Identification, method development, validation, and characterization of Aza sugars by an ion-chromatography, high-resolution mass spectrometer, and LC-MS/MS
Tóm tắt
Aza sugars are organi c sugars having nitrogen containing polyhydroxyl sugar molecules. These molecules are active pharmaceutical ingredients; these are not well separated and eluted early in the HPLC and UPLC columns due to high polar nature. Aza sugars are having high conductivity hence the ion chromatography validated method has been established for the castanospermin and celgosivir along with its degradation studies (impurities). An ion chromatography with conductivity detector-cation column was used to determine the assay of castanospermin and celgosivir as in the form of bulk active pharmaceutical ingredients. The degradation impurities were identified and characterized by using the UPLC-TOF and the LCMS/MS techniques. An ion chromatography method was developed and determined the assay for castanospermin and celgosivir as in the form of bulk active pharmaceutical ingredients with the specificity of the miglitol and 1-deoxynojirimycin. Validation was performed for assay of the castanospermin and celgosivir. The method precision %RSD results at 0.25 mg/mL concentration of castanospermin and celgosivir were 1.1 and 0.7 respectively. The linearity was performed from 25 to 200% (w.r.t 0.25 mg/mL); the results were 1.000 and 0.999 coefficient for the castanospermin and celgosivir respectively. The recovery studies, robustness, ruggedness, and solution stability results were within the acceptance limits of the ICHQ2 (R1) guidelines. The stress study for the castanospermin and celgosivir active pharmaceutical ingredients was performed by using 0.5N HCl solution, 0.5N NaOH solution, 3.0% H202 solution, UV-visible and the thermal conditions. The castanospermin was degraded as 20.8% of n-oxide impurity, and celgosivir was degraded as 10.0% n-oxide impurity under 3.0% H202 solution. In base degradation, the celgosivir was back converted completely to castanospermin. These n-oxide impurities were identified and characterized by using UPLC-TOF and LCMS/MS techniques after collection from the ion chromatography. Castanospermin and celgosivir are stable in remaining stress conditions. From the present study, it was found that robust analytical ion chromatography technique is used for the determination of assay in Aza sugar, especially assay for the castanospermin and celgosivir with minimum usage of test sample 0.25 mg/mL and used green chemistry solvents. The study also explains that the unique degradation of castanospermin and celgosivir under oxidative and base hydrolysis, Oxidative degradation impurities were identified and characterized as n-oxides of its respective castanospermin and celgosivir active pharmaceutical ingredients by using HRMS and LC-MS/MS.
Tài liệu tham khảo
Balakumaran K, Janagili M, Rajana N, Papureddy S, Anireddy J. Development and Validation of Miglitol and Its Impurities by RP-HPLC and Characterization Using Mass Spectrometry Techniques. Sci Pharm. 2016;84(4):654-70. https://doi.org/10.3390/scipharm84040654.
Belley M, Leger S, Roy P, Xiang YB, Labelle M, Guay D, Miglitol D. MedlinePlus Drug Information. MedlinePlus. National Institutes of Health. 2013. Retrieved 13 April 2013. European Patent 0480717B1, April 15 1998.
Budavari S, O'Neil MJ, Smith A, PE Heckelman, editors. The Merck Index: An Encyclopedia of Chemicals, Drugs and Biologicals. Eleventh Edition. Rahway: Merck & Co. Inc.; 1989.
Cahours X, Daali Y, Cherkaoui S, Veuthey JL. Simultaneous analysis of poly hydroxylated alkaloids by capillary electrophoresis using borate complexation and evaluation of sweeping technique for sensitivity improvement. Chromatographia. 2002;55:211–6.
Chittora NC, Shrivastava A, Jain A. New RP-HPLC method of miglitol in tablet dosage form including forced degradation studies and estimation in spiked rabbit plasma. J Young Pharm. 2009;1:364–70.
Council of Europe. European Pharmacopoeia (Ph. Eur.), 8th ed. Strasbourg: Council of Europe; 2015.
Dhole SM, Khedekar PB, Amnerkar ND. Validated high performance liquid chromatography method for determination of miglitol in tablet dosage form. Pharm Methods. 2012;3(2):68–72. https://doi.org/10.4103/2229-4708.103875.
