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Mar. Drugs 2013, 11(2), 274-299; doi:10.3390/md11020274

Synthesis, DNA Binding and Antitumor Evaluation of Styelsamine and Cystodytin Analogues

School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand
Author to whom correspondence should be addressed.
Received: 4 December 2012 / Revised: 16 January 2013 / Accepted: 21 January 2013 / Published: 28 January 2013
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A series of N-14 sidechain substituted analogues of styelsamine (pyrido[4,3,2-mn]acridine) and cystodytin (pyrido[4,3,2-mn]acridin-4-one) alkaloids have been prepared and evaluated for their DNA binding affinity and antiproliferative activity towards a panel of human tumor cell lines. Overall it was found that styelsamine analogues were stronger DNA binders, with the natural products styelsamines B and D having particularly high affinity (Kapp 5.33 × 106 and 3.64 × 106 M−1, respectively). In comparison, the cystodytin iminoquinone alkaloids showed lower affinity for DNA, but were typically just as active as styelsamine analogues at inhibiting proliferation of tumor cells in vitro. Sub-panel selectivity towards non-small cell lung, melanoma and renal cancer cell lines were observed for a number of the analogues. Correlation was observed between whole cell activity and clogP, with the most potent antiproliferative activity being observed for 3-phenylpropanamide analogues 37 and 41 (NCI panel average GI50 0.4 μM and 0.32 μM, respectively) with clogP ~4.0–4.5. View Full-Text
Keywords: marine natural products; styelsamine; cystodytin; pyridoacridine; DNA binding marine natural products; styelsamine; cystodytin; pyridoacridine; DNA binding

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Fong, H.K.H.; Copp, B.R. Synthesis, DNA Binding and Antitumor Evaluation of Styelsamine and Cystodytin Analogues. Mar. Drugs 2013, 11, 274-299.

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