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Quinol derivatives as potential trypanocidal agents

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Quinol derivatives as potential trypanocidal agents. / Capes, Amy; Patterson, Stephen; Wyllie, Susan; Hallyburton, Irene; Collie, Iain T.; McCarroll, Andrew J.; Stevens, Malcolm F. G.; Frearson, Julie A.; Wyatt, Paul G.; Fairlamb, Alan H.; Gilbert, Ian H.

In: Bioorganic & Medicinal Chemistry, Vol. 20, No. 4, 15.02.2012, p. 1607-1615.

Research output: Contribution to journalArticle

Harvard

Capes, A, Patterson, S, Wyllie, S, Hallyburton, I, Collie, IT, McCarroll, AJ, Stevens, MFG, Frearson, JA, Wyatt, PG, Fairlamb, AH & Gilbert, IH 2012, 'Quinol derivatives as potential trypanocidal agents' Bioorganic & Medicinal Chemistry, vol 20, no. 4, pp. 1607-1615.

APA

Capes, A., Patterson, S., Wyllie, S., Hallyburton, I., Collie, I. T., McCarroll, A. J., Stevens, M. F. G., Frearson, J. A., Wyatt, P. G., Fairlamb, A. H., & Gilbert, I. H. (2012). Quinol derivatives as potential trypanocidal agents. Bioorganic & Medicinal Chemistry, 20(4), 1607-1615doi: 10.1016/j.bmc.2011.12.018

Vancouver

Capes A, Patterson S, Wyllie S, Hallyburton I, Collie IT, McCarroll AJ et al. Quinol derivatives as potential trypanocidal agents. Bioorganic & Medicinal Chemistry. 2012 Feb 15;20(4):1607-1615.

Author

Capes, Amy; Patterson, Stephen; Wyllie, Susan; Hallyburton, Irene; Collie, Iain T.; McCarroll, Andrew J.; Stevens, Malcolm F. G.; Frearson, Julie A.; Wyatt, Paul G.; Fairlamb, Alan H.; Gilbert, Ian H. / Quinol derivatives as potential trypanocidal agents.

In: Bioorganic & Medicinal Chemistry, Vol. 20, No. 4, 15.02.2012, p. 1607-1615.

Research output: Contribution to journalArticle

Bibtex - Download

@article{d998177883244538b4af42f1239205fb,
title = "Quinol derivatives as potential trypanocidal agents",
author = "Amy Capes and Stephen Patterson and Susan Wyllie and Irene Hallyburton and Collie, {Iain T.} and McCarroll, {Andrew J.} and Stevens, {Malcolm F. G.} and Frearson, {Julie A.} and Wyatt, {Paul G.} and Fairlamb, {Alan H.} and Gilbert, {Ian H.}",
year = "2012",
volume = "20",
number = "4",
pages = "1607--1615",
journal = "Bioorganic & Medicinal Chemistry",
issn = "0968-0896",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Quinol derivatives as potential trypanocidal agents

A1 - Capes,Amy

A1 - Patterson,Stephen

A1 - Wyllie,Susan

A1 - Hallyburton,Irene

A1 - Collie,Iain T.

A1 - McCarroll,Andrew J.

A1 - Stevens,Malcolm F. G.

A1 - Frearson,Julie A.

A1 - Wyatt,Paul G.

A1 - Fairlamb,Alan H.

A1 - Gilbert,Ian H.

AU - Capes,Amy

AU - Patterson,Stephen

AU - Wyllie,Susan

AU - Hallyburton,Irene

AU - Collie,Iain T.

AU - McCarroll,Andrew J.

AU - Stevens,Malcolm F. G.

AU - Frearson,Julie A.

AU - Wyatt,Paul G.

AU - Fairlamb,Alan H.

AU - Gilbert,Ian H.

PY - 2012/2/15

Y1 - 2012/2/15

N2 - <p>Quinols have been developed as a class of potential anti-cancer compounds. They are thought to act as double Michael acceptors, forming two covalent bonds to their target protein(s). Quinols have also been shown to have activity against the parasite Trypanosoma brucei, the causative organism of human African trypanosomiasis, but they demonstrated little selectivity over mammalian MRC5 cells in a counter-screen. In this paper, we report screening of further examples of quinols against T. brucei. We were able to derive an SAR, but the compounds demonstrated little selectivity over MRC5 cells. In an approach to increase selectivity, we attached melamine and benzamidine motifs to the quinols, because these moieties are known to be selectively concentrated in the parasite by transporter proteins. In general these transporter motif-containing analogues showed increased selectivity; however they also showed reduced levels of potency against T. brucei. (C) 2011 Elsevier Ltd. All rights reserved.</p>

AB - <p>Quinols have been developed as a class of potential anti-cancer compounds. They are thought to act as double Michael acceptors, forming two covalent bonds to their target protein(s). Quinols have also been shown to have activity against the parasite Trypanosoma brucei, the causative organism of human African trypanosomiasis, but they demonstrated little selectivity over mammalian MRC5 cells in a counter-screen. In this paper, we report screening of further examples of quinols against T. brucei. We were able to derive an SAR, but the compounds demonstrated little selectivity over MRC5 cells. In an approach to increase selectivity, we attached melamine and benzamidine motifs to the quinols, because these moieties are known to be selectively concentrated in the parasite by transporter proteins. In general these transporter motif-containing analogues showed increased selectivity; however they also showed reduced levels of potency against T. brucei. (C) 2011 Elsevier Ltd. All rights reserved.</p>

KW - Inhibitors

KW - Medicinal chemistry

KW - Trypanosoma brucei

KW - P2 transporter

KW - Quinols

KW - HUMAN AFRICAN TRYPANOSOMIASIS

KW - CANCER CELL-LINES

KW - THERAPEUTIC AGENTS

KW - ANTITUMOR QUINOLS

KW - BRUCEI

KW - THIOREDOXIN

KW - BENZOTHIAZOLE

KW - APOPTOSIS

KW - TARGET

KW - CYCLOADDITIONS

UR - http://ukpmc.ac.uk/articles/PMC3281193

U2 - 10.1016/j.bmc.2011.12.018

DO - 10.1016/j.bmc.2011.12.018

M1 - Article

JO - Bioorganic & Medicinal Chemistry

JF - Bioorganic & Medicinal Chemistry

SN - 0968-0896

IS - 4

VL - 20

SP - 1607

EP - 1615

ER -

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