Biophysical Studies on the Effect of the 13 Position Substitution of the Anticancer Alkaloid Berberine on Its DNA Binding
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
Biophysical Studies on the Effect of the 13 Position Substitution of the Anticancer Alkaloid Berberine on Its DNA Binding
|
|
| Creator |
Bhowmik, Debipreeta
Hossain, Maidul Buzzetti, Franco D’Auria, Rosaria Lombardi, Paolo Kumar, G Suresh |
|
| Subject |
Chemistry
|
|
| Description |
The structural effects and thermodynamics of
the DNA binding of six berberine analogues with alkyl chains
of varying length and a terminal phenyl group at the C-13
position were investigated. All the analogues bound DNA
noncooperatively in contrast to the cooperative binding of
berberine. The binding affinity was higher and the effect of the
chain length was only up to (CH2)3, after which the binding
affinity decreased slightly. Intercalative binding with strong
stabilization of the DNA helix was revealed. Binding resulted in
the weakening of the base stacking with moderate conformational changes within the B-form. The binding was entropy driven in
each case, the entropy contribution to the free energy increasing with the chain length up to the threshold (CH2)3. The
complexation was dominated by nonpolyelectrolytic forces in each case; polyelectrolytic forces contributed only a quarter to the
total free energy at 50 mM [Na+]. Overall, the phenylalkyl substitution at the C-13 position considerably enhanced the DNA
binding and was highest for the analogue with (CH2)3. Structural and thermodynamic data on the DNA binding aspects of the
substituted berberines are presented in comparison with berberine.
|
|
| Date |
2012
|
|
| Type |
Article
PeerReviewed |
|
| Format |
application/pdf
|
|
| Identifier |
http://www.eprints.iicb.res.in/1521/1/JOURNAL_OF_PHYSICAL_CHEMISTRY_B__116__(7)2314%2D2324;2012[49].pdf
Bhowmik, Debipreeta and Hossain, Maidul and Buzzetti, Franco and D’Auria, Rosaria and Lombardi, Paolo and Kumar, G Suresh (2012) Biophysical Studies on the Effect of the 13 Position Substitution of the Anticancer Alkaloid Berberine on Its DNA Binding. The Journal of Physical Chemistry B, 116 (7). pp. 2314-2324. |
|
| Relation |
http://dx.doi.org/10.1021/jp210072a
http://www.eprints.iicb.res.in/1521/ |
|