New triorganotin(IV) derivatives of dipeptides as anti-inflammatory-antimicrobial agents.
New triorganotin(IV) derivatives of dipeptides with general formulae R(3)Sn(HL), where R = Me and/or n-Bu and/or Ph and HL is the monoanion of glycylglycine (H(2)L-1), glycylvaline (H(2)L-2), glycylleucine (H(2)L-3), glycyltryptophane (H(2)L-4) and glycyltyrosine (H(2)L-5) have been synthesized and characterized on the basis of infrared, multinuclear NMR and (119)Sn Mossbauer 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(3)Sn(Gly-Val) displays a potent cardiovascular activity. Moreover, most of the compounds displayed appreciable antibacterial activities when compared with ampicillin and norfloxacin. Compounds Ph(3)Sn(Gly-Gly) and Ph(3)Sn(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.
Nath
Mala
M
Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, India. malanfcy@iitr.ernet.in
Pokharia
Sandeep
S
Eng
George
G
Song
Xueqing
X
Kumar
Ashok
A
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D001419:Bacteria / Q000187:drug effects; D002319:Cardiovascular System / Q000187:drug effects; D002351:Carrageenan / Q000633:toxicity; D002415:Cats; D004285:Dogs; D004487:Edema / Q000188:drug therapy / Q000276:immunology; D005260:Female; D007928:Lethal Dose 50; D008297:Male; D008826:Microbial Sensitivity Tests; D009947:Organotin Compounds / Q000138:chemical synthesis / Q000494:pharmacology* / Q000633:toxicity; D051381:Rats
D000900:Anti-Bacterial Agents; D000893:Anti-Inflammatory Agents; D009947:Organotin Compounds; D002351:Carrageenan