N,N-Dimethylaniline and Zno nanoparticles mediated photochemical transformation of metronidazole

Abstract: The present study evaluates the photochemical behavior of a nitroimidazole derivative drug metronidazole in presence of N,N dimethylaniline and ZnO nanoparticles. The photochemical behavior was examined in a photochemical reactor by irradiating with a light of 254 and 310 nm. After completion of reaction one photoproduct was obtained. The photoproduct was isolated by using column chromatography and the structure of the isolated photoproduct was established by different spectroscopic techniques. This study provides the probable mechanism of the photochemical transformation of metronidazole in presence of an electron donor and in presence of ZnO NPs. During the photochemical transformation the nitro group of metronidazole was reduced in the amine group by a series of electron transfer processes. The ZnO nanoparticles are very efficient catalysts, and they degrade almost 90% metronidazole in the 60 min of UV irradiation. The photocatalytic mechanism of the ZnO nanoparticles is also discussed.

How to cite this paper

 Ahmad, W & Negi, P. (2023). N,N-Dimethylaniline and Zno nanoparticles mediated photochemical transformation of metronidazole.Current Chemistry Letters, 12(4), 733-738.

Refrences

1. Kowalska J., Rok J., Rzepka Z., Wrześniok D. (2021) Drug-Induced Photosensitivity-From Light and Chemistry to Biological Reactions and Clinical Symptoms. Pharmaceuticals (Basel)., 26 723.
2. Jodłowski P. J., Chlebda D. K., Jędrzejczyk, R. J., Dziedzicka A., Kuterasiński Ł., Sitarz M. (2018) Characterisation of well-adhered ZrO2 layers produced on structured reactors using the sonochemical sol–gel method. Applied Surface Science., 427 563-574.
3. Ali A. E., Salem W. M., Younes S. M., Kaid M. (2020) Modeling climatic effect on physiochemical parameters and microorganisms of Stabilization Pond Performance. Heliyon., 6 e04005.
4. Bound J.P., Voulvolis N. (2004) Pharmaceuticals in the aquatic environment-a comparison of risk assessment strategies. Chemosphere., 56 1143–1155.
5. Ravina M., Campanella L., Kiwi J. (2002) Accelerated mineralization of drug Diclofenac via Fenton reactions in a concentric photo-reactor. Water Res. 36 3553–3560.
6. Ahmad W., Singh A., Jaiswal K. K., Gupta P. (2021) Green Synthesis of Photocatalytic TiO2 Nanoparticles for Potential Application in Photochemical Degradation of Ornidazole. Journal of Inorganic and Organometallic Polymers and Materials.,10 614-623.
7. Jodłowski P.J., Kuterasiński Ł., Jędrzejczyk R.J., Chlebda D., Gancarczyk A., Basąg S., Chmielarz L. (2017) DeNOx Abatement Modelling over Sonically Prepared Copper USY and ZSM5 Structured Catalysts. Catalysts. 7(7) 205
8. Ahmad W., Zaheer M. R., Gupta A. (2016) Photodegradation of trimeprazine triggeredby self-photogenerated singlet molecular oxygen. Journal of Saudi Chemical Society., 20 543–546.
9. Ray R.S., Agrawal N., Misra R.B., Farooq M. (2006) Radiation-induced in vitro phototoxic potential of some fluoroquinolones. Drug Chem. Toxicol., 29 25–38.
10. Ahmad W. (2014) Photoinduced Aromatization of Asymmetrically Substituted1,4-Dihydropyridine Derivative Drug Cilnidipine. International Journal of Photochemistry. http://dx.doi.org/10.1155/2014/176989
11. Cosa G, Scaiano J.C. (2004) Laser techniques in the study of drug photochemistry. Photochemistry and Photobiology., 80 159–174.
12. Quintero B, Miranda M.A. (2000) Mechanisms of photosensitization induced by drugs: a general survey. Ars Pharmaceutica., 41 27–46.
