The abnormal cytotoxicities of 2,5-diaziridinyl-1,4-benzoquinone-3-phenyl esters.

Di Francesco; M. Angela; Robert H. J. Hargreaves; Timothy Wallace; Stephen P. Mayalarp; Ali Hazrati; John A. Hartley; John Butler

The abnormal cytotoxicities of 2,5-diaziridinyl-1,4-benzoquinone-3-phenyl esters.

Di Francesco, M. Angela, Robert H. J. Hargreaves, Timothy Wallace, Stephen P. Mayalarp, Ali Hazrati, John A. Hartley, John Butler

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

Abstract

Several derivs. of 2,5-diaziridinyl-3-phenyl-1,4-benzoquinone have been synthesized and their cytotoxicities in six different human cancer cell lines (H460, H596, HT29, BE, K562 and A2780) have been detd. It was obsd. that certain phenol-ester derivs. were significantly more cytotoxic in all of the cell lines investigated. These esters were shown to be cleaved by esterases to form a stable meta-phenol and an unstable para-phenol. The meta-phenol was also highly cytotoxic. Several of these compds. were studied in detail using DNA crosslinking, clonogenic, apoptosis and flow cytometry assays. It is proposed that although the phenol-esters and the phenols can efficiently cross-link DNA, this mechanism alone is not sufficient to explain the toxicities of these compds.

Original language	English
Pages (from-to)	347-359
Number of pages	12
Journal	Anti-Cancer Drug Design
Volume	15
Issue number	5
Publication status	Published - 2001

Keywords

Structure-activity relationship (DNA-crosslinking; diaziridinyl benzoquinone Ph esters: prepn. and abnormal cytotoxicity); DNA Role: BPR (Biological process), BSU (Biological study, unclassified), BIOL (Biological study), PROC (Process) (crosslinked; diaziridinyl benzoquinone Ph esters: prepn. and abnormal cytotoxicity); Antitumor agents; Apoptosis; Cytotoxic agents (diaziridinyl benzoquinone Ph esters: prepn. and abnormal cytotoxicity)

UN SDGs

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

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title = "The abnormal cytotoxicities of 2,5-diaziridinyl-1,4-benzoquinone-3-phenyl esters.",

abstract = "Several derivs. of 2,5-diaziridinyl-3-phenyl-1,4-benzoquinone have been synthesized and their cytotoxicities in six different human cancer cell lines (H460, H596, HT29, BE, K562 and A2780) have been detd. It was obsd. that certain phenol-ester derivs. were significantly more cytotoxic in all of the cell lines investigated. These esters were shown to be cleaved by esterases to form a stable meta-phenol and an unstable para-phenol. The meta-phenol was also highly cytotoxic. Several of these compds. were studied in detail using DNA crosslinking, clonogenic, apoptosis and flow cytometry assays. It is proposed that although the phenol-esters and the phenols can efficiently cross-link DNA, this mechanism alone is not sufficient to explain the toxicities of these compds.",

keywords = "Structure-activity relationship (DNA-crosslinking; diaziridinyl benzoquinone Ph esters: prepn. and abnormal cytotoxicity); DNA Role: BPR (Biological process), BSU (Biological study, unclassified), BIOL (Biological study), PROC (Process) (crosslinked; diaziridinyl benzoquinone Ph esters: prepn. and abnormal cytotoxicity); Antitumor agents; Apoptosis; Cytotoxic agents (diaziridinyl benzoquinone Ph esters: prepn. and abnormal cytotoxicity)",

author = "Di Francesco and M. Angela and Hargreaves, {Robert H. J.} and Timothy Wallace and Mayalarp, {Stephen P.} and Ali Hazrati and Hartley, {John A.} and John Butler",

year = "2001",

language = "English",

volume = "15",

pages = "347--359",

journal = "Anti-Cancer Drug Design",

publisher = "Cognizant Communication Corporation",

number = "5",

}

TY - JOUR

T1 - The abnormal cytotoxicities of 2,5-diaziridinyl-1,4-benzoquinone-3-phenyl esters.

AU - Francesco, Di

AU - Angela, M.

AU - Hargreaves, Robert H. J.

AU - Wallace, Timothy

AU - Mayalarp, Stephen P.

AU - Hazrati, Ali

AU - Hartley, John A.

AU - Butler, John

PY - 2001

Y1 - 2001

N2 - Several derivs. of 2,5-diaziridinyl-3-phenyl-1,4-benzoquinone have been synthesized and their cytotoxicities in six different human cancer cell lines (H460, H596, HT29, BE, K562 and A2780) have been detd. It was obsd. that certain phenol-ester derivs. were significantly more cytotoxic in all of the cell lines investigated. These esters were shown to be cleaved by esterases to form a stable meta-phenol and an unstable para-phenol. The meta-phenol was also highly cytotoxic. Several of these compds. were studied in detail using DNA crosslinking, clonogenic, apoptosis and flow cytometry assays. It is proposed that although the phenol-esters and the phenols can efficiently cross-link DNA, this mechanism alone is not sufficient to explain the toxicities of these compds.

AB - Several derivs. of 2,5-diaziridinyl-3-phenyl-1,4-benzoquinone have been synthesized and their cytotoxicities in six different human cancer cell lines (H460, H596, HT29, BE, K562 and A2780) have been detd. It was obsd. that certain phenol-ester derivs. were significantly more cytotoxic in all of the cell lines investigated. These esters were shown to be cleaved by esterases to form a stable meta-phenol and an unstable para-phenol. The meta-phenol was also highly cytotoxic. Several of these compds. were studied in detail using DNA crosslinking, clonogenic, apoptosis and flow cytometry assays. It is proposed that although the phenol-esters and the phenols can efficiently cross-link DNA, this mechanism alone is not sufficient to explain the toxicities of these compds.

KW - Structure-activity relationship (DNA-crosslinking; diaziridinyl benzoquinone Ph esters: prepn. and abnormal cytotoxicity); DNA Role: BPR (Biological process), BSU (Biological study, unclassified), BIOL (Biological study), PROC (Process) (crosslinked; diaz

M3 - Article

VL - 15

SP - 347

EP - 359

JO - Anti-Cancer Drug Design

JF - Anti-Cancer Drug Design

IS - 5

ER -

The abnormal cytotoxicities of 2,5-diaziridinyl-1,4-benzoquinone-3-phenyl esters.

Abstract

Keywords

UN SDGs

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