CN106083993A - Parents' polypeptide amine dendrimer and preparation method thereof - Google Patents
Parents' polypeptide amine dendrimer and preparation method thereof Download PDFInfo
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- 239000000412 dendrimer Substances 0.000 title claims abstract description 51
- 229920000736 dendritic polymer Polymers 0.000 title claims abstract description 51
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 150000001412 amines Chemical class 0.000 title abstract description 5
- 102000004196 processed proteins & peptides Human genes 0.000 title description 4
- 108090000765 processed proteins & peptides Proteins 0.000 title description 4
- 229920001184 polypeptide Polymers 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229910001868 water Inorganic materials 0.000 claims abstract description 24
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004472 Lysine Substances 0.000 claims abstract description 12
- 241000219000 Populus Species 0.000 claims abstract description 11
- 239000000835 fiber Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 8
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 7
- 239000012046 mixed solvent Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 20
- 238000001338 self-assembly Methods 0.000 claims description 19
- 239000000376 reactant Substances 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 208000035126 Facies Diseases 0.000 claims description 15
- 229940125904 compound 1 Drugs 0.000 claims description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 235000002639 sodium chloride Nutrition 0.000 claims description 14
- 239000011780 sodium chloride Substances 0.000 claims description 14
- 238000003786 synthesis reaction Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 11
- 238000000746 purification Methods 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 229940125782 compound 2 Drugs 0.000 claims description 8
- 238000007710 freezing Methods 0.000 claims description 8
- 230000008014 freezing Effects 0.000 claims description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 8
- 238000004440 column chromatography Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 238000005406 washing Methods 0.000 claims description 6
- 229940126214 compound 3 Drugs 0.000 claims description 5
- 229940125898 compound 5 Drugs 0.000 claims description 5
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims description 5
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000012265 solid product Substances 0.000 claims description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims description 3
- 239000012230 colorless oil Substances 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- -1 methoxyl group Chemical group 0.000 claims description 3
- 230000002572 peristaltic effect Effects 0.000 claims description 3
- LYUXBTAUKJETMS-KRWDZBQOSA-N (4-nitrophenyl) (2s)-2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate Chemical compound CC(C)(C)OC(=O)NCCCC[C@H](NC(=O)OC(C)(C)C)C(=O)OC1=CC=C([N+]([O-])=O)C=C1 LYUXBTAUKJETMS-KRWDZBQOSA-N 0.000 claims description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000103 lithium hydride Inorganic materials 0.000 claims description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- 239000012295 chemical reaction liquid Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 230000006698 induction Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 238000006555 catalytic reaction Methods 0.000 abstract description 2
- 238000013270 controlled release Methods 0.000 abstract description 2
- 230000032050 esterification Effects 0.000 abstract description 2
- 238000005886 esterification reaction Methods 0.000 abstract description 2
- 230000008288 physiological mechanism Effects 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 238000001514 detection method Methods 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- NCQXXVRTDHWOSP-UHFFFAOYSA-N CNC1=CN(C=C1)NC Chemical compound CNC1=CN(C=C1)NC NCQXXVRTDHWOSP-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 description 1
- 102000006395 Globulins Human genes 0.000 description 1
- 108010044091 Globulins Proteins 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001967 indiganyl group Chemical group [H][In]([H])[*] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000002127 nanobelt Substances 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K19/00—Hybrid peptides, i.e. peptides covalently bound to nucleic acids, or non-covalently bound protein-protein complexes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Peptides Or Proteins (AREA)
Abstract
The invention discloses the preparation method of class parents' chirality amine dendrimer.This parents' amine dendrimer is prepared by esterification by lysine dendrimers and alkyloxy-ethers dendrimers.Parents' dendrimers in the present invention, induction due to chiral structure, parents' dendrimers (MeG2 LysG3) that the poplar bundles lysine of secondary poplar bundles alkyloxy-ethers and three generations is constituted carries out Supramolecular Assembling in the mixed solvent of oxolane and water, the spiral fiber of ordered arrangement is can observe under atomic force microscope, and by changing hydrophilic and hydrophobic and the algebraically of poplar bundles primitive of this molecule periphery group, the assembly of available different shape, dendrimer in the present invention is not only at drug controlled release, there is important application prospect in the fields such as catalysis and intellectual material, the various physiological mechanisms disclosed in life process are had great significance simultaneously.