13. Gupta A., Iqbal J., Ahmad W. (2014) Photoinduced electron transfer photodegradation of photosensitivediuretic drug-xipamide. Journal of Taibah University for Science., 8 64–70.
14. Lau A. H., Lam N. P., Piscitelli S. C. (1992) Clinical pharmacokinetics of metronidazole and other nitroimidazole antiinfectives. Clin Pharmacokinet., 23 328–364
15. Lanzky P.F, Halling-Sørensen B. (1997) The toxic effect of the antibiotic metronidazole on aquatic organisms. Chemosphere. 35 2553–2561.
16. Bendesky A, Mene’ndez D. (2002) Is Metronidazole carcinogenic? Mutat Res., 511 133–144.
17. Dobias L., Cerna M., Rossner P. (1994) Genotoxicity and carcinogenicity of metronidazole. Mutat Res-Rev Genetic Toxicol., 317 177–194.
18. Ebele AJ, Oluseyi T, Drage D.S., Harrad S. (2020) Occurrence, seasonal variation and human exposure to pharmaceuticals and personal care products in surface water, groundwater and drinking water in Lagos State, Nigeria. Emerg Contam 6:124–132.
19. Ahmad W., Singh A., Jaiswal K. K., Gupta P. (2021) Green Synthesis of Photocatalytic TiO2 Nanoparticles for Potential Application in Photochemical Degradation of Ornidazole. Journal of Inorganic and Organometallic Polymers and Materials., 31 614-623. https://doi.org/10.1007/s10904-020-01703-6.
20. Ahmad W., Kaur N., Joshi H. C. (2022) Photocatalytic behavior of NiO nanoparticles towards photocatalytic degradation of paracetamol. Materials Today: Proceedings., https://doi.org/10.1016/j.matpr.2022.09.075.
21. der Beek T., Weber F.A., Bergmann A., Hickmann S., Ebert I., Hein A., Küster A. (2016) Pharmaceuticals in the environment—Global occurrences and perspectives. J Environ Toxicol Chem 35(4):823–835.
22. Baeissa E.S. (2016) Photocatalytic degradation of methylene blue dye under visible light irradiation using In/ZnO nanocomposite. Front Nanosci Nanotechnol., 2 1–5.
23. Ebele A.J., Abdallah M.A.E., Harrad S. (2017) Pharmaceuticals and personal care products (PPCPs) in the freshwater aquatic environment. J Emerg Contam., 3(1) 1–16.
24. Starling M.C.V., Amorim C.C., Leão M.M.D. (2019) Occurrence, control and fate of contaminants of emerging concern in environmental compartments in Brazil. J Hazard Mater., 372 17–36.
25. Huerta B., Rodriguez-Mozaz S., Nannou C., Nakis L., Ruhí A., Acuña V., Sabater S., Barcelo D. (2016) Determination of a broad spectrum of pharmaceuticals and endocrine disruptors in bioflm from a waste water treatment plant-impacted river. Sci Total Environ., 540 241–249.
26. Assi N, Mehrdad S.A.A., Bakhtiari H., Manuchehri N.Q.S. (2014) Photo catalytic property of ZnO and Mn-ZnO nanoparticles in removal of Cibacet Turquoise blue G from aquatic solution. Int J Nano Dimens., 5 145–154.
27. Mardani HR, Forouzani M, Ziari M, Biparva P. (2015) Visible light photo-degradation of methylene blue over Fe or Cu promoted ZnO nanoparticles. Spectrochim Acta A Mol Biomol Spectrosc 141 27–33.
28. Jurablu S., Farahmandjou M., Firoozabadi T.P. (2015) Sol–gel synthesis of zinc oxide (ZnO) nanoparticles: study of structural and optical properties. J Sci Islam Rep Iran 26 281–285.
29. Ahmad W., Shekhawat B. (2019) Photochemistry of Levofloxacin antibiotics: Direct photodegradation and antimicrobial activity changes. Research Journal of Chemistry and Environment., 23 113-116.
30. Ahmad W. (2019) Role of Copper (II) ion, in the Photochemical and Photosensitizing Properties of Zomepirac.12;2359-2362. DOI: 10.5958/0974-360X.2019.00395.0.