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生命之色的转变——原卟啉IX在化学生物学中的合成进展与新兴应用

The Red Color of Life Transformed - Synthetic Advances and Emerging Applications of Protoporphyrin IX in Chemical Biology.

作者信息

Sitte Elisabeth, Senge Mathias O

机构信息

School of Chemistry Trinity College Dublin The University of Dublin Trinity Biomedical Sciences Institute 152-160 Pearse Street 2 Dublin Ireland.

Institute for Advanced Study (TUM-IAS) Technische Universität München Lichtenberg-Str. 2a 85748 Garching Germany.

出版信息

European J Org Chem. 2020 Jun 16;2020(22):3171-3191. doi: 10.1002/ejoc.202000074. Epub 2020 Mar 30.

DOI:10.1002/ejoc.202000074
PMID:32612451
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7319466/
Abstract

Protoporphyrin IX (PPIX) is the porphyrin scaffold of heme b, a ubiquitous prosthetic group of proteins responsible for oxygen binding (hemoglobin, myoglobin), electron transfer (cytochrome c) and catalysis (cytochrome P450, catalases, peroxidases). PPIX and its metallated derivatives frequently find application as therapeutic agents, imaging tools, catalysts, sensors and in light harvesting. The vast toolkit of accessible porphyrin functionalization reactions enables easy synthetic modification of PPIX to meet the requirements for its multiple uses. In the past few years, particular interest has arisen in exploiting the interaction of PPIX and its synthetic derivatives with biomolecules such as DNA and heme-binding proteins to evolve molecular devices with new functions as well as to uncover potential therapeutic toeholds. This review strives to shine a light on the most recent developments in the synthetic chemistry of PPIX and its uses in selected fields of chemical biology.

摘要

原卟啉IX（PPIX）是血红素b的卟啉骨架，血红素b是一种普遍存在的蛋白质辅基，负责氧结合（血红蛋白、肌红蛋白）、电子转移（细胞色素c）和催化作用（细胞色素P450、过氧化氢酶、过氧化物酶）。PPIX及其金属化衍生物经常被用作治疗剂、成像工具、催化剂、传感器以及用于光捕获。大量可及的卟啉官能化反应工具包使得对PPIX进行简便的合成修饰成为可能，以满足其多种用途的需求。在过去几年中，人们对利用PPIX及其合成衍生物与生物分子（如DNA和血红素结合蛋白）之间的相互作用来开发具有新功能的分子装置以及揭示潜在的治疗切入点产生了特别的兴趣。本综述旨在阐明PPIX合成化学的最新进展及其在化学生物学特定领域中的应用。

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