Probing structural requirements for human topoisomerase I inhibition by a novel N1-Biphenyl fluoroquinolone

Fluoroquinolones substituted with N-1 biphenyl and napthyl groups were discovered to act as catalytically inhibitors of human topoisomerases I and II, and to possess anti-proliferative activity in vivo. Structural requirements for these novel quinolones to inhibit catalytic activity of human topoiso...

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Vydáno v:	European journal of medicinal chemistry Ročník 172; s. 109 - 130
Hlavní autoři:	Delgado, Justine L., Lentz, Sarah R.C., Kulkarni, Chaitanya A., Chheda, Pratik R., Held, Hailey A., Hiasa, Hiroshi, Kerns, Robert J.
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	ISSY-LES-MOULINEAUX Elsevier Masson SAS 15.06.2019 Elsevier
Témata:	Anti-cancer Biphenyl Compounds - chemical synthesis Biphenyl Compounds - chemistry Biphenyl Compounds - pharmacology Catalytic inhibitors Chemistry, Medicinal DNA Topoisomerases, Type I - metabolism Dose-Response Relationship, Drug Fluoroquinolones Fluoroquinolones - chemical synthesis Fluoroquinolones - chemistry Fluoroquinolones - pharmacology hTopoI inhibitor Humans Life Sciences & Biomedicine Molecular Structure Pharmacology & Pharmacy Science & Technology Structure-Activity Relationship Topoisomerase Topoisomerase I Inhibitors - chemical synthesis Topoisomerase I Inhibitors - chemistry Topoisomerase I Inhibitors - pharmacology Fluoroquinolones Topoisomerase hTopoI inhibitor Anti-cancer Catalytic inhibitors MECHANISM BIPHENYL ROLES MODE hTopol inhibitor DNA GYRASE DERIVATIVES
ISSN:	0223-5234, 1768-3254, 1768-3254
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Abstract	Fluoroquinolones substituted with N-1 biphenyl and napthyl groups were discovered to act as catalytically inhibitors of human topoisomerases I and II, and to possess anti-proliferative activity in vivo. Structural requirements for these novel quinolones to inhibit catalytic activity of human topoisomerase I have not been explored. In this work novel derivatives of the N-1 biphenyl fluoroquinolone were designed, synthesized and evaluated to understand structural requirements of the C-3 carboxylic acid, C-6 fluorine, C-7 aminomethylpyrrolidine, C-8 methoxy, and the N-1 biphenyl functional groups for hTopoI inhibition. Characterization of each analog for inhibition of hTopoI catalytic inhibition reveals critical insight into structural requirements of these novel quinolones for activity. Additionally, results of DNA binding and modeling studies suggest that N-1 biphenyl fluoroquinolones intercalate between the DNA base pairs with the N-1 biphenyl functional group, rather than the quinolone core, and that this mode of DNA intercalation contributes to inhibition of hTopoI by these novel structures. The results presented here support further development and evaluation of N-1 biphenyl fluoroquinolone analogs as a novel class of anti-cancer agents that act through catalytic inhibition of hTopoI. [Display omitted] •Novel quinolones act as catalytic inhibitors of hTopoI.•C-7 amine required for hTopoI catalytic inhibition.•N-1 biphenyl functional group intercalates between DNA base pairs.•Mechanism of DNA intercalation by N-1 biphenyl fluoroquinolones contributes to hTopoI inhibition.•Novel hTopoI inhibitors that do not increase DNA breaks.
