Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors
Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-ba...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Ganeshpurkar, Ankit [verfasserIn] Kumar, Devendra [verfasserIn] Singh, Sushil Kumar [verfasserIn] |
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2017 |
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| Schlagwörter: |
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| Übergeordnetes Werk: |
Enthalten in: International journal of biological macromolecules - New York, NY [u.a.] : Elsevier, 1979, 107, Seite 1491-1500 |
|---|---|
| Übergeordnetes Werk: |
volume:107 ; pages:1491-1500 |
| DOI / URN: |
10.1016/j.ijbiomac.2017.10.008 |
|---|
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ELV000711985 |
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| 245 | 1 | 0 | |a Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors |
| 264 | 1 | |c 2017 | |
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| 520 | |a Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34μM, 29.61μM, 28.39μM, 31.4 and 32.11μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. | ||
| 650 | 4 | |a Phenylglycine | |
| 650 | 4 | |a Sulfonamide | |
| 700 | 1 | |a Kumar, Devendra |e verfasserin |4 aut | |
| 700 | 1 | |a Singh, Sushil Kumar |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t International journal of biological macromolecules |d New York, NY [u.a.] : Elsevier, 1979 |g 107, Seite 1491-1500 |h Online-Ressource |w (DE-627)30089502X |w (DE-600)1483284-7 |w (DE-576)259270814 |x 1879-0003 |7 nnns |
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| 912 | |a GBV_ILN_2020 | ||
| 912 | |a GBV_ILN_2021 | ||
| 912 | |a GBV_ILN_2025 | ||
| 912 | |a GBV_ILN_2026 | ||
| 912 | |a GBV_ILN_2027 | ||
| 912 | |a GBV_ILN_2031 | ||
| 912 | |a GBV_ILN_2034 | ||
| 912 | |a GBV_ILN_2037 | ||
| 912 | |a GBV_ILN_2038 | ||
| 912 | |a GBV_ILN_2039 | ||
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| 912 | |a GBV_ILN_2111 | ||
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| 912 | |a GBV_ILN_2113 | ||
| 912 | |a GBV_ILN_2116 | ||
| 912 | |a GBV_ILN_2118 | ||
| 912 | |a GBV_ILN_2119 | ||
| 912 | |a GBV_ILN_2122 | ||
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| 912 | |a GBV_ILN_2147 | ||
| 912 | |a GBV_ILN_2148 | ||
| 912 | |a GBV_ILN_2152 | ||
| 912 | |a GBV_ILN_2153 | ||
| 912 | |a GBV_ILN_2188 | ||
| 912 | |a GBV_ILN_2190 | ||
| 912 | |a GBV_ILN_2232 | ||
| 912 | |a GBV_ILN_2336 | ||
| 912 | |a GBV_ILN_2507 | ||
| 912 | |a GBV_ILN_2522 | ||
| 912 | |a GBV_ILN_4035 | ||
| 912 | |a GBV_ILN_4037 | ||
| 912 | |a GBV_ILN_4112 | ||
| 912 | |a GBV_ILN_4125 | ||
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| 912 | |a GBV_ILN_4326 | ||
| 912 | |a GBV_ILN_4333 | ||
| 912 | |a GBV_ILN_4334 | ||
| 912 | |a GBV_ILN_4335 | ||
| 912 | |a GBV_ILN_4338 | ||
| 912 | |a GBV_ILN_4393 | ||
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2017 |
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| allfields |
10.1016/j.ijbiomac.2017.10.008 doi (DE-627)ELV000711985 (ELSEVIER)S0141-8130(17)32053-6 DE-627 ger DE-627 rda eng 540 570 DE-600 BIODIV DE-30 fid 35.80 bkl 58.30 bkl Ganeshpurkar, Ankit verfasserin aut Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors 2017 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34μM, 29.61μM, 28.39μM, 31.4 and 32.11μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. Phenylglycine Sulfonamide Kumar, Devendra verfasserin aut Singh, Sushil Kumar verfasserin aut Enthalten in International journal of biological macromolecules New York, NY [u.a.] : Elsevier, 1979 107, Seite 1491-1500 Online-Ressource (DE-627)30089502X (DE-600)1483284-7 (DE-576)259270814 1879-0003 nnns volume:107 pages:1491-1500 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-BIODIV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2098 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.80 Makromolekulare Chemie 58.30 Biotechnologie AR 107 1491-1500 |
| spelling |
