Photo-induced radical thiol-ene chemistry: a versatile toolbox for peptide-based drug design

被引：49
作者：
Ahangarpour, Marzieh [1 ,2 ]
Kavianinia, Iman [1 ,2 ,3 ]
Harris, Paul W. R. [1 ,2 ,3 ]
Brimble, Margaret A. [1 ,2 ,3 ]
机构：
[1] Univ Auckland, Sch Chem Sci, 23 Symonds St, Auckland 1010, New Zealand
[2] Univ Auckland, Maurice Wilkins Ctr Mol Biodiscovery, 3 Symonds St, Auckland 1010, New Zealand
[3] Univ Auckland, Sch Biol Sci, 3A Symonds St, Auckland 1010, New Zealand
来源：
CHEMICAL SOCIETY REVIEWS | 2021年 / 50卷 / 02期
关键词：
GLYCOSYLATION; ALBUMIN;
D O I：
10.1039/d0cs00354a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
While the global market for peptide/protein-based therapeutics is witnessing significant growth, the development of peptide drugs remains challenging due to their Low oral bioavailability, poor membrane permeability, and reduced metabolic stability. However, a toolbox of chemical approaches has been explored for peptide modification to overcome these obstacles. In recent years, there has been a revival of interest in photoinduced radical thiol-ene chemistry as a powerful tool for the construction of therapeutic peptides.
引用
收藏
页码：898 / 944
页数：47
相关论文
共 415 条
[1]   Natural Cyclic Peptides as an Attractive Modality for Therapeutics: A Mini Review [J].
Abdalla, Muna Ali ;
McGaw, Lyndy J. .
MOLECULES, 2018, 23 (08)
[2]   A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].
Agard, NJ ;
Prescher, JA ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047
[3]   Regulating the regulator: post-translational modification of RAS [J].
Ahearn, Ian M. ;
Haigis, Kevin ;
Bar-Sagi, Dafna ;
Philips, Mark R. .
NATURE REVIEWS MOLECULAR CELL BIOLOGY, 2012, 13 (01) :39-51
[4]   Synthesis of cyclic, multivalent Arg-Gly-Asp using sequential thiol-ene/thiol-yne photoreactions [J].
Aimetti, Alex A. ;
Feaver, Kristen R. ;
Anseth, Kristi S. .
CHEMICAL COMMUNICATIONS, 2010, 46 (31) :5781-5783
[5]   On-resin peptide macrocyclization using thiol-ene click chemistry [J].
Aimetti, Alex A. ;
Shoemaker, Richard K. ;
Lin, Chien-Chi ;
Anseth, Kristi S. .
CHEMICAL COMMUNICATIONS, 2010, 46 (23) :4061-4063
[6]   Intramolecular hydrogen bonding to improve membrane permeability and absorption in beyond rule of five chemical space [J].
Alex, Alexander ;
Millan, David S. ;
Perez, Manuel ;
Wakenhut, Florian ;
Whitlock, Gavin A. .
MEDCHEMCOMM, 2011, 2 (07) :669-674
[7]   Stapled Peptides Inhibitors: A New Window for Target Drug Discovery [J].
Ali, Ameena M. ;
Atmaj, Jack ;
Van Oosterwijk, Niels ;
Groves, Matthew R. ;
Domling, Alexander .
COMPUTATIONAL AND STRUCTURAL BIOTECHNOLOGY JOURNAL, 2019, 17 :263-281
[8]   MEDI0382, a GLP-1/glucagon receptor dual agonist, meets safety and tolerability endpoints in a single-dose, healthy-subject, randomized, Phase 1 study [J].
Ambery, Philip D. ;
Klammt, Sebastian ;
Posch, Maximillian G. ;
Petrone, Marcella ;
Pu, Wenji ;
Rondinone, Cristina ;
Jermutus, Lutz ;
Hirshberg, Boaz .
BRITISH JOURNAL OF CLINICAL PHARMACOLOGY, 2018, 84 (10) :2325-2335
[9]   Influence of Phenotypic Dissociation in Bacillus subtilis Strain ET-1 on Iturin A Production [J].
Ambrico, Alfredo ;
Trupo, Mario ;
Magarelli, Rosaria A. .
CURRENT MICROBIOLOGY, 2019, 76 (12) :1487-1494
[10]   Total chemical synthesis of glycocin F and analogues: S-glycosylation confers improved antimicrobial activity [J].
Amso, Zaid ;
Bisset, Sean W. ;
Yang, Sung-Hyun ;
Harris, Paul W. R. ;
Wright, Tom H. ;
Navo, Claudio D. ;
Patchett, Mark L. ;
Norris, Gillian E. ;
Brimble, Margaret A. .
CHEMICAL SCIENCE, 2018, 9 (06) :1686-1691
12345678910