Synthesis, structural examination, molecular interaction analysis, invitro and insilico anticancer activity investigation of a new curcumin derivative: 1- (4 – chlorobenzoyl) - 3, 5 - bis ((E) - 4 - methoxybenzylidene) piperidin - 4 – one

• Published in: Chemical physics impact 2024-06, Vol.8, p.100559, Article 100559
• Main Authors: Fathima, A. Anish, Kumaravel, Varuna, Jonathan, D. Reuben, Sadasivam, Senthil Kumar, Yuvashri, R., Usha, G.
• Format: Article
• Language: English
• Subjects: Anticancer activity; Curcumin derivative; FTIR; In-silico investigation; NMR; SCXRD
• ISSN: 2667-0224; 2667-0224
• DOI: 10.1016/j.chphi.2024.100559

•A new curcumin derivative has been synthesized using Claisen-Schmidt condensation reaction and Schotten-Baumann reaction methods.•Single crystal XRD reveals that the compound crystallized in monoclinic crystal system with P21/c space group.•The obtained crystal was characterized and analyzed using NMR, FTIR, FT-Raman spectra UV, PL, and TG/DTA thermograms.•Various non-covalent interactions and energy frameworks analysis have been visualized using crystal explorer 17.5.•In-vitro and in-silico investigation have been performed and found to exhibit potential anticancer activity against breast cancer. The title material, C28H24ClNO4, was synthesized using the Claisen-Schmidt condensation reaction and Schotten-Baumann reaction methods and crystallized. Geometrical parameters were determined for the grown crystal using the Single Crystal X-Ray Diffraction (SCXRD) technique. The title compound has been characterized and anzalyzed for its optical properties via1H1 and 13C NMR, FT-Raman, and FT-IR, UV and PL spectra. The melting point and thermal stability have been investigated using TG/DTA thermograms.Hirshfeld surfaces were developed in order to observe and quantify short contacts, CH…π and π...π stacking interactions. To determine how various interactions influence the overall Hirshfeld surface, 2D fingerprint plots were created, and it was discovered that the H…H contact's contribution was the most significant. Cytotoxic effect on HEK293 cell lines was performed and found to be highly toxic. To determine the compound's efficacy as an anticancer agent, a research was conducted using MCF-7 cell lines. Molecular docking simulation revealed that the title material (ligand) fits well at the active site of the target protein with PDB ID: 1M17. Pharmacokinetic, and ADMET properties revealed that the compound is exceedingly orally active, and after further biological and pharmaceutical investigations, the compound can be recommended as a drug candidate. [Display omitted]