10.1016/j.ijbiomac.2017.10.008 doi (DE-627)ELV000711985 (ELSEVIER)S0141-8130(17)32053-6 DE-627 ger DE-627 rda eng 540 570 DE-600 BIODIV DE-30 fid 35.80 bkl 58.30 bkl Ganeshpurkar, Ankit verfasserin aut Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors 2017 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34μM, 29.61μM, 28.39μM, 31.4 and 32.11μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. Phenylglycine Sulfonamide Kumar, Devendra verfasserin aut Singh, Sushil Kumar verfasserin aut Enthalten in International journal of biological macromolecules New York, NY [u.a.] : Elsevier, 1979 107, Seite 1491-1500 Online-Ressource (DE-627)30089502X (DE-600)1483284-7 (DE-576)259270814 1879-0003 nnns volume:107 pages:1491-1500 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-BIODIV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2098 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.80 Makromolekulare Chemie 58.30 Biotechnologie AR 107 1491-1500 |
| allfields_unstemmed |
10.1016/j.ijbiomac.2017.10.008 doi (DE-627)ELV000711985 (ELSEVIER)S0141-8130(17)32053-6 DE-627 ger DE-627 rda eng 540 570 DE-600 BIODIV DE-30 fid 35.80 bkl 58.30 bkl Ganeshpurkar, Ankit verfasserin aut Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors 2017 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34μM, 29.61μM, 28.39μM, 31.4 and 32.11μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. Phenylglycine Sulfonamide Kumar, Devendra verfasserin aut Singh, Sushil Kumar verfasserin aut Enthalten in International journal of biological macromolecules New York, NY [u.a.] : Elsevier, 1979 107, Seite 1491-1500 Online-Ressource (DE-627)30089502X (DE-600)1483284-7 (DE-576)259270814 1879-0003 nnns volume:107 pages:1491-1500 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-BIODIV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2098 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.80 Makromolekulare Chemie 58.30 Biotechnologie AR 107 1491-1500 |
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10.1016/j.ijbiomac.2017.10.008 doi (DE-627)ELV000711985 (ELSEVIER)S0141-8130(17)32053-6 DE-627 ger DE-627 rda eng 540 570 DE-600 BIODIV DE-30 fid 35.80 bkl 58.30 bkl Ganeshpurkar, Ankit verfasserin aut Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors 2017 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34μM, 29.61μM, 28.39μM, 31.4 and 32.11μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. Phenylglycine Sulfonamide Kumar, Devendra verfasserin aut Singh, Sushil Kumar verfasserin aut Enthalten in International journal of biological macromolecules New York, NY [u.a.] : Elsevier, 1979 107, Seite 1491-1500 Online-Ressource (DE-627)30089502X (DE-600)1483284-7 (DE-576)259270814 1879-0003 nnns volume:107 pages:1491-1500 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-BIODIV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2098 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.80 Makromolekulare Chemie 58.30 Biotechnologie AR 107 1491-1500 |
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10.1016/j.ijbiomac.2017.10.008 doi (DE-627)ELV000711985 (ELSEVIER)S0141-8130(17)32053-6 DE-627 ger DE-627 rda eng 540 570 DE-600 BIODIV DE-30 fid 35.80 bkl 58.30 bkl Ganeshpurkar, Ankit verfasserin aut Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors 2017 nicht spezifiziert zzz rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34μM, 29.61μM, 28.39μM, 31.4 and 32.11μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. Phenylglycine Sulfonamide Kumar, Devendra verfasserin aut Singh, Sushil Kumar verfasserin aut Enthalten in International journal of biological macromolecules New York, NY [u.a.] : Elsevier, 1979 107, Seite 1491-1500 Online-Ressource (DE-627)30089502X (DE-600)1483284-7 (DE-576)259270814 1879-0003 nnns volume:107 pages:1491-1500 GBV_USEFLAG_U SYSFLAG_U GBV_ELV FID-BIODIV SSG-OLC-PHA GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_31 GBV_ILN_32 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_74 GBV_ILN_90 GBV_ILN_95 GBV_ILN_100 GBV_ILN_101 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_224 GBV_ILN_370 GBV_ILN_602 GBV_ILN_702 GBV_ILN_2001 GBV_ILN_2003 GBV_ILN_2004 GBV_ILN_2005 GBV_ILN_2007 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2015 GBV_ILN_2020 GBV_ILN_2021 