Description
Technical field
The present invention relates to class parents' chirality dendrimers and preparation method thereof.
Background technology
Parents' dendrimers is nearest a kind of novel organic synthesis macromolecular material, and this type of molecular structure is regular, molecule
Measuring single, unimolecule yardstick is at Nano grade, and surface has the functional group of very high-density, the most also has similar globulin
Structure, has the advantages such as good water solublity and biodegradability, in drug release, genetic engineering, tissue repair and disease
The fields such as diagnosis play an important role, and therefore parents' dendrimers has broad application prospects at biomedical sector.
Parents' dendrimers is with hydrophilic head and the structure of hydrophobic tail, and it is vulnerable to hydrogen bond, Van der Waals force, electrostatic interaction, π-π heap
Long-pending, hydrophobe and surface tension of liquid etc. drive, and in a solvent or carry out self assembly on interface, and obtain a series of microfacies
Structure, such as spherical, bar-shaped, the composite micelle etc. of vesicle or bigger.Percec et al. (S.Zhang, H.J.Sun,
A.D.Hughes,R.O.Moussodia,A.Bertin,Y.Chen,D.J.Pochan,P.A.Heiney,M.L.Klein,
V.Percec, PNAS., 2014,111,9058-9063) report and parents' dendrimers with adhoc basis structure is injected
In water or buffer solution, molecule carries out self assembly and obtains the vesicle of size uniformity, and by changing the concentration assembling solution, point
Son is self-assembly of many bilayer vesicles of single bilayer vesicle and similar Bulbus Allii Cepae structure scalably.
But when chirality primitive is incorporated into parents' molecule, due to the induction of chiral structure, parents' molecule can be layered
Ground carries out self assembly thus obtains the different forms such as fiber, banding, spiral, superhelix and tubulose.Ihara and Liu Minghua et al.
Introducing multiple chiral element on parents' molecule based on Pidolidone or D-Glu, research finds that the chirality of chirality primitive can
Be delivered to supermolecule nano structure (M.Takafuji, Y.Kira, H.Tsuji, S.Sawada, H.Hachisako, H.Ihara,
Tetrahedron., 2007,63,7489-7494, C.Liu, Q.Jin, K.Lv, L.Zhang, M.Liu,
.Chem.Commun.2014,50,3702-3705,Q.Jin,L.Zhang,M.Liu,Chem.-Eur.J.2013,19,9234-
9241.) organogel, such as formed in DMSO at pyridine meta substituted Pidolidone parents' molecule is capable of detecting when relatively
Strong section pauses signal, and clearly observe under transmission electron microscope(TEM) deviously nano belt (P.Duan, X.Zhu,
M.Liu,.Chem.Commun.2011,47,5569-5571；).
Self assembly about parents' chiral molecule at present is studied more, and makes some progress, but by chirality
Element is incorporated in parents' dendrimers, but rarely has report studying the work of chiral induction parents' dendritic macromole self assembly
Road.
Summary of the invention
One of the object of the invention is to provide class chirality parents' amine dendrimer.
The two of the object of the invention are the preparation methoies of this chirality parents' dendrimer.
The three of the object of the invention are the Supramolecular Assemblings of such parents' chirality dendrimer.
It is the secondary of hydroxyl and three generations's lysine dendrimer that the present invention uses liquid phase synthesizing method to obtain epipole, from different
End group and the alkyloxy-ethers dendrimers of different algebraically carry out esterification, finally give described parents' dendrimer.
