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Bioorg Med Chem Lett. 2015 Nov 15;25(22):5142-6. doi: 10.1016/j.bmcl.2015.10.004. Epub 2015 Oct 9.

Design and synthesis of aloe-emodin derivatives as potent anti-tyrosinase, antibacterial and anti-inflammatory agents.

Author information

1
Department of Biology and Chemical Engineering, Shaoyang University, Shao Shui Xi Road, Shaoyang 422100, China. Electronic address: syuliujb@163.com.
2
Department of Biology and Chemical Engineering, Shaoyang University, Shao Shui Xi Road, Shaoyang 422100, China.

Abstract

Twenty aloe-emodin derivatives were designed, synthesized, and their biological activities were evaluated. Some compounds displayed potent tyrosinase inhibitory activities, especially, compounds with thiosemicarbazide moiety showed more potent inhibitory effects than the other compounds. The structure-activity relationships (SARs) were preliminarily discussed. The inhibition mechanism of selected compounds 1 and 13 were investigated. The results showed compound 1 was reversible inhibitor, however, compound 13 was irreversible. Kinetic analysis indicated that compound 1 was competitive tyrosinase inhibitor. Furthermore, the antibacterial activities and anti-inflammatory activities of some selected compounds were also screened. The results showed that compound 3 exhibited more potent antibacterial activity than the aloe-emodin, compounds 5 and 6 possessed more potent anti-inflammatory activities than the diacerein.

KEYWORDS:

Aloe-emodin derivatives; Anti-inflammatory activity; Antibacterial activity; Tyrosinase inhibitory activities

PMID:
26471089
DOI:
10.1016/j.bmcl.2015.10.004
[Indexed for MEDLINE]

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