Butler, Jennifer S., Woods, Julie A., Farrer, Nicola J., Newton, Mark E. and Sadler, P. J.. (2012) Tryptophan switch for a photoactivated platinum anticancer complex. Journal of the American Chemical Society, Vol.134 (No.40). pp. 16508-16511. ISSN 0002-7863

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Abstract

The octahedral PtIV complex trans,trans,trans-[Pt(N3)2(OH)2(py)2] (1) is potently cytotoxic to cancer cells when irradiated with visible (blue) light. We show that the acute photocytotoxicity can be switched off by low doses (500 μM) of the amino acid l-tryptophan. EPR and NMR spectroscopic experiments using spin traps show that l-Trp quenches the formation of azidyl radicals, probably by acting as an electron donor. l-Trp is well-known as a mediator of electron transfer between distant electron acceptor/donor centers in proteins, and such properties may make the free amino acid clinically useful for controlling the activity of photochemotherapeutic azido PtIV drugs. Since previous work has demonstrated the ability of photoactivated 1 to platinate DNA, this suggests that the high potency of such photoactive platinum complexes is related to their dual attack on cancer cells by radicals and PtII photoproducts.

Item Type:	Journal Article
Subjects:	Q Science > QP Physiology R Medicine > RC Internal medicine > RC0254 Neoplasms. Tumors. Oncology (including Cancer)
Divisions:	Faculty of Science > Chemistry Faculty of Science > Physics
Library of Congress Subject Headings (LCSH):	Tryptophan, Antineoplastic agents, Photochemistry, Platinum -- Therapeutic use
Journal or Publication Title:	Journal of the American Chemical Society
Publisher:	American Chemical Society
ISSN:	0002-7863
Date:	2012
Volume:	Vol.134
Number:	No.40
Page Range:	pp. 16508-16511
Identification Number:	10.1021/ja3074159
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Open Access
Funder:	European Research Council (ERC), Engineering and Physical Sciences Research Council (EPSRC)
Grant number:	247450 (ERC), EP/G006792/1 (EPSRC)
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URI:	http://wrap.warwick.ac.uk/id/eprint/51991

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