One class parents' chirality dendrimers, it is characterised in that the structural formula of this dendrimers is one of following:
1.
2.
3.
4.
A kind of method preparing above-mentioned parents' dendrimer, it is characterised in that concretely comprising the following steps of the method:
A. under cryosel bath and inert atmosphere, at the lysine tetrahydrochysene furan to nitro-activating ester (Boc-Lys (boc)-ONp)
Mutter in (THF), be sequentially added into sodium borohydride (NaBH4) and the tetrahydrofuran solution of lithium chloride (LiCl), stirring to reaction is completely；
Add water to, no longer till effervescent, then with saturated aqueous common salt, reactant liquor be washed, then organic facies is carried out in system
Being dried, solvent evaporated after filtration, separated purification obtains colorless oil compound 2, and its structural formula is:
Described compound 1, LiCl and NaBH4Mol ratio be: 1:5:8；
B., in ice bath, step a gained compound 2 is dissolved in oxolane, and adds the HCl of 25wt%, under room temperature
Stirring is complete to reaction, stopped reaction, reactant liquor deionized water and DCM washing, aqueous phase liquid nitrogen freezing, is finally dried,
To its structural formula of compound as white solid 3 it is:
Described compound 2 with the mol ratio ratio of the HCl of 25wt% is: 1:20～1:30；；
C., in ice bath, step b gained compound 3 is dissolved in H2O and N,N-dimethylformamide (DMF) (V/V=1:2)
In mixed solvent, in system, then add DIPEA (DIEA), then in system, be slowly added dropwise compound 1
DMF solution, completely, stopped reaction, reactant liquor saturated aqueous common salt washs 3 times, and regulates pH to 5, then nothing in reaction to reaction
Organic facies is dried by water magnesium sulfate, is spin-dried for solvent after filtration, and separated purification obtains white foam product 4, its structure
Formula is:
The mol ratio of described compound 3, DIEA and compound 1 is: 1:10:3；
D., in ice bath, step c gained compound 4 is dissolved in THF, in system, then adds the HCl of 25wt%, room
The lower stirring of temperature is extremely reacted completely, stopped reaction, reactant liquor deionized water and DCM washing, and aqueous phase uses liquid nitrogen freezing 10min,
Rear dry, obtain compound as white solid 5, its structural formula is:
Described compound 4 with the mol ratio of the HCl of 25wt% is: 1:20～1:30；
F., in ice bath, step d gained compound 5 is dissolved in H2The mixed solvent of O and DMF (V/V=1:2), adds DIEA,
Being slowly added dropwise the DMF solution of compound 1 again in system, to reaction completely, stopped reaction, reactant liquor saturated aqueous common salt washs
3 times, and regulate pH to 5, then organic facies is dried by anhydrous magnesium sulfate, is spin-dried for solvent after filtration, separated purification obtains white
Color solid product 6；Its structural formula is:
The mol ratio of described compound 5, DIEA and compound 1 is: 1:10:6；
G. a generation and the synthesis of secondary alkyloxy-ethers B (MeG1)
By a generation alkyloxy-ethers poplar bundles primitive A (MeG1-COOMe) (reference literature Li, W. that core epipole is ester group；
Zhang,A.；Schl ü ter, the synthesis of A.D.Chem.Commun.2008,5523-5525) it is dissolved in THF and H2O (V/V=1:1)
In, in system, then it is slowly added dropwise a water lithium hydride (LiOH.H2O) aqueous solution, under room temperature, stirring is to reaction completely, reaction
After liquid washs with saturated aqueous common salt, adjust PH to 5 with potassium acid sulfate, after organic facies is dried by anhydrous magnesium sulfate, revolve after filtration
Dry solvent, purifies through column chromatography chromatogram and obtains colourless transparent liquid B, and its structural formula is:
The mol ratio of described compound A and Lithium hydroxide monohydrate is: 1:8～1:10.
