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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/4101
Title: Effect of adenosine on the supramolecular architecture and activity of 5-fluorouracil
Authors: Singh U.P.
Kashyap S.
Singh H.J.
Mishra B.K.
Roy, Partha
Chakraborty A.
Published in: Journal of Molecular Structure
Abstract: The reactions of adenosine (Ad) with 5-halouracils (5XU where X = F for 1, Cl for 2, Br for 3 and I for 4) resulted in the formation of co-crystals 1-4 in monoclinic with P2 1 space group. Despite of great variation in the halo substituent at the 5th position of the uracil, each structure contains the same number and same type of non-covalent interactions i.e., primary N-H⋯N, N-H⋯O, O-H⋯N, O-H⋯O hydrogen bonds and secondary C-H⋯O and X⋯O interactions within these motifs as well as with neighboring molecules. As compared to Ad the size of cavity increases in co-crystal 1 to accommodate the 5FU as a guest. With the variation of halogen from fluoro to iodo on the uracil, the orientation of the molecules remains the same with a slight difference in the dihedral angle in all the co-crystals 1-4. This study demonstrates that hydrogen-bonded interactions between adenosine and halouracils provide a supramolecular assembly to these co-crystals. Computational studies illustrate that the size of the halo substituents on uracil has no effect on the hydrogen bond interaction energy. It further reveals that the orientation of molecules remain same in both solid phase as well as in the gaseous phase. The antitumor and DNA cleavage activity studies show that the antitumor activity of 5-fluorouracil against MCF-7 breast cancer decreases in the presence of adenosine. © 2012 Elsevier B.V. All rights reserved.
Citation: Journal of Molecular Structure (2012), 1014(): 47-56
URI: https://doi.org/10.1016/j.molstruc.2012.01.035
http://repository.iitr.ac.in/handle/123456789/4101
Issue Date: 2012
Keywords: 5-Halouracils
Antitumor and DNA cleavage activity
Supramolecular architecture
ISSN: 222860
Author Scopus IDs: 57203181883
26537562100
15133015200
55512610300
35509207200
8507454000
Author Affiliations: Singh, U.P., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India
Kashyap, S., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India
Singh, H.J., Department of Chemistry, DDU Gorakhpur University, Gorakhpur 273 009, India
Mishra, B.K., Department of Chemistry, DDU Gorakhpur University, Gorakhpur 273 009, India
Roy, P., Department of Biotechnology, Indian Institute of Technology Roorkee, Roorkee 247 667, India
Chakraborty, A., Department of Biotechnology, Indian Institute of Technology Roorkee, Roorkee 247 667, India
Funding Details: The authors gratefully acknowledge CSIR, New Delhi, India for financial assistance in form of SRF to SK. Appendix A
Corresponding Author: Singh, U.P.; Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247 667, India; email: udaipfcy@iitr.ernet.in
Appears in Collections:Journal Publications [BT]
Journal Publications [CY]

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