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Int. J. Mol. Sci. 2017, 18(3), 544; doi:10.3390/ijms18030544

d-Amino Acid Position Influences the Anticancer Activity of Galaxamide Analogs: An Apoptotic Mechanism Study

1
College of Pharmacy, Jinan University, Guangzhou 510632, China
2
Key Laboratory of Biomaterials of Guangdong Higher Education Institutes, Department of Biomedical Engineering, Jinan University, Guangzhou 510632, China
3
Department of Chemistry, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, China
*
Authors to whom correspondence should be addressed.
Academic Editor: Anthony Lemarié
Received: 5 December 2016 / Revised: 10 February 2017 / Accepted: 27 February 2017 / Published: 10 March 2017
(This article belongs to the Section Bioactives and Nutraceuticals)
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Abstract

Galaxamide, an extract from Galaxaura filamentosa, is a cyclic pentapeptide containing five l-leucines. Due to the particular cyclic structure and the excellent anticancer activity, synthesis of Galaxamide and its analogs and their subsequent bio-applications have attracted great attention. In the present work, we synthesized six Galaxamide analogs by replacing one of the l-leucines with phenylalanine and varying the d-amino acid position. The anticancer effect of the synthesized Galaxamide analogs was tested against four in vitro human cancer cell lines, human hepatocellular cells (HepG2), human breast cancer cell (MCF-7), human breast adenocarcinoma cells (MDA-MB-435) and a human cervical carcinoma cell line (Hela). Results showed that Galaxamide analogs with different d-amino acid positions displayed distinct anticancer potential. The Galaxamide analog containing d-amino acid at position 5 (Analog-6) presented the strongest anticancer activity. The mechanism study revealed that Analog-6 could cause the early apoptosis of HepG2 cells by inhibiting their growth in the sub-G1 stage of the cell cycle and induce the chromatin condensation and fragmentation, which can be seen as 68% of HepG2 cells inhibited in the sub-G1 stage. Moreover, a mitochondria-mediated pathway was found to be involved in the apoptotic process of Analog-6 on HepG2 cells. View Full-Text
Keywords: Galaxamide analogs; cyclopeptide; d-amino acid; anticancer; mechanism Galaxamide analogs; cyclopeptide; d-amino acid; anticancer; mechanism
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Bai, D.; Yu, S.; Zhong, S.; Zhao, B.; Qiu, S.; Chen, J.; Lunagariya, J.; Liao, X.; Xu, S. d-Amino Acid Position Influences the Anticancer Activity of Galaxamide Analogs: An Apoptotic Mechanism Study. Int. J. Mol. Sci. 2017, 18, 544.

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