JP6356374B2 - 加水分解ヒアルロン酸誘導体及びカチオン系殺菌剤を含有するコンタクトレンズ用液剤 - Google Patents
加水分解ヒアルロン酸誘導体及びカチオン系殺菌剤を含有するコンタクトレンズ用液剤 Download PDFInfo
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- JP6356374B2 JP6356374B2 JP2018518806A JP2018518806A JP6356374B2 JP 6356374 B2 JP6356374 B2 JP 6356374B2 JP 2018518806 A JP2018518806 A JP 2018518806A JP 2018518806 A JP2018518806 A JP 2018518806A JP 6356374 B2 JP6356374 B2 JP 6356374B2
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- hyaluronic acid
- acid derivative
- hydrolyzed hyaluronic
- contact lens
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 title claims description 121
- 239000000882 contact lens solution Substances 0.000 title claims description 17
- 125000002091 cationic group Chemical group 0.000 title claims description 15
- 239000000417 fungicide Substances 0.000 title claims description 10
- 230000000855 fungicidal effect Effects 0.000 title claims description 8
- 239000000126 substance Substances 0.000 claims description 35
- 239000000017 hydrogel Substances 0.000 claims description 17
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052710 silicon Inorganic materials 0.000 claims description 10
- 239000010703 silicon Substances 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000645 desinfectant Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical class CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical class C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- 229920002674 hyaluronan Polymers 0.000 description 44
- 229960003160 hyaluronic acid Drugs 0.000 description 44
- 239000000243 solution Substances 0.000 description 30
- 238000007654 immersion Methods 0.000 description 28
- 239000000463 material Substances 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 229920002413 Polyhexanide Polymers 0.000 description 13
- 238000001179 sorption measurement Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 229920002385 Sodium hyaluronate Polymers 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- 229940010747 sodium hyaluronate Drugs 0.000 description 10
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 10
- 238000000585 Mann–Whitney U test Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
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- UURVHRGPGCBHIC-UHFFFAOYSA-N 3-(ethenoxycarbonylamino)propanoic acid 4-[[[[[[[[[[[[[[[[[[[[[[[[[[[4-ethenoxycarbonyloxybutyl(dimethyl)silyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]butyl ethenyl carbonate 1-ethenylpyrrolidin-2-one ethenyl N-[3-tris(trimethylsilyloxy)silylpropyl]carbamate Chemical compound C=CN1CCCC1=O.OC(=O)CCNC(=O)OC=C.C[Si](C)(C)O[Si](CCCNC(=O)OC=C)(O[Si](C)(C)C)O[Si](C)(C)C.C[Si](C)(CCCCOC(=O)OC=C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)CCCCOC(=O)OC=C UURVHRGPGCBHIC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 6
