Design and microwave-assisted synthesis of tri- and dialkyltin(IV) hippurates, characterization, in vitro anti-cancer and in vivo anti-inflammatory activities

Abstract

Microwave-assisted reactions of triorganotin(IV)/diorganotin(IV) chlorides/oxides with hippuric acid (HHA), in 1:1 or 1:2 molar ratio resulted R<inf>3</inf>Sn(HA) (R = Ph (1b), n-Bu (2b), and Me (3b))/R<inf>2</inf>Sn(HA)<inf>2</inf> (R = n-Oct (4b), n-Bu (5b), and Me (6b)); (HA = anion of hippuric acid). However, all complexes (1a-6a) were also synthesized under conventional thermal conditions for comparison. IR, ESI-MS, and NMR (1H, 13C and 119Sn) spectroscopic studies revealed that R<inf>3</inf>Sn(HA) (1-3) and R<inf>2</inf>Sn(HA)<inf>2</inf> (4, 5) exhibit trigonal-bipyramidal and tetrahedral geometry, respectively (except dimethyltin(IV) hippurate (6) exhibiting octahedral geometry). All complexes (1b-6b) have been screened in vitro against five cancer cell lines of human origin, viz. MCF-7 (mammary cancer), HEK-293 (kidney cancer), PC-3 (prostate cancer), HCT-15 (colon cancer), and HepG-2 (liver cancer). Compounds 1b and 3b exhibited good anti-cancer activity against MCF-7, HEK-293, and PC-3 cell lines, while 6b showed better activity against PC-3 and HepG-2 cell lines. Toxicity and in vivo anti-inflammatory activity of all (1b-6b) complexes in Swiss albino mice have also been carried out. Compound 1b exhibited the highest anti-inflammatory activity among the studied complexes. © 2014 Springer Science+Business Media New York.