Tri- and diorganotin(IV) complexes of biologically important orotic acid: synthesis, spectroscopic studies, in vitro anti-cancer, DNA fragmentation, enzyme assays and in vivo anti-inflammatory activities.

Abstract

Tri-and diorganotin(IV) orotates of general formula, R(n)Sn(H(2)Or)(m) [n = 3/2, m = 1/2, R = Me, n-Bu, n-Oct and Ph; H(2)Or(-) = monoanion of orotic acid (H(3)Or)] (n-Bu(2)Sn(HOr) as an exception) have been synthesized. On the basis of various spectroscopic studies it is revealed that R(3)Sn(H(2)Or) and R(2)Sn(H(2)Or)(2) exhibit distorted trigonal-bipyramidal and distorted octahedral geometry, respectively, and n-Bu(2)Sn(HOr) shows both five and six coordination geometry around tin. In vitro anti-cancer screening against MCF-7 (mammary), HEK-293 (kidney), PC-3 (prostate), HCT-15 (colon) and HepG-2 (liver) cancer cell lines suggest that the n-Oct(2)Sn(H(2)Or)(2) is the most active complex among all of the studied complexes. DNA fragmentation and antioxidant enzyme assays suggest that cytotoxic effect of the complexes is selectively mediated through the induction of apoptosis. They also exhibit low toxicity and good anti-inflammatory activity (in vivo).

• Authors: Mala Nath, Monika Vats, Partha Roy
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 59 Pg. 310-21 (Jan 2013) ISSN: 1768-3254 [Electronic] France
• PMID: 23266665 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2012 Elsevier Masson SAS. All rights reserved.

Chemical References

• Anti-Inflammatory Agents
• Antineoplastic Agents
• Organotin Compounds
• Orotic Acid
• Tin

Topics

• Animals
• Anti-Inflammatory Agents (chemical synthesis, chemistry, pharmacology)
• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Apoptosis (drug effects)
• Cell Line, Tumor
• DNA Fragmentation (drug effects)
• Enzyme Activation (drug effects)
• Humans
• Infusions, Parenteral
• Mice
• Molecular Structure
• Organotin Compounds (chemical synthesis, chemistry, pharmacology)
• Orotic Acid (chemistry)
• Tin (chemistry)