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Data from Miami University provide new insights into cancer
2009 JUL 20 - (NewsRx.com) -- "4-Acetoxy-4-(benzothiazol-2-yl)-2,5-cyclohexadien-1-one, 1, a quinol derivative that exhibits significant anti-tumor activity against human breast, colon, and renal cancer cell lines, undergoes hydrolysis in aqueous solution to generate an oxenium ion intermediate, 3, that is selectively trapped by N-3(-) in an aqueous environment. The 4-(benzothiazol-2-yl) substituent slows the rate of ionization of I compared to analogues with 4-phenyl or 4-(p-tolyl) substituents, 4a or 4b," scientists in the United States report. "However, once generated, 3 is somewhat more selective than the 4-phenyl-substituted cation 5a. Calculations performed at the B3LYP/6-31G(d) level agree that the 4-(benzothiazol-2-yl) substituent does significantly stabilize 3. The structure of the major isolated azide adduct, 4-(6-azidobenzothiazol-2-yl)phenol, 9, confirms that the positive charge is highly delocalized in 3. The results of hydrolysis of 1 show that the 4-(benzothiazol-2-yi) substituent has a significant inductive electron-withdrawing effect as well as a significant resonance effect that is electron-donating. Photolysis of I in aqueous solution generates the quinol 2 as one of several photolysis products. The presence of the quinol suggests that photolysis also leads, in part, to generation of 3, but photoionization of 1 is significantly less efficient than is the case for the esters 4a and 4b. This study proves that 3 is generated by ionization of I in an aqueous environment. A significant number of other 2-benzothiazole derivatives that are not quinols, including ring-substituted derivatives of 2-(4-aminophenyl)benzothiazole 15, are under development as anti-tumor agents as well," wrote Y.T. Wang and colleagues, Miami University. The researchers concluded: "The possible generation of the reactive intermediate 17 by hydrolysis of the putative metabolite 16 is under investigation.." Wang and colleagues published their study in the Journal of Organic Chemistry (Hydrolysis and Photolysis of 4-Acetoxy-4-(Benzothiazol-2-yl)-2,5-cyclohexadien-1-one, a Model Anti-Tumor Quinol Ester. Journal of Organic Chemistry, 2009;74(12):4463-4471). For additional information, contact M. Novak, Miami University, Dept. of Chemical & Biochemistry, Oxford, OH 45056, USA. The publisher's contact information for the Journal of Organic Chemistry is: American Chemical Society, 1155 16th St., NW, Washington, DC 20036, USA. Keywords: United States, Oxford, Anticancer Therapy, Kidney, Nephrology, Oncology, Renal Cancer, Renal Carcinoma, Therapy, Treatment, Miami University. This article was prepared by Biotech Business Week editors from staff and other reports. Copyright 2009, Biotech Business Week via NewsRx.com.
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