Synthesis of Novel Anticancer Drugs Derived from 4‐nitrobenzaldehyde, and Investigation of Responsive Drug Delivery Systems Based on Carbon Quantum Dots.

Author:

Daniel Sobhi12ORCID,Binu Ann Maria K.3,Sunish K. S.3,Joy Jain2,Sivan Unnikrishnan45,Menon Athira M.4

Affiliation:

1. Postgraduate and Research Department of Chemistry Maharaja's College Ernakulam, Kerala India

2. Research and Postgraduate Department of Chemistry T.M. Jacob Memorial Government College Manimalakunnu, Kerala India

3. Postgraduate and Research department of Zoology Maharaja's College Ernakulam, Kerala India

4. Centre for Neuroscience Department of Biotechnology Cochin University of Science and Technology Kerala India

5. FFE Kerala University of Fisheries and Ocean Studies Kerala India

Abstract

AbstractThe present work describes the synthesis two novel derivatives of 4‐nitrobenzaldehyde through a single pot microwave assisted green synthetic method and the characterization of the synthesized drugs using UV, IR,1HNMR, Mass spectra and CHN analysis. The structure optimization of the synthesized anticancer agents was carried out using Gaussian 9. Also carbon quantum dots (CQDs) derived from amino acid precursors were synthesized (Cystine and threonine) by microwave assisted method, followed by the integration of CQDS together with 4‐nitrobenzaldehyde and its novel derivatives. The drugs were subjected to targeted drug delivery applications in cancer cell lines (PC3) The MTT assay results revealed that the CQDs conjugated with 4‐nitrobenzaldehye (D1) and one of the derivatives (D3) exhibited greater cytotoxic effects on PC3 cells compared to L929 cells. The outcomes demonstrated that this novel derivative could kill cancer cells as effectively as 4‐nitrobenzaldehyde conjugated with CQDs. Also, the potential cytotoxicity of drugs D1 and D3 were further confirmed by the apoptosis assay using flow cytometry, which also explains that apoptosis is the mechanism underlying cell death in PC3 cancer cells. The autofluorescence test were also carried out in PC3 cells lines and the drugs D1 and D3 showed significant autofluorescence in PE−A (29.9 % and 34.7 %), in Alexa Fluor‐488 (32.6 % and61.1 %) and in Bv510‐A (16.6 % and 23.2 %) respectively. Thus, the synergistic effect of CQDs together with 4‐nitrobenzaldehyde and its derivative drug D3 are indeed a promising medication towards the localized drug delivery applications in prostate cancer cells as well as the autofluorescence results will explore novel arenas in bioimaging applications.

Publisher

Wiley

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