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Enhanced DNA Binding of 9-o-Amino Alkyl Ether Analogs from the Plant Alkaloid Berberine

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Title Enhanced DNA Binding of 9-o-Amino Alkyl Ether Analogs
from the Plant Alkaloid Berberine
 
Creator Islam, Md. Maidul
Basu, Anirban
Hossain, Maidul
Sureshkumar, Gopalsamy
Hotha, Srinivas
Kumar, G Suresh
 
Subject Chemistry
 
Description To understand the structure–activity relationship of isoquinoline alkaloids, absorption, fluorescence, circular
dichroism, and thermodynamics were employed to study the interaction of five C-9-o-amino alkyl ether analogs
from the plant alkaloid berberine with double-stranded calf thymus DNA. The C-9 derivatization resulted in
dramatic enhancements in the fluorescence emission of these compounds. The most remarkable changes in the
spectral and binding properties were in the BC4 and BC5 derivatives. Interactions of these analogs, which have
an additional recognition motif with DNA, were evaluated through different spectroscopic and calorimetric
titration experiments. The analogs remarkably enhanced the DNA binding affinity and the same was directly
dependent on the alkyl chain length. The analog with six alkyl chains enhanced the DNA binding affinity by
about 33 times compared with berberine. The binding became more entropically driven with increasing chain
length. These results may be of potential use in the design of berberine derivatives and understanding of the
structure–activity relationship for improved therapeutic applications.
 
Date 2011
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/75/1/DNA_AND_CELL_BIOLOGY%2C_30(2)%2C123%2D133%2C2011[92].pdf
Islam, Md. Maidul and Basu, Anirban and Hossain, Maidul and Sureshkumar, Gopalsamy and Hotha, Srinivas and Kumar, G Suresh (2011) Enhanced DNA Binding of 9-o-Amino Alkyl Ether Analogs from the Plant Alkaloid Berberine. DNA and Cell Biology, 30 (2). pp. 123-133.
 
Relation http://dx.doi.org/10.1089/dna.2010.1109
http://www.eprints.iicb.res.in/75/