- NLAIHECABDOZBR-UHFFFAOYSA-M sodium 2,2-bis(2-methylprop-2-enoyloxymethyl)butyl 2-methylprop-2-enoate 2-hydroxyethyl 2-methylprop-2-enoate 2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O.CC(=C)C(=O)OCCO.CCC(COC(=O)C(C)=C)(COC(=O)C(C)=C)COC(=O)C(C)=C NLAIHECABDOZBR-UHFFFAOYSA-M 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000008213 purified water Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- FRKCSSCVWLUYQH-UHFFFAOYSA-N 3-(6,7-dimethoxy-4-methyl-3-oxoquinoxalin-2-yl)propanehydrazide Chemical compound N1=C(CCC(=O)NN)C(=O)N(C)C2=C1C=C(OC)C(OC)=C2 FRKCSSCVWLUYQH-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 229960004926 chlorobutanol Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 238000001215 fluorescent labelling Methods 0.000 description 3
- 230000003204 osmotic effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 2
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 2
- 229920001287 Chondroitin sulfate Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- -1 alkyl hyaluronate Chemical compound 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940059329 chondroitin sulfate Drugs 0.000 description 2
- 230000000249 desinfective effect Effects 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000002997 ophthalmic solution Substances 0.000 description 2
- 229940054534 ophthalmic solution Drugs 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
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- 235000019155 vitamin A Nutrition 0.000 description 2
- 239000011719 vitamin A Substances 0.000 description 2
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- LZODAFXCYFDVTK-UHFFFAOYSA-N 3-(6,7-dimethoxy-4-methyl-3-oxo-1,2-dihydroquinoxalin-2-yl)propanehydrazide Chemical compound N1C(CCC(=O)NN)C(=O)N(C)C2=C1C=C(OC)C(OC)=C2 LZODAFXCYFDVTK-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 1
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- 206010015150 Erythema Diseases 0.000 description 1
- 241000318162 Hyaloria Species 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
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- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
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- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
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- 210000004087 cornea Anatomy 0.000 description 1
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- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
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- 239000010893 paper waste Substances 0.000 description 1
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- 230000002335 preservative effect Effects 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 229940046008 vitamin d Drugs 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
- A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
- A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12
- A61L12/141—Biguanides, e.g. chlorhexidine
- A61L12/142—Polymeric biguanides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
- A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
- A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12
- A61L12/141—Biguanides, e.g. chlorhexidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
