Synthesis, spectroscopic, X-ray crystal structure, biological and DNA interaction studies of organotin(IV) complexes of 2-(4-ethoxybenzylidene) butanoic acid

Muhammad Tariq; Niaz Muhammad; Saqib Ali; Jafir Hussain Shirazi; Muhammad Nawaz Tahir; Nasir Khalid

doi:10.1016/j.saa.2013.11.065

Synthesis, spectroscopic, X-ray crystal structure, biological and DNA interaction studies of organotin(IV) complexes of 2-(4-ethoxybenzylidene) butanoic acid

Spectrochim Acta A Mol Biomol Spectrosc. 2014 Mar 25:122:356-64. doi: 10.1016/j.saa.2013.11.065. Epub 2013 Nov 21.

Authors

Muhammad Tariq¹, Niaz Muhammad², Saqib Ali³, Jafir Hussain Shirazi⁴, Muhammad Nawaz Tahir⁵, Nasir Khalid⁶

Affiliations

¹ Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. Electronic address: mtnazir@yahoo.com.
² Department of Chemistry, Abdul Wali Khan University, Mardan, Pakistan.
³ Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. Electronic address: drsa54@yahoo.com.
⁴ Department of Microbiology, Quaid-i-Azam University, Islamabad 45320, Pakistan.
⁵ Department of Physics, University of Sargodha, Sargodha, Pakistan.
⁶ Chemistry Division, Pakistan Institute of Nuclear Science and Technology, Nilore, Islamabad, Pakistan.

PMID: 24322756
DOI: 10.1016/j.saa.2013.11.065

Abstract

Six organotin(IV) carboxylates of the type R2SnL2 [R=CH3 (1), n-C4H9 (2), n-C8H17 (3)] and R3SnL [R=CH3 (4), n-C4H9 (5), C6H5 (6), where L=2-(4-ethoxybenzylidene) butanoic acid, have been synthesized and characterized by elemental analysis, FT-IR and NMR ((1)H, (13)C). The complex (1) was also analyzed by single crystal X-ray analysis. The complexes were screened for antimicrobial, cytotoxic and anti-tumor activities. The results showed significant activity in each area of the activity with few exceptions. DNA interactions studies of ligand HL and representative complex 2 were investigated by UV-Visible absorption spectroscopy and viscosity measurements. The results showed that both ligand HL and complex 2 interact with SS-DNA via intercalation as well as minor groove binding.

Keywords: Antimicrobial activity; Antitumor activity; Cytotoxic activity; Distannoxane.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Anti-Infective Agents / chemistry
Anti-Infective Agents / pharmacology
Antifungal Agents / pharmacology
Antineoplastic Agents / pharmacology
Artemia / drug effects
Bacteria / drug effects
Benzylidene Compounds / chemical synthesis*
Benzylidene Compounds / chemistry
Benzylidene Compounds / metabolism*
Benzylidene Compounds / toxicity
Butyrates / chemical synthesis*
Butyrates / chemistry
Butyrates / metabolism*
Butyrates / toxicity
Butyric Acid / chemical synthesis*
Butyric Acid / chemistry
Butyric Acid / metabolism*
Butyric Acid / toxicity
Cell Death / drug effects
Crystallography, X-Ray
DNA / metabolism*
Fishes
Fungi / drug effects
Ligands
Magnetic Resonance Spectroscopy
Male
Microbial Sensitivity Tests
Organotin Compounds / chemical synthesis*
Organotin Compounds / chemistry
Organotin Compounds / metabolism*
Organotin Compounds / toxicity
Plant Tumors
Spectroscopy, Fourier Transform Infrared
Viscosity / drug effects

Substances

2-(4-ethoxybenzylidene)butanoic acid
Anti-Infective Agents
Antifungal Agents
Antineoplastic Agents
Benzylidene Compounds
Butyrates
Ligands
Organotin Compounds
Butyric Acid
DNA