Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide

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

doi:10.1016/j.ejmech.2009.02.004

Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide

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

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

22 Citations (Scopus)

Abstract

Several new TOP1-targeting agents were prepared using as an intermediate the N,N,N-trimethyl quaternary ammonium salt 2 of ARC-111. Direct displacement of the quaternary ammonium group with hydroxide, cyclopropylamine, imidazole, 1H-1,2,3-triazole, alkylethylenediamines, ethanolamine, and polyhydroxylated alkylamines provides a convenient means for furthering insight into the structure-activity relationships within this series of non-camptothecin TOP1-targeting agents. The relative TOP1-targeting activities and cytotoxicities were evaluated in RPMI8402 and P388 cells and their camptothecin-resistant variants. Their potential to serve as substrates for the efflux transporters MDR1 and BCRP, which are associated with multidrug resistance, was also assessed.

Original language	English
Pages (from-to)	3433-3438
Number of pages	6
Journal	European Journal of Medicinal Chemistry
Volume	44
Issue number	9
DOIs	https://doi.org/10.1016/j.ejmech.2009.02.004
Publication status	Published - Sept 2009
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

5H-Dibenzo[c,h][1,6]naphthyridin-6-ones
ARC-111
Antitumor
Cytotoxic activity
Multidrug resistance
Quaternary ammonium salts
TOP1-targeting agents

ASJC Scopus subject areas

Drug Discovery
Pharmacology
Organic Chemistry

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10.1016/j.ejmech.2009.02.004

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Feng, W., Satyanarayana, M., Tsai, Y. C., Liu, A. A., Liu, L. F., & LaVoie, E. J. (2009). Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide. European Journal of Medicinal Chemistry, 44(9), 3433-3438. https://doi.org/10.1016/j.ejmech.2009.02.004

Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide. / Feng, Wei; Satyanarayana, Mavurapu; Tsai, Yuan Chin et al.
In: European Journal of Medicinal Chemistry, Vol. 44, No. 9, 09.2009, p. 3433-3438.

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

Feng, W, Satyanarayana, M, Tsai, YC, Liu, AA, Liu, LF & LaVoie, EJ 2009, 'Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide', European Journal of Medicinal Chemistry, vol. 44, no. 9, pp. 3433-3438. https://doi.org/10.1016/j.ejmech.2009.02.004

Feng W, Satyanarayana M, Tsai YC, Liu AA, Liu LF, LaVoie EJ. Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide. European Journal of Medicinal Chemistry. 2009 Sept;44(9):3433-3438. doi: 10.1016/j.ejmech.2009.02.004

Feng, Wei ; Satyanarayana, Mavurapu ; Tsai, Yuan Chin et al. / Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide. In: European Journal of Medicinal Chemistry. 2009 ; Vol. 44, No. 9. pp. 3433-3438.

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title = "Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide",

abstract = "Several new TOP1-targeting agents were prepared using as an intermediate the N,N,N-trimethyl quaternary ammonium salt 2 of ARC-111. Direct displacement of the quaternary ammonium group with hydroxide, cyclopropylamine, imidazole, 1H-1,2,3-triazole, alkylethylenediamines, ethanolamine, and polyhydroxylated alkylamines provides a convenient means for furthering insight into the structure-activity relationships within this series of non-camptothecin TOP1-targeting agents. The relative TOP1-targeting activities and cytotoxicities were evaluated in RPMI8402 and P388 cells and their camptothecin-resistant variants. Their potential to serve as substrates for the efflux transporters MDR1 and BCRP, which are associated with multidrug resistance, was also assessed.",

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

year = "2009",

month = sep,

doi = "10.1016/j.ejmech.2009.02.004",

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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.

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AB - Several new TOP1-targeting agents were prepared using as an intermediate the N,N,N-trimethyl quaternary ammonium salt 2 of ARC-111. Direct displacement of the quaternary ammonium group with hydroxide, cyclopropylamine, imidazole, 1H-1,2,3-triazole, alkylethylenediamines, ethanolamine, and polyhydroxylated alkylamines provides a convenient means for furthering insight into the structure-activity relationships within this series of non-camptothecin TOP1-targeting agents. The relative TOP1-targeting activities and cytotoxicities were evaluated in RPMI8402 and P388 cells and their camptothecin-resistant variants. Their potential to serve as substrates for the efflux transporters MDR1 and BCRP, which are associated with multidrug resistance, was also assessed.

KW - 5H-Dibenzo[c,h][1,6]naphthyridin-6-ones

KW - ARC-111

KW - Antitumor

KW - Cytotoxic activity

KW - Multidrug resistance

KW - Quaternary ammonium salts

KW - TOP1-targeting agents

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Novel topoisomerase I-targeting antitumor agents synthesized from the N,N,N-trimethylammonium derivative of ARC-111, 5H-2,3-dimethoxy-8,9-methylenedioxy-5-[(2-N,N,N-trimethylammonium)ethyl]dibenzo[c,h][1,6]naphthyridin-6-one iodide

Abstract

UN SDGs

Keywords

ASJC Scopus subject areas

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