RU2014123260A - Гликополисиалирование белков, не являющихся белками свертывания крови - Google Patents
Гликополисиалирование белков, не являющихся белками свертывания крови Download PDFInfo
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- RU2014123260A RU2014123260A RU2014123260/04A RU2014123260A RU2014123260A RU 2014123260 A RU2014123260 A RU 2014123260A RU 2014123260/04 A RU2014123260/04 A RU 2014123260/04A RU 2014123260 A RU2014123260 A RU 2014123260A RU 2014123260 A RU2014123260 A RU 2014123260A
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- growth factors
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- 102000004169 proteins and genes Human genes 0.000 title claims abstract 7
- 108090000623 proteins and genes Proteins 0.000 title claims abstract 7
- 230000023555 blood coagulation Effects 0.000 title claims abstract 5
- 238000000034 method Methods 0.000 claims abstract 17
- 102000003886 Glycoproteins Human genes 0.000 claims abstract 11
- 108090000288 Glycoproteins Proteins 0.000 claims abstract 11
- 125000000837 carbohydrate group Chemical group 0.000 claims abstract 8
- 239000002253 acid Substances 0.000 claims abstract 6
- 239000003102 growth factor Substances 0.000 claims abstract 5
- 235000018102 proteins Nutrition 0.000 claims abstract 5
- 102000007644 Colony-Stimulating Factors Human genes 0.000 claims abstract 4
- 108010071942 Colony-Stimulating Factors Proteins 0.000 claims abstract 4
- 150000001720 carbohydrates Chemical class 0.000 claims abstract 4
- 229940047120 colony stimulating factors Drugs 0.000 claims abstract 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims abstract 4
- 102000002467 interleukin receptors Human genes 0.000 claims abstract 4
- 108010093036 interleukin receptors Proteins 0.000 claims abstract 4
- 230000021615 conjugation Effects 0.000 claims abstract 3
- 102000011022 Chorionic Gonadotropin Human genes 0.000 claims abstract 2
- 108010062540 Chorionic Gonadotropin Proteins 0.000 claims abstract 2
- 102000004127 Cytokines Human genes 0.000 claims abstract 2
- 108090000695 Cytokines Proteins 0.000 claims abstract 2
- 102000018386 EGF Family of Proteins Human genes 0.000 claims abstract 2
- 108010066486 EGF Family of Proteins Proteins 0.000 claims abstract 2
- 102000018233 Fibroblast Growth Factor Human genes 0.000 claims abstract 2
- 108050007372 Fibroblast Growth Factor Proteins 0.000 claims abstract 2
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 claims abstract 2
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 claims abstract 2
- 102000015611 Hypothalamic Hormones Human genes 0.000 claims abstract 2
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- 108060003951 Immunoglobulin Proteins 0.000 claims abstract 2
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- 102000014150 Interferons Human genes 0.000 claims abstract 2
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- 108010009583 Transforming Growth Factors Proteins 0.000 claims abstract 2
- 101800004564 Transforming growth factor alpha Proteins 0.000 claims abstract 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract 2
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- 230000003213 activating effect Effects 0.000 claims abstract 2
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims abstract 2
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- 102000018358 immunoglobulin Human genes 0.000 claims abstract 2
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- 229940047124 interferons Drugs 0.000 claims abstract 2
- 229940047122 interleukins Drugs 0.000 claims abstract 2
- 239000002523 lectin Substances 0.000 claims abstract 2
- 239000000049 pigment Substances 0.000 claims abstract 2
- 235000021118 plant-derived protein Nutrition 0.000 claims abstract 2
- 229940097325 prolactin Drugs 0.000 claims abstract 2
- 125000005629 sialic acid group Chemical group 0.000 claims abstract 2
- 230000008467 tissue growth Effects 0.000 claims abstract 2
- 102000003390 tumor necrosis factor Human genes 0.000 claims abstract 2