GBV_ILN_2025 GBV_ILN_2026 GBV_ILN_2027 GBV_ILN_2031 GBV_ILN_2034 GBV_ILN_2037 GBV_ILN_2038 GBV_ILN_2039 GBV_ILN_2044 GBV_ILN_2048 GBV_ILN_2049 GBV_ILN_2050 GBV_ILN_2055 GBV_ILN_2056 GBV_ILN_2059 GBV_ILN_2061 GBV_ILN_2064 GBV_ILN_2065 GBV_ILN_2068 GBV_ILN_2070 GBV_ILN_2086 GBV_ILN_2098 GBV_ILN_2106 GBV_ILN_2108 GBV_ILN_2111 GBV_ILN_2112 GBV_ILN_2113 GBV_ILN_2116 GBV_ILN_2118 GBV_ILN_2119 GBV_ILN_2122 GBV_ILN_2129 GBV_ILN_2143 GBV_ILN_2144 GBV_ILN_2147 GBV_ILN_2148 GBV_ILN_2152 GBV_ILN_2153 GBV_ILN_2188 GBV_ILN_2190 GBV_ILN_2232 GBV_ILN_2336 GBV_ILN_2507 GBV_ILN_2522 GBV_ILN_4035 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4242 GBV_ILN_4251 GBV_ILN_4305 GBV_ILN_4313 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4326 GBV_ILN_4333 GBV_ILN_4334 GBV_ILN_4335 GBV_ILN_4338 GBV_ILN_4393 35.80 Makromolekulare Chemie 58.30 Biotechnologie AR 107 1491-1500 |
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Enthalten in International journal of biological macromolecules 107, Seite 1491-1500 volume:107 pages:1491-1500 |
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Ganeshpurkar, Ankit @@aut@@ Kumar, Devendra @@aut@@ Singh, Sushil Kumar @@aut@@ |
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Ganeshpurkar, Ankit |
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Ganeshpurkar, Ankit ddc 540 fid BIODIV bkl 35.80 bkl 58.30 misc Phenylglycine misc Sulfonamide Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors |
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540 570 DE-600 BIODIV DE-30 fid 35.80 bkl 58.30 bkl Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors Phenylglycine Sulfonamide |
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ddc 540 fid BIODIV bkl 35.80 bkl 58.30 misc Phenylglycine misc Sulfonamide |
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Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors |
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Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors |
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design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors |
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Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors |
| abstract |
Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34μM, 29.61μM, 28.39μM, 31.4 and 32.11μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. |
| abstractGer |
Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34μM, 29.61μM, 28.39μM, 31.4 and 32.11μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. |
| abstract_unstemmed |
Metalloproteases are a class of proteases having metal ion(s) at their catalytic sites. Bacterial collagenases are involved in human gas gangrene, periodontal diseases, food etc. The Clostridium collagenase occurs in two isoforms COL_G and Col_H. The present work is based on the protein structure-based approach for the development of collagenase inhibitors. The sequence analysis and structural alignment of both isoforms showed significant similarity in active site except aspartate switch present in Col_H. The homology model was developed and validated for Col_H peptidase domain with open aspartate switch followed by the docking of designed ligands. Compound 8b showed better interaction due to the presence of the nitro group. The N-benzyl-arylsulfonyl-phenylglycine derivatives were synthesized and characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis. The compounds were evaluated for C. histolyticum collagenase inhibitory activity using gelatin-ninhydrin based assay. Compounds 5b, 3b, 11b, 6b and 8b with IC50 of 24.34μM, 29.61μM, 28.39μM, 31.4 and 32.11μM respectively were found to be more active. Further, The Ki of most active compound 5b was found to be 22.02μM showing the competitive mode of inhibition of the enzyme. The activity of the derivatives showed correlation with the docking results. |
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Design, synthesis and collagenase inhibitory activity of some novel phenylglycine derivatives as metalloproteinase inhibitors |
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| score |
7.3999157 |