Biological activity and molecular docking studies of curcumin-related α,β-unsaturated carbonyl-based synthetic compounds as anticancer agents and mushroom tyrosinase inhibitors

Bukhari Syed Nasir Abbas, Ibrahim Jantan, Oya Unsal Tan, Muhammad Sher, M. Naeem-Ul-Hassan, Hua Li Qin

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Hyperpigmentation in human skin and enzymatic browning in fruits, which are caused by tyrosinase enzyme, are not desirable. Investigations in the discovery of tyrosinase enzyme inhibitors and search for improved cytotoxic agents continue to be an important line in drug discovery and development. In present work, a new series of 30 compounds bearing α,β-unsaturated carbonyl moiety was designed and synthesized following curcumin as model. All compounds were evaluated for their effects on human cancer cell lines and mushroom tyrosinase enzyme. Moreover, the structure-activity relationships of these compounds are also explained. Molecular modeling studies of these new compounds were carried out to explore interactions with tyrosinase enzyme. Synthetic curcumin-like compounds (2a-b) were identified as potent anticancer agents with 81-82% cytotoxicity. Five of these newly synthesized compounds (1a, 8a-b, 10a-b) emerged to be the potent inhibitors of mushroom tyrosinase, providing further insight into designing compounds useful in fields of food, health, and agriculture.

Original languageEnglish
Pages (from-to)5538-5547
Number of pages10
JournalJournal of Agricultural and Food Chemistry
Volume62
Issue number24
DOIs
Publication statusPublished - 18 Jun 2014

Fingerprint

Curcumin
curcumin
Monophenol Monooxygenase
antineoplastic agents
Agaricales
Bioactivity
Antineoplastic Agents
mushrooms
bioactive properties
enzymes
enzymatic browning
health foods
enzyme inhibitors
structure-activity relationships
skin (animal)
Bearings (structural)
Enzymes
cytotoxicity
Hyperpigmentation
cell lines

Keywords

  • antibrowning
  • Curcuma longa
  • cytotoxicity
  • melanogenesis
  • synthesis

ASJC Scopus subject areas

  • Agricultural and Biological Sciences(all)
  • Chemistry(all)

Cite this

Biological activity and molecular docking studies of curcumin-related α,β-unsaturated carbonyl-based synthetic compounds as anticancer agents and mushroom tyrosinase inhibitors. / Syed Nasir Abbas, Bukhari; Jantan, Ibrahim; Unsal Tan, Oya; Sher, Muhammad; Naeem-Ul-Hassan, M.; Qin, Hua Li.

In: Journal of Agricultural and Food Chemistry, Vol. 62, No. 24, 18.06.2014, p. 5538-5547.

Research output: Contribution to journalArticle

Syed Nasir Abbas, Bukhari ; Jantan, Ibrahim ; Unsal Tan, Oya ; Sher, Muhammad ; Naeem-Ul-Hassan, M. ; Qin, Hua Li. / Biological activity and molecular docking studies of curcumin-related α,β-unsaturated carbonyl-based synthetic compounds as anticancer agents and mushroom tyrosinase inhibitors. In: Journal of Agricultural and Food Chemistry. 2014 ; Vol. 62, No. 24. pp. 5538-5547.
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