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims abstract 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
- 230000001590 oxidative effect Effects 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 102000003951 Erythropoietin Human genes 0.000 claims 2
- 108090000394 Erythropoietin Proteins 0.000 claims 2
- 241000872931 Myoporum sandwicense Species 0.000 claims 2
- 229940105423 erythropoietin Drugs 0.000 claims 2
- 239000012634 fragment Substances 0.000 claims 2
- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims 1
- 102000016911 Deoxyribonucleases Human genes 0.000 claims 1
- 108010053770 Deoxyribonucleases Proteins 0.000 claims 1
- 102000002464 Galactosidases Human genes 0.000 claims 1
- 108010093031 Galactosidases Proteins 0.000 claims 1
- 229930003268 Vitamin C Natural products 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 102000005936 beta-Galactosidase Human genes 0.000 claims 1
- 108010005774 beta-Galactosidase Proteins 0.000 claims 1
- 229960000182 blood factors Drugs 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000001268 conjugating effect Effects 0.000 claims 1
- 102000013361 fetuin Human genes 0.000 claims 1
- 108060002885 fetuin Proteins 0.000 claims 1
- 102000037865 fusion proteins Human genes 0.000 claims 1
- 108020001507 fusion proteins Proteins 0.000 claims 1
- 238000011534 incubation Methods 0.000 claims 1
- 239000012011 nucleophilic catalyst Substances 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 235000019154 vitamin C Nutrition 0.000 claims 1
- 239000011718 vitamin C Substances 0.000 claims 1
- -1 α-galactoside Proteins 0.000 claims 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 1
- 239000000122 growth hormone Substances 0.000 abstract 1
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Abstract
1. Способ конъюгации полисиаловой кислоты (PSA) или модифицированной PSA (mPSA) с окисленной углеводной частью гликопротеина, отличного от белка свертывания крови, содержащего углеводную группу, включающий контактирование окисленной углеводной части с PSA или mPSA в условиях, которые обеспечивают конъюгацию,где указанная PSA или mPSA содержат гидразидную группу и между окисленной углеводной частью и гидразидной группой на PSA или mPSA образуется гидразоновая связь.2. Способ по п. 1, где PSA или mPSA представляет собой коломиновую кислоту или модифицированную коломиновую кислоту.3. Способ по п. 1 или 2, где PSA или mPSA содержит 2-500 звеньев сиаловой кислоты.4. Способ по п. 1 или 2, где гликопротеин выбран из цитокинов, таких как интерлейкины, альфа-, бета- и гамма-интерфероны, колониестимулирующих факторов, включая гранулоцитарные колониестимулирующие факторы, фибробластных факторов роста, тромбоцитарных факторов роста, активирующего фосфолипазу белка (PUP), инсулина, растительных белков, таких как лектины и рицины, факторов некроза опухоли и родственных аллельных форм, растворимых форм рецепторов фактора некроза опухоли, рецепторов интерлейкинов и растворимых форм рецепторов интерлейкинов, факторов роста, тканевых факторов роста, трансформирующих факторов роста, таких как TGFα или TGFβ, и эпидермальных факторов роста, гормонов, соматомединов, пигментарных гормонов, гипоталамических рилизинг-факторов, антидиуретических гормонов, пролактина, хорионического гонадотропина, фоликулостимулирующего гормона, тиреотропного гормона, тканевого активатора плазминогена и иммуноглобулинов, таких как IgG, IgE, IgM, IgA и IgD, моноклональных антител, эритроп�
Claims (14)
1. Способ конъюгации полисиаловой кислоты (PSA) или модифицированной PSA (mPSA) с окисленной углеводной частью гликопротеина, отличного от белка свертывания крови, содержащего углеводную группу, включающий контактирование окисленной углеводной части с PSA или mPSA в условиях, которые обеспечивают конъюгацию,
где указанная PSA или mPSA содержат гидразидную группу и между окисленной углеводной частью и гидразидной группой на PSA или mPSA образуется гидразоновая связь.
2. Способ по п. 1, где PSA или mPSA представляет собой коломиновую кислоту или модифицированную коломиновую кислоту.
3. Способ по п. 1 или 2, где PSA или mPSA содержит 2-500 звеньев сиаловой кислоты.
