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De novo design of chiral organotin cancer drug candidates: Validation of enantiopreferential binding to molecular target DNA and 5′-GMP by UV–visible, fluorescence, 1H and 31P NMR

Paper ID Volume ID Publish Year Pages File Format Full-Text
30702 44497 2011 8 PDF Available
Title
De novo design of chiral organotin cancer drug candidates: Validation of enantiopreferential binding to molecular target DNA and 5′-GMP by UV–visible, fluorescence, 1H and 31P NMR
Abstract

N,N-bis[(R-/S-)-1-benzyl-2-ethoxyethane] tin (IV) complexes were synthesized by applying de novo design strategy by the condensation reaction of (R-/S-)2-amino-2-phenylethanol and dibromoethane in presence of dimethyltin dichloride and thoroughly characterized by elemental analysis, conductivity measurements, IR, ESI-MS, 1H, 13C and 119Sn, multinuclear NMR spectroscopy and XRD study. Enantioselective and specific binding profile of R-enantiomer 1 in comparison to S-enantiomer 2 with ultimate molecular target CT-DNA was validated by UV–visible, fluorescence, circular dichroism, 1H and 31P NMR techniques. This was further corroborated well by interaction of 1 and 2 with 5′-GMP.

► De novo synthesis of N,N-bis[(R-/S-)-1-benzyl-2-ethoxyethane] tin (IV) complexes. ► Elemental analysis, IR, ESI-MS, 1H, 13C and 119Sn, NMR spectroscopy and XRD study. ► 2J [1H–117/119Sn] coupling constant. ► Chiral discrimination of R- and S-enantiomer with CT DNA by employing biophysical techniques. ► R-enantiomer complex binds more avidly to DNA as compared to S-enantiomer complex.

Keywords
Organotin complexes; CT-DNA binding studies; NMR validation with 5′-GMP; 119Sn NMR
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De novo design of chiral organotin cancer drug candidates: Validation of enantiopreferential binding to molecular target DNA and 5′-GMP by UV–visible, fluorescence, 1H and 31P NMR
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology B: Biology - Volume 105, Issue 3, 2 December 2011, Pages 167–174
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
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Any Questions? feel free to contact us