Synthesis of Novel Bis-imino and Bis-amino Curcuminoids for Evaluation of Their Anticancer and Antibacterial Activity

Priyanka Mathur; Meera Mori; Hitarthi Vyas; Kartik Mor; Jalpa Jagtap; Sumita Vadher; Komal Vyas; Ranjitsinh Devkar; Arpita Desai

doi:10.1021/acsomega.2c06177

Synthesis of Novel Bis-imino and Bis-amino Curcuminoids for Evaluation of Their Anticancer and Antibacterial Activity

ACS Omega. 2022 Dec 2;7(49):45545-45555. doi: 10.1021/acsomega.2c06177. eCollection 2022 Dec 13.

Authors

Priyanka Mathur¹, Meera Mori¹, Hitarthi Vyas², Kartik Mor¹, Jalpa Jagtap¹, Sumita Vadher¹, Komal Vyas³, Ranjitsinh Devkar², Arpita Desai¹

Affiliations

¹ Department of Chemistry, Faculty of Science, The Maharaja Sayajirao University of Baroda, Vadodara 390002, Gujarat, India.
² Department of Zoology, Faculty of Science, The Maharaja Sayajirao University of Baroda, Vadodara 390002, Gujarat, India.
³ Department of Chemistry, Sardar Patel University,Vallabh Vidyanagar 388120, Gujarat, India.

Abstract

A new set of curcumin analogues with a Schiff base moiety were synthesized from a bis-aldehyde derivative of hydroxybenzylidene cyclohexanone and various alicyclic and aromatic amines. The single crystals of compound 2 (bis-aldehyde), compound 3b (bis-cyclohexylimino derivative), and compound 3c (bis-1-imino piperidyl derivative) were developed. The said bis-imino and bis-amino curcuminoids were tested for anticancer activity against MCF-7 utilizing the conventional MTT assay. These Schiff bases had significantly higher anticancer efficacy than curcumin and methotrexate against MCF-7 cell lines. Compounds 3k, 3b, and 3l have the highest efficacy among all synthesized curcuminoids. The MTT results are in accordance with the binding affinities found by docking the said molecules with HER2 Tyrosine Kinase (HER2-TK). Compound 3b is identified as a promising HER2-TK inhibitor and also shows effective inhibition against Gram-positive bacteria Staphylococcus aureus.