New triorganotin(IV) derivatives of dipeptides as anti-inflammatory–antimicrobial agents

Abstract

New triorganotin(IV) derivatives of dipeptides with general formulae R 3Sn(HL), where R = Me and/or n-Bu and/or Ph and HL is the monoanion of glycylglycine (H 2L-1), glycylvaline (H 2L-2), glycylleucine (H 2L-3), glycyltryptophane (H 2L-4) and glycyltyrosine (H 2L-5) have been synthesized and characterized on the basis of infrared, multinuclear NMR and 119Sn Mössbauer spectroscopic studies. All the newly synthesized compounds were examined for their in vivo anti-inflammatory activity (using the carrageenan-induced paw edema bioassay in rats), acute toxicity (LD 50) and cardiovascular activity. These compounds were also screened for their in vitro antimicrobial activity against Staphylococcus aureus Mau (29/58) and (78/71), Bacillus subtilis (18/64), Escherichia coli (326/71), Candida albicans (Pn-10), Microsporum gypseum and Euglena gracillis. The results revealed that triphenyltin(IV) derivatives exhibited anti-inflammatory activity comparable to that of phenylbutazone with high safety margin (LD 50 > 500 mg kg –1). Further Ph 3Sn(Gly-Val) displays a potent cardiovascular activity. Moreover, most of the compounds displayed appreciable antibacterial activities when compared with ampicillin and norfloxacin. Compounds Ph 3Sn(Gly-Gly) and Ph 3Sn(Gly-Val) are the most distinctive derivatives identified in the present study because of their promising in vivo anti-inflammatory activity and in vitro antibacterial activity against gram-positive and -negative bacteria.