Design, Synthesis, In Silico Screening, and Antiproliferative Activity of Novel 1,2,3-Triazole Tethered Dibenzosuberane Conjugates

• Published in: Biotechnology and bioprocess engineering Vol. 28; no. 5; pp. 761 - 773
• Main Authors: Kant, Ravi, Saini, Keshav Kumar, Upadhyay, Ravindra Kumar, Singh, Yogender, Reddy, Y. Veera Manohara, Singh, Shishu Pal, Kareem, M. Abdul, Dasegowda, K. R., Prabhavati, H., Kumar, Rakesh, Park, Jong Pil, Kumar, Lalita S.
• Format: Journal Article
• Language: English
• Published: Seoul The Korean Society for Biotechnology and Bioengineering 01.10.2023; Springer Nature B.V; 한국생물공학회
• Subjects: active sites; Anticancer properties; Antifungal agents; antineoplastic activity; Antiproliferatives; Antitumor activity; Binding; Biotechnology; Cell lines; Chemistry; Chemistry and Materials Science; computer simulation; Conjugates; Cytotoxicity; human cell lines; Industrial and Production Engineering; Infrared spectroscopy; Magnetic resonance spectroscopy; magnetism; Mass spectrometry; Mass spectroscopy; Molecular docking; NMR; NMR spectroscopy; Nuclear magnetic resonance; prediction; Proteins; Research Paper; Synthesis; toxicity testing; Triazoles; 생물공학; dibenzosuberone; docking; isatin; 1,2,3-triazoles; antiproliferative activity
• ISSN: 1226-8372; 1976-3816
• DOI: 10.1007/s12257-023-0077-5

To explore novel and potent compounds with anticancer activity, two series of 1H-1,2,3-triazole tethered dibenzosuberane conjugates ( 5a-i and 5j-n ) were synthesized using a linear and convergent approach. The synthesized novel compounds were screened for their in vitro antiproliferative activity against HepG2 cell lines using the MTT assay to explore their binding interactions with the 5EQG protein. IC 50 values revealed that the most active combination against HepG2 cell lines was triazole tethered with an ortho chloro-substituted aryl ring ( 5g ) (IC 50 : 99.64 µg/mL). The other compounds in the series exhibited comparable cytotoxic activities against HepG2 cell lines. The results were substantiated by molecular docking studies. The majority of the compounds demonstrated high binding affinity for the active site of the targeted protein. In addition, in silico drug-likeness prediction by the ADMET method has been explored with these compounds. All synthesized novel derivatives were characterized by mass spectrometry, infrared spectroscopy, 1 H-nuclear magnetic resonance (NMR) spectroscopy, and 13 C-NMR spectroscopy.