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Preparation and Immunological Evaluation of Organic Acid Salts of Levamisole
Corresponding Author(s) : Jianhua Wang
Asian Journal of Chemistry,
Vol. 26 No. 3 (2014): Vol 26 Issue 3
Abstract
Four kinds of organic acid salts of levamisole were prepared from levamisole hydrochloride and organic acids (L-ascorbic acid, tartaric acid, citric acid and ferulic acid) by solvent crystallization method, respectively. The salts were characterized by elemental analysis, UV-VIS, FTIR, ESI-MS, DSC-TGA, solubility in water, melting point, optical rotation and pH in water. The immunosuppressed mice models were established by intraperitoneal injection of cyclophosphamide to verify and compare the effects of levamisole hydrochloride and organic acid salts of levamisole on immune functions of immunosuppressed mice. The results showed while significantly increasing the contents of serum IgM and IgG and the immune organ indexes in cyclophosphamide-induced immunosuppressed mice, levamisole ferulate and levamisole tartrate presented higher increases in IgG contents and immune organ indexes than other salts did. Thus, it could be concluded that levamisole ferulate and levamisole tartrate were more effective on immune enhancement than other salts.
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- P.B. Faanes, P. Dillon and Y.S. Choi, Clin. Exp. Immunol., 27, 502 (1977).
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References
P.B. Faanes, P. Dillon and Y.S. Choi, Clin. Exp. Immunol., 27, 502 (1977).
E. Soppi, O. Lassila, M.K. Viljanen and O.P. Lehtonen, Clin. Exp. Immunol., 38, 609 (1979).
Z.I. Qureshi, L.A. Lodhi and H. Jamil, Vet. Arhiv., 70, 59 (2000).
H.A.C.C. Perera and A. Pathiratne, In eds.: M.G. Bondad-Reantaso, C.V. Mohan, M. Crumlish and R.P. Subasinghe, Enhancement of immune responses in Indian carp, Catla catla, following adiministration of levamisole by immersion, Diseases in Asian Aquaculture VI. Fish Health Section, Asian Fisheries Society, Manila, Philippines, pp. 129-142 (2008).
S.M. Aly, O. Abd-Allah, A. Mahmoud and H. Gafer, Mediter. Aquacult. J., 1, 8 (2010).
P. Stasiak, M. Sznitowska, C. Ehrhardt, M. Luczyk-Juzwa and P. Grieb, AAPS PharmSciTech, 11, 1636 (2010); doi:10.1208/s12249-010-9545-2.
J.N. Hemenway, P. Jarho, J.T. Henri, S.K. Nair, D. VanderVelde, G.I. Georg and V.J. Stella, J. Pharm. Sci., 99, 1810 (2010); doi:10.1002/jps.21952.
N.H. Nam, Y. Kim, Y.J. You, D.H. Hong, H.M. Kim and B.Z. Ahn, Bioorg. Med. Chem., 11, 1021 (2003); doi:10.1016/S0968-0896(02)00514-X.
P. Hewawasam, M. Ding, N. Chen, D. King, J. Knipe, L. Pajor, A. Ortiz, V.K. Gribkoff and J. Starrett, Bioorg. Med. Chem. Lett., 13, 1695 (2003); doi:10.1016/S0960-894X(03)00296-8.
B. Mizrahi and A.J. Domb, AAPS PharmSciTech, 10, 453 (2009); doi:10.1208/s12249-009-9228-z.
S. Miyazaki, M. Oshiba and T. Nadai, Chem. Pharm. Bull. (Tokyo), 29, 883 (1981); doi:10.1248/cpb.29.883.
Y. Ueda, J.D. Matiskella, J. Golik, T.P. Connolly, T.W. Hudyma, S. Venkatesh, M. Dali, S.-H. Kang, N. Barbour, R. Tejwani, S. Varia, J. Knipe, M. Zheng, M. Mathew, K. Mosure, J. Clark, L. Lamb, I. Medin, Q. Gao, S. Huang, C.-P. Chen and J.J. Bronson, Bioorg. Med. Chem. Lett., 13, 3669 (2003); doi:10.1016/j.bmcl.2003.08.029.
H. Thakuria, A. Pramanik, B.M. Borah and G. Das, Tetrahedron Lett., 47, 3135 (2006); doi:10.1016/j.tetlet.2006.02.137.
H. Darius, T. Münzel, K. Huber, E. Sultan and U. Walter, J. Kardiol., 16, 412 (2009).
N. Kumar, Shishu, G. Bansal, S. Kumar and A.K. Jana, AAPS Pharm. Sci. Tech., 13, 863 (2012); doi: 10.1208/s12249-012-9804-5.
Z. Rahman, A.S. Zidan, R. Samy, V.A. Sayeed and M.A. Khan, AAPS Pharm. Sci. Tech., 13, 793 (2012); doi:10.1208/s12249-012-9800-9.
K.H. Cho and H.G. Choi, Pharm. Dev. Technol., 39, 901 (2013); doi:10.3109/03639045.2012.717295.
H.J. Vial, S. Wein, C. Farenc, C. Kocken, O. Nicolas, M.L. Ancelin, F. Bressolle, A. Thomas and M. Calas, Proc. Natl. Acad. Sci. USA, 101, 15458 (2004); doi:10.1073/pnas.0404037101.
O. Nicolas, D. Margout, N. Taudon, S. Wein, M. Calas, H.J. Vial and F.M.M. Bressolle, Antimicrob. Agents Chemother., 49, 3631 (2005); doi:10.1128/AAC.49.9.3631-3639.2005.
G. Shi, X. Wang, L. Tao et al., Effects of organic acid in Folium Isatidis on the immune organ index and activity of enzymes involved in free radicals of immunosuppressed mice. In: International Conference on Human Health and Biomedical Engineering (HHBE), IEEE Piscataway NJ, USA, p. 227-300 (2011).
J.D. Buhr and G. Widmann, Application handbook thermal analysis: Pharmaceuticals & food, ed. by Lu L. M., Shanghai, Donghua University Press, p. 1-10 (2011).
A. Winkelstein, Blood, 41, 273 (1973).
J.F. Xu, J.M. Qu, L.X. He and Z.L. Ou, Chin. Med. J. (Engl.), 119, 1421 (2006).
X. He, X.J. Yang and Y.M. Guo, Anim. Feed Sci. Technol., 139, 186 (2007); doi:10.1016/j.anifeedsci.2007.01.009.
K. Mccutcheon, E. O'Hara and D. Fei, Immunol. Invest., 34, 199 (2005).
K. Kawabata, T. Yamamoto, A. Hara, M. Shimizu, Y. Yamada, K. Matsunaga, T. Tanaka and H. Morie, Cancer Lett., 157, 15 (2000); doi:10.1016/S0304-3835(00)00461-4.
Y. Song, J. Yang, W.L. Bai and W. Ji, Phytother. Res., 25, 909 (2011); doi:10.1002/ptr.3354.
R.K. Verbeeck, I. Kanfer and R.B. Walker, Eur. J. Pharm. Sci., 28, 1 (2006).
S. Hansen, M. Vulic', J. Min, T.J. Yen, M.A. Schumacher, R.G. Brennan and K. Lewis, PLoS ONE, 7, e39185 (2012); doi:10.1371/journal.pone.0039185.