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

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 mea...

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Bibliographic Details
Published in:Journal of photochemistry and photobiology. B, Biology Biology, 2011-12, Vol.105 (3), p.167-174
Main Authors: Arjmand, Farukh, Sharma, Girish Chandra, Sayeed, Fatima, Muddassir, Mohd, Tabassum, Sartaj
Format: Article
Language:English
Subjects:
Absorption
Animals
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - metabolism
Antineoplastic Agents - pharmacology
Cattle
Circular Dichroism
DNA - chemistry
DNA - metabolism
Drug Design
Guanosine Monophosphate - metabolism
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Targeted Therapy
Nucleic Acid Conformation - drug effects
Organotin Compounds - chemical synthesis
Organotin Compounds - chemistry
Organotin Compounds - metabolism
Organotin Compounds - pharmacology
Osmolar Concentration
Reproducibility of Results
Spectrometry, Fluorescence
Spectrophotometry, Ultraviolet
Spectrum Analysis - methods
Stereoisomerism
Substrate Specificity
X-Ray Diffraction
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Summary: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, (1)H, (13)C and (119)Sn, 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, (1)H and (31)P NMR techniques. This was further corroborated well by interaction of 1 and 2 with 5'-GMP.
ISSN:1873-2682
DOI:10.1016/j.jphotobiol.2011.08.001