Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors

Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors Publisher Pubmed

Ghafari S¹ ; Ranjbar S² ; Larijani B³ ; Amini M¹ ; Biglar M⁴ ; Mahdavi M³ ; Bakhshaei M⁵ ; Khoshneviszadeh M⁶ ; Sakhteman A⁵ ; Khoshneviszadeh M⁶

Show Affiliations

1. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
2. Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
3. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
4. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
5. Department of Medicinal Chemistry, School of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Iran
6. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

Source: International Journal of Biological Macromolecules Published:2019

Abstract

Tyrosinase enzyme plays a crucial role in melanin biosynthesis and enzymatic browning process of vegetables and fruits. Hence, tyrosinase inhibitors are important in the fields of medicine, cosmetics and agriculture. In this study, novel N-(2-morpholinoethyl)cinnamamide derivatives bearing different substituents on phenyl ring were designed, synthesized and evaluated for their tyrosinase diphenolase inhibitory activity. The compounds were found to be better tyrosinase inhibitors (IC50s were in micro molar range) than cinnamic acid. (E)-3-(3-chlorophenyl)-N-(2-morpholinoethyl)acrylamide (B6) exhibited the highest inhibition with IC50 value of 15.2 ± 0.6 μM which was comparable to that of kojic acid. The inhibition kinetic analysis of B6 indicated that the compound was a mixed-type tyrosinase inhibitor. In silico ADME prediction indicated that B6 might show more skin penetration than kojic acid. Molecular docking analysis confirmed that the active inhibitors well accommodated in the mushroom tyrosinase active site and it was also revealed that B6 formed the most stable drug-receptor complex with the target protein. Therefore, cinnamamide B6 could be introduced as a potent tyrosinase inhibitor that might be a promising lead in cosmetics, medicine and food industry. © 2019

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Mohammad Mahdavi (6)

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Style	Citing Format
MLA	Ghafari S, et al.. "Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors." International Journal of Biological Macromolecules, vol. 135, no. , 2019, pp. 978-985.
APA	Ghafari S, Ranjbar S, Larijani B, Amini M, Biglar M, Mahdavi M, Bakhshaei M, Khoshneviszadeh M, Sakhteman A, Khoshneviszadeh M (2019). Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors. International Journal of Biological Macromolecules, 135(), 978-985.
Chicago	Ghafari S, Ranjbar S, Larijani B, Amini M, Biglar M, Mahdavi M, Bakhshaei M, Khoshneviszadeh M, Sakhteman A, Khoshneviszadeh M. "Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors." International Journal of Biological Macromolecules 135, no. (2019): 978-985.
Harvard	Ghafari S et al. (2019) 'Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors', International Journal of Biological Macromolecules, 135(), pp. 978-985.
Vancouver	Ghafari S, Ranjbar S, Larijani B, Amini M, Biglar M, Mahdavi M, et al.. Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors. International Journal of Biological Macromolecules. 2019;135():978-985.
BibTex	@article{ author = {Ghafari S and Ranjbar S and Larijani B and Amini M and Biglar M and Mahdavi M and Bakhshaei M and Khoshneviszadeh M and Sakhteman A and Khoshneviszadeh M}, title = {Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors}, journal = {International Journal of Biological Macromolecules}, volume = {135}, number = {}, pages = {978-985}, year = {2019} }
RIS	TY - JOUR AU - Ghafari S AU - Ranjbar S AU - Larijani B AU - Amini M AU - Biglar M AU - Mahdavi M AU - Bakhshaei M AU - Khoshneviszadeh M AU - Sakhteman A AU - Khoshneviszadeh M TI - Novel Morpholine Containing Cinnamoyl Amides As Potent Tyrosinase Inhibitors JO - International Journal of Biological Macromolecules VL - 135 IS - SP - 978 EP - 985 PY - 2019 ER -

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