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

• Published in: European journal of medicinal chemistry Vol. 40; no. 3; pp. 289 - 298
• Main Authors: Nath, Mala, Pokharia, Sandeep, Eng, George, Song, Xueqing, Kumar, Ashok
• Format: Journal Article
• Language: English
• Published: ISSY-LES-MOULINEAUX Elsevier Masson SAS 01.03.2005; Elsevier
• Subjects: Acute toxicity; Animals; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - pharmacology; Anti-Bacterial Agents - toxicity; Anti-inflammatory activity; Anti-Inflammatory Agents - chemical synthesis; Anti-Inflammatory Agents - pharmacology; Anti-Inflammatory Agents - toxicity; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antimicrobial activity; Bacteria - drug effects; Biological and medical sciences; Bones, joints and connective tissue. Antiinflammatory agents; Cardiovascular activity; Cardiovascular System - drug effects; Carrageenan - toxicity; Cats; Chemistry, Medicinal; Dipeptide; Dogs; Edema - drug therapy; Edema - immunology; Female; General aspects; Lethal Dose 50; Life Sciences & Biomedicine; Male; Medical sciences; Microbial Sensitivity Tests; Organotin Compounds - chemical synthesis; Organotin Compounds - pharmacology; Organotin Compounds - toxicity; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Rats; Science & Technology; Triorganotin; Dipeptide; Anti-inflammatory activity; Cardiovascular activity; Antimicrobial activity; Triorganotin; Acute toxicity; INFECTION ANTIFUNGAL ACTIVITIES; triorganotin; VIVO; dipeptide; ORGANOMETALLIC COMPLEXES; TRYPANOCIDAL ACTIVITY; antimicrobial activity; SOLID-STATE; anti-inflammatory activity; IN-VITRO; cardiovascular activity; acute toxicity; AMINO-ACIDS; BIOLOGICAL MOLECULES; ORGANOTIN-DRUG INTERACTIONS; VITRO ANTITUMOR-ACTIVITY; Peptides; Toxicity; Acute; Antiinflammatory agent; In vitro; Biological activity; Antimicrobial agent; Dipeptides; Circulatory system; Tin Organic compounds; Chemical synthesis; Organic stannane
• ISSN: 0223-5234; 1768-3254
• DOI: 10.1016/j.ejmech.2004.11.001

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.