Synthesis, characterization, biological activities, crystal structure and DNA binding of organotin(IV) 5-chlorosalicylates

Abstract

New organotin(IV) carboxylates, R 2 SnL 2 (R = n-Bu: 1), R 2 Sn(Cl)L (R = n-Bu: 2) and R 3 SnL (R = Me: 3; n-Bu: 4; Ph: 5), have been synthesized by stirring 5-chloro-2-hydroxybenzoic acid HL with KOH and R 2 SnCl 2 (R = n-Bu)/R 3 SnCl (R = Me, n-Bu, Ph) in methanol at room temperature. The complexes along with ligand have been characterized by FT-IR, ( 1 H, 13 C) NMR, EI-MS and single crystal XRD crystallography. FT-IR data indicated bidentate coordination of carboxylate. NMR data suggested six-or five-coordinate geometry of organotin(IV) carboxylates. Single crystal XRD of 1 demonstrated skew-trapezoidal geometry around the tin center, with the basal plane occupied by four oxygens and the two butyl groups lying in distorted axial position. Complexes 1, 2 and 5 exhibited interaction with SS-DNA (salmon sperm) and suggests intercalating mode of binding. The complexes displayed significant antimicrobial activities against bacterial and fungal strains as compared to free ligand. The hemolytic activity of the complexes was lower compared to Triton-X 100 (positive control, 100% lysis) and higher than PBS (negative control, 0% lysis). Complex 4 was the most potent inhibitor of bacterial/fungal growth.

Diorganotin(IV) Complexes with Monohydrate Disodium Salt of Iminodiacetic Acid: Synthesis, Characterization, Crystal Structure and Biological Activities

“…The peaks showed rich ion distribution with characteristic isotopic patterns for Sn; each metal ion appeared in the spectrum as a series of peaks close to each other because tin has 10 isotopes. The EI-MS spectra could not display the molecular ion peak; the data thus support the earlier reports 20 that in the mass spectra of the organometallic compounds with [ …”

“…The inocula with 1´10 8 spores/mL were used for further analysis. 20 The fungal strains (Alternaria alternata, Ganoderma lucidum, Penicillium notatum, Trichoderma harzianum, and Aspergillus niger) were cultured overnight at 28°C using potato dextrose agar. The pure cultures were maintained in sabouraud dextrose agar (SDA) medium in slants and petri plates which were presterilized in hot air oven at 180°C for 3 hours.…”

“…18 The carbonyl stretching frequencies of the ligand were shifted to lower wave number in complexes, which is ascribed to metal carboxylate coordination in accordance with earlier reports. 19,20 The mode of tin-carboxylate interaction was predicted from Du = uCOO (asym) -uCOO (sym) value which varies depending upon the coordination geometry around Sn(IV). The Du value of Na 2 L (164 cm -1 ) was greatly shifted towards a higher frequency (263-286 cm -1 ) in complexes, which indicates a monodentate binding mode of the carboxylate ion for tin.…”

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“…Generally hypsochromism and red shift are associated with intercalative binding of the complex to the double helix of DNA due to strong intercalation between the complex and the base pairs of DNA. The extent of hypsochromism is commonly consistent with the strength of the intercalative interaction [25].…”

Synthesis, Characterization and DNA Binding Studies of Zn(II)/Cu(II) Complexes with 2,2`-Diphenyl Acetic Acid/2-(4-Hydroxyphenyl)Acetic Acid Ligand Precursors and Nitrogen Bases

“…The mode of interaction of zinc/copper complexes with salmon sperm DNA (SS-DNA) was determined by the comparison of the absorbance and the shifts in a wavelength range of 200-400 cm -1 with and without DNA. The spectra were recorded at different DNA concentrations by keeping the concentration of the complexes (solvent, DMSO) constant [25]. The DNA binding activities owed to the nature of coordinated metal and aromatic ligand precursor.…”