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Computational studies of 1:2 complex between retinol propionate and β cyclodextrin

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Abstract

[M05-2X/6-31G*:PM3MM] and [B3LYP/6-31G*:PM3] ONIOM2 methods have been used to investigate the vitamin A propionate/β cyclodextrin complex with 1:2 stoichiometry. Both methods give almost the same lowest energy minimum. The minimum energy structure of the complex is found in good agreement with experimental data. In this configuration, the major structure of propionate of vitamin A (PVA) is embedded inside the two cavities of βCD while the propionate group is kept outside. However, the three methyl groups of PVA are positioned in the free space between both βCD molecules. The driving forces for complexation are dominated by Van der Waals interactions between PVA and the βCD molecules assisted with multiple hydrogen bond interactions between the two cyclodextrin molecules. These interactions were investigated using the natural bond orbital approach.

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References

  1. Loveday, S.M., Singh, H.: Trends in food science & technology 19, 657–668 (2008)

    Article  CAS  Google Scholar 

  2. Weisse, S.: Doctorat thesis serie N° 741 Faculté de Pharmacie de Chatenay-Malabry Université de Paris XI (2002)

  3. Villiers, A.: Sur la fermentation de la fécule par l’action du ferment butyriqué. C.R. Hebd. Seances Acad. Sci. 112, 536–538 (1891)

    Google Scholar 

  4. Frömming, K.H., Szejtli, J.: Cyclodextrins in Pharmacy. Kluwer Academic Publishers, Dordrecht (1994)

    Google Scholar 

  5. Attoui Yahia, O., Khatmi, D.E.: J Mol. Struct. (Theochem) 912, 38–43 (2009)

    Article  CAS  Google Scholar 

  6. Loftsson, T., Jarho, P., Másson, M., Järvinen, T.: Expert Opin Drug. Deliv. 2, 335–351 (2005)

    Article  CAS  Google Scholar 

  7. Huang, M.J., Quan, Z., Liu, Y.M: Int. J. Quantum Chem. 109, 81–90 (2009)

  8. Palmieri, F., Wehrlé, P., Duportail, G., Stamm, A.: Drug Dev. Ind. Pharm. 18(19), 2117 (1992)

    Article  Google Scholar 

  9. Muñoz-Botella, S., Martín, M.A., Del Castillo, B., Lerner, D.A., Menéndez, J.C.: Analytica. Chimica. Acta. 468, 161–170 (2002)

  10. Stewart, J.J.P.: MOPAC2009, Stewart Computational Chemistry. Colorado Springs, CO, USA. http://OpenMOPAC.net (2008)

  11. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A.Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C.,Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzewski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghavachari K, Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cioslowski, J., Stefanov, B.B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayakkara, A., Challacombe, M., Gill, P.M.W., Johnson, B., Chen, W., M. Wong, M.W., Gonzalez, C., Pople, J.A.: Gaussian 03, Revision E.01. Gaussian Inc., Pittsburgh PA (2009)

  12. Barbiric, D.J., de Rossi, R.H., Castro, E.A.: J. Mol. Struct. (Theochem) 537, 234–235 (2001)

    Article  Google Scholar 

  13. Matei, I., Nicolae, A., Hillebrand, M.: J. Incl. Phenom. Macrocycl. Chem. 57, 597–601 (2007)

    Article  CAS  Google Scholar 

  14. Yan, C., Xiu, Z., Li, X., Teng, H., Hao, C.: J. Incl. Phenom. Macrocycl. Chem. 58, 337 (2007)

    Article  CAS  Google Scholar 

  15. Dapprich, S., Koma′romi, I., Byun, K.S., Morokuma, K., Frisch, M.J.: J. Mol. Struct. (Theochem) 461–462, 1–21 (1999)

    Article  Google Scholar 

  16. Kuno, M., Hannongbua, S., Morokuma, K.: Chem. Phys. Lett. 380, 456–463 (2003)

    Article  CAS  Google Scholar 

  17. James, C., Amal Raj, A., Reghunathan, R., Joe, I.H., Jayakumar, V.S.: J. Raman Spectrosc. 37, 1381 (2006)

    Article  CAS  Google Scholar 

  18. Liu, J.N., Chen, Z.R., Yuan, S.F.: J. Zhejiang Univ. Sci. B6, 584 (2005)

    Article  Google Scholar 

  19. Szafran, M., Komasa, A., Adamska, E.B.: J. Mol. Struct. (Theochem) 827, 101 (2007)

    CAS  Google Scholar 

  20. Kavitha, E., Sundaraganesan, N., Sebastian, S., Kurt, M.: Spectrochim. Acta Part A 77, 612–619 (2010)

    Article  CAS  Google Scholar 

  21. Zhao, Y., Truhlar, D.G.: Org. Lett. 8, 5753 (2006)

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Badji-Mokhtar University, BP. 12, Annaba, Algeria

    Nassima Mallem, Soraya Benghodbane & Ouassila Attoui Yahia

  2. Department of Chemistry, Faculty of Science, Guelma’s University, Guelma, Algeria

    Djameleddine Khatmi

  3. Faculty of Engineering Science, LR3MI, Badji-Mokhtar University, BP. 12, Annaba, Algeria

    Salaheddine Azzouz

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  1. Nassima Mallem
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  2. Djameleddine Khatmi
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  3. Salaheddine Azzouz
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  4. Soraya Benghodbane
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  5. Ouassila Attoui Yahia
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Correspondence to Nassima Mallem.

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Mallem, N., Khatmi, D., Azzouz, S. et al. Computational studies of 1:2 complex between retinol propionate and β cyclodextrin. J Incl Phenom Macrocycl Chem 73, 305–312 (2012). https://doi.org/10.1007/s10847-011-0057-9

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  • DOI: https://doi.org/10.1007/s10847-011-0057-9

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