title: Pharmacological investigations and Petra/Osiris/Molinspiration (POM) analyses of newly synthesized potentially bioactive organotin(IV) carboxylates.
abstract: A series of organotin(IV) carboxylate complexes: [Me2SnL2] (1), [n-Bu2SnL2] (2), [n-Oct2SnL2] (3), [Me3SnL] (4), [n-Bu3SnL] (5) and [Ph3SnL] (6), where L=3-(4-fluorophenyl)acrylic acid, have been successfully synthesized and characterized by FT-IR, NMR ((1)H, (13)C) and single crystal analysis. The ligand coordinates to tin atom via carboxylate group. Compound 4 was also analyzed by single crystal XRD analysis. Crystallographic data for trimethyltin(IV) complex showed that the tin has approximate trigonal bipyramidal geometry with the CH3 groups in the trigonal plane. The carboxylate groups bridge the adjacent tin atoms, resulting in polymeric chains. FT-IR and NMR data also support the 5-coordination geometry for the triorganotin(IV) derivatives. In the case of the diorganotin(IV) derivatives a six-coordinate geometry at the tin atom is proposed from spectroscopic data. The Me-Sn-Me bond angle in complexes 1 and 4 was determined from the (2)J[(119)Sn-(1)H] value as 138.4° and 111° that falls in the range of 5-coordinated trigonal bipyramidal and 6-coordinated octahedral geometries, respectively. The synthesized compounds were screened for their biological activities including antibacterial, antifungal and cytotoxicity. The compounds 4-6 exhibit excellent antibacterial, antifungal and cytotoxic activities. The cytotoxicity data reveals that the HL and 1-3 are almost non-toxic and exhibited LD50 values in the range 73.45-675.1μg/mL while 4-6 are found to be cytotoxic to mildly cytotoxic with LD50 values in the range 6.43-13.49μg/mL. The compound interacts with DNA via intercalation of aromatic ring into the base pairs of DNA resulting in hypochromism and minor red shift.
authors.affiliation: Institute of Chemical Sciences, Bahauddin Zakariya University Multan, 60000, Pakistan. Electronic address: mtnazir@yahoo.com.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Tariq
authors.affiliation: Department of Chemistry, University of Science & Technology, Bannu, Pakistan. Electronic address: m.siraj09@yahoo.com.
authors.forename: Muhammad
authors.initials: M
authors.lastname: Sirajuddin
authors.affiliation: Department of Chemistry, Quaid-i-Azam University Islamabad, 45320, Pakistan. Electronic address: drsa54@hotmail.com.
authors.forename: Saqib
authors.initials: S
authors.lastname: Ali
authors.affiliation: Chemistry Division, Pakistan Institute of Nuclear Science and Technology, P.O. Nilore, Islamabad, Pakistan.
authors.forename: Nasir
authors.initials: N
authors.lastname: Khalid
authors.affiliation: Department of Physics, University of Sargodha, Pakistan.
authors.forename: Muhammad Nawaz
authors.initials: MN
authors.lastname: Tahir
authors.affiliation: Department of Chemistry, University of Science & Technology, Bannu, Pakistan.
authors.forename: Hizbullah
authors.initials: H
authors.lastname: Khan
authors.affiliation: Institute of Chemical Sciences, Bahauddin Zakariya University Multan, 60000, Pakistan.
authors.forename: Tariq Mahmood
authors.initials: TM
authors.lastname: Ansari
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D002264:Carboxylic Acids / Q000737:chemistry*; D045744:Cell Line, Tumor; D018360:Crystallography, X-Ray; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009947:Organotin Compounds / Q000737:chemistry / Q000494:pharmacology*; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D002264:Carboxylic Acids; D009947:Organotin Compounds
keywords: Antimicrobial activity; Cytotoxicity; DNA interaction; Organotin(IV) carboxylate; Single crystal