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Studies on phenothiazines: New microtubule-interacting compounds with phenothiazine A-ring as potent antineoplastic agents.

Abstract：

:New phenothiazine derivatives 6-20 have been designed, synthesized and evaluated in vitro for their ability to inhibit tubulin polymerization and antiproliferative activity against 60 cancer cell lines, including several multi-drug resistant (MDR) tumor cell lines. The phenothiazine unit may successfully replace the classical 3,4,5-trimethoxyphenyle A ring of parent combretastatin A-4 or phenstatin, confirming previous studies. The most promising structural modulations have been realized on the B ring, the 2'-fluoro-4'-methoxy substitution in compound 6 and the 2'-trifluoromethyl-4'-methoxy substitution in compound 7 providing the best antitubulin and antitumor activity in the current study. Compounds 6-8 and 16 exhibited more important cell growth inhibition than parent phenstatin 2 on human colon Duke's type D, colorectal adenocarcinoma COLO 205 and on human kidney adenocarcinoma A498 cell lines. 10-Methylphenothiazine derivatives 19 and 20 did not show biological activity but exerted bright fluorescence and solvatochromism effects. These molecules deserve further chemical efforts in order to provide valuable tools for biophysical studies.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Ghinet A,Moise IM,Rigo B,Homerin G,Farce A,Dubois J,Bîcu E

doi

10.1016/j.bmc.2016.04.001

subject

Has Abstract

pub_date

2016-05-15 00:00:00

pages

2307-17

issue

10

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(16)30223-1

journal_volume

24

pub_type

杂志文章

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