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Charge density and electrostatic potential of hepatitis C anti-viral agent andrographolide: an experimental and theoretical study

Manjula, Saravanan and Kalaiarasi, Chinnasamy and Pavan, Mysore S and Hathwar, Venkatesha R and Kumaradhas, Poomani (2018) Charge density and electrostatic potential of hepatitis C anti-viral agent andrographolide: an experimental and theoretical study. In: ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 74 (6). pp. 693-704.

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Official URL: https://doi.org/10.1107/S2052520618014981

Abstract

Andrographolide (AGH) is a hepatitis C anti-viral agent which targets the host cell by covalently binding with the NF-kappa Breceptor. The experimental electron density distribution study of AGH has been carried out from high-resolution X-ray diffraction data collected at 110.2 (3) K. The unit-cell packing of AGH was stabilized by strong O-H center dot center dot center dot O and weak C-H center dot center dot center dot O types of intermolecular interactions. The dissociation energy of the strong hydrogen bond O2-H22 center dot center dot center dot O1 is very high, 32 kJ mol(-1). The percentage occupancy of H center dot center dot center dot H interactions is found to be maximum (68.5%) when it comparing with the other types of interactions occurring in the AGH crystalline phase. The atomic valance index (V-topo) of the C16 atom is low compared with other carbon atoms; this shows that C16 could be the possible reactive location of the AGH molecule. All atoms in the OH groups have very low V-topo values; this indicates their role in strong hydrogen bonding interactions. The electrostatic potential (ESP) surface of AGH shows the polarization of the C16=C17 bond and ESP contour map shows several maxima at the vicinity of the C16 atom; these results strongly demonstrate that the C16 atom is the reactive location of the AGH molecule. The molecular covalent docking analysis of AGH with the NF-kappa B receptor has been performed and confirmed this result. The highly electronegative region around gamma-butyrolactone can be helpful for initial alignment of the AGH molecule in NF-kappa B receptor active site. The atomic volumes of the hydrogen atoms which participate in the H center dot center dot center dot H interaction are found to be low.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to INT UNION CRYSTALLOGRAPHY
Keywords: andrographolide; electron density; hydrogen bonding; electrostatic potential; intermolecular interactions
Department/Centre: Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Depositing User: Francis Jayakanth
Date Deposited: 10 Feb 2019 09:45
Last Modified: 10 Feb 2019 09:45
URI: http://eprints.iisc.ac.in/id/eprint/61372

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