دورية أكاديمية
أعرض في EDS

2H-chromene and 7H-furo-chromene derivatives selectively inhibit tumour associated human carbonic anhydrase IX and XII isoforms.

التفاصيل البيبلوغرافية
العنوان: 2H-chromene and 7H-furo-chromene derivatives selectively inhibit tumour associated human carbonic anhydrase IX and XII isoforms.
المؤلفون: Sequeira L; Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, Italy.; CIQUP-IMS/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Porto, Portugal., Distinto S; Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, Italy., Meleddu R; Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, Italy., Gaspari M; Department of Experimental and Clinical Medicine, Research Centre for Advanced Biochemistry and Molecular Biology, 'Magna Græcia' University of Catanzaro, Catanzaro, Italy., Angeli A; Department of NEUROFARBA, Section of Pharmaceutical Sciences, University of Florence, Florence, Italy., Cottiglia F; Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, Italy., Secci D; Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, Italy., Onali A; Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, Italy., Sanna E; Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, Italy., Borges F; CIQUP-IMS/Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Porto, Portugal., Uriarte E; Department of Organic Chemistry, Faculty of Pharmacy, University of Santiago de Compostela, Santiago de Compostela, Spain., Alcaro S; Department of Health Sciences, 'Magna Græcia' University of Catanzaro, Catanzaro, Italy., Supuran CT; Department of NEUROFARBA, Section of Pharmaceutical Sciences, University of Florence, Florence, Italy., Maccioni E; Department of Life and Environmental Sciences, University of Cagliari, Cittadella Universitaria, Monserrato, Italy.
المصدر: Journal of enzyme inhibition and medicinal chemistry [J Enzyme Inhib Med Chem] 2023 Dec; Vol. 38 (1), pp. 2270183. Date of Electronic Publication: 2023 Oct 23.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Taylor & Francis Country of Publication: England NLM ID: 101150203 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1475-6374 (Electronic) Linking ISSN: 14756366 NLM ISO Abbreviation: J Enzyme Inhib Med Chem Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Basingstoke, UK : Taylor & Francis, c2002-
مواضيع طبية MeSH: Carbonic Anhydrases*/metabolism , Neoplasms*/drug therapy , Neoplasms*/pathology, Humans ; Carbonic Anhydrase IX ; Carbonic Anhydrase I ; Carbonic Anhydrase II ; Structure-Activity Relationship ; Carbonic Anhydrase Inhibitors/pharmacology ; Carbonic Anhydrase Inhibitors/chemistry ; Antigens, Neoplasm/chemistry ; Benzopyrans/pharmacology ; Isoenzymes/metabolism ; Molecular Structure
مستخلص: Tumour associated carbonic anhydrases (CAs) IX and XII have been recognised as potential targets for the treatment of hypoxic tumours. Therefore, considering the high pharmacological potential of the chromene scaffold as selective ligand of the IX and XII isoforms, two libraries of compounds, namely 2H-chromene and 7H-furo-chromene derivatives, with diverse substitution patterns were designed and synthesised. The structure of the newly synthesised compounds was characterised and their inhibitory potency and selectivity towards human CA off target isoforms I, II and cancer-associated CA isoforms IX and XII were evaluated. Most of the compounds inhibit CA isoforms IX and XII with no activity against the I and II isozymes. Thus, while the potency was influenced by the substitution pattern along the chromene scaffold, the selectivity was conserved along the series, confirming the high potential of both 2H-chromene and 7H-furo-chromene scaffolds for the design of isozyme selective inhibitors.
References: Bioorg Chem. 2022 Nov;128:106071. (PMID: 35932498)
J Clin Pathol. 2021 Feb 22;:. (PMID: 33619217)
Nat Rev Drug Discov. 2008 Feb;7(2):168-81. (PMID: 18167490)
Curr Pharm Des. 2008;14(7):603-14. (PMID: 18336305)
J Med Chem. 2010 Jan 14;53(1):335-44. (PMID: 19911821)
Anticancer Agents Med Chem. 2017;17(3):395-403. (PMID: 26902599)
Br J Cancer. 2020 Jan;122(2):157-167. (PMID: 31819195)
Metabolites. 2017 Nov 11;7(4):. (PMID: 29137134)
Expert Opin Ther Pat. 2018 Oct;28(10):729-740. (PMID: 30074415)
