JP5683268B2 - 生物活性アニリンコポリマー - Google Patents
生物活性アニリンコポリマー Download PDFInfo
- Publication number
- JP5683268B2 JP5683268B2 JP2010526842A JP2010526842A JP5683268B2 JP 5683268 B2 JP5683268 B2 JP 5683268B2 JP 2010526842 A JP2010526842 A JP 2010526842A JP 2010526842 A JP2010526842 A JP 2010526842A JP 5683268 B2 JP5683268 B2 JP 5683268B2
- Authority
- JP
- Japan
- Prior art keywords
- industry
- copolymer
- aniline
- group
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims description 156
- 229920001577 copolymer Polymers 0.000 title description 159
- 230000000975 bioactive effect Effects 0.000 title 1
- 229920000767 polyaniline Polymers 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 55
- 241000894006 Bacteria Species 0.000 claims description 48
- 230000000845 anti-microbial effect Effects 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 235000013305 food Nutrition 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 18
- -1 handles Substances 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 239000011521 glass Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 claims description 11
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 229920001971 elastomer Polymers 0.000 claims description 10
- 239000005060 rubber Substances 0.000 claims description 10
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- 241000194033 Enterococcus Species 0.000 claims description 8
- 241000233866 Fungi Species 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- ZMCBYSBVJIMENC-UHFFFAOYSA-N tricaine Chemical compound CCOC(=O)C1=CC=CC(N)=C1 ZMCBYSBVJIMENC-UHFFFAOYSA-N 0.000 claims description 8
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 claims description 6
- 241000191940 Staphylococcus Species 0.000 claims description 6
- 229920001519 homopolymer Polymers 0.000 claims description 6
- 238000004806 packaging method and process Methods 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 241000607142 Salmonella Species 0.000 claims description 5
- 241000223230 Trichosporon Species 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- 239000004033 plastic Substances 0.000 claims description 5
- 241000228212 Aspergillus Species 0.000 claims description 4
- 241000588914 Enterobacter Species 0.000 claims description 4
- 241000588722 Escherichia Species 0.000 claims description 4
- 241000589902 Leptospira Species 0.000 claims description 4
- 241000589516 Pseudomonas Species 0.000 claims description 4
- 241001493065 dsRNA viruses Species 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 3
- 241000235389 Absidia Species 0.000 claims description 3
- 241000606750 Actinobacillus Species 0.000 claims description 3
- 241000701242 Adenoviridae Species 0.000 claims description 3
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 3
- 241000335423 Blastomyces Species 0.000 claims description 3
- 241000588807 Bordetella Species 0.000 claims description 3
- 241000714198 Caliciviridae Species 0.000 claims description 3
- 241000606161 Chlamydia Species 0.000 claims description 3
- 241000223203 Coccidioides Species 0.000 claims description 3
- 241000711573 Coronaviridae Species 0.000 claims description 3
- 241000186216 Corynebacterium Species 0.000 claims description 3
- 241001527609 Cryptococcus Species 0.000 claims description 3
- 241001480035 Epidermophyton Species 0.000 claims description 3
- 241000588698 Erwinia Species 0.000 claims description 3
- 241000710781 Flaviviridae Species 0.000 claims description 3
- 241000223218 Fusarium Species 0.000 claims description 3
- 241000700739 Hepadnaviridae Species 0.000 claims description 3
- 241000700586 Herpesviridae Species 0.000 claims description 3
- 241000228402 Histoplasma Species 0.000 claims description 3
- 241000588748 Klebsiella Species 0.000 claims description 3
- 241000589248 Legionella Species 0.000 claims description 3
- 208000007764 Legionnaires' Disease Diseases 0.000 claims description 3
- 241000186781 Listeria Species 0.000 claims description 3
- 241001480037 Microsporum Species 0.000 claims description 3
- 241000699670 Mus sp. Species 0.000 claims description 3
- 241000186359 Mycobacterium Species 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 241000588653 Neisseria Species 0.000 claims description 3
- 241000712464 Orthomyxoviridae Species 0.000 claims description 3
- 241001631646 Papillomaviridae Species 0.000 claims description 3
- 241001537205 Paracoccidioides Species 0.000 claims description 3
- 241000711504 Paramyxoviridae Species 0.000 claims description 3