AbstractList	Fluoroquinolones substituted with N-1 biphenyl and napthyl groups were discovered to act as catalytically inhibitors of human topoisomerases I and II, and to possess anti-proliferative activity in vivo. Structural requirements for these novel quinolones to inhibit catalytic activity of human topoisomerase I have not been explored. In this work novel derivatives of the N-1 biphenyl fluoroquinolone were designed, synthesized and evaluated to understand structural requirements of the C-3 carboxylic acid, C-6 fluorine, C-7 aminomethylpyrrolidine, C-8 methoxy, and the N-1 biphenyl functional groups for hTopoI inhibition. Characterization of each analog for inhibition of hTopoI catalytic inhibition reveals critical insight into structural requirements of these novel quinolones for activity. Additionally, results of DNA binding and modeling studies suggest that N-1 biphenyl fluoroquinolones intercalate between the DNA base pairs with the N-1 biphenyl functional group, rather than the quinolone core, and that this mode of DNA intercalation contributes to inhibition of hTopoI by these novel structures. The results presented here support further development and evaluation of N-1 biphenyl fluoroquinolone analogs as a novel class of anti-cancer agents that act through catalytic inhibition of hTopoI. Fluoroquinolones substituted with N-1 biphenyl and napthyl groups were discovered to act as catalytically inhibitors of human topoisomerases I and II, and to possess anti-proliferative activity in vivo. Structural requirements for these novel quinolones to inhibit catalytic activity of human topoisomerase I have not been explored. In this work novel derivatives of the N-1 biphenyl fluoroquinolone were designed, synthesized and evaluated to understand structural requirements of the C-3 carboxylic acid, C-6 fluorine, C-7 aminomethylpyrrolidine, C-8 methoxy, and the N-1 biphenyl functional groups for hTopol inhibition. Characterization of each analog for inhibition of hTopol catalytic inhibition reveals critical insight into structural requirements of these novel quinolones for activity. Additionally, results of DNA binding and modeling studies suggest that N-1 biphenyl fluoroquinolones intercalate between the DNA base pairs with the N-1 biphenyl functional group, rather than the quinolone core, and that this mode of DNA intercalation contributes to inhibition of hTopol by these novel structures. The results presented here support further development and evaluation of N-1 biphenyl fluoroquinolone analogs as a novel class of anti-cancer agents that act through catalytic inhibition of hTopol. (C) 2019 Elsevier Masson SAS. All rights reserved. Fluoroquinolones substituted with N-1 biphenyl and napthyl groups were discovered to act as catalytically inhibitors of human topoisomerases I and II, and to possess anti-proliferative activity in vivo. Structural requirements for these novel quinolones to inhibit catalytic activity of human topoisomerase I have not been explored. In this work novel derivatives of the N-1 biphenyl fluoroquinolone were designed, synthesized and evaluated to understand structural requirements of the C-3 carboxylic acid, C-6 fluorine, C-7 aminomethylpyrrolidine, C-8 methoxy, and the N-1 biphenyl functional groups for hTopoI inhibition. Characterization of each analog for inhibition of hTopoI catalytic inhibition reveals critical insight into structural requirements of these novel quinolones for activity. Additionally, results of DNA binding and modeling studies suggest that N-1 biphenyl fluoroquinolones intercalate between the DNA base pairs with the N-1 biphenyl functional group, rather than the quinolone core, and that this mode of DNA intercalation contributes to inhibition of hTopoI by these novel structures. The results presented here support further development and evaluation of N-1 biphenyl fluoroquinolone analogs as a novel class of anti-cancer agents that act through catalytic inhibition of hTopoI.Fluoroquinolones substituted with N-1 biphenyl and napthyl groups were discovered to act as catalytically inhibitors of human topoisomerases I and II, and to possess anti-proliferative activity in vivo. Structural