Total synthesis and modification of proline-rich cyclopeptides Phakellistatins 17 and 18 isolated from marine sponge

被引：7
|
作者：
Wu, Ming-hao [1 ,2 ]
Li, Yu-lei [1 ,2 ]
Chang, Qi [1 ,2 ]
Zhao, Xia [1 ,2 ]
Chen, Qing [1 ]
机构：
[1] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Minist Educ, Qingdao 266003, Peoples R China
[2] Qingdao Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao 266237, Peoples R China
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 45期
关键词：
Phakellistatin; Cyclic peptide; Proline-rich; Solid-phase/solution synthesis; Modification; SOLID-PHASE SYNTHESIS; CYCLIC-PEPTIDES; ANTIBACTERIAL; RESISTANCE; INHIBITORS; DISCOVERY;
D O I：
10.1016/j.tetlet.2018.09.059
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Phakellistatins 17 and 18, two naturally occurring cyclic proline-rich peptides from marine sponge, were synthesized by utilizing a two-step solid-phase/solution synthesis strategy for the first time. Phakellistatin 18 exhibited a weak inhibitory activity against human lung carcinoma cell (A549) and human hepatoma (BEL-7042). In order to improve the activity of Phakellistatin 18, two of its analogues which contain sulfonyl fluoride group (P18-1) and arginine substituted derivative (P18-2) were also synthesized respectively. The spectral data of Phakellistatins 17 and 18 were identical to that reported for the natural products. Analogues P18-1 and P18-2 were identified by means of HR-QTOF-MS, H-1 NMR and C-13 NMR. More importantly, analogue P18-1 exhibited significantly enhanced cytotoxicity against BEL-7042 cancer cells compared with Phakellistatin 18, suggesting that the sulfonyl fluoride group in the parent peptide may contribute to the improvement of antitumor activity. This strategy provides a reference method for improving the activity of natural peptides. reserved. (C) 2018 Published by Elsevier Ltd.
引用
收藏
页码：4011 / 4014
页数：4
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