- 241000701945 Parvoviridae Species 0.000 claims description 3
- 241000228143 Penicillium Species 0.000 claims description 3
- 241000709664 Picornaviridae Species 0.000 claims description 3
- 241001631648 Polyomaviridae Species 0.000 claims description 3
- 241000605894 Porphyromonas Species 0.000 claims description 3
- 241000700625 Poxviridae Species 0.000 claims description 3
- 241000702247 Reoviridae Species 0.000 claims description 3
- 241000712907 Retroviridae Species 0.000 claims description 3
- 241000711931 Rhabdoviridae Species 0.000 claims description 3
- 241000607768 Shigella Species 0.000 claims description 3
- 241000194017 Streptococcus Species 0.000 claims description 3
- 241000710924 Togaviridae Species 0.000 claims description 3
- 241000223238 Trichophyton Species 0.000 claims description 3
- 241000607734 Yersinia <bacteria> Species 0.000 claims description 3
- 108700010877 adenoviridae proteins Proteins 0.000 claims description 3
- 238000004378 air conditioning Methods 0.000 claims description 3
- 239000000919 ceramic Substances 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 230000036541 health Effects 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 238000009928 pasteurization Methods 0.000 claims description 3
- 239000002985 plastic film Substances 0.000 claims description 3
- 229920006255 plastic film Polymers 0.000 claims description 3
- 244000144977 poultry Species 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- 235000014102 seafood Nutrition 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 230000002485 urinary effect Effects 0.000 claims description 3
- 210000002700 urine Anatomy 0.000 claims description 3
- 239000002023 wood Substances 0.000 claims description 3
- 241000606125 Bacteroides Species 0.000 claims description 2
- 241001148534 Brachyspira Species 0.000 claims description 2
- 241000589876 Campylobacter Species 0.000 claims description 2
- 241000450599 DNA viruses Species 0.000 claims description 2
- 241000187831 Dermatophilus Species 0.000 claims description 2
- 241000186811 Erysipelothrix Species 0.000 claims description 2
- 241000606790 Haemophilus Species 0.000 claims description 2
- 241000555676 Malassezia Species 0.000 claims description 2
- 241000235395 Mucor Species 0.000 claims description 2
- 241000204031 Mycoplasma Species 0.000 claims description 2
- 241000191992 Peptostreptococcus Species 0.000 claims description 2
- 241000186429 Propionibacterium Species 0.000 claims description 2
- 241000235527 Rhizopus Species 0.000 claims description 2
- 241001149962 Sporothrix Species 0.000 claims description 2
- 241000607598 Vibrio Species 0.000 claims description 2
- 238000001356 surgical procedure Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims 1
- 241000222290 Cladosporium Species 0.000 claims 1
- 241000222831 Phialophora <Chaetothyriales> Species 0.000 claims 1
- 229950000244 sulfanilic acid Drugs 0.000 claims 1
- 239000000725 suspension Substances 0.000 description 34
- 229920002451 polyvinyl alcohol Polymers 0.000 description 26
- 229920001817 Agar Polymers 0.000 description 25
- 241000191967 Staphylococcus aureus Species 0.000 description 25
- 239000008272 agar Substances 0.000 description 25
- 244000005700 microbiome Species 0.000 description 24
- 239000004372 Polyvinyl alcohol Substances 0.000 description 23
- 230000000844 anti-bacterial effect Effects 0.000 description 22
- 229920000642 polymer Polymers 0.000 description 21
- 125000000623 heterocyclic group Chemical group 0.000 description 20
- 230000000694 effects Effects 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 13
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 13
- 230000001580 bacterial effect Effects 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 12
- 239000004926 polymethyl methacrylate Substances 0.000 description 12
- 241000700605 Viruses Species 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 229920000775 emeraldine polymer Polymers 0.000 description 11
- 241000222122 Candida albicans Species 0.000 description 10
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 10
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- 229940095731 candida albicans Drugs 0.000 description 10
- 230000002401 inhibitory effect Effects 0.000 description 10
- 239000002054 inoculum Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 9
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 8
- 241001360526 Escherichia coli ATCC 25922 Species 0.000 description 8
