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9-O-N-Aryl/arylalkyl Amino Carbonyl Methyl Substituted Berberine Analogues induce Self-Structure in Polyadenylic Acid

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Title 9-O-N-Aryl/arylalkyl Amino Carbonyl Methyl Substituted Berberine Analogues
induce Self-Structure in Polyadenylic Acid
 
Creator Basu, Anirban
Jaisankar , P
Kumar, G Suresh
 
Subject Chemistry
 
Description This manuscript describes the interaction of 9-O-substituted analogues of the plant alkaloid berberine
with single stranded (ss) poly(A). Three new analogues of berberine with aryl/arylalkyl amino
carbonyl methyl substituents at the 9-position of the isoquinoline chromophore were evaluated for
their binding to ss poly(A) by a wide variety of biophysical techniques. The results indicated that
these analogues exhibited several-fold higher binding affinities than berberine. The Scatchard binding
isotherms revealed that all the analogues retained the cooperative binding mode of berberine.
Circular dichroism and FTIR studies unequivocally established the strong interaction potential of the
analogues to ss poly(A). Optical melting and the unique dilution experiments revealed that these
analogues induced self-structure formation in poly(A) and the nature of the substituent was
important for the ease of formation of self-structure. Energetics of the binding suggested an entropy
driven binding for the analogues in sharp contrast to the enthalpy driven binding of berberine. The
introduction of the aryl/arylalkyl amino carbonyl methyl substituent thus switched the enthalpy
driven binding of berberine to entropy dominated binding. Salt and temperature dependent
calorimetric studies established the involvement of multiple weak noncovalent interactions in the
binding process. The study also revealed that the spacer length at the 9-position had an important role
in the self-structure induction.
 
Date 2012
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/1675/1/RSC_ADVANCES___2_(20)_7714%2D7723;2012[148].pdf
Basu, Anirban and Jaisankar , P and Kumar, G Suresh (2012) 9-O-N-Aryl/arylalkyl Amino Carbonyl Methyl Substituted Berberine Analogues induce Self-Structure in Polyadenylic Acid. RSC Advances, 2 (20). pp. 7714-7723.
 
Relation http://dx.doi.org/10.1039/c2ra20841e
http://www.eprints.iicb.res.in/1675/