H., under cryosel bath and inert atmosphere, in dichloromethane (DCM) solution of step f gained compound 6, add successively
Entering compound B, DMAP and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, stirring reaction is extremely
Completely, reactant liquor saturated aqueous common salt washs 3 times, and organic facies is spin-dried for solvent after being dried, more separated purification obtains in reaction
White solid C, the mol ratio of described compound B and compound 6 is 1:2～1:3, is parents' dendrimer.
The condition of described parents' chirality dendrimers self assembly is: by peristaltic pump to the tetrahydrochysene furan of parents' dendrimers
Muttering water filling in solution, the final volume of oxolane and water is than for 1:20.
The described parents being made up of the poplar bundles lysine (MeG2-LysG3) of secondary poplar bundles alkyloxy-ethers and three generations
The self assembly in the mixed solvent of water and oxolane of chirality dendrimers, the spiral fiber of available ordered arrangement.
Described parents' chirality dendrimers, when the end group on alkyloxy-ethers is become relative hydrophobic from hydrophilic methoxyl group
Ethyoxyl time, EtG2-LysG3 self assembly can get intensive short and Random fiber.
Described parents' chirality dendrimers, reduces the algebraically of alkyloxy-ethers, by the secondary generation that is reduced to, MeG1-LysG3
Self assembly forms relative distribution and short and unordered fiber too；
Described parents' chirality dendrimers, reduces alkyloxy-ethers and the algebraically of lysine simultaneously, and MeG1-LysG2 then obtains
The nanoparticle that size is the most homogeneous.
This type of macromole is with peptides dendrimers and the structure of parents' molecule and performance, and can carry out supermolecule
Self assembly, forms the spiral fiber with regular ordered arrangement.Dendrimer in the present invention not only drug controlled release,
There is important application prospect in the fields such as catalysis and intellectual material, have the various physiological mechanisms disclosed in life process simultaneously
Important meaning.
Parents' chirality dendrimers of the present invention, changes hydrophilic and hydrophobic and the poplar bundles base of parents' dendrimers peripheral groups
Unit's algebraically, the assembly of available different shape.When the end group on alkyloxy-ethers is become the ethoxy of relative hydrophobic from methoxyl group
During base, parents' dendrimers (EtG2-LysG3) self assembly can get intensive short and Random fiber；Reduce the algebraically of alkyloxy-ethers,
Parents' dendrimers (MeG1-LysG3) self assembly forms relative distribution and short and unordered fiber too；But ought drop simultaneously
Low alkyloxy-ethers and the algebraically of lysine, parents' dendrimers (MeG1-LysG2) self assembly then obtain diameter dimension 55～
The particle of 100nm.
The present invention compared with prior art, has and the most obviously highlights substantive distinguishing features and remarkable advantage:
1. the present invention is obtaining three generations's branch lysine by liquid phase synthesizing method, and relatively conventional solid-phase synthesis yield is more
High；
2. the parents' molecule hydrophobic part in the present invention is polypeptide dendrimers, has good biocompatibility and biology
The advantages such as degradability；
3. chirality primitive is incorporated in parents' dendrimers by the present invention, from little molecule, chirality can be delivered to supermolecule and receive
Rice structure.
Accompanying drawing explanation
Fig. 1 is the synthesis schematic diagram of LysG3.
Fig. 2 is the synthesis schematic diagram of MeG1.
Fig. 3 is the synthesis schematic diagram of MeG1-LysG3.
Fig. 4 is the hydrogen nuclear magnetic resonance spectrogram (DMSO) of MeG1-LysG3.
Fig. 5 is the hydrogen nuclear magnetic resonance spectrogram (CDCl of MeG1-LysG33)。
Fig. 6 is the hydrogen nuclear magnetic resonance spectrogram (DMSO) of MeG1-LysG3.