- 241000192125 Firmicutes Species 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 239000002131 composite material Substances 0.000 description 8
- 230000000855 fungicidal effect Effects 0.000 description 8
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 241000589875 Campylobacter jejuni Species 0.000 description 7
- 241000588724 Escherichia coli Species 0.000 description 7
- 230000000843 anti-fungal effect Effects 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 238000011081 inoculation Methods 0.000 description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 description 7
- 239000011707 mineral Substances 0.000 description 7
- 235000010755 mineral Nutrition 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000004599 antimicrobial Substances 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 238000011068 loading method Methods 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 229940121375 antifungal agent Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 230000036457 multidrug resistance Effects 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical group [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 5
- 239000001230 potassium iodate Substances 0.000 description 5
- 229940093930 potassium iodate Drugs 0.000 description 5
- 235000006666 potassium iodate Nutrition 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 4
- FUADXEJBHCKVBN-UHFFFAOYSA-N (3-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 FUADXEJBHCKVBN-UHFFFAOYSA-N 0.000 description 4
- OJZQOQNSUZLSMV-UHFFFAOYSA-N (3-aminophenyl)methanol Chemical compound NC1=CC=CC(CO)=C1 OJZQOQNSUZLSMV-UHFFFAOYSA-N 0.000 description 4
- FEDLEBCVFZMHBP-UHFFFAOYSA-N 2-amino-3-methylphenol Chemical compound CC1=CC=CC(O)=C1N FEDLEBCVFZMHBP-UHFFFAOYSA-N 0.000 description 4
- BNNICQAVXPXQAH-UHFFFAOYSA-N 2-amino-4-bromobenzoic acid Chemical compound NC1=CC(Br)=CC=C1C(O)=O BNNICQAVXPXQAH-UHFFFAOYSA-N 0.000 description 4
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 4
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 4
- KWXIPEYKZKIAKR-UHFFFAOYSA-N 2-amino-4-hydroxy-6-methylpyrimidine Chemical compound CC1=CC(O)=NC(N)=N1 KWXIPEYKZKIAKR-UHFFFAOYSA-N 0.000 description 4
- SZCPTRGBOVXVCA-UHFFFAOYSA-N 2-amino-6-chlorobenzoic acid Chemical compound NC1=CC=CC(Cl)=C1C(O)=O SZCPTRGBOVXVCA-UHFFFAOYSA-N 0.000 description 4
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 4
- YAZSBRQTAHVVGE-UHFFFAOYSA-N 2-aminobenzenesulfonamide Chemical compound NC1=CC=CC=C1S(N)(=O)=O YAZSBRQTAHVVGE-UHFFFAOYSA-N 0.000 description 4
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 4
- BSRGUEWPSFZQCV-UHFFFAOYSA-N 2-aminophenol;3-aminophenol Chemical compound NC1=CC=CC(O)=C1.NC1=CC=CC=C1O BSRGUEWPSFZQCV-UHFFFAOYSA-N 0.000 description 4
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 4
- CKQHAYFOPRIUOM-UHFFFAOYSA-N 3'-Aminoacetophenone Chemical compound CC(=O)C1=CC=CC(N)=C1 CKQHAYFOPRIUOM-UHFFFAOYSA-N 0.000 description 4
- MKARNSWMMBGSHX-UHFFFAOYSA-N 3,5-dimethylaniline Chemical compound CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 4
- BYHMLZGICSEKIY-UHFFFAOYSA-N 3-amino-2-methylbenzoic acid Chemical compound CC1=C(N)C=CC=C1C(O)=O BYHMLZGICSEKIY-UHFFFAOYSA-N 0.000 description 4
- NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 4
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 4
- RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 4
- BRBUBVKGJRPRRD-UHFFFAOYSA-N 4,6-dimethylpyridin-2-amine Chemical compound CC1=CC(C)=NC(N)=C1 BRBUBVKGJRPRRD-UHFFFAOYSA-N 0.000 description 4
- QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 108090000204 Dipeptidase 1 Proteins 0.000 description 4
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 108010059993 Vancomycin Proteins 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 244000052616 bacterial pathogen Species 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 102000006635 beta-lactamase Human genes 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 4
- 229920000126 latex Polymers 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 229960003085 meticillin Drugs 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 4
- 229960003165 vancomycin Drugs 0.000 description 4
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 4
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 3
- LMDPYYUISNUGGT-UHFFFAOYSA-N 2-(2-aminophenyl)acetonitrile Chemical compound NC1=CC=CC=C1CC#N LMDPYYUISNUGGT-UHFFFAOYSA-N 0.000 description 3
- XUSKZLBLGHBCLD-UHFFFAOYSA-N 2-(3-aminophenyl)acetic acid Chemical compound NC1=CC=CC(CC(O)=O)=C1 XUSKZLBLGHBCLD-UHFFFAOYSA-N 0.000 description 3
