Controlling the Uptake of Diarylethene-Based Cell-Penetrating Peptides into Cells Using Light

被引:7
作者
Schober, Tim [1 ]
Wehl, Ilona [2 ]
Afonin, Sergii [3 ]
Babii, Oleg [3 ]
Iampolska, Anna [4 ,5 