requirements for these novel quinolones to inhibit catalytic activity of human topoisomerase I have not been explored. In this work novel derivatives of the N-1 biphenyl fluoroquinolone were designed, synthesized and evaluated to understand structural requirements of the C-3 carboxylic acid, C-6 fluorine, C-7 aminomethylpyrrolidine, C-8 methoxy, and the N-1 biphenyl functional groups for hTopoI inhibition. Characterization of each analog for inhibition of hTopoI catalytic inhibition reveals critical insight into structural requirements of these novel quinolones for activity. Additionally, results of DNA binding and modeling studies suggest that N-1 biphenyl fluoroquinolones intercalate between the DNA base pairs with the N-1 biphenyl functional group, rather than the quinolone core, and that this mode of DNA intercalation contributes to inhibition of hTopoI by these novel structures. The results presented here support further development and evaluation of N-1 biphenyl fluoroquinolone analogs as a novel class of anti-cancer agents that act through catalytic inhibition of hTopoI. Fluoroquinolones substituted with N-1 biphenyl and napthyl groups were discovered to act as catalytically inhibitors of human topoisomerases I and II, and to possess anti-proliferative activity in vivo. Structural requirements for these novel quinolones to inhibit catalytic activity of human topoisomerase I have not been explored. In this work novel derivatives of the N-1 biphenyl fluoroquinolone were designed, synthesized and evaluated to understand structural requirements of the C-3 carboxylic acid, C-6 fluorine, C-7 aminomethylpyrrolidine, C-8 methoxy, and the N-1 biphenyl functional groups for hTopoI inhibition. Characterization of each analog for inhibition of hTopoI catalytic inhibition reveals critical insight into structural requirements of these novel quinolones for activity. Additionally, results of DNA binding and modeling studies suggest that N-1 biphenyl fluoroquinolones intercalate between the DNA base pairs with the N-1 biphenyl functional group, rather than the quinolone core, and that this mode of DNA intercalation contributes to inhibition of hTopoI by these novel structures. The results presented here support further development and evaluation of N-1 biphenyl fluoroquinolone analogs as a novel class of anti-cancer agents that act through catalytic inhibition of hTopoI. [Display omitted] •Novel quinolones act as catalytic inhibitors of hTopoI.•C-7 amine required for hTopoI catalytic inhibition.•N-1 biphenyl functional group intercalates between DNA base pairs.•Mechanism of DNA intercalation by N-1 biphenyl fluoroquinolones contributes to hTopoI inhibition.•Novel hTopoI inhibitors that do not increase DNA breaks. Fluoroquinolones substituted with N-1 biphenyl and napthyl groups were discovered to act as catalytically inhibitors of human topoisomerases I and II, and to possess anti-proliferative activity in vivo. Structural requirements for these novel quinolones to inhibit catalytic activity of human topoisomerase I have not been explored. In this work novel derivatives of the N-1 biphenyl fluoroquinolone were designed, synthesized and evaluated to understand structural requirements of the C-3 carboxylic acid, C-6 fluorine, C-7 aminomethylpyrrolidine, C-8 methoxy, and the N-1 biphenyl functional groups for hTopoI inhibition. Characterization of each analog for inhibition of hTopoI catalytic inhibition reveals critical insight into structural requirements of these novel quinolones for activity. Additionally, results of DNA binding and modeling studies suggest that N-1 biphenyl fluoroquinolones intercalate between the DNA base pairs with the N-1 biphenyl functional group, rather than the quinolone core, and that this mode of DNA intercalation contributes to inhibition of hTopoI by these novel structures. The results presented here support further development and evaluation of N-1 biphenyl fluoroquinolone analogs as a novel class of anti-cancer agents that act through catalytic inhibition of hTopoI.
Author	Delgado, Justine L. Chheda, Pratik R. Held, Hailey A. Lentz, Sarah R.C. Hiasa, Hiroshi Kerns, Robert J. Kulkarni, Chaitanya A.