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000002033 PVDF binder Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 230000002292 Radical scavenging effect Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000007760 free radical scavenging Effects 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 230000010534 mechanism of action Effects 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 102000020235 metallo-beta-lactamase Human genes 0.000 description 3
- 108060004734 metallo-beta-lactamase Proteins 0.000 description 3
- 229960001019 oxacillin Drugs 0.000 description 3
- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 description 3
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 230000003612 virological effect Effects 0.000 description 3
- KHMNCHDUSFCTGK-UHFFFAOYSA-N 2-aminophenylacetic acid Chemical compound NC1=CC=CC=C1CC(O)=O KHMNCHDUSFCTGK-UHFFFAOYSA-N 0.000 description 2
- DWJXWSIJKSXJJA-UHFFFAOYSA-N 4-n-[4-(4-aminoanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1NC(C=C1)=CC=C1NC1=CC=C(N)C=C1 DWJXWSIJKSXJJA-UHFFFAOYSA-N 0.000 description 2
- KBZFDRWPMZESDI-UHFFFAOYSA-N 5-aminobenzene-1,3-dicarboxylic acid Chemical compound NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KBZFDRWPMZESDI-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 241000712892 Arenaviridae Species 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 244000309727 Salmonella enterica serotype Enteritidis Species 0.000 description 2
- 241000700618 Vaccinia virus Species 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 150000003927 aminopyridines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000001332 colony forming effect Effects 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 210000000416 exudates and transudate Anatomy 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- 229920000763 leucoemeraldine polymer Polymers 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000002068 microbial inoculum Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000002121 nanofiber Substances 0.000 description 2
- 229920006173 natural rubber latex Polymers 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- WPUWNCWLDZMYSC-UHFFFAOYSA-N 1-fluoropropan-2-ol Chemical compound CC(O)CF WPUWNCWLDZMYSC-UHFFFAOYSA-N 0.000 description 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 1
- GVOYKJPMUUJXBS-UHFFFAOYSA-N 2-(aminomethyl)aniline Chemical compound NCC1=CC=CC=C1N GVOYKJPMUUJXBS-UHFFFAOYSA-N 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 206010011409 Cross infection Diseases 0.000 description 1
- 201000007336 Cryptococcosis Diseases 0.000 description 1
- 241000221204 Cryptococcus neoformans Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000943303 Enterococcus faecalis ATCC 29212 Species 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000186779 Listeria monocytogenes Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000235048 Meyerozyma guilliermondii Species 0.000 description 1
- UTSPFQMVKZBYEB-UHFFFAOYSA-N NC1=C(CC#N)C=CC=C1.NC1=C(CN)C=CC=C1 Chemical compound NC1=C(CC#N)C=CC=C1.NC1=C(CN)C=CC=C1 UTSPFQMVKZBYEB-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 241000150350 Peribunyaviridae Species 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000001237 Raman spectrum Methods 0.000 description 1
- 241000223252 Rhodotorula Species 0.000 description 1
- 241000831652 Salinivibrio sharmensis Species 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- 229960005274 benzocaine Drugs 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 201000011529 cardiovascular cancer Diseases 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000013553 cell monolayer Substances 0.000 description 1
- VZDYWEUILIUIDF-UHFFFAOYSA-J cerium(4+);disulfate Chemical compound [Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VZDYWEUILIUIDF-UHFFFAOYSA-J 0.000 description 1
- 229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001523 electrospinning Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940032049 enterococcus faecalis Drugs 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012458 free base Chemical class 0.000 description 1
- 235000012055 fruits and vegetables Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000004264 monolayer culture Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- KKOYWVUHKUNECX-UHFFFAOYSA-M potassium iodic acid chloride Chemical compound [Cl-].I(=O)(=O)O.[K+] KKOYWVUHKUNECX-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003244 pro-oxidative effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000001974 tryptic soy broth Substances 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/06—Nitrogen directly attached to an aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