- A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
- A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12
- A61L12/143—Quaternary ammonium compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/04—Artificial tears; Irrigation solutions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Eyeglasses (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Description
加水分解ヒアルロン酸誘導体を含有する、ハイドロゲルコンタクトレンズ又はシリコンハイドロゲルコンタクトレンズ用液剤であって
前記加水分解ヒアルロン酸誘導体は、
炭素数6以上20以下の直鎖状又は分岐状のアルキル基又はアルケニル基とグリセリンとのモノエーテルを側鎖に有することを特徴とするコンタクトレンズ用液剤に関する。
[化1]に示される加水分解ヒアルロン酸誘導体のソフトコンタクトレンズ(SCL)への吸着性を、以下の手順によって評価した。加水分解ヒアルロン酸誘導体として、[化1]に示される加水分解ヒアルロン酸誘導体であるキューピー株式会社製ヒアロリペア(登録商標)を使用した。加水分解ヒアルロン酸としては、キューピー株式会社製ヒアロオリゴ(登録商標、ヒアルロン酸を加水分解して得られる平均分子量1万以下の低分子ヒアルロン酸)を使用した。ヒアルロン酸ナトリウムとして、キューピー株式会社製HA-LQを使用した。
[1. 使用する試液の調製]
(1) 7.6mM加水分解ヒアルロン酸誘導体水溶液の調製
200mLビーカーに精製水50mLと[化1]に示される加水分解ヒアルロン酸誘導体(加水分解ヒアルロン酸アルキル(C12-13)グリセリル)380mgを入れ、攪拌溶解した。
25mLメスフラスコに1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride(EDC)を225mg加え、精製水でメスアップした。
100mLビーカーにN,N-ジメチルホルムアミド30mLと1,2,3,4-テトラヒドロ-6,7-ジメトキシ-1-メチル-2-オキソキノキサリン-3-プロピオン酸ヒドラジド(DMEQ-ヒドラジド)37.2mgを加え、攪拌溶解した。
7.6mM加水分解ヒアルロン酸誘導体水溶液に対して、ピリジン1.5mL、9mM EDC水溶液5mL、1.24mM DMEQ-ヒドラジド溶液25mLの順に攪拌しながら添加した。その後、室温・遮光環境下で2時間攪拌した。2時間後、さらに50mLの精製水を加え、再び10分間攪拌した。
透析膜に蛍光標識化反応後液を加え、5Lの精製水中で攪拌を行い、透析を実施した。12時間の透析を4回繰り返した。精製水は、毎回交換された。
透析終了後の溶液をナス型フラスコに移し、エバポレーターで溶液を蒸発乾固させた。ナス型フラスコの内壁に付着している蛍光標識化された加水分解ヒアルロン酸誘導体をかき取り、サンプリングを行った。このサンプルを蛍光標識化サンプル1と称する。
SCL素材として、従来型のハイドロゲルレンズ素材であるetafilcon A(FDAグループIV)、及びシリコンハイドロゲルレンズ素材であるsenofilcon A(FDAグループI)とbalafilcon A(FDAグループIII)を選択した。蛍光標識化サンプル1〜3を終濃度50ppmとしてPBSに溶解させた溶液に、各SCLを浸漬した。対照試験として、各SCLをPBSに浸漬した。各SCLは一晩、各溶液に浸漬後、実際の装着を想定しPBSに8時間浸漬する条件でサイクル処理を行った。
ガラスプレート上の2か所にマウンティングメディウムを滴下し、二等分に切断したSCLを滴下箇所に載せ、カバーガラスを被せた。これを蛍光顕微鏡用の検体とした。検体を蛍光顕微鏡(オリンパス株式会社製、倒立型リサーチ顕微鏡 IX71)にセットした後、拡大倍率4倍、カメラシャッター速度200msの機器設定で、フィルターWU(励起波長:330-385nm、蛍光波長:420nm以上)を用いて、SCL 1枚につき4枚写真を撮影した。その後、SCL上の蛍光強度を測定し、画像解析ソフトImage-Jを用いて測定結果を解析した。写真上のコンタクトレンズ部をランダムに4箇所選択し、Image-J内で蛍光強度を測定した後、蛍光強度の平均値及び標準偏差を算出した。測定結果は、対照試験サンプル(PBSに浸漬させたSCL)の蛍光強度を1とした時の相対値で示され、Mann-Whitney U検定によって統計解析した。
[化1]に示される加水分解ヒアルロン酸誘導体を吸着したSCLの親水性を、以下の手順によって評価した。
ポリヘキサメチレンビグアナイド(PHMB)は、塩素又はアルコール類を含有せず、無臭、無脱色性及び低刺激性であり、有機物汚れが付着していても効果が低減しにくく、広範囲の最近に対して殺菌効果が高いカチオン系殺菌剤として、SCL保存液にも汎用されている。しかし、PHMBがSCLに吸着されると、SCL装着時の不快感を引き起こしかねない。そこで、[化1]に示される加水分解ヒアルロン酸誘導体によって、SCL表面へのPHMB吸着を抑制し得るかについて、以下の試験を行った。
素材がLotrafilcon BあるSCLを15人の被験者の両眼に日中装着し、夜間は[化1]に示される加水分解ヒアルロン酸誘導体50ppmを含有するA液又は[化1]に示される加水分解ヒアルロン酸誘導体50ppmを含有しないB液に浸漬することを1週間継続した。その後、15人の被験者の両眼を眼科医が検査し、SPK(点状表層角膜炎)スコアを測定した。
Claims (6)
- 加水分解ヒアルロン酸誘導体を含有する、ハイドロゲルコンタクトレンズ又はシリコンハイドロゲルコンタクトレンズ用液剤であって、
前記加水分解ヒアルロン酸誘導体は、
炭素数6以上20以下の直鎖状又は分岐状のアルキル基又はアルケニル基とグリセリンとのモノエーテルを側鎖に有することを特徴とするコンタクトレンズ用液剤。 - カチオン系殺菌剤として、
アレキシジン塩、クロルヘキシジン塩、ポリヘキサメチレンビグアニド塩及び第4級アンモニウム塩からなる群より選択される1種以上をさらに含有する、
請求項1に記載のコンタクトレンズ用液剤。 - ソフトコンタクトレンズ用液剤である、請求項1又は2に記載のコンタクトレンズ用液剤。
- 前記加水分解ヒアルロン酸誘導体の濃度が5ppm以上5000ppm以下である、請求項1乃至3に記載のコンタクトレンズ用液剤。
- 前記カチオン系消毒剤の濃度が0.5ppm以上50ppm以下である、請求項2乃至4のいずれか1項に記載のコンタクトレンズ用液剤。
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