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Interaction of Dialkyltin(IV) Bishydroxamates with 5′‐AMP or DNA:the Impact of Carbon Chain Length to Coordination Properties
Author(s) -
SHANG XianMei,
WU JiZhou,
LI QingShan
Publication year - 2008
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200890118
Subject(s) - chemistry , dna , hyperchromicity , phosphate , stereochemistry , crystallography , adenosine , nuclear magnetic resonance spectroscopy , carbon chain , biochemistry , organic chemistry
Two diorganotin(IV) complexes, [Me 2 Sn(4‐FC 6 H 4 C(O)NHO) 2 ] ( 1 ) and [Bu 2 Sn(4‐FC 6 H 4 C(O)NHO) 2 ] ( 2 ), were synthesized. The action mode of the diorganotin(IV) complexes with adenosine‐5′‐monophosphate (5′‐AMP) or DNA under different conditions and different time was investigated by high‐solution 1 H NMR and 31 P NMR technology and UV spectroscopy. The complexes 1 and 2 which have different carbon chain lengths exhibited different action modes with mononucleotide or DNA. The interaction of 2 with 5′‐AMP resulted in significant chemical shift of H(8), H(2) and 31 P. A hyperchromic effect of DNA could be observed due to the interaction of 2 with DNA, while interaction of 1 with 5′‐AMP or DNA could only cause obvious change of chemical shift of 31 P. The results indicate that the complex 2 is the first case which could selectively bind to both the N(1) atom of the base and the phosphate oxygen atom of 5′‐AMP near a physiological condition, and may further destroy the helical structure of DNA, while 1 may merely bind to the phosphate oxygen atom of 5′‐AMP and cause the contraction of the DNA helical structure. The results first reveal that the organic group R may not only help the membrane transference of the diorganotin compounds but also play an important role in the action mode with DNA.