Research Article | Volume 13, Supplement 1, September, 2023

A novel chiral HPLC and LC-MS/MS method development for the triazole antifungal compound

R. Sangamithra S. N. Meyyanathan B. Babu   

Open Access   

Published:  Sep 20, 2023

DOI: 10.7324/JAPS.2023.118532
Abstract

The objective of the present study was to separate and develop a chiral high-performance liquid chromatography (HPLC) and sensitive liquid chromatography-tandem mass spectrometry (LC-MS/MS) technique to estimate the (+) and (-) enantiomers of Albaconazole and validate the individual enantiomer of the drug. Albaconazole is used to treat anti-fungal diseases. The stationary phase was reverse phase Chiralpak IG-3 (250 × 4.6 mm, 5 μm) and (100 × 4.6 mm, 3 μm), whereas the isocratic mobile phase was ethanol and diethyl amine (100:0.1% v/v ratio HPLC) Acetonitrile and 10 mM ammonium bicarbonate (90:10 v/v ratio LC-MS/MS) and the flow rate was 1.0 and 0.5 ml/minute. The resolution of the (+) and (-) enantiomers were monitored using HPLC diode array detector (DAD) 240 signal and LC-electrospray ionization-MS/MS in positive transition at 432.0 m/z (M + H) for Albaconazole. The retention time of the (+) and (−) enantiomers of the drug was 6.952 and 9.955 minutes and 2.905 and 3.780 minutes by HPLC and LC-MS/MS. The major benefits of the LC-MS/MS are related to its improved selectivity, precision and accuracy and the lower variability in comparison to the HPLC-DAD. This study provided a rapid, sensitive and novel selective method to evaluate the (+) and (-) enantiomers in active pharmaceutical ingredients by HPLC and LC-MS/MS.


Keyword:     Albaconazole  enantiomers HPLC LC-ESI-MS/MS and validation


Citation:

Sangamithra R, Meyyanathan SN, Babu B. A novel chiral HPLC and LC-MS/MS method development for the triazole antifungal compound. J Appl Pharm Sci, 2023; 13(Suppl 1):001–008. https://doi.org/10.7324/JAPS.2023.11853

Copyright: © The Author(s). This is an open-access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

HTML Full Text

Reference

Amjad M, Sumrra SH, Akram MS, Chohan ZH. Metal-based ethanolamine-derived compounds: a note on their synthesis, characterization and bioactivity. J Enzyme Inhib Med Chem, 2016; 4(31):88-97. https://doi.org/10.1080/14756366.2016.1220375

Ates H, Younes AA, Mangelings D, Vander Heyden Y. Enantioselectivity of polysaccharide-based chiral selectors in polar organic solvents chromatography: implementation of chlorinated selectors in a separation strategy J Pharm Biomed Anal, 2013; 74:1-3. https://doi.org/10.1016/j.jpba.2012.09.025

Azhari NR, Hui BY, Zain NN, Suah FB. Enantiomeric separation of azole antifungal compounds using chromatographic and electrophoretic techniques: a mini review. Sains Malays, 2020; 49(11):2699-714. https://doi.org/10.17576/jsm-2020-4911-09

Bhanderi BB, Yadav MM, Roy A. Antifungal drug resistance-concerns for veterinarians. Vet World, 2009; 2(5):204. https://doi.org/10.5455/vetworld.2009.204-207

Bhowmick D, Sang Y, Santra K, Halbauer M, Capua E, Paltiel Y, Naaman R, Tassinari F. Simultaneous high-purity enantiomeric resolution of conglomerates using magnetic substrates. Cryst Growth Des, 2021; 21(5):2925-31. https://doi.org/10.1021/acs.cgd.1c00093

Brauer VS, Rezende CP, Pessoni AM, De Paula RG, Rangappa KS, Nayaka SC, Gupta VK, Almeida F. Antifungal agents in agriculture: friends and foes of public health. Biomolecules, 2019; 9(10):521. https://doi.org/10.3390/biom9100521

Gazzinelli BP, Brêtas CM, César IC. Development of a stability-indicating assay method by HPLC-DAD and MS characterization of forced degradation products of ravuconazole. J Chromatogr Sci, 2022; 60(2):157-63. https://doi.org/10.1093/chromsci/bmab064

Ghannoum MA, Rice LB. Antifungal agents: mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance. Clin Microbiol Rev, 1999; 12(4):501-17. https://doi.org/10.1128/CMR.12.4.501

Hassan AU, Sumrra SH, Zafar MN, Nazar MF, Mughal EU, Zafar MN, Iqbal M. New organosulfur metallic compounds as potent drugs: synthesis, molecular modeling, spectral, antimicrobial, drug likeness and DFT analysis. Mol Divers, 2022; 26(1):51-72. https://doi.org/10.1007/s11030-020-10157-4

ICH. Q3B validation of analytical procedures: methodology. International Conference on Harmonization, 1996. [Online] Available via https://www.fda.gov/downloads/drugs/guidances/ucm073384. pdf (Accessed 20 August 2019).

Liu Y, Tian A, Wang X, Qi J, Wang F, Ma Y, Ito Y, Wei Y. Fabrication of chiral amino acid ionic liquid modified magnetic multifunctional nanospheres for centrifugal chiral chromatography separation of racemates. J Chromatogr A, 2015; 26(1400):40-6. https://doi.org/10.1016/j.chroma.2015.04.045

Maertens JA. History of the development of azole derivatives. Clin Microbiol Infect, 2004; 10:1. https://doi.org/10.1111/j.1470-9465.2004.00841.x

Mukherjee AS, Bera AJ. Importance of chirality and chiral chromatography in pharmaceutical industry: a detailed study. J Chem Pharm Sci, 2012; 2(4):334-46.

Scorzoni L, de Paula e Silva AC, Marcos CM, Assato PA, de Melo WC, de Oliveira HC, Costa-Orlandi CB, Mendes-Giannini MJ, Fusco-Almeida AM. Antifungal therapy: new advances in the understanding and treatment of mycosis. Front Microbiol, 2017; (23):8-36. https://doi.org/10.3389/fmicb.2017.00036

Shekar R, Sinha BN, Mukhopadhya A, Degani MS. Chiral HPLC method for the novel triazole antitubercular compound MSDRT 12. Chromatographia, 2014; 77(5):511-6. https://doi.org/10.1007/s10337-013-2613-5

Sumrra SH, Zafar W, Imran M, Chohan ZH. A review on the biomedical efficacy of transition metal triazole compounds. J Coord Chem, 2022; 75(3-4):293-334. https://doi.org/10.1080/00958972.2022.2059359

Sumrra SH, Zafar W, Javed H, Zafar M, Hussain MZ, Imran M, Nadeem MA. Facile synthesis, spectroscopic evaluation and antimicrobial screening of metal endowed triazole compounds. Biometals, 2021; 34:1329-51. https://doi.org/10.1007/s10534-021-00345-6

Zafar W, Sumrra SH, Chohan ZH. A review: pharmacological aspects of metal based 1, 2, 4-triazole derived Schiff bases. Eur J Med Chem, 2021; 15(222):113602. https://doi.org/10.1016/j.ejmech.2021.113602

Zhang Y, Wu DR, Wang-Iverson DB, Tymiak AA. Enantioselective chromatography in drug discovery. Drug Disco, 2005; 10(8):571-7. https://doi.org/10.1016/S1359-6446(05)03407-0

Article Metrics
88 Views 69 Downloads 157 Total

Year

Month

Related Search

By author names