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Isolation and Characterization of Novel Degradation Product of Pidotimod
Corresponding Author(s) : Madhuri Baghel
Asian Journal of Chemistry,
Vol. 34 No. 9 (2022): Vol 34 Issue 9
Abstract
A synthetic dipeptide, pidotimod (3-L-pyroglutamyl-L-thiaziolidine-4-carboxylic acid, PTD) is an immunomodulator and it possesses anti-infective activity against variety of infections. The objective of this study was to explore into and identify pidotimod’s major degradation product. Pidotimod was degraded in ICH prescribed stress conditions. pidotimod was degraded 90% in 1.0 N NaOH at 80 ºC for 6 h and the degradation product (DP2) was determined using HPLC. The HPLC method was used to separate the primary and subsidiary degradation products and carried out on a C18 column with a mobile phase of ammonium acetate buffer (pH 4.5; 10 mM) and MeOH/ACN (90:10 v/v) at a ratio of 97:03 v/v at 40 ºC, flow rate of 1.0 mL/min, and detection at 215 nm. IR, NMR and LC-MS-MS were used to identify degradation product (DP2) as 3,8-dihydroxy-tetrahydro-bisthiazolo[3,4,4a,3′,4′-d]pyrazine-5,10-dione.
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- M. D’Amato, D. Paris, A. Molino, P. Cuomo, A. Fulgione, N. Sorrentino, L. Palomba, M. Maniscalco and A. Motta, Front. Pharmacol., 10, 1115 (2019); https://doi.org/10.3389/fphar.2019.01115
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- T. Crimella, R. Orlandi, G. Bocchiola, U. Anders and R. Stradi, Arzneimittelforschung, 44, 1405 (1994).
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- M. Baghel and S.J. Rajput, Indo Am. J. Pharm. Res., 06, 6182 (2016).
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References
M. D’Amato, D. Paris, A. Molino, P. Cuomo, A. Fulgione, N. Sorrentino, L. Palomba, M. Maniscalco and A. Motta, Front. Pharmacol., 10, 1115 (2019); https://doi.org/10.3389/fphar.2019.01115
G.V. Zuccotti and C. Mameli, Int. J. Pediatr., 39, 75 (2013); https://doi.org/10.1186/1824-7288-39-75
F. Mailland, G. Signorelli and G. Coppi, Drugs Future, 16, 1096 (1991); https://doi.org/10.1358/dof.1991.016.12.158317
C. Mameli, A. Pasinato, M. Picca, G. Bedogni, S. Pisanelli and G.V. Zuccotti, Pharmacol. Res., 97, 79 (2015); https://doi.org/10.1016/j.phrs.2015.04.007
C. Giagulli, M. Noerder, M. Avolio, P.D. Becker, S. Fiorentini, C.A. Guzman and A. Caruso, Int. Immunopharmacol., 9, 1366 (2009); https://doi.org/10.1016/j.intimp.2009.08.010
K. Masihi, Int. J. Antimicrob. Agents, 14, 181 (2000); https://doi.org/10.1016/S0924-8579(99)00161-2
P. Riboldi, M. Gerosa and P. Meroni, Int. J. Immunopathol. Pharmacol., 22, 255 (2009); https://doi.org/10.1177/039463200902200201
L. Ye, Y. Luo and X. Ou, China Pharmacy, 1, 17 (2012).
H. Chen, M. Shen and L. Chen, Chromatographia, 73, 767 (2011); https://doi.org/10.1007/s10337-011-1930-9
Y. Zhang, Z. Xiong, F. Qin, S. Lu, W. Liu and F. Li, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 877, 2566 (2009); https://doi.org/10.1016/j.jchromb.2009.06.038
H. Lou, Z. Ruan and B. Jiang, Arzneimittelforschung, 62, 99 (2012); https://doi.org/10.1055/s-0031-1297983
G. Coppi and M. Barchielli, J. Chromatogr. B Biomed. Appl., 563, 385 (1991); https://doi.org/10.1016/0378-4347(91)80046-F
J.H. Huang, X.H. Huang, K. Wang, J.C. Li, X.F. Xie, C.L. Shen, L.J. Li and Q.S. Zheng, Biomed. Pharmacother., 67, 475 (2013); https://doi.org/10.1016/j.biopha.2013.03.009
L. Junfang, China Pharmacy, 31, 28 (2009).
A. Magni, G. Signorelli and G. Bocchiola, Arzneimittelforschung, 44, 1402 (1994); https://doi.org/10.1002/chin.199524213
T. Crimella, R. Orlandi, G. Bocchiola, U. Anders and R. Stradi, Arzneimittelforschung, 44, 1405 (1994).
L.X. Zhang, T.J. Yin, W.Y. Shen, Y. Cheng, C.P. Jiang and X.Y. Zhang, Zhongguo Yaoke Daxue Xuebao, 42, 238 (2011).
M. Baghel and S.J. Rajput, Indo Am. J. Pharm. Res., 06, 6182 (2016).
X. Dou, X. Su, Y. Wang, Y. Chen and W. Shen, Chirality, 27, 802 (2015); https://doi.org/10.1002/chir.22493
M. Baghel and S. Rajput, J. Chromatogr. Sci., 55, 899 (2017); https://doi.org/10.1093/chromsci/bmx047
M. Baghel and S. Rajput, Biomed. Chromatogr., 32, e4146 (2018); https://doi.org/10.1002/bmc.4146