SDRP Journal of Computational Chemistry & Molecular Modelling

Molecular modeling investigation of 2-, 3-, and 4-aminobenzoic acids in ?- and ?-cyclodextrins

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

  1. L. Szente, J. Szejtli, Adv. Drug Deliv. Rev. 36 (1999) 17. 00092-1

    View Article           

  2. D.O. Thompson, Critical Reviews in Therapeutic Drug Carrier Systems, 14 (1997) 1. PMid:9043816

    View Article      PubMed/NCBI     

  3. K. Uekama, F. Hirayama, T. Irie, Chem. Rev. 98 (1998) 2045. PMid:11848959

    View Article      PubMed/NCBI     

  4. T. Loftsson, M. Brewster, J. Pharm. Sci. 85 (1996) 1017. PMid:8897265

    View Article      PubMed/NCBI     

  5. T. Loftsson, H. Fridriksdo?ttir, A.M. Sigurdardo?ttir, H. Ueda, Int. J. Pharm. 110 (1994) 169. 90155-4

    View Article           

  6. G. Ganzerli, L. van Santvliet, E. Verschuren, A. Ludwig, Pharmazie 51 (1996) 357.

  7. 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.

  8. 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.

  9. 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 Article           

  10. P. Mura, M.T. Faucci, A. Manderioli, G. Bramanti, J. Incl. Phenom. 39 (2001) 131.

    View Article           

  11. E. 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 Article           

  12. G. Piel, B. Pirotte, I. Delneuville, P. Neven, G. Llabres, J. Elarg?`, L. Delatore, J. Pharm. Sci. 86 (1997) 475. PMid:9109052

    View Article      PubMed/NCBI     

  13. M. 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.

  14. E. Redenti, L. Szente, J. Szejtli, J. Pharm. Sci. 90 (2001) 979. PMid:11536201

    View Article      PubMed/NCBI     

  15. S. Gouin, Trends in Food Science and Technology, 15 (2004) 330.

    View Article           

  16. B.L. Zeller, F.Z. Saleeb, R.D. Ludescher, Trends in Food Science and Technology, 9 (1999) 389. 00007-2

    View Article           

  17. P.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.

  18. G. Venkatesh, T. Sivasankar, M. Karthick, N. Rajendiran, J Incl Phenom Macrocycl Chem., 77 (2013) 309.

    View Article           

  19. M. Jude Jenita, A. Antony Muthu Prabhu & N. Rajendiran, Ind. J. Chem. 51A (2012) 1686.

  20. N. Rajendiran, G. Venkatesh, Supramolecular Chemistry, 26(2014) 783. Antony Muthu Prabhu & N. Rajendiran, J Fluoresc, 22 (2012) 1461. PMid:22752432

  21. T. Sivasankar, A. Antony Muthu Prabhu, N. Rajendiran, J Mol Struc., 1028 (2012) 57.

    View Article           

  22. R.K. Sankaranarayanan and N. Rajendiran, J. Experimental Nanoscience, 10 (2015) 407

    View Article           

  23. L. Liu, Q.X. Guo, J. Incl. Phenom. Macrocycl. Chem. 50 (2004) 95.

    View Article           

  24. A.A. Rafati, S.M. Hashemianzadeh, Z.B. Nojini, M.A. Safarpour, J. Mol. Liqs. 135 (2007) 153.

    View Article           

  25. 25. 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. 26. R.K. Sankaranarayanan, A. Antony Muthu Prabhu, N. Rajendiran, J. Mol. Liqs. 161 (2011) 107.

    View Article           

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