4. Способ по п. 1 или 2, где гликопротеин выбран из цитокинов, таких как интерлейкины, альфа-, бета- и гамма-интерфероны, колониестимулирующих факторов, включая гранулоцитарные колониестимулирующие факторы, фибробластных факторов роста, тромбоцитарных факторов роста, активирующего фосфолипазу белка (PUP), инсулина, растительных белков, таких как лектины и рицины, факторов некроза опухоли и родственных аллельных форм, растворимых форм рецепторов фактора некроза опухоли, рецепторов интерлейкинов и растворимых форм рецепторов интерлейкинов, факторов роста, тканевых факторов роста, трансформирующих факторов роста, таких как TGFα или TGFβ, и эпидермальных факторов роста, гормонов, соматомединов, пигментарных гормонов, гипоталамических рилизинг-факторов, антидиуретических гормонов, пролактина, хорионического гонадотропина, фоликулостимулирующего гормона, тиреотропного гормона, тканевого активатора плазминогена и иммуноглобулинов, таких как IgG, IgE, IgM, IgA и IgD, моноклональных антител, эритропоэтина (EPO), факторов крови, отличных от белков свертывания крови, галактозидаз, α-галактозидаз, β-галактозидаз, ДНКаз, фетуина, их фрагментов и любых слитых белков, содержащих любой из упомянутых выше белков или их фрагментов.
5. Способ по п. 1 или 2, включающий окисление углеводной части путем инкубации гликопротеина с перйодатом натрия (NaIO4).
6. Способ по п. 1 или 2, включающий окисление PSA или mPSA с образованием альдегидной группы на концевом звене PSA или mPSA и реакцию окисленного PSA или mPSA с гидразидным линкером.
7. Способ согласно п. 6, включающий окисления PSA или mPSA с использованием NaIO4.
8. Способ по п. 1 или 2, включающий контактирование окисленной углеводной части с PSA или mPSA в буфере, содержащем нуклеофильный катализатор, выбранный из анилина или производных анилина.
9. Способ по п. 1 или 2, где указанная PSA или mPSA содержит гидразидную группу и между окисленной углеводной частью и гидразидной группой на PSA или mPSA образуется гидразоновая связь.
10. Способ по п. 9, где гидразидная группа образуется путем реакции окисленного PSA или mPSA с гидразидным линкером.
11. Способ по п. 1 или 2, дополнительно включающий восстановление гидразоновой связи в конъюгированном гликопротеине путем инкубации в присутствии восстановителя.
12. Способ по п. 11, где восстанавливающее соединение представляет собой цианоборгидрид натрия (NaCNBH3) или аскорбиновую кислоту (витамин C).
13. Конъюгированный гликопротеин, получаемый способом по любому из предшествующих пунктов.
14. Конъюгированный гликопротеин, отличный от белка свертывания крови, включающий:
(a) гликопротеин и
(b) по меньшей мере одну гидразид-PSA или гидразид-mPSA, связанную с гликопротеином согласно (а), где указанная гидразид-PSA или гидразид-mPSA присоединена к гликопротеину через одну или несколько углеводных частей.
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CN113677360A (zh) * | 2019-02-04 | 2021-11-19 | 艾克森埃缇克生物科学公司 | 使用糖聚唾液酸化治疗性蛋白的方法 |
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RU2016121611A (ru) | 2018-11-29 |
SG10201401194VA (en) | 2014-07-30 |
CN104530182A (zh) | 2015-04-22 |
JP2018024882A (ja) | 2018-02-15 |
CN106110311A (zh) | 2016-11-16 |
US20190314516A1 (en) | 2019-10-17 |
RU2744370C2 (ru) | 2021-03-05 |
JP2015227385A (ja) | 2015-12-17 |
RU2016121611A3 (ru) | 2019-12-10 |
JP2018035192A (ja) | 2018-03-08 |
US20180200380A1 (en) | 2018-07-19 |
EP3093029A8 (en) | 2016-12-28 |
EP3093029A1 (en) | 2016-11-16 |
US10350301B2 (en) | 2019-07-16 |
HUE028056T2 (en) | 2016-11-28 |
PT2459224T (pt) | 2016-09-05 |
JP2020037701A (ja) | 2020-03-12 |
ES2856055T3 (es) | 2021-09-27 |
US20160361430A1 (en) | 2016-12-15 |
JP6208269B2 (ja) | 2017-10-04 |
PL2459224T3 (pl) | 2017-08-31 |
JP7071093B2 (ja) | 2022-05-18 |
NZ623810A (en) | 2015-10-30 |
RU2662807C2 (ru) | 2018-07-31 |
US10772968B2 (en) | 2020-09-15 |
JP2021042244A (ja) | 2021-03-18 |
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US11040109B2 (en) | 2021-06-22 |
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