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光控二噻吩乙烯修饰的环肽：在斑马鱼胚胎中光开关体内毒性

Light-controllable dithienylethene-modified cyclic peptides: photoswitching the in vivo toxicity in zebrafish embryos.

作者信息

Afonin Sergii, Babii Oleg, Reuter Aline, Middel Volker, Takamiya Masanari, Strähle Uwe, Komarov Igor V, Ulrich Anne S

机构信息

Institute of Biological Interfaces (IBG-2), Karlsruhe Institute of Technology (KIT), POB 3640, 76021 Karlsruhe, Germany.

Institute of Organic Chemistry (IOC), KIT, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany.

出版信息

Beilstein J Org Chem. 2020 Jan 7;16:39-49. doi: 10.3762/bjoc.16.6. eCollection 2020.

DOI:10.3762/bjoc.16.6
PMID:31976015
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6964649/
Abstract

This study evaluates the embryotoxicity of dithienylethene-modified peptides upon photoswitching, using 19 analogues based on the β-hairpin scaffold of the natural membranolytic peptide gramicidin S. We established an in vivo assay in two variations (with ex vivo and in situ photoisomerization), using larvae of the model organism and determined the toxicities of the peptides in terms of 50% lethal doses (LD). This study allowed us to: (i) demonstrate the feasibility of evaluating peptide toxicity with larvae at 3-4 days post fertilization, (ii) determine the phototherapeutic safety windows for all peptides, (iii) demonstrate photoswitching of the whole-body toxicity for the dithienylethene-modified peptides in vivo, (iv) re-analyze previous structure-toxicity relationship data, and (v) select promising candidates for potential clinical development.

摘要

本研究使用基于天然膜溶解肽短杆菌肽S的β-发夹支架的19种类似物，评估了光开关作用下二噻吩乙烯修饰肽的胚胎毒性。我们建立了两种变体的体内试验（离体和原位光异构化），使用模式生物的幼虫，并根据50%致死剂量（LD）确定肽的毒性。这项研究使我们能够：（i）证明在受精后3-4天用幼虫评估肽毒性的可行性，（ii）确定所有肽的光治疗安全窗口，（iii）证明体内二噻吩乙烯修饰肽的全身毒性的光开关作用，（iv）重新分析以前的结构-毒性关系数据，以及（v）选择有潜力用于临床开发的有前景的候选物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/43b2565eadbe/Beilstein_J_Org_Chem-16-39-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/a42eec4d6a4d/Beilstein_J_Org_Chem-16-39-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/a3fccf86e70f/Beilstein_J_Org_Chem-16-39-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/115458e78a81/Beilstein_J_Org_Chem-16-39-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/4f0427b75906/Beilstein_J_Org_Chem-16-39-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/43b2565eadbe/Beilstein_J_Org_Chem-16-39-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/a42eec4d6a4d/Beilstein_J_Org_Chem-16-39-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/a3fccf86e70f/Beilstein_J_Org_Chem-16-39-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/115458e78a81/Beilstein_J_Org_Chem-16-39-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/4f0427b75906/Beilstein_J_Org_Chem-16-39-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35cb/6964649/43b2565eadbe/Beilstein_J_Org_Chem-16-39-g006.jpg

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