- C08G73/0266—Polyanilines or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/24—Polysulfonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pest Control & Pesticides (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Apparatus For Disinfection Or Sterilisation (AREA)
Description
n=1、2または3であり、
R1は、独立して、以下のものからなる群より選択され:
C1〜C6アルキル、
C1〜C6アルコキシル、
ハロ、
−CO2R2、
−SO3R2、
−PO3HR2、
−COR4、
−CH2COOR4、
−CN、
−CH2OH、
−CH2NH2、
−CH2CN、
−OH、
−SO2NH2;
R2は、水素、C1〜C6アルキル、アルカリ金属、アンモニウム、および置換されたアンモニウム塩から選択され;
R4は、水素、C1〜C6アルキル、フェニルから選択される。
xは1および0の間の整数であり、且つ、mは重合度を示す。前記化合物は、それ自体でポリアニリンでないのが好ましい。
n=1、2または3であり、
R1は、独立して、以下のものからなる群より選択され:
C1〜C6アルキル、
C1〜C6アルコキシル、
ハロ、
−CO2R2、
−SO3R2、
−PO3HR2、
−COR4、
−CH2COOR4、
−CN、
−CH2OH、
−CH2NH2、
−CH2CN、
−OH、
−SO2NH2;
R2は、水素、C1〜C6アルキル、アルカリ金属、アンモニウム、および置換されたアンモニウム塩から選択され;
R4は、水素、C1〜C6アルキル、フェニルから選択される。
n=1、2または3であり、
R1は、独立して、以下のものからなる群より選択され:
C1〜C6アルキル、
C1〜C6アルコキシル、
ハロ、
−CO2R2、
−SO3R2、
−PO3HR2、
−COR4、
−CH2COOR4、
−CN、
−CH2OH、
−CH2NH2、
−CH2CN、
−OH、
−SO2NH2;
R2は、水素、C1〜C6アルキル、アルカリ金属、アンモニウム、および置換されたアンモニウム塩から選択され;
R4は、水素、C1〜C6アルキル、フェニルから選択される。
n=1、2または3であり、
R1は、独立して、以下のものからなる群より選択され:
C1〜C6アルキル、
C1〜C6アルコキシル、
ハロ、
−CO2R2、
−SO3R2、
−PO3HR2、
−COR4、
−CH2COOR4、
−CN、
−CH2OH、
−CH2NH2、
−CH2CN、
−OH、
−SO2NH2;
R2は、水素、C1〜C6アルキル、アルカリ金属、アンモニウム、および置換されたアンモニウム塩から選択され;
R4は、水素、C1〜C6アルキル、フェニルから選択される。
アニリンと3−アミノ安息香酸との1:1コポリマー(3ABAPANI)、またはアニリンとアントラニル酸との1:1コポリマー(OABAPANI)の合成を、3.88mLのアニリン、それぞれ5.85gの3−アミノ安息香酸またはアントラニル酸、8.64gのヨウ素酸カリウム(KIO3)および240mLの1.25M塩酸を使用して実施した。
PANIのEB形は、1586、1493、1305、1162、および828cm−1に強い吸収ピークを有している。PANIのプロトン化された塩の形(ES)においては、キノイド単位に起因する1586cm−1および1162cm−1〜1574cm−1および1135cm−1への吸収帯のシフトが観察された。
ラマンスペクトルは、PANIのES形およびEB形のそれと同様の吸収帯を示した。コポリマーのES形において1336cm−1に現れる吸収帯は、カチオンラジカル種のC−N伸縮と同定された。ESの場合のアミン変角吸収帯である、1414cm−1でのN−H変角もまた観察された。
PANI/NMP溶液のUV−VISスペクトルには、〜330nmのピーク(ベンゼノイドピーク;Bと呼ばれる)および〜630nmの第二のピーク(キノイドピーク;Qと呼ばれる)の二つ特異的ピークが存在する。3EABPANIサンプルの方がより良好な溶解性を示す。
コポリマーのDPPHフリーラジカル捕捉活性、およびそれぞれのコポリマーで捕捉されたDPPHラジカルあたりのアニリン単位の比率を表2に示す。
本発明の化合物を、以下の細菌の菌株に対して試験した:Staphylococcus aureus ATCC 25923(ATCC=アメリカ培養細胞系統保存機関(American Type Culture Collection)(グラム陽性菌)、Escherichia coli ATCC 25922(グラム陰性菌)、Pseudomonas aeruginosa ATCC 27853(グラム陰性菌)、Salmonella enterica血清型エンテリチディス(2種の抗生物質耐性菌株;グラム陰性菌)、Enterococcus faecalis(バンコマイシン耐性菌株;グラム陽性菌)、Staphylococcus sciuri(オキサシリン耐性菌株、多剤耐性;グラム陽性菌)、Enterobacter属(多剤耐性菌株;グラム陰性菌)、Pseudomonas aeruginosa(多剤耐性菌株;グラム陰性菌)、Campylobacter jejuni(菌株A;グラム陰性菌)、Campylobacter jejuni(菌株B;グラム陰性菌)、Salmonella enterica血清型エンテリチディス(広域スペクトルベータラクタマーゼ陽性分離菌、多剤耐性;グラム陰性菌)、Escherichia coli(広域スペクトルベータラクタマーゼ陽性分離菌及び多剤耐性;グラム陰性菌)、Pseudomonas aeruginosa(メタロベータラクタマーゼ陽性及び多剤耐性;グラム陰性菌)、Staphylococcus aureus(メチシリン耐性、多剤耐性;グラム陽性菌)、Listeria monocytogenes ATCC BAA−751(グラム陽性菌)、Bacillus subtilis ATCC 6633(グラム陽性菌)、およびEnterococcus faecalis ATCC 29212(グラム陽性菌)。
本発明の化合物を、以下の酵母およびカビ菌株に対して試験した:Candida albicans、Cryptococcus neoformans、Candida guilliermondii、Candida parapsilosis、Candida kefyr、Candida glabrata、Aspergillus flavus、およびAspergillus niger。
コポリマー粉体についてのMICは、微量希釈試験法を用いて求めた。その方法は、ふた付きの無菌の平底96ウェルポリスチレン非組織培養処理マイクロタイタープレート(マイクロプレート)中で、最終容積100μLで、以下のようにして実施した。
*MDR=多剤耐性、すなわち作用機構の異なる3種以上の抗微生物剤に耐性あり;ESBL=広域スペクトルベータラクタマーゼ;MBL=メタロベータラクタマーゼ;VR=バンコマイシン耐性;MR=メチシリン/オキサシリン耐性。
滅菌後、ならびにa)グラム陰性のEscherichia coli ATCC 25922およびPseudomonas aeruginosa ATCC 27853、ならびにb)グラム陽性のStaphylococcus aureus ATCC 25923細菌で処理した後の、3ABAPANI(ES)、3EABPANI(ES)、OABAPANI(ES)、PANI(ES)、SO3HPANI(ES)、3ABAPANI(EB)およびPANI(EB)のFTIRスペクトルを記録した。その結果は、すべてのサンプルにおいて、C−C伸縮キノイドおよび脱プロトン化吸収帯が、9cm−1までシフトしていることを示している。理論に束縛されることなく言えば、これらの結果から、異なる極性の電荷を担持するポリマー分子と微生物たとえば(一例として)E.coli細菌との間の静電的付着によって、図1に見られるように、細菌の壁面が破壊され、細菌の内容物が漏れだし、それによって細菌を死滅させることが示唆されている。
以下の表6に示したコポリマーから、平均重量100±5mg、直径1.5cmのタブレットを作製した。Staphylococcus aureus ATCC 25923について、抗微生物活性の試験をした。
「静菌(static)」または「抑制」効果とは、薬剤/物質が微生物の増殖を抑制することを意味しているが、その一方で、殺菌/殺真菌/殺ウイルスという用語は、その薬剤/物質が微生物を死滅させるということを意味している。細菌のStaphylococcus aureus ATCC 25923、Escherichia coli ATCC 25922、Pseudomonas aeruginosa ATCC 27853、および酵母のCandida albicansに対する3ABAPANI(ES)およびPANI(ES)の作用機構を調べた。
本発明において最も有効なアニリンコポリマーであった3ABAPANI(ES)について、微生物の死滅速度の面から、動態学的検討を行った。ガラスチューブに、5mLのBHIブロスで2%3ABAPANI(ES)の懸濁液を作製し、オートクレーブ中121℃で滅菌した。次いで、懸濁液に微生物を播種した。CFU滴定後ゼロ時間で、微生物の初期接種量を計算すると、Staphylococcus aureus ATCC 25923では3.4×105cfu/mL、Escherichia coli ATCC 25922では3.8×105cfu/mL、Pseudomonas aeruginosa ATCC 27853では3.8×105cfu/mL、そしてCandida albicansでは1.4×105cfu/mLであった。時間間隔を置いて100μLのサンプルを採取し、BHIブロスを用いて段階的に10倍希釈し、それぞれの希釈液から100μLを、BHI寒天表面プレート全体の上にガラス棒を用いて拡げた。そのBHI寒天プレートを35℃で48時間インキュベートした後、コロニーを計数した。最小検出レベルは100コロニーであった。
