Structure elucidation and inhibitory effects of self-assembled organotin(IV) esters of p-tolyl acetic acid on bacterial, fungal, brine shrimp, and potato tumor cells

Drug Chem Toxicol. 2010 Apr;33(2):183-92. doi: 10.3109/01480540903203992.

Abstract

Biologically active new organotin(IV) acetates (1-6) of p-tolyl acetic acid have been synthesized and characterized by multinuclear nuclear magnetic resonance ((1)H, (13)C) and mass spectrometry. The X-ray crystallographic data of compounds (3 and 4) were also collected. These studies show that in diorganotin(IV) compounds (compounds 1, 2, 3, and 6), tin exists in skew trapezoidal geometry with four strong and two weaker bonds, whereas triorganotin(IV) carboxylates (compounds 4 and 5) have four and five coordinated geometries in solution and solid form, respectively. These compounds were screened for a range of biological activities. Antibacterial activities were determined against six pathogenic bacterial strains, three Gram-positive and three Gram-negative; the activities were measured in terms of inhibition zones (mm). Antifungal activities were determined against six pathogenic fungal strains, cytotoxicity by the brine shrimp lethality assay, and antitumor activities by the crown gall tumor inhibition (potato disc) assay.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Acetates / pharmacology
  • Acetic Acid / chemistry
  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology
  • Anti-Infective Agents / chemistry*
  • Anti-Infective Agents / pharmacology
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Artemia / drug effects
  • Crystallography, X-Ray
  • Esters
  • Fungi / drug effects
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Longevity / drug effects
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Organotin Compounds / chemistry*
  • Organotin Compounds / pharmacology
  • Plant Tumors
  • Solanum tuberosum
  • Spectroscopy, Fourier Transform Infrared
  • Toluene / chemistry

Substances

  • Acetates
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antifungal Agents
  • Antineoplastic Agents
  • Esters
  • Organotin Compounds
  • Toluene
  • Acetic Acid