DNA threading agents: Effect of sidechain bulk on DNA binding and cytotoxicity of 9-anilinoacridine-4-carboxamides

Mark Searcey; P. Noel Martin; Nicola M. Howarth; Bernie Madden; Laurence P. G. Wakelin

doi:10.1016/0960-894X(96)00325-3

DNA threading agents: Effect of sidechain bulk on DNA binding and cytotoxicity of 9-anilinoacridine-4-carboxamides

Mark Searcey, P. Noel Martin, Nicola M. Howarth, Bernie Madden, Laurence P. G. Wakelin

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

8 Citations (Scopus)

Abstract

A series of 9-anilinoacridine-4-carboxamides with cycloalkyl sidechains has been synthesised to study the effect of sidechain bulk on the DNA binding properties and biological activity of these potential threading intercalators. With sidechains larger than cyclohexane the pKa of the acridine is exceptionally low, so that DNA binding is restricted to pHs below 5. The compounds are cytotoxic to human colon carcinoma cells in the μM range irrespective of their ability to bind to DNA.

Original language	English
Pages (from-to)	1831-1836
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	6
Issue number	15
DOIs	https://doi.org/10.1016/0960-894X(96)00325-3
Publication status	Published - 6 Aug 1996
Externally published	Yes

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abstract = "A series of 9-anilinoacridine-4-carboxamides with cycloalkyl sidechains has been synthesised to study the effect of sidechain bulk on the DNA binding properties and biological activity of these potential threading intercalators. With sidechains larger than cyclohexane the pKa of the acridine is exceptionally low, so that DNA binding is restricted to pHs below 5. The compounds are cytotoxic to human colon carcinoma cells in the μM range irrespective of their ability to bind to DNA.",

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AU - Searcey, Mark

AU - Martin, P. Noel

AU - Howarth, Nicola M.

AU - Madden, Bernie

AU - Wakelin, Laurence P. G.

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AB - A series of 9-anilinoacridine-4-carboxamides with cycloalkyl sidechains has been synthesised to study the effect of sidechain bulk on the DNA binding properties and biological activity of these potential threading intercalators. With sidechains larger than cyclohexane the pKa of the acridine is exceptionally low, so that DNA binding is restricted to pHs below 5. The compounds are cytotoxic to human colon carcinoma cells in the μM range irrespective of their ability to bind to DNA.

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DO - 10.1016/0960-894X(96)00325-3

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SN - 0960-894X

IS - 15

ER -

DNA threading agents: Effect of sidechain bulk on DNA binding and cytotoxicity of 9-anilinoacridine-4-carboxamides

Abstract

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