動態学(死滅速度または死滅率)の場合とまったく同じ方法であるが、ただし接種数だけを変化させて、接種数の影響を調べた。ガラスチューブに、5mLのBHIブロスで2%3ABAPANI(ES)を含む懸濁液を作製し、オートクレーブ中121℃で滅菌した。次いで、懸濁液に微生物を播種した。CFU滴定後ゼロ時間のところで、微生物の初期接種量を計算すると、Staphylococcus aureus ATCC 25923の場合で1.2×1010cfu/mLであった。時間間隔を置いて100μLのサンプルを採取し、BHIブロスを用いて段階的に10倍希釈し、それぞれの希釈液から100μLを、BHI寒天表面プレート全体の上にガラス棒を用いて拡げた。そのBHI寒天プレートを35℃で48時間インキュベート後、コロニーを計数した。最小検出レベルは100コロニーであった。
有機物担持がアニリンコポリマーの抗微生物活性におよぼす影響を調べるために、接種数がアニリンコポリマーの抗微生物活性におよぼす影響を調べるために先に記載した手順を一般的に使用した。ガラスチューブにBHIブロスで作製し、オートクレーブ中121℃で滅菌した3ABAPANI(ES)の懸濁液をヒト血漿と混合した。得られた混合物を、室温で30分間静置した。次いで、その混合物に微生物を接種した。その最終容積は5mLであり、それにはBHIブロス、最終濃度2%の3ABAPANI(ES)、および最終濃度20%、10%または5%のヒト血漿が含まれていた。一方、CFU滴定後ゼロ時間での微生物の初期接種量を計算すると、Staphylococcus aureus ATCC 25923の場合で1.2×1010cfu/mL、Escherichia coli ATCC 25922の場合で5.7×1011cfu/mL、Pseudomonas aeruginosa ATCC 27853の場合で3.84×1011cfu/mL、そしてCandida albicansの場合で8.1×107cfu/mLであった。時間間隔を置いて100μLのサンプルを採取し、BHIブロスを用いて段階的に10倍希釈し、それぞれの希釈液から100μLを、BHI寒天表面プレート全体の上にガラス棒を用いて拡げた。そのBHI寒天プレートを35℃で48時間インキュベート後、コロニーを計数した。最小検出レベルは100コロニーであった。
MBC(最小殺菌濃度、最小殺真菌濃度(MFC)に同じ)を、初期微生物接種量の生存を0.1%以下(死滅が99.9%)とするような最低の薬剤濃度と定義する。図12に示すように、この定義を本発明の結果に対して適用すると、初期接種量がLog108.99であったものが、8時間後にLog106.32、24時間後にはLog105.41となっているので、10%血漿の存在下での3ABAPANI(ES)は24時間後であっても、(静真菌性作用のみでなく)殺真菌性作用を示した。
NACがコポリマーの抗微生物活性におよぼす影響を、Staphylococcus aureus ATCC 25923に対しての3ABAPANI(ES)により調べた。
ポリメタクリル酸メチル(PMMA)の上にコーティングしたθ4(ポリビニルアルコール−PVAおよび0.7重量%PANI)のフィルムと、PMMAの上にコーティングしたρ2(PVAおよび0.2重量%Poly3ABA)のフィルムを切断して、約1×1cmの小片とした。アニリンコポリマーまたはポリアニリンで覆われたフィルムの側が最上部になるように注意しながら、それらのフィルムを無菌のプラスチック製ペトリ皿の底部に置いた。
オートクレーブ処理したポリマーの3ABAPANI(ES)およびPANI(ES)の懸濁液を、細胞培養増殖培地(DMEM)で、2、1および0.4%(w/v)の濃度で調製した。ワクシニアウイルス(WR株)をDMEM中で段階的に希釈して、最終濃度が1mLあたり103〜105個の間の感染性粒子数になるようにした。ウイルスのアリコートを等容のポリマー懸濁液(およびポリマーを含まないDMEMの対照物)と混合し、室温で1時間穏やかに撹拌しながらインキュベートしてから、等容のそれぞれの懸濁液を直接添加して、CV−I細胞の単層培養物を複製させた。1時間後にその接種物を除去し、その細胞を5%のウシ胎児血清を含むDMEMで覆った。2日後にその培地を取り出し、細胞を0.5%クリスタルバイオレットで染色した。ウイルス懸濁液の感染力を、プラーク数を計数することにより求め、それぞれのポリマーの出発濃度について、(ポリマーを含まない対照との比較で)感染力の低下を求めた。
Claims (7)
- 前記化合物が、N−メチル−2−ピロリドン、ピリジン、2,6−ジメチルピリジン、2,4,6−トリメチルピリジン、ジメチルスルホキシド、N,N−ジメチルアセトアミド(無水)、テトラヒドロフラン、およびジメチルホルムアミドからなる群より選択される溶媒に、少なくとも0.05mg/mLの溶解度を有している、請求項1に記載の使用。
- 前記化合物が、3−アミノ安息香酸のホモポリマー、または3−アミノベンゼンスルホン酸のホモポリマーである、請求項1に記載の使用。
- 前記式(I)の化合物が、3−アミノ安息香酸、2−アミノ安息香酸、3−アミノ安息香酸エチルおよびスルファニル酸からなる群より選択される、請求項3に記載の使用。
- 前記抗微生物性物質が、Bordetella、Neisseria、Legionella、Pseudomonas、Salmonella、Shigella、Erwinia、Enterobacter、Escherichia、Vibrio、Haemophilus、Actinobacillus、Klebsiella、Staphylococcus、Streptococcus、Enterococcus、Corynebacterium、Listeria、Bacillus、Mycobacterium、Enterococcus、Leptospira、Serpulina、Mycoplasma、Bacteroides、Yersinia、Chlamydia、Porphyromonas、Pasteurella、Peptostreptococcus、Propionibacterium、Dermatophilus、Campylobacter、およびErysipelothrixからなる群より選択される細菌に対して有効である、または、Aspergillus、Blastomyces、Candida、Coccidioides、Cryptococcus、Epidermophyton、Histoplasma、Microsporum、Mucor、Rhizopus、Sporothrix、Trichophyton、Paracoccidioides、Absidia、Fusarium、Penicillium、Torulopsis、Trichosporon、Rhodotorula、Malassezia、Cladosporium、Fonsecea、およびPhialophoraからなる群より選択される真菌の属に対して有効である、または、Parvoviridae、Papillomaviridae、Polyomaviridae、Adenoviridae、Hepadnaviridae、Herpesviridae、Poxviridae、Picornaviridae、Caliciviridae、Reoviridae、Togaviridae、Flaviviridae、Coronaviridae、Orthomyxoviridae、Paramyxoviridae、Rhabdoviridae、Filoviridae、Bunyaviridae、Arenaviridae、およびRetroviridaeからなる群より選択される系統に属するDNAおよびRNAウイルスに対して有効である、請求項1乃至請求項5のいずれか一項に記載の使用。
- 前記抗微生物性物質が、健康産業、食品産業、包装産業、水関連産業、繊維産業、プラスチック産業、ガラス産業、紙産業、ゴム産業、セラミック産業、ペイント産業、木材産業、家禽産業、水産食品産業、スポーツ産業、および農産業において採用される対象物に用いられ、かつ、前記対象物が、包帯、尿カテーテル、内視鏡、医用機器、病院の備品、マスク、フロア、食品袋、食品加工表面および装置、ピペット、コンピューターのキーボードおよびマウス、プラスチックフィルムラップ、化粧品、ハンドル、水タンク、浄水のための膜、洗面所、ドアハンドル、排水管、給水管、イヤピース、靴の中敷き、プール、尿または便または血小板のためのバッグ、エアコンユニット、濾過設備、低温殺菌設備および備品を含む群から選択される、請求項1乃至請求項6のいずれか一項に記載の使用。
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NZ56209207A NZ562092A (en) | 2007-09-28 | 2007-09-28 | Antimicrobial effect of copolymers of aniline with 3-amino benzoic acid, anthranilic acid and ethyl 3-amino benzoate |
NZ562092 | 2007-09-28 | ||
NZ565987 | 2008-02-15 | ||
NZ56598708 | 2008-02-15 | ||
NZ570475 | 2008-06-06 | ||
NZ57047508 | 2008-06-06 | ||
PCT/NZ2008/000254 WO2009041837A1 (en) | 2007-09-28 | 2008-09-26 | Bioactive aniline copolymers |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010540514A JP2010540514A (ja) | 2010-12-24 |
JP2010540514A5 JP2010540514A5 (ja) | 2013-09-12 |
JP5683268B2 true JP5683268B2 (ja) | 2015-03-11 |
