8,9-Methylenedioxybenzo[i]phenanthridines: Topoisomerase I-targeting activity and cytotoxicity

Dajie Li; Baoping Zhao; Sai Peng Sim; Tsai Kun Li; Angela Liu; Leroy-Fong Liu; Edmond J. LaVoie

doi:10.1016/S0968-0896(03)00394-8

8,9-Methylenedioxybenzo[i]phenanthridines: Topoisomerase I-targeting activity and cytotoxicity

Dajie Li, Baoping Zhao, Sai Peng Sim, Tsai Kun Li, Angela Liu, Leroy-Fong Liu, Edmond J. LaVoie

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

Abstract

Substituted benzo[i]phenanthridines that have incorporated within their structure an 8,9-methylenedioxy group can exhibit topoisomerase I-targeting activity. Structure-activity studies were performed to examine the influence of saturation at the 11,12-positions of several substituted 8,9-methylenedioxybenzo[i]phenanthridines. The activities of these dihydro analogues were compared to those of their unsaturated analogues. In addition, the influence of varying substituents at the 2- and 3-positions within the A-ring of these 8,9-methylenedioxybenzo[i]phenanthridines on their relative potency as topoisomerase I-targeting agents and cell proliferation as determined using the MTT assay was investigated. 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and its 11,12-dihydro derivative were among the more potent analogues evaluated with regard to topoisomerase I-targeting activity and cytotoxicity.

Original language	English
Pages (from-to)	3795-3805
Number of pages	11
Journal	Bioorganic and Medicinal Chemistry
Volume	11
Issue number	17
DOIs	https://doi.org/10.1016/S0968-0896(03)00394-8
Publication status	Published - Aug 15 2003
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Biology
Organic Chemistry
Drug Discovery
Pharmaceutical Science

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title = "8,9-Methylenedioxybenzo[i]phenanthridines: Topoisomerase I-targeting activity and cytotoxicity",

abstract = "Substituted benzo[i]phenanthridines that have incorporated within their structure an 8,9-methylenedioxy group can exhibit topoisomerase I-targeting activity. Structure-activity studies were performed to examine the influence of saturation at the 11,12-positions of several substituted 8,9-methylenedioxybenzo[i]phenanthridines. The activities of these dihydro analogues were compared to those of their unsaturated analogues. In addition, the influence of varying substituents at the 2- and 3-positions within the A-ring of these 8,9-methylenedioxybenzo[i]phenanthridines on their relative potency as topoisomerase I-targeting agents and cell proliferation as determined using the MTT assay was investigated. 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and its 11,12-dihydro derivative were among the more potent analogues evaluated with regard to topoisomerase I-targeting activity and cytotoxicity.",

author = "Dajie Li and Baoping Zhao and Sim, {Sai Peng} and Li, {Tsai Kun} and Angela Liu and Leroy-Fong Liu and LaVoie, {Edmond J.}",

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AU - Li, Dajie

AU - Zhao, Baoping

AU - Sim, Sai Peng

AU - Li, Tsai Kun

AU - Liu, Angela

AU - Liu, Leroy-Fong

AU - LaVoie, Edmond J.

PY - 2003/8/15

Y1 - 2003/8/15

N2 - Substituted benzo[i]phenanthridines that have incorporated within their structure an 8,9-methylenedioxy group can exhibit topoisomerase I-targeting activity. Structure-activity studies were performed to examine the influence of saturation at the 11,12-positions of several substituted 8,9-methylenedioxybenzo[i]phenanthridines. The activities of these dihydro analogues were compared to those of their unsaturated analogues. In addition, the influence of varying substituents at the 2- and 3-positions within the A-ring of these 8,9-methylenedioxybenzo[i]phenanthridines on their relative potency as topoisomerase I-targeting agents and cell proliferation as determined using the MTT assay was investigated. 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and its 11,12-dihydro derivative were among the more potent analogues evaluated with regard to topoisomerase I-targeting activity and cytotoxicity.

AB - Substituted benzo[i]phenanthridines that have incorporated within their structure an 8,9-methylenedioxy group can exhibit topoisomerase I-targeting activity. Structure-activity studies were performed to examine the influence of saturation at the 11,12-positions of several substituted 8,9-methylenedioxybenzo[i]phenanthridines. The activities of these dihydro analogues were compared to those of their unsaturated analogues. In addition, the influence of varying substituents at the 2- and 3-positions within the A-ring of these 8,9-methylenedioxybenzo[i]phenanthridines on their relative potency as topoisomerase I-targeting agents and cell proliferation as determined using the MTT assay was investigated. 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and its 11,12-dihydro derivative were among the more potent analogues evaluated with regard to topoisomerase I-targeting activity and cytotoxicity.

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