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Carvacrol derivatives as mushroom tyrosinase inhibitors; synthesis, kinetics mechanism and molecular docking studies.
PLoS One. 2017; 12(5):e0178069.Plos

Abstract

The present work describesthe development of highly potent mushroom tyrosinase inhibitor better than the standard kojic acid. Carvacrol derivatives 4a-f and 6a-d having substituted benzoic acid and cinnamic acidresidues were synthesized with the aim to possess potent tyrosinase inhibitory activity.The structures of the synthesized compounds were ascertained by their spectroscopic data (FTIR, 1HNMR, 13CNMR and Mass Spectroscopy).Mushroom tyrosinase inhibitory activity of synthesized compounds was determined and it was found that one of the derivative 6c possess higher activity (IC50 0.0167μM) than standard kojic acid (IC50 16.69μM). The derivatives 4c and 6b also showed good tyrosinase inhibitory activity with (IC50 16.69μM) and (IC50 16.69μM) respectively.Lineweaver-Burk and Dixon plots were used for the determination of kinetic mechanism of the compounds 4c and 6b and 6c. The kinetic analysis revealed that compounds 4c and 6b showed mixed-type inhibition while 6c is a non-competitive inhibitor having Ki values19 μM, 10 μM, and 0.05 μMrespectively. The enzyme inhibitory kinetics further showed thatcompounds 6b and 6c formed irreversible enzyme inhibitor complex while 4c bind reversibly with mushroom tyrosinase.The docking studies showed that compound 6c have maximum binding affinity against mushroom tyrosinase (PDBID: 2Y9X) with binding energy value (-7.90 kcal/mol) as compared to others.The 2-hydroxy group in compound 6c interacts with amino acid HIS85 which is present in active binding site. The wet lab results are in good agreement with the dry lab findings.Based upon our investigation we may propose that the compound 6c is promising candidate for the development of safe cosmetic agent.

Authors+Show Affiliations

Department of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan.Department of Biochemistry & Biotechnology (Baghdad-ul-Jadeed Campus), The Islamia University of Bahawalpur, Bahawalpur, Pakistan.Deapertment of Pharmaceutical Chemistry, Riphah Institute of Pharmaceutical Sciences, Riphah International University, Islamabad, Pakistan.Department of Biology, College of Natural Sciences, Kongju National University, Gongju, Republic of Korea.Department of Pharmacy, Faculty of Pharmacy, BahauddinZakria University, Multan Pakistan.Department of Biology, Allama Iqbal Open University, Islamabad, Pakistan.Department of Pharmacy, Faculty of Pharmacy, BahauddinZakria University, Multan Pakistan.School of Chemical Sciences & Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, Bangi, Selangor, Malaysia.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28542395

Citation

Ashraf, Zaman, et al. "Carvacrol Derivatives as Mushroom Tyrosinase Inhibitors; Synthesis, Kinetics Mechanism and Molecular Docking Studies." PloS One, vol. 12, no. 5, 2017, pp. e0178069.
Ashraf Z, Rafiq M, Nadeem H, et al. Carvacrol derivatives as mushroom tyrosinase inhibitors; synthesis, kinetics mechanism and molecular docking studies. PLoS ONE. 2017;12(5):e0178069.
Ashraf, Z., Rafiq, M., Nadeem, H., Hassan, M., Afzal, S., Waseem, M., Afzal, K., & Latip, J. (2017). Carvacrol derivatives as mushroom tyrosinase inhibitors; synthesis, kinetics mechanism and molecular docking studies. PloS One, 12(5), e0178069. https://doi.org/10.1371/journal.pone.0178069
Ashraf Z, et al. Carvacrol Derivatives as Mushroom Tyrosinase Inhibitors; Synthesis, Kinetics Mechanism and Molecular Docking Studies. PLoS ONE. 2017;12(5):e0178069. PubMed PMID: 28542395.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Carvacrol derivatives as mushroom tyrosinase inhibitors; synthesis, kinetics mechanism and molecular docking studies. AU - Ashraf,Zaman, AU - Rafiq,Muhammad, AU - Nadeem,Humaira, AU - Hassan,Mubashir, AU - Afzal,Samina, AU - Waseem,Muhammad, AU - Afzal,Khurram, AU - Latip,Jalifah, Y1 - 2017/05/23/ PY - 2017/02/28/received PY - 2017/05/08/accepted PY - 2017/5/26/entrez PY - 2017/5/26/pubmed PY - 2017/9/19/medline SP - e0178069 EP - e0178069 JF - PloS one JO - PLoS ONE VL - 12 IS - 5 N2 - The present work describesthe development of highly potent mushroom tyrosinase inhibitor better than the standard kojic acid. Carvacrol derivatives 4a-f and 6a-d having substituted benzoic acid and cinnamic acidresidues were synthesized with the aim to possess potent tyrosinase inhibitory activity.The structures of the synthesized compounds were ascertained by their spectroscopic data (FTIR, 1HNMR, 13CNMR and Mass Spectroscopy).Mushroom tyrosinase inhibitory activity of synthesized compounds was determined and it was found that one of the derivative 6c possess higher activity (IC50 0.0167μM) than standard kojic acid (IC50 16.69μM). The derivatives 4c and 6b also showed good tyrosinase inhibitory activity with (IC50 16.69μM) and (IC50 16.69μM) respectively.Lineweaver-Burk and Dixon plots were used for the determination of kinetic mechanism of the compounds 4c and 6b and 6c. The kinetic analysis revealed that compounds 4c and 6b showed mixed-type inhibition while 6c is a non-competitive inhibitor having Ki values19 μM, 10 μM, and 0.05 μMrespectively. The enzyme inhibitory kinetics further showed thatcompounds 6b and 6c formed irreversible enzyme inhibitor complex while 4c bind reversibly with mushroom tyrosinase.The docking studies showed that compound 6c have maximum binding affinity against mushroom tyrosinase (PDBID: 2Y9X) with binding energy value (-7.90 kcal/mol) as compared to others.The 2-hydroxy group in compound 6c interacts with amino acid HIS85 which is present in active binding site. The wet lab results are in good agreement with the dry lab findings.Based upon our investigation we may propose that the compound 6c is promising candidate for the development of safe cosmetic agent. SN - 1932-6203 UR - https://www.unboundmedicine.com/medline/citation/28542395/Carvacrol_derivatives_as_mushroom_tyrosinase_inhibitors L2 - http://dx.plos.org/10.1371/journal.pone.0178069 DB - PRIME DP - Unbound Medicine ER -