AuthorAffiliation	2 Department of Pharmacology, University of Minnesota Medical School, 6-120 Jackson Hall, 321 Church Street SE, Minneapolis, Minnesota 55455, U.S.A 1 Division of Medicinal and Natural Products Chemistry, Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, University of Iowa, 115 S Grand Ave., S321 Pharmacy Building, Iowa City, Iowa 52242, U.S.A
AuthorAffiliation_xml	– name: 2 Department of Pharmacology, University of Minnesota Medical School, 6-120 Jackson Hall, 321 Church Street SE, Minneapolis, Minnesota 55455, U.S.A – name: 1 Division of Medicinal and Natural Products Chemistry, Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, University of Iowa, 115 S Grand Ave., S321 Pharmacy Building, Iowa City, Iowa 52242, U.S.A
Author_xml	– sequence: 1 givenname: Justine L. surname: Delgado fullname: Delgado, Justine L. organization: Division of Medicinal and Natural Products Chemistry, Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, University of Iowa, 115 S Grand Ave., S321 Pharmacy Building, Iowa City, IA, 52242, USA – sequence: 2 givenname: Sarah R.C. surname: Lentz fullname: Lentz, Sarah R.C. organization: Department of Pharmacology, University of Minnesota Medical School, 6-120 Jackson Hall, 321 Church Street SE, Minneapolis, MN, 55455, USA – sequence: 3 givenname: Chaitanya A. orcidid: 0000-0002-6836-0518 surname: Kulkarni fullname: Kulkarni, Chaitanya A. organization: Division of Medicinal and Natural Products Chemistry, Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, University of Iowa, 115 S Grand Ave., S321 Pharmacy Building, Iowa City, IA, 52242, USA – sequence: 4 givenname: Pratik R. orcidid: 0000-0001-5788-3324 surname: Chheda fullname: Chheda, Pratik R. organization: Division of Medicinal and Natural Products Chemistry, Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, University of Iowa, 115 S Grand Ave., S321 Pharmacy Building, Iowa City, IA, 52242, USA – sequence: 5 givenname: Hailey A. surname: Held fullname: Held, Hailey A. organization: Department of Pharmacology, University of Minnesota Medical School, 6-120 Jackson Hall, 321 Church Street SE, Minneapolis, MN, 55455, USA – sequence: 6 givenname: Hiroshi surname: Hiasa fullname: Hiasa, Hiroshi organization: Department of Pharmacology, University of Minnesota Medical School, 6-120 Jackson Hall, 321 Church Street SE, Minneapolis, MN, 55455, USA – sequence: 7 givenname: Robert J. orcidid: 0000-0001-5371-403X surname: Kerns fullname: Kerns, Robert J. email: robert-kerns@uiowa.edu organization: Division of Medicinal and Natural Products Chemistry, Department of Pharmaceutical Sciences and Experimental Therapeutics, College of Pharmacy, University of Iowa, 115 S Grand Ave., S321 Pharmacy Building, Iowa City, IA, 52242, USA
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Keywords	Fluoroquinolones Topoisomerase hTopoI inhibitor Anti-cancer Catalytic inhibitors MECHANISM BIPHENYL ROLES MODE hTopol inhibitor DNA GYRASE DERIVATIVES
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Snippet	Fluoroquinolones substituted with N-1 biphenyl and napthyl groups were discovered to act as catalytically inhibitors of human topoisomerases I and II, and to...
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SubjectTerms	Anti-cancer Biphenyl Compounds - chemical synthesis Biphenyl Compounds - chemistry Biphenyl Compounds - pharmacology Catalytic inhibitors Chemistry, Medicinal DNA Topoisomerases, Type I - metabolism Dose-Response Relationship, Drug Fluoroquinolones Fluoroquinolones - chemical synthesis Fluoroquinolones - chemistry Fluoroquinolones - pharmacology hTopoI inhibitor Humans Life Sciences & Biomedicine Molecular Structure Pharmacology & Pharmacy Science & Technology Structure-Activity Relationship Topoisomerase Topoisomerase I Inhibitors - chemical synthesis Topoisomerase I Inhibitors - chemistry Topoisomerase I Inhibitors - pharmacology
Title	Probing structural requirements for human topoisomerase I inhibition by a novel N1-Biphenyl fluoroquinolone
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