Durantel D. Celgosivir, an alpha-glucosidase I inhibitor for the potential treatment of HCV infection. Curr Opin Investig Drugs. 2009;10(8):860-70.
Hohenschutz LD, Bell EA, Jewess PJ, Leworthy DP, Pryce RJ, Arnold E, Clardy J. Castanospermin, a 1,6,7,8-tetrahydroxyoctahydroindolizine alkaloid, from seeds of castanospermin australe. Photochemistry. 1981;20(4):811–4. https://doi.org/10.1016/0031-9422(81)85181-3.
Ibrahim FA, Ali FA. Kinetic determination of acarbose and miglitol in bulk and pharmaceutical formulations using alkaline potassium permanganate. Int J Biomed Sci. 2007;3:20–30.
International Conference on Harmonization. Q2 (R1), Validation of Analytical Procedures: Text and Methodology. ICH Guidelines; 2005.
International Conference on Harmonization. Q1B, Photo stability Testing of New Drug Substances and Products. ICH Guidelines; 1996.
Japan Intl. Research Center for Agricultural Sciences. A simple, selective, and rapid method of high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD) to quantify DNJ in mulberry-based food products, Postharvest Science and Technology Div. Tsukuba: Japan Intl. Research Center for Agricultural Sciences; 2010. https://doi.org/10.1111/j.1750-3841.2010.01528.
Kimura T, Nakagawa K, Saito Y, Yamagishi K, Suzuki M, Yamaki K, Shinmoto H, Miyazawa T. Simple and rapid determination of 1-deoxynojirimycin in mulberry leaves. Biofactors. 2004;22(1-4):341-5.
Li X, Wang Y, Wang J, Fawcett JP, Zhao L, Gu J. Determination of miglitol in human plasma by liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrum. 2007;21:247–51. https://doi.org/10.1016/j.jchromb.2005.09.021.
Nirogi RV, Kandikere VN, Shukla M, Mudigonda K, Maurya S, Boosi RK, Yerramilli A. Liquid chromatographic tandem mass spectrometry method for the quantification of miglitol in human plasma. Arzneimittelforschung. 2006;56:328–36.
Rajana N, Lasker R, Venkatesh P, Yarbagi K, Balakumaran K, Babu JM. A novel assay method of 1-deoxy nojirimycine (DNJ) by ion chromatography. Int J Pharm Sci Res. 2016;7(4):1580–9. https://doi.org/10.13040/IJPSR.0975-8232.7(4).1580-89.
Rudraprasad Reddy J, Pramod Kumar R, Appa rao KMCh, Ramakrishna K. A sensitive UPLC method development and validation with LC-MS compatible for the determination of 1-Deoxynojirimycin in mulberry leaves using fluorescence detection. Am J Pharm Tech Res. 2014;4(3). ISSN: 2249-3387.
Saul R, Ghidoni JJ, Molyneux RJ, Elbein AD. Castanospermine inhibits alpha-glucosidase activities and alters glycogen distribution in animals. PNAS. 1985;82(1):93–7. https://doi.org/10.1073/pnas.82.1.93. PMC 396977. PMID 3881759.
The United States Pharmacopoeia 39 and National Formulary 34, Asian ed. United States Pharmacopoeia. Rockville: Convection; 2016.
Wang F, Jin XZ, Xiu-mei D. Determination of miglitol in human plasma by HPLC-MS/ESI. Chin Pharm J. 2005;40:51–3.
Whitby K, Pierson TC, Geiss B, Lane K, Engle M, Zhou Y, Doms RW, Diamond MS. Castanospermin, a potent inhibitor of dengue virus infection in vitro and in vivo. J Virol. 2005;79(14):8698–706. https://doi.org/10.1128/JVI.79.14.8698-8706. PMC 1168722. PMID. 15994763
Whitby K, Taylor D, Patel D, Ahmed P, Tyms AS. Action of celgosivir (6 O-butanoyl castanospermine) against the pestivirus BVDV: implications for the treatment of hepatitis C. Antivir Chem Chemother. 2004;15(3):141-51.