J. Thulasidhasan, M. Jude Jenita
Molecular modeling investigation of 2-, 3-, and 4-aminobenzoic acids in α- and β-cyclodextrins
Co-Authors
Citation
RAJENDIRAN, Molecular modeling investigation of 2-, 3-, and 4-aminobenzoic acids in ?- and ?-cyclodextrins(2016)SDRP Journal of Computational Chemistry & Molecular Modelling 1(1)
Abstract
Geometry optimizations of neutral, monocation and monoanion of 2-aminobenzoic acid (2ABA), 3-aminobenzoic acid (3ABA) and 4-aminobenzoic acid (4ABA) with ?-, and ?-cyclodextrins (?-CD, and ?-CD) were carried out using semi-empirical PM3 method. PM3 calculations were performed upon the inclusion complexation of ?-CD, ?-CD with neutral, monoanion and monocation species of 2ABA, 3ABA and 4ABA. The negative Gibbs energy and enthalpy changes for the inclusion complexes indicated that the formation of these complexes is spontaneous and exothermic. Hydrogen bonding interactions played a major role in the ABA:CD inclusion process. The dipole moment values for guests increased when they entered into the CD cavity which is an indication of the increase of the polarity and the formation of complex. The computational results indicated that the formation of all the inclusion complexes were enthalpy driven process.
References
L. Szente, J. Szejtli, Adv. Drug Deliv. Rev. 36 (1999) 17. 00092-1
View ArticleD.O. Thompson, Critical Reviews in Therapeutic Drug Carrier Systems, 14 (1997) 1. PMid:9043816
View Article PubMed/NCBIK. Uekama, F. Hirayama, T. Irie, Chem. Rev. 98 (1998) 2045. PMid:11848959
View Article PubMed/NCBIT. Loftsson, M. Brewster, J. Pharm. Sci. 85 (1996) 1017. PMid:8897265
View Article PubMed/NCBIT. Loftsson, H. Fridriksdo?ttir, A.M. Sigurdardo?ttir, H. Ueda, Int. J. Pharm. 110 (1994) 169. 90155-4
View ArticleG. Ganzerli, L. van Santvliet, E. Verschuren, A. Ludwig, Pharmazie 51 (1996) 357.
E. Fenyvesi, M. Vikmon, J. Szeman, J. Szejtli, P. Ventura, M. Pasini, in: T. Osa (Ed.), Proceedings of Seventh International Symposium on Cyclodextrins, Academic Society of Japan, (1994) 414.
M. Vikmon, J. Szeman, J. Szejtli, M. Pasini, E. Redenti, P. Ventura, in: T. Osa (Ed.), Proceedings of Seventh International Symposium on Cyclodextrins, Academic Society of Japan, (1994) 480.
M.T. Esclusa-Diaz, M. Gayo-Otero, M.B. Pe?rez-Marcos, J.L. Vila-Jato, J.J. Torres-Labandeira, Int. J. Pharm. 142 (1996) 183. 04666-2
View ArticleP. Mura, M.T. Faucci, A. Manderioli, G. Bramanti, J. Incl. Phenom. 39 (2001) 131.
View ArticleE. Redenti, L. Szente, J. Szejtli, J. Pharm. Sci. 89 (2000) 1. 1520-6017(200001)89:1<1::AID-JPS1>3.0.CO;2-W
View ArticleG. Piel, B. Pirotte, I. Delneuville, P. Neven, G. Llabres, J. Elarg?`, L. Delatore, J. Pharm. Sci. 86 (1997) 475. PMid:9109052
View Article PubMed/NCBIM. Vikmon, I. Kolbe, J. Szejtli, E. Redenti, P. Ventura, in: J.J. Torres Labandeira, J.L. Vila Jato (Eds.), Proceedings of Ninth International Symposium on Cyclodextrins, Kluwer, Dordecht, (1999) 281.
E. Redenti, L. Szente, J. Szejtli, J. Pharm. Sci. 90 (2001) 979. PMid:11536201
View Article PubMed/NCBIS. Gouin, Trends in Food Science and Technology, 15 (2004) 330.
View ArticleB.L. Zeller, F.Z. Saleeb, R.D. Ludescher, Trends in Food Science and Technology, 9 (1999) 389. 00007-2
View ArticleP.M.M. Schrooyen, R. van der Meer, C.G. De Kruif, Proceedings of the Nutrition Society, 60 (2001) 475. Antony Muthu Prabhu, and N. Rajendiran, J. Indian Chem Soc. 90 (2013) 1127.
G. Venkatesh, T. Sivasankar, M. Karthick, N. Rajendiran, J Incl Phenom Macrocycl Chem., 77 (2013) 309.
View ArticleM. Jude Jenita, A. Antony Muthu Prabhu & N. Rajendiran, Ind. J. Chem. 51A (2012) 1686.
N. Rajendiran, G. Venkatesh, Supramolecular Chemistry, 26(2014) 783. Antony Muthu Prabhu & N. Rajendiran, J Fluoresc, 22 (2012) 1461. PMid:22752432
PubMed/NCBIT. Sivasankar, A. Antony Muthu Prabhu, N. Rajendiran, J Mol Struc., 1028 (2012) 57.
View ArticleR.K. Sankaranarayanan and N. Rajendiran, J. Experimental Nanoscience, 10 (2015) 407
View ArticleL. Liu, Q.X. Guo, J. Incl. Phenom. Macrocycl. Chem. 50 (2004) 95.
View ArticleA.A. Rafati, S.M. Hashemianzadeh, Z.B. Nojini, M.A. Safarpour, J. Mol. Liqs. 135 (2007) 153.
View Article25. R. Castro, M.J. Berardi, E. Cordova, M.O. de Olza, A.E. Kaifer, J.D. Evanseck, J. Am. Chem. Soc. 118 (1996) 10257. Antony Muthu Prabhu, G. Venkatesh, N. Rajendiran, J Fluoresc, 20 (2010) 1199.
26. R.K. Sankaranarayanan, A. Antony Muthu Prabhu, N. Rajendiran, J. Mol. Liqs. 161 (2011) 107.
View Article