Family
ID=40511647
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010526842A Active JP5683268B2 (ja) | 2007-09-28 | 2008-09-26 | 生物活性アニリンコポリマー |
Country Status (7)
Country | Link |
---|---|
US (4) | US20100196306A1 (ja) |
EP (1) | EP2190285B1 (ja) |
JP (1) | JP5683268B2 (ja) |
CN (1) | CN101808514B (ja) |
AU (1) | AU2008305815B2 (ja) |
CA (1) | CA2700712A1 (ja) |
WO (1) | WO2009041837A1 (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011136977A (ja) * | 2009-06-16 | 2011-07-14 | Sekisui Chem Co Ltd | Rnaウイルス感染阻止塗料用組成物、rnaウイルス感染阻止塗料及びrnaウイルス感染阻止製品 |
CN102079837A (zh) * | 2010-11-11 | 2011-06-01 | 天津工业大学 | 卤代聚苯胺共混杀菌膜及其制备方法 |
NZ615718A (en) | 2011-04-05 | 2015-04-24 | Auckland Uniservices Ltd | Polymerization method and product |
CN102669158B (zh) * | 2012-04-13 | 2014-02-12 | 昆明理工大学 | 一种亚锡盐配合物抗菌材料及其制备方法 |
CN102786685B (zh) * | 2012-08-08 | 2014-02-26 | 东华大学 | 一种导电木材的制备方法 |
CN103242525B (zh) * | 2013-05-20 | 2015-08-26 | 昆明理工大学 | 一种聚邻羟基苯酚抗菌材料及其制备方法 |
CN104001483B (zh) * | 2014-05-15 | 2016-02-24 | 昆明理工大学 | 一种吸附抗生素的高分子材料及其制备方法和应用 |
CN106010218A (zh) * | 2016-06-23 | 2016-10-12 | 合肥奇腾农业科技有限公司 | 一种防水地板及其制作方法 |
DE102018107149A1 (de) * | 2018-03-26 | 2019-09-26 | Kautex Textron Gmbh & Co. Kg | Antimikrobielle Bevorratung von Wasser oder wässrigen Lösungen insbesondere in Kraftfahrzeugen |
EP3590343A1 (fr) * | 2018-07-04 | 2020-01-08 | Centre National de la Recherche Scientifique | Materiaux et dispositifs biocides |
CN111500063B (zh) * | 2019-01-31 | 2021-12-14 | 中国科学技术大学 | 一种聚苯胺导电水凝胶及其制备方法和超级电容器 |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5232631A (en) * | 1991-06-12 | 1993-08-03 | Uniax Corporation | Processible forms of electrically conductive polyaniline |
US5227092A (en) * | 1991-07-10 | 1993-07-13 | Allied-Signal Inc. | Process for forming conjugated backbone block copolymers |
JP3051244B2 (ja) * | 1991-12-27 | 2000-06-12 | 三菱レイヨン株式会社 | アニリン系共重合体スルホン化物とその製法 |
JP3043981B2 (ja) * | 1995-12-26 | 2000-05-22 | 健一 森田 | 活性酸素発生剤およびそれを用いた活性酸素発生方法 |
TW464661B (en) * | 1996-06-10 | 2001-11-21 | Nippon Catalytic Chem Ind | Water-soluble electrically-conductive polyaniline and method for production thereof and antistatic agent using water-soluble electrically-conductive polymer |
US5959072A (en) * | 1998-01-26 | 1999-09-28 | Conpoly Technology Co., Ltd. | Wastewater-recyclable process for producing a polyaniline resin powder |
JP2000212554A (ja) * | 1998-11-20 | 2000-08-02 | Idemitsu Kosan Co Ltd | 蛍光変換媒体及びそれを用いた表示装置 |
US6572843B1 (en) * | 1998-12-01 | 2003-06-03 | Novozymes, A/S | Method for treating hair |
JP2001070426A (ja) * | 1999-06-30 | 2001-03-21 | Kenichi Morita | 活性酸素発生剤 |
US6403052B1 (en) * | 2000-05-10 | 2002-06-11 | Ken-ichi Morita | Method for generation of active oxygen in an oxygen-containing gas phase |
FR2798933B1 (fr) * | 1999-09-23 | 2002-02-15 | Commissariat Energie Atomique | Procede de preparation de copolymeres solubles a base d'aniline et d'aniline modifiee et leur utilisation dans des materiaux a rigidite dielectrique amelioree |
JP2003159596A (ja) * | 2001-11-28 | 2003-06-03 | Kenichi Morita | 活性汚泥殺菌膜及びその製造方法並びに汚泥処理装置 |
JP3858777B2 (ja) * | 2002-07-09 | 2006-12-20 | 株式会社デンソー | ポリアニリンからなる構造体を用いた活性酸素発生方法 |
JP2004099406A (ja) * | 2002-09-12 | 2004-04-02 | Oxyd Ltd | 活性酸素発生方法および装置 |
JP2004115965A (ja) * | 2002-09-26 | 2004-04-15 | Oxyd Ltd | 脱臭・殺菌作用を持つ紙 |
WO2006004653A2 (en) * | 2004-06-28 | 2006-01-12 | The Ohio State University | Synthesis of nanofibers of polyaniline and substituted derivatives |
WO2006016193A1 (en) * | 2004-08-07 | 2006-02-16 | Oled-T Limited | Electroluminescent materials and devices |
US20060165746A1 (en) * | 2005-01-24 | 2006-07-27 | Arie Markus | Formulations containing microencapsulated essential oils |
CN1844245A (zh) * | 2005-04-06 | 2006-10-11 | 中国科学院金属研究所 | 一种抗菌材料 |
DE102005049388A1 (de) * | 2005-10-15 | 2007-04-19 | Dechema Gesellschaft Für Chemische Technik Und Biotechnologie E.V. | Verfahren zur Vermeidung oder Verminderung von Biofilmen auf einer Oberfläche |
CN1810850A (zh) * | 2006-01-04 | 2006-08-02 | 扬州大学 | 导电高聚物-苯胺与间氨基苯酚共聚物及合成方法 |
DE102007056423A1 (de) * | 2007-11-23 | 2009-06-04 | Süd-Chemie AG | Herstellung und Verwendung neuer Polyaniline zur Wasserbehandlung |
-
2008
- 2008-09-26 EP EP08833179.8A patent/EP2190285B1/en active Active
- 2008-09-26 CA CA2700712A patent/CA2700712A1/en not_active Abandoned
- 2008-09-26 WO PCT/NZ2008/000254 patent/WO2009041837A1/en active Application Filing
- 2008-09-26 CN CN200880109599.5A patent/CN101808514B/zh active Active
