Molecular docking studies and biological evaluation of chalcone based pyrazolines as tyrosinase inhibitors and potential anticancer agents

Hua Li Qin, Zhen Peng Shang, Ibrahim Jantan, Oya Unsal Tan, Muhammad Ajaz Hussain, Muhammad Sher, Bukhari Syed Nasir Abbas

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Studies on the discovery of tyrosinase enzyme inhibitors and exploration for better cytotoxic agents remain an important line in drug discovery and development. A series of synthetic chalcones and pyrazoline derivatives was evaluated for their inhibitory effects on the diphenolase activity of mushroom tyrosinase. The effects of these compounds on proliferation and microtubule assembly were also evaluated in seven different cancer cell lines. The results revealed that some of the synthetic compounds showed significant inhibitory activity, with four compounds being more potent tyrosinase inhibitors than the reference standard inhibitor kojic acid. Several compounds were toxic to cancer cell lines. Compound 1a was found to possess the highest anticancer activity towards all cell lines with an IC<inf>50</inf> in the range of 0.9-2.2 μM. Seven of the compounds showed considerable tubulin polymerization activity at a concentration of 25 μM. Molecular modeling studies of these synthetic compounds were performed to investigate their interactions with the tyrosinase enzyme. The structure-activity relationship (SAR) study using in-silico analysis matched well with the in vitro tumour cell inhibitory activity.

Original languageEnglish
Pages (from-to)46330-46338
Number of pages9
JournalRSC Advances
Volume5
Issue number57
DOIs
Publication statusPublished - 2015

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Chalcone
Monophenol Monooxygenase
Antineoplastic Agents
Cells
Enzymes
Chalcones
Molecular modeling
Poisons
Cytotoxins
Enzyme Inhibitors
Tubulin
Tumors
Polymerization
Derivatives
Acids

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Molecular docking studies and biological evaluation of chalcone based pyrazolines as tyrosinase inhibitors and potential anticancer agents. / Qin, Hua Li; Shang, Zhen Peng; Jantan, Ibrahim; Tan, Oya Unsal; Hussain, Muhammad Ajaz; Sher, Muhammad; Syed Nasir Abbas, Bukhari.

In: RSC Advances, Vol. 5, No. 57, 2015, p. 46330-46338.

Research output: Contribution to journalArticle

Qin, Hua Li ; Shang, Zhen Peng ; Jantan, Ibrahim ; Tan, Oya Unsal ; Hussain, Muhammad Ajaz ; Sher, Muhammad ; Syed Nasir Abbas, Bukhari. / Molecular docking studies and biological evaluation of chalcone based pyrazolines as tyrosinase inhibitors and potential anticancer agents. In: RSC Advances. 2015 ; Vol. 5, No. 57. pp. 46330-46338.
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AU - Sher, Muhammad

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