Abstract
Five stable isomers of antiviral ribavirin agent were theoretically determined in gas and aqueous solution by using the hybrid B3LYP/6-31G* method. Here, the solvent effects were studied with the self consistent reaction field (SCRF) methodology employing the polarized continuum (PCM) and the universal solvation model (SM). Structural, electronic and topological properties were reported for all isomers while the vibrational analyses were performed only for those two polymorphic structures experimentally observed in the solid phase by X-ray diffraction. Calculations have evidenced that C2 correspond to the polymorphic V1 structure while C5 to the polymorphic V2 structure. The high dipole moment values predicted for C2 and C5 in both media could probably explain their presences in the solid. Experimental available IR and Raman spectra of ribavirin in the solid state and normal internal coordinates were employed together with the scaled quantum mechanical force field (SQMFF) approach to perform the complete vibrational assignments in both media. Here, the 81 vibration modes expected for C2 and C5 in both media were completely assigned. The frontier orbitals studies reveal that C5 is the less reactive in both media. Here, the gap value observed for C5 is in agreement with the value recently reported for ribavirin by using B3LYP/6-311++G** calculations.
Highlights
Ribavirin or virazole is an antiviral drug whose chemical name is 1- -D-ribofuranosyl-1,2,4-triazole-3carboxamide and, as it present activity on various DNA and RNA viruses, in particular orthomyxoviruses, paramyxoviruses (measles, respiratory syncytial virus (RSV)) and arenaviruses (Lassa, Junin, etc.), as reported by De Clercq [1] their study is of great chemical, pharmacological and medicinal interest
Five stable isomers of antiviral ribavirin agent were theoretically determined in gas and aqueous solution by using the hybrid B3LYP/6-31G* method
We have compared the properties of ribavirin in the two studied media with those computed properties by us for other antiviral drugs such as, thymidine [14,18], dideoxynucleoside zalcitabine [46], 5-trifluoromethyluracil [47] and cidofovir and brincidofovir [48] in order to observe the relationships that exist between the hydrophobic and hydrophilic sites and the different groups because it is very important to understand the mechanisms of interaction of this antiviral agent with the receptors sites
Summary
Ribavirin or virazole is an antiviral drug whose chemical name is 1- -D-ribofuranosyl-1,2,4-triazole-3carboxamide and, as it present activity on various DNA and RNA viruses, in particular orthomyxoviruses (influenza A and B), paramyxoviruses (measles, respiratory syncytial virus (RSV)) and arenaviruses (Lassa, Junin, etc.), as reported by De Clercq [1] their study is of great chemical, pharmacological and medicinal interest. The temperature effects on the FTIR spectra of Ribavirin were recently reported by Topala [19], the IR spectrum at room temperature by Kumar [20] and new studies by Near-Infrared and Raman Spectroscopies [21,22] were recently reported but, in this latter work all isomers were not studied and the complete assignments of their vibrational spectra were not performed by using their force fields In this context, in order to characterize completely this antiviral substance, in relation to their interesting biological activities, the aims of the present work are the studies of the structural, electronic, topological and vibrational properties of all isomers in gas phase and, especially in aqueous solution, because it is known that ribavirin are soluble in water. We have compared the properties of ribavirin in the two studied media with those computed properties by us for other antiviral drugs such as, thymidine [14,18], dideoxynucleoside zalcitabine [46], 5-trifluoromethyluracil [47] and cidofovir and brincidofovir [48] in order to observe the relationships that exist between the hydrophobic and hydrophilic sites and the different groups because it is very important to understand the mechanisms of interaction of this antiviral agent with the receptors sites
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