Electronic structure analysis of isomeric preferences of canonical and zwitterionic forms of lornoxicam

Nathavad, Zankhana P.; Bhatia, Sonam; Dhaked, Devendra K.; Bharatam, Prasad V.

doi:10.1016/j.comptc.2013.09.011

Cited by 5 publications

(2 citation statements)

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“…This is confirmed from Table in which the relative energy values between C1 and Z3 ; C1 and Z4 are reduced under implicit solvent conditions. Several studies are reported on the possible equilibrium between canonical and zwitterionic structures of amino acids and some important drug like molecules . As discussed in the introduction section, minimum seven water molecules are required to reduce the energy difference between canonical and zwitterionic form of glycine, however, one water molecule is sufficient to achieve the same in the case of arginine.…”

Section: Microsolvationmentioning

confidence: 99%

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Electronic structure and conformational analysis of P218: An antimalarial drug candidate

Abbat

Bharatam

2016

Int J of Quantum Chemistry

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P218 is one of the very important and recent lead compounds for antimalarial research. The 3D structural and electronic details of P218 are not available. In this article, quantum chemical studies to understand the possible 3D structures of P218 are reported and compared with 3D structures from the active site cavities of hDHFR and PfDHFR. The neutral P218, can adopt open chain as well as cyclic arrangements. Under implicit solvent condition a zwitterionic‐cyclic conformer is found to be quite possible. Microsolvation studies using explicit water molecules indicate that one water molecule may bridge the two ends of zwitterionic‐cyclic P218. It was observed that the protonation occurs preferentially at N1 position of the 2,4‐diaminopyrimidine ring, with a proton affinity of 274.49 kcal/mol (implicit solvent phase) and 236.35 kcal/mol (gas phase). A dimer of P218 may be zwitterionic dimer, the dimer formation can release upto ∼28.60 kcal/mol (implicit solvent phase).

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Section: Microsolvationmentioning

confidence: 99%

“…The canonical vs . zwitterionic states of amino acids are subjects of extensive study . It was reported that in the presence of seven explicit water molecules the zwitterionic form of glycine becomes more stable than its canonical form .…”

Section: Introductionmentioning

confidence: 99%