12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents

Wei Feng; Mavurapu Satyanarayana; Yuan Chin Tsai; Angela A. Liu; Leroy F. Liu; Edmond J. LaVoie

doi:10.1016/j.bmc.2009.02.023

12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents

Wei Feng, Mavurapu Satyanarayana, Yuan Chin Tsai, Angela A. Liu, Leroy F. Liu, Edmond J. LaVoie

Research output: Contribution to journal › Article

16 Citations (Scopus)

Abstract

2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and a few of its 12-substituted analogs are active as TOP1-targeting agents. Studies were performed to further evaluate the potential of this series of non-camptothecin TOP1-targeting agents. The influence of a hydroxymethyl, formyl, N,N-dimethylaminomethyl, 2-(N,N-dimethylamino)ethyl, 3-(N,N-dimethylamino)propyl), and 4-(N,N-dimethylamino)butyl substituent at the 12-position on TOP1-targeting activity and tumor cell growth was evaluated. In addition, the relative pharmacologic activities of the 12-carboxamide analog, as well as its N-methyl and N,N-dimethyl derivatives were assessed.

Original language	English
Pages (from-to)	2877-2885
Number of pages	9
Journal	Bioorganic and Medicinal Chemistry
Volume	17
Issue number	7
DOIs	https://doi.org/10.1016/j.bmc.2009.02.023
Publication status	Published - Apr 1 2009
Externally published	Yes

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Keywords

Benzo[i]phenanthridines
Cytotoxicity
Structure-activity
Topoisomerase I

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Organic Chemistry
Molecular Medicine
Molecular Biology
Clinical Biochemistry
Biochemistry

Cite this

Feng, W., Satyanarayana, M., Tsai, Y. C., Liu, A. A., Liu, L. F., & LaVoie, E. J. (2009). 12-Substituted 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridines as novel topoisomerase I-targeting antitumor agents. Bioorganic and Medicinal Chemistry, 17(7), 2877-2885. https://doi.org/10.1016/j.bmc.2009.02.023

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abstract = "2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and a few of its 12-substituted analogs are active as TOP1-targeting agents. Studies were performed to further evaluate the potential of this series of non-camptothecin TOP1-targeting agents. The influence of a hydroxymethyl, formyl, N,N-dimethylaminomethyl, 2-(N,N-dimethylamino)ethyl, 3-(N,N-dimethylamino)propyl), and 4-(N,N-dimethylamino)butyl substituent at the 12-position on TOP1-targeting activity and tumor cell growth was evaluated. In addition, the relative pharmacologic activities of the 12-carboxamide analog, as well as its N-methyl and N,N-dimethyl derivatives were assessed.",

keywords = "Benzo[i]phenanthridines, Cytotoxicity, Structure-activity, Topoisomerase I",

author = "Wei Feng and Mavurapu Satyanarayana and Tsai, {Yuan Chin} and Liu, {Angela A.} and Liu, {Leroy F.} and LaVoie, {Edmond J.}",

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AU - Feng, Wei

AU - Satyanarayana, Mavurapu

AU - Tsai, Yuan Chin

AU - Liu, Angela A.

AU - Liu, Leroy F.

AU - LaVoie, Edmond J.

PY - 2009/4/1

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N2 - 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and a few of its 12-substituted analogs are active as TOP1-targeting agents. Studies were performed to further evaluate the potential of this series of non-camptothecin TOP1-targeting agents. The influence of a hydroxymethyl, formyl, N,N-dimethylaminomethyl, 2-(N,N-dimethylamino)ethyl, 3-(N,N-dimethylamino)propyl), and 4-(N,N-dimethylamino)butyl substituent at the 12-position on TOP1-targeting activity and tumor cell growth was evaluated. In addition, the relative pharmacologic activities of the 12-carboxamide analog, as well as its N-methyl and N,N-dimethyl derivatives were assessed.

AB - 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and a few of its 12-substituted analogs are active as TOP1-targeting agents. Studies were performed to further evaluate the potential of this series of non-camptothecin TOP1-targeting agents. The influence of a hydroxymethyl, formyl, N,N-dimethylaminomethyl, 2-(N,N-dimethylamino)ethyl, 3-(N,N-dimethylamino)propyl), and 4-(N,N-dimethylamino)butyl substituent at the 12-position on TOP1-targeting activity and tumor cell growth was evaluated. In addition, the relative pharmacologic activities of the 12-carboxamide analog, as well as its N-methyl and N,N-dimethyl derivatives were assessed.

KW - Benzo[i]phenanthridines

KW - Cytotoxicity

KW - Structure-activity

KW - Topoisomerase I

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10.1016/j.bmc.2009.02.023