The use of analytical methods for quality control of promising active pharmaceutical ingredients among derivatives of 4-oxoquinoline- 3-propanoic acids
DOI:
https://doi.org/10.24959/nphj.16.2144Keywords:
antimicrobial resistance, quinolin-4-one, propanoic acid, standardization, quality control, NMR, LC-MS/MSAbstract
Due to a global increase of microbial resistance to antimicrobial drugs the search for new antibiotics is vital for modern medicinal chemistry. 3-Quinolin-4-one propanoic acids have the molecular similarity with fluoroquinolone antibiotics and are prospective scaffold to create antimicrobial drugs. On the example of 3-(2-methyl-4-oxo-1,4-dihydroquinoline-3-yl) propanoic acid the analytical methods that can be used for quality control of promising active pharmaceutical ingredients (API) among derivatives of 3-(2-methyl-4 oxo-1,4-dihydroquinoline-3-yl) propanoic acids have been analyzed and tested. The necessity of their inclusion in the list of control methods of 13C NMR-spectroscopy, due to which the problem of the tautomeric forms of 3-(2-methyl-4-oxo-1,4-dihydroquinoline-3-yl) propanoic acid is uniquely solved, has been shown. Specific related substances, which are by-products of the synthesis of 3-(2-methyl-4-oxo-1,4-dihydroquinoline-3-yl) propanoic acid – 1,2,3,4,9,10- hexahydroacridine-2,9-dione and 6a-hydroxy-5,6,6a, 8,9,14,15,16a, 17,18-decahydro-7,16-dioxa -5.14-diazaheptacene-9,18-dione, have been identified using liquid chromatography-mass spectrometry (LC-MS/MS). Recommendations for the use of UV- and IR-spectroscopy to develop quality control methods for 3-(2-methyl-4-oxo-1,4-dihydroquinoline-3-yl) propanoic acid have been proposed.
References
Державна фармакопея України / Державне підприємство «Науково-експертний фармакопейний центр». – 1-е вид. – Доп. 2. – Х.: РІРЕГ, 2008. – 617 с.
Державна фармакопея України / Державне підприємство «Науково експертний фармакопейний центр». – 1-е вид. – Доп. 4. – Х.: РІРЕГ, 2011. – 538 с.
2016 U.S. Pharmacopoeia-National Formulary [USP 39 NF 34]. Vol. 1. Rockville, Md: United States Pharmacopeial Convention, Inc, 2015.
Deak D., Outterson K., Powers J.H. et al. // Annals of Internal Medicine. – 2016. – Vol. 165, №5. – P. 363.
European Pharmacopoeia, 8-th ed. Directorate for the Quality of Medicines and Healthcare of the Council of Europe. – Strasbourg, France, 2013. – P. 1231.
Global Action Plan on Antimicrobial Resistance / WHO. – 2015.
Günther H. NMR-spectroscopy: basic principles, concepts and applications in chemistry. – John Wiley & Sons, 2013.
JChem 16.11.14.0, 2016, ChemAxon. (http://www.chemaxon.com).
Maggiora, Vogt M., Stumpfe D., et al. // J. of Med. Chem. – 2014. – Vol. 57, №8. – P. 3186-3204.
Premanandh J., Samara B.S., Mazen A.N. // Frontiers in Microbiol. – 2015. – Vol. 6. – P. 1536.
Santajit S., Indrawattana N. // BioMed Res. International. – 2016. – Vol. 2016. – P. 1-8.
Zubkov V.O., Osolodchenko T.P., Ruschak N.I. et al. // J. of Organic and Pharmac. Chem. – 2015. – Vol. 13, №4 (52). – P. 20-26.
Zubkov V.O., Rozhenko О.B., Ruschak N.I. et al. // J. of Organic and Pharmac. Chem. – 2011. – Vol. 14, №2. – P. 53-59.
Zubkov V.O., Tsapko T.O., Gritsenko I.S et al. // J. of Organic and Pharmac. Chem. – 2011. – Vol. 9, №4. – P. 38-41.
Downloads
Published
Issue
Section
License
Copyright (c) 2016 National University of Pharmacy
This work is licensed under a Creative Commons Attribution 4.0 International License.
Authors who publish with this journal agree to the following terms:- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).