- 2008-09-26 JP JP2010526842A patent/JP5683268B2/ja active Active
- 2008-09-26 US US12/680,113 patent/US20100196306A1/en not_active Abandoned
- 2008-09-26 AU AU2008305815A patent/AU2008305815B2/en active Active
-
2013
- 2013-04-26 US US13/871,164 patent/US20140105849A1/en not_active Abandoned
-
2015
- 2015-05-15 US US14/713,981 patent/US20150320042A1/en not_active Abandoned
-
2016
- 2016-04-29 US US15/142,032 patent/US9992996B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
EP2190285A4 (en) | 2013-12-11 |
EP2190285A1 (en) | 2010-06-02 |
CN101808514B (zh) | 2016-06-08 |
AU2008305815B2 (en) | 2014-11-13 |
US20140105849A1 (en) | 2014-04-17 |
US9992996B2 (en) | 2018-06-12 |
US20160235059A1 (en) | 2016-08-18 |
CA2700712A1 (en) | 2009-04-02 |
EP2190285B1 (en) | 2019-03-20 |
AU2008305815A1 (en) | 2009-04-02 |
WO2009041837A1 (en) | 2009-04-02 |
CN101808514A (zh) | 2010-08-18 |
US20100196306A1 (en) | 2010-08-05 |
JP2010540514A (ja) | 2010-12-24 |
US20150320042A1 (en) | 2015-11-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5683268B2 (ja) | 生物活性アニリンコポリマー | |
Hendessi et al. | Antibacterial sustained-release coatings from halloysite nanotubes/waterborne polyurethanes | |
Qu et al. | Effects of norspermidine on Pseudomonas aeruginosa biofilm formation and eradication | |
Liu et al. | Characterization and antibacterial properties of genipin-crosslinked chitosan/poly (ethylene glycol)/ZnO/Ag nanocomposites | |
Wang et al. | Integration of antifouling and bactericidal moieties for optimizing the efficacy of antibacterial coatings | |
EP3747932A1 (en) | Branched polyamino acid bacteriostatic agent and application thereof | |
Gregorova et al. | Lignin-containing polyethylene films with antibacterial activity | |
US8415408B2 (en) | Germs resisting and self cleaning infiltration thin film and manufacturing method thereof | |
Liang et al. | In situ synthesis of biocompatible imidazolium salt hydrogels with antimicrobial activity | |
CN115175968B (zh) | 抗菌聚合物组合物 | |
Sang et al. | Synthesis and preservative application of quaternized carboxymethyl chitosan containing guanidine groups | |
Li et al. | Biocidal poly (vinyl alcohol) films incorporated with N-halamine siloxane | |
Werner et al. | Antimicrobial and antifouling polymeric coating mitigates persistence of Pseudomonas aeruginosa biofilm | |
CN102017979A (zh) | 一种聚胍吡啶硫酮酸盐抗菌剂及其制备方法 | |
Cao et al. | Synthesis of non-water soluble polymeric guanidine derivatives and application in preparation of antimicrobial regenerated cellulose | |
Ahmadi et al. | Antimicrobial polymer nanocomposite films and coatings | |
Campos et al. | Antibacterial activity of chitosan solutions for wound dressing | |
WO2022026495A1 (en) | Antimicrobial silk nanoparticles and methods for making and using the same | |
WO2011131773A1 (en) | Novel antimicrobial composition, use and preparation thereof | |
JP5603701B2 (ja) | 抗菌性組成物及びその用途 | |
CN116940641A (zh) | 制备抗微生物涂料组合物的方法、抗微生物涂料组合物及其用于赋予基材表面抗微生物特性的用途 | |
NZ562092A (en) | Antimicrobial effect of copolymers of aniline with 3-amino benzoic acid, anthranilic acid and ethyl 3-amino benzoate | |
CN112825858B (zh) | 2,5呋喃二甲醛肟在抗菌除霉消毒剂中的应用 | |
JP7475765B2 (ja) | 抗菌性高分子組成物 | |
CN107549174A (zh) | 一种含杂环结构的季铵盐表面活性剂杀菌剂 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110629 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20110629 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20130124 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130205 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130502 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130513 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130604 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130611 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130703 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130710 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20130805 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20140408 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140807 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20140814 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20140909 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141017 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20141202 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20141208 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150106 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150113 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5683268 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |