Second generation specific-enzyme-activated rotaxane propeptides

被引：45

作者：

Fernandes, Antony ^{[2
,3
]}

Viterisi, Aurelien ^{[2
]}

Aucagne, Vincent ^{[1
]}

Leigh, David A. ^{[2
]}

Papot, Sebastien ^{[3
]}

机构：

[1] CNRS, Ctr Biophys Mol, UPR 4301, F-45071 Orleans 2, France

[2] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland

[3] Univ Poitiers, CNRS, Lab Synth & Reactivite Subst Nat, UMR 6514, F-86022 Poitiers, France

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 15期

基金：

英国工程与自然科学研究理事会;

关键词：

MOLECULAR MACHINE; PEPTIDE ROTAXANES; TERMINAL ALKYNES; POLYROTAXANE; DELIVERY; RELEASE; SHUTTLE; STATION; AZIDES; DNA;

D O I：

10.1039/c2cc17458h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A [2] rotaxane, in which the peptidic axle is protected from degradation by the macrocyclic sheath and terminated with a novel glycosidase-cleavable stopper, is rendered water-soluble by derivatisation with tetra(ethylene glycol) (TetEG) or glucosylated tetra(ethylene glycol) (Glc-TetEG) chains using the CuAAC 'click' reaction. The Glc-TetEG-derivatised rotaxane propeptide is > 50 000 times more soluble in aqueous media than the parent rotaxane. Activation of the water-soluble rotaxane propeptide with a beta-galactosidase efficiently releases the parent peptide.

引用

收藏

页码：2083 / 2085

页数：3

相关论文

共 35 条

[11] A new pH-switchable dimannosyl[c2]daisy chain molecular machine [J].

Coutrot, Frederic ;

Romuald, Camille ;

Busseron, Eric .

ORGANIC LETTERS, 2008, 10 (17) :3741-3744

[12] A new glycorotaxane molecular machine based on an anilinium and a triazolium station [J].

Coutrot, Frederic ;

Busseron, Eric .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) :4784-4787

[13] A very efficient synthesis of a mannosyl orthoester [2]rotaxane and mannosidic [2]rotaxanes [J].

Coutrot, Frederic ;

Busseron, Eric ;

Montero, Jean-Louis .

ORGANIC LETTERS, 2008, 10 (05) :753-756

[14] Controlling the Chair Conformation of a Mannopyranose in a Large-Amplitude [2]Rotaxane Molecular Machine [J].

Coutrot, Frederic ;

Busseron, Eric .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (21) :5186-5190

[15] Hydrogen bond-assembled fullerene molecular shuttle [J].

Da Ros, T ;

Guldi, DM ;

Morales, AF ;

Leigh, DA ;

Prato, M ;

Turco, R .

ORGANIC LETTERS, 2003, 5 (05) :689-691

[16] Host-[2] rotaxanes as cellular transport agents [J].

Dvornikovs, V ;

House, BE ;

Kaetzel, M ;

Dedman, JR ;

Smithrud, DB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (27) :8290-8301

[17] Rotaxane-Based Propeptides: Protection and Enzymatic Release of a Bioactive Pentapeptide [J].

Fernandes, Anthony ;

Viterisi, Aurelien ;

Coutrot, Frederic ;

Potok, Stephanie ;

Leigh, David A. ;

Aucagne, Vincent ;

Papot, Sebastien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (35) :6443-6447

[18] The application of CuAAC 'click' chemistry to catenane and rotaxane synthesis [J].

Haenni, Kevin D. ;

Leigh, David A. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1240-1251

[19] Glycylglycine rotaxanes - The hydrogen bond directed assembly of synthetic peptide rotaxanes [J].

Leigh, DA ;

Murphy, A ;

Smart, JP ;

Slawin, AMZ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (07) :728-732

[20] In vitro assessment of a novel polyrotaxane-based drug delivery system integrated with a cell-penetrating peptide [J].

Moon, Cheol ;

Kwon, Young Min ;

Lee, Won Kyu ;

Park, Yoon Jeong ;

Yang, Victor C. .

JOURNAL OF CONTROLLED RELEASE, 2007, 124 (1-2) :43-50

← 1 2 3 4 →