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Pharmacological investigations and Petra/Osiris/Molinspiration (POM) analyses of newly synthesized potentially bioactive organotin(IV) carboxylates

Paper ID Volume ID Publish Year Pages File Format Full-Text
29894 44445 2016 10 PDF Available
Title
Pharmacological investigations and Petra/Osiris/Molinspiration (POM) analyses of newly synthesized potentially bioactive organotin(IV) carboxylates
Abstract

•Synthesis of novel organotin(IV) carboxylates•FT-IR, NMR and single crystal X-ray characterization•Biological applications•DNA interaction study•POM analyses

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 (1H, 13C) 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 2J[119Sn–1H] 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 73.45–675.1 μg/mL while 4–6 are found to be cytotoxic to mildly cytotoxic with LD50 values in the range 6.43–13.49 μg/mL. The compound interacts with DNA via intercalation of aromatic ring into the base pairs of DNA resulting in hypochromism and minor red shift.

Graphical abstractA series of organotin(IV) compounds were synthesized and characterized successfully. The synthesized compounds interact with SS-DNA via intercalation mode of interaction.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Organotin(IV) carboxylate; Single crystal; Antimicrobial activity; Cytotoxicity; DNA interaction
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Pharmacological investigations and Petra/Osiris/Molinspiration (POM) analyses of newly synthesized potentially bioactive organotin(IV) carboxylates
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology B: Biology - Volume 158, May 2016, Pages 174–183
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us