Med Chem. 2020;16(8):1099-1111. (PMID: 31448715)
J Enzyme Inhib Med Chem. 2017 Dec;32(1):68-73. (PMID: 27775452)
J Enzyme Inhib Med Chem. 2019 Dec;34(1):644-650. (PMID: 30727781)
Br J Clin Pharmacol. 2022 May;88(5):2019-2034. (PMID: 34820879)
ACS Med Chem Lett. 2018 Jun 06;9(7):725-729. (PMID: 30034608)
Bioorg Med Chem Lett. 2014 Feb 1;24(3):835-8. (PMID: 24393580)
J Enzyme Inhib Med Chem. 2019 Dec;34(1):1526-1533. (PMID: 31431095)
Gene. 2017 Aug 5;623:33-40. (PMID: 28433659)
Int J Mol Sci. 2020 Jun 29;21(13):. (PMID: 32610556)
JAMA Oncol. 2015 Jul;1(4):505-27. (PMID: 26181261)
J Med Chem. 2011 Mar 24;54(6):1896-902. (PMID: 21361354)
Radiol Oncol. 2020 Feb 19;54(1):1-13. (PMID: 32074075)
Bioorg Chem. 2018 Oct;80:94-98. (PMID: 29894892)
Curr Med Chem. 2010;17(13):1325-38. (PMID: 20166938)
Proc Natl Acad Sci U S A. 1998 Jun 23;95(13):7608-13. (PMID: 9636197)
Int J Mol Sci. 2023 Mar 12;24(6):. (PMID: 36982496)
Chest. 2022 Jun;161(6):1675-1686. (PMID: 35026298)
Cancer Metastasis Rev. 2019 Jun;38(1-2):65-77. (PMID: 31076951)
Drug Metab Rev. 2008;40(2):355-75. (PMID: 18464049)
J Ethnopharmacol. 2017 May 5;203:27-38. (PMID: 28341244)
Molecules. 2018 Apr 30;23(5):. (PMID: 29710858)
CA Cancer J Clin. 2020 Jan;70(1):7-30. (PMID: 31912902)
Nucleic Acids Res. 2000 Jan 1;28(1):235-42. (PMID: 10592235)
Bioorg Med Chem. 2013 Mar 15;21(6):1377-8. (PMID: 23452985)
J Chem Inf Model. 2009 Oct;49(10):2382-7. (PMID: 19799409)
Future Med Chem. 2019 May;11(9):1057-1082. (PMID: 31140865)
Metabolites. 2018 Feb 28;8(1):. (PMID: 29495652)
Bioorg Med Chem Lett. 2015 Aug 15;25(16):3281-4. (PMID: 26073006)
Biochem J. 2005 Nov 15;392(Pt 1):83-92. (PMID: 16083424)
Cancer Epidemiol. 2016 Oct;44:203-221. (PMID: 27460784)
PeerJ. 2018 Feb 26;6:e4412. (PMID: 29503769)
Chem Biol Interact. 2016 Jul 25;254:11-23. (PMID: 27174134)
Biochem Soc Trans. 2010 Feb;38(Pt 1):50-3. (PMID: 20074034)
J Med Chem. 2020 Jul 9;63(13):7392-7409. (PMID: 32463228)
J Enzyme Inhib Med Chem. 2020 Dec;35(1):539-548. (PMID: 31948300)
J Enzyme Inhib Med Chem. 2021 Dec;36(1):1988-1995. (PMID: 34482770)
Br J Haematol. 2008 Jun;141(6):757-63. (PMID: 18355382)
Arch Pharm (Weinheim). 2015 Dec;348(12):875-88. (PMID: 26462142)
Biochem Biophys Res Commun. 2001 Nov 2;288(3):666-9. (PMID: 11676494)
Future Med Chem. 2011 Jul;3(9):1165-80. (PMID: 21806379)
J Histochem Cytochem. 2000 Dec;48(12):1601-8. (PMID: 11101628)
Nature. 2022 Mar;603(7899):166-173. (PMID: 35197630)
N Engl J Med. 2022 Jul 7;387(1):9-20. (PMID: 35665782)
Bioorg Chem. 2020 Oct;103:104163. (PMID: 32890989)
J Biol Chem. 1971 Apr 25;246(8):2561-73. (PMID: 4994926)
Lancet Glob Health. 2020 Feb;8(2):e180-e190. (PMID: 31862245)
J Enzyme Inhib Med Chem. 2021 Dec;36(1):685-692. (PMID: 33602041)
Med Res Rev. 2018 Sep;38(6):1799-1836. (PMID: 29635752)
Subcell Biochem. 2014;75:9-30. (PMID: 24146372)
Cancers (Basel). 2020 Jul 19;12(7):. (PMID: 32707666)
Biochemistry. 1996 Apr 16;35(15):5083-92. (PMID: 8664301)
J Mol Biol. 2009 Jan 30;385(4):1207-20. (PMID: 19071134)
Acc Chem Res. 2000 Dec;33(12):889-97. (PMID: 11123888)
J Med Chem. 2015 Nov 25;58(22):9004-9. (PMID: 26522624)
J Enzyme Inhib Med Chem. 2020 Dec;35(1):325-329. (PMID: 31813300)
Physiol Rev. 1967 Oct;47(4):595-781. (PMID: 4964060)
Mini Rev Med Chem. 2020;20(17):1754-1766. (PMID: 32386492)
J Am Chem Soc. 2009 Mar 4;131(8):3057-62. (PMID: 19206230)
Adv Clin Chem. 2006;42:167-216. (PMID: 17131627)
Med Res Rev. 2020 Nov;40(6):2485-2565. (PMID: 32691504)
J Enzyme Inhib Med Chem. 2016 Oct;31(5):689-94. (PMID: 26118417)
فهرسة مساهمة: Keywords: Human carbonic anhydrase IX and XII; cancer; coumarin derivatives; docking; selective inhibitors
المشرفين على المادة: EC 4.2.1.1 (Carbonic Anhydrase IX)
EC 4.2.1.1 (Carbonic Anhydrases)
0 (5,7-dimethoxy-2-methyl-2H-benzopyran)
EC 4.2.1.- (Carbonic Anhydrase I)
EC 4.2.1.- (Carbonic Anhydrase II)
0 (Carbonic Anhydrase Inhibitors)
0 (Antigens, Neoplasm)
0 (Benzopyrans)
0 (Isoenzymes)
تواريخ الأحداث: Date Created: 20231023 Date Completed: 20231102 Latest Revision: 20240411
رمز التحديث: 20240411
مُعرف محوري في PubMed: PMC11003494
DOI: 10.1080/14756366.2023.2270183
PMID: 37870190
قاعدة البيانات: MEDLINE
الوصف
تدمد:1475-6374
DOI:10.1080/14756366.2023.2270183