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Position Effect of Fatty Acid Modification on the Cytotoxicity and Antimetastasis Potential of the Cytotoxic Peptide Lycosin-I.

Abstract：

:Peptide modification with fatty acids is an effective method to improve peptide performance. We previously investigated the fatty acid modification of R-lycosin-I, a cytotoxic peptide derived from lycosin-I from the venom of the spider Lycosa singoriensis. In this study, we further investigated the position effects of fatty acid modification of lycosin-I. Dodecanoic acid was covalently coupled to the α/ε-amino group of one of the seven Lys residues of lycosin-I, generating eight different lipopeptides. Although all the lipopeptides had significantly improved cytotoxicity compared with lycosin-I, they displayed different cytotoxic potencies and profiles, which might be explained by multifactors including charge, size, helicity, hydrophobicity, and so forth. Of the eight lipopeptides, L-C12 demonstrated highest cytotoxicity and antimetastasis activity in two-dimensional cells, tumor spheroids, subcutaneous transplantation mouse models, and experimental melanoma metastasis mouse models. Collectively, our finding indicated that fatty acid modification position plays important roles in physiochemical parameters and biological activities of cytotoxic peptides.

journal_name

J Med Chem

journal_title

Journal of medicinal chemistry

authors

Zhang P,Jian C,Jian S,Zhang Q,Sun X,Nie L,Liu B,Li F,Li J,Liu M,Liang S,Zeng Y,Liu Z

doi

10.1021/acs.jmedchem.9b01126

subject

Has Abstract

pub_date

2019-12-26 00:00:00

pages

11108-11118

issue

24

eissn

0022-2623

issn

1520-4804

journal_volume

62

pub_type

杂志文章

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