Fig. 7 is the hydrogen nuclear magnetic resonance spectrogram (DMSO) of MeG1-LysG3.
Fig. 8 is the dynamic light scattering data of four kinds of parents' dendrimers.
Fig. 9 is the self assembly AFM figure of four kinds of parents' dendrimers.
Detailed description of the invention:
Embodiment 1:
The present invention relates to the preparation of MeG1-LysG3.Synthetic route is with reference to accompanying drawing Fig. 1, Fig. 2, Fig. 3, and other parents' branch divides
The preparation of son is with reference to this syntheti c route.
1. the synthesis of three generations's lysine
1) synthesis of compound 2 (Boc-LysG1-OL)
Compound 1 (3.00g, 6.42mmol) is dissolved in dry THF (20mL), repeatedly uses high-purity N2Bleed-inflate
Circulate 3 times, system is placed in cryosel bath and cools down 30min；Then in system, it is sequentially added into LiCl (2.18g, 51.33mmol)
And NaBH4(1.21g, 32.08mmol), uses high-purity N the most repeatedly2Bleed-inflation cycle 3 times, reaction overnight.Detect with TLC plate
Reaction completely, stopped reaction, add water to no longer (remove remaining NaBH till effervescent in system4), then use saturated food
Reactant liquor is washed by saline, then is dried organic facies with anhydrous magnesium sulfate, solvent evaporated after filtration, through column chromatography color
Spectrum purification obtains colorless oil compound 2 (1.86g, 87%).
2) synthesis of compound 3 (LL-OL.2HCl)
Compound 2 (1.86g, 5.59mmol) is dissolved in THF (20mL), system is placed in ice bath cooling 30min, then
In system, add the HCl (24.48g, 167.85mmol) of 25%, stir 1h under ice bath, remove ice bath, under room temperature, stir 3h；
With the detection reaction of TLC plate completely, stopped reaction, reactant liquor deionized water and DCM washing, aqueous phase liquid nitrogen freezing 10min,
It is dried with freezer dryer afterwards, obtains compound as white solid 3 (1.04g, 90%).
3) synthesis of compound 4 (Boc-LLG2-OL)
Compound 3 (1.04g, 5.07mmol) is dissolved in H2O (10mL) and DMF (10mL), puts into system in ice bath cold
But 20min, then adds DIEA (3.28g, 25.35mmol), freezing stirring 10min in system, by compound 1 (7.11g,
15.21mmol) it is dissolved in DMF (30mL), then the compound 1 dissolved is slowly dropped in system, reaction overnight；With TLC
Completely, stopped reaction, reactant liquor saturated aqueous common salt washs 3 times, and adjusts PH to 5 with potassium acid sulfate, more anhydrous in plate detection reaction
Organic facies is dried by magnesium sulfate, is spin-dried for solvent after filtration, purifies through column chromatography chromatogram and obtains white solid product 4
(3.96g, 90%).
4) synthesis of compound 5 (LL-OL.4HCl)
By compound 4 (1g, 1.27mmol), be dissolved in THF (20mL), system be placed in ice bath cooling 30min, then to
System adds the HCl (5.56g, 38.02mmol) of 25%, stirs 1h under ice bath, remove ice bath, stir 3h under room temperature, with TLC
Plate detection reaction is complete, stopped reaction, reactant liquor deionized water and DCM washing, aqueous phase liquid nitrogen freezing 10min, finally uses
Freezer dryer is dried, and obtains compound as white solid 5 (0.61g, 90%).
5) synthesis of compound 6 (Boc-LysG3)
Compound 5 (0.61g, 1.14mmol) is dissolved in H2O (10mL) and DMF (10mL), puts into system in ice bath cold
But 20min, then adds DIEA (1.48g, 11.41mmol), freezing stirring 10min in system, by compound 1 (2.67g,
5.71mmol) it is dissolved in DMF (30mL), then the compound 1 dissolved is slowly dropped in system, reaction overnight；With TLC plate
Completely, stopped reaction, reactant liquor saturated aqueous common salt washs 3 times, and adjusts PH to 5, more anhydrous sulfur with potassium acid sulfate in detection reaction
Organic facies is dried by acid magnesium, is spin-dried for solvent after filtration, through column chromatography chromatogram purify obtain white solid product 6 (1.82g,
93%).
2. the synthesis of generation alkyloxy-ethers B (MeG1)
By a generation alkyloxy-ethers poplar bundles primitive A (G1-COOMe) (reference literature Li, W. that core is ester group；Zhang,A.；
Schl ü ter, the synthesis of A.D.Chem.Commun.2008,5523-5525) weigh 1g and be dissolved in THF (10mL) and H2O(10mL)
In, then will be dissolved with LiOH.H2In the slow above-mentioned solution of 20mL aqueous solution of O (6.06g), stir two hours and extremely react completely,
After reactant liquor washs with saturated aqueous common salt, adjust PH to 5 with potassium acid sulfate, after organic facies is dried by anhydrous magnesium sulfate, filter
After be spin-dried for solvent, through column chromatography chromatogram purify obtain colourless transparent liquid A (2.89g, 76%).
3. the synthesis of compound C (MeG1-LysG3)
Weigh Compound 6 (200mg) is dissolved in dry DCM (10mL), repeatedly uses high-purity N2Bleed-inflation cycle 3 times,
System is placed in cryosel bath and cools down 20min；Then be sequentially added in system compound B (214mg), 1,4-dimethylamino pyrrole
(DMAP, 4.31mg) and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC HCl 27.36mg), again
Repeatedly use high-purity N2Bleed-inflation cycle 3 times, react 72h；With the detection reaction of TLC plate completely, stopped reaction, reactant liquor is with full
With brine It 3 times, then use anhydrous MgSO4Organic facies is dried, is spin-dried for solvent after filtration, carries with through column chromatography chromatogram
Pure obtain white solid C (110mg, 40%).
Example 2:
Take the THF solution 100uL of 0.5mg/mL MeG2-LysG3, by peristaltic pump with the speed of 1.6uL/s in solution
Water filling 2mL Watson distilled water, stands three days.Solution dialysis is removed organic solvent THF, to obtain the aqueous solution of assembly,
Solution is dropped in preparation atomic force microscope (AFM) sample on mica sheet, is observing assembling volume morphing at AFM.
Claims (7)
1. class parents' chirality dendrimers, it is characterised in that the structural formula of this dendrimers is one of following:
a.
b.
c.
d.
。
2. the method preparing parents' dendrimer according to claim 1, it is characterised in that the method concrete
Step is:
A. under cryosel bath and inert atmosphere, at the lysine oxolane to nitro-activating ester (Boc-Lys (Boc)-ONp)
(THF) in, being sequentially added into sodium borohydride (NaBH4) and the tetrahydrofuran solution of lithium chloride (LiCl), stirring to reaction is completely；To
System adds water to, no longer till effervescent, then with saturated aqueous common salt, reactant liquor is washed, then organic facies is done
Dry, solvent evaporated after filtration, separated purification obtains colorless oil compound 2, described compound 1, LiCl and NaBH4
Mol ratio is: 1:5:8；
B. in ice bath, step a gained compound 2 is dissolved in oxolane, and adds the HCl of 25wt%, stir under room temperature
To reaction completely, stopped reaction, reactant liquor deionized water and dichloromethane DCM washing, aqueous phase liquid nitrogen freezing, finally do
Dry, obtain compound as white solid 3;Described compound 2 with the mol ratio of the HCl of 25wt% is: 1:20 ~ 1:30；
C., in ice bath, step b gained compound 3 is dissolved in water and DMF DMF mixing by the volume ratio of 1:2
In bonding solvent, in system, then add DIPEA DIEA, then in system, be slowly added dropwise the DMF of compound 1
Solution, completely, stopped reaction, reactant liquor saturated aqueous common salt washs 3 times, and regulates pH to 5, then anhydrous slufuric acid in reaction to reaction
Organic facies is dried by magnesium, is spin-dried for solvent after filtration, and separated purification obtains white foam product 4,
Described compound 3, the mol ratio of compound 1 and DIEA be: 1:3:10；
D., in ice bath, step c gained compound 4 is dissolved in THF, in system, then adds the HCl of 25wt%, room temperature
Lower stirring is complete to reaction, stopped reaction, reactant liquor deionized water and DCM washing, aqueous phase liquid nitrogen freezing 10 min, finally
Being dried, obtain compound as white solid 5, described compound 4 with the mol ratio of the HCl of 25wt% is: 1:20 ~ 1:30；
F. in ice bath, step d gained compound 5 is dissolved in water and the DMF mixed solvent by the volume ratio of 1:2, adds N, N-bis-
Wopropyl ethyl amine DIEA, then in system, it is slowly added dropwise the DMF solution of compound 1, to reaction completely, stopped reaction, reaction
Liquid saturated aqueous common salt washs 3 times, and regulates pH to 5, then organic facies is dried by anhydrous magnesium sulfate, is spin-dried for molten after filtration
Agent, separated purification obtains white solid product 6, and the mol ratio of described compound 5, DIEA and compound 1 is: 1:10:6；
G. a generation and the synthesis of secondary alkyloxy-ethers B (MeG1)
Generation alkyloxy-ethers poplar bundles primitive A (MeG1-COOMe) that core epipole is ester group is dissolved in THF and water by the volume of 1:1
In the mixed liquor of ratio, being then slowly added dropwise the aqueous solution of a water lithium hydride in system, under room temperature, stirring is to reaction completely, reaction
After liquid washs with saturated aqueous common salt, adjust PH to 5 with potassium acid sulfate, after organic facies is dried by anhydrous magnesium sulfate, revolve after filtration
Dry solvent, purifies through column chromatography chromatogram and obtains colourless transparent liquid B, and the mol ratio of described compound A and Lithium hydroxide monohydrate is:
1:8 ~ 1:10.
H., under cryosel bath and inert atmosphere, in dichloromethane (DCM) solution of step f gained compound 6, it is sequentially added into
Compound B, DMAP and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, stirring reaction is to instead
Should be complete, reactant liquor saturated aqueous common salt washs 3 times, and organic facies is spin-dried for solvent after being dried, more separated purification obtains white
Color solid C, the mol ratio of described compound B and compound 6 is 1:2 ~ 1:3, is parents' dendrimer.
3. the condition of the parents' chirality dendrimers self assembly as described in claim 1 is: divided to parents' branch by peristaltic pump
Water filling in the tetrahydrofuran solution of son, the final volume of oxolane and water ratio is for 1:20.
4. as described in claim 1 by poplar bundles lysine (MeG2-LysG3) structure of secondary poplar bundles alkyloxy-ethers and three generations
The parents' chirality dendrimers self assembly in the mixed solvent of water and oxolane become, the spiral of available ordered arrangement is fine
Dimension.
5. the parents' chirality dendrimers as described in claim 1, when the end group on alkyloxy-ethers is become by hydrophilic methoxyl group
During for the ethyoxyl of relative hydrophobic, EtG2-LysG3 self assembly can get intensive short and Random fiber.
6. the parents' chirality dendrimers as described in claim 1, reduces the algebraically of alkyloxy-ethers, be secondary be reduced to a generation,
MeG1-LysG3 self assembly forms relative distribution and short and unordered fiber too.
7. the parents' chirality dendrimers as described in claim 1, reduces alkyloxy-ethers and the algebraically of lysine, MeG1-simultaneously
LysG2 then obtains the diameter dimension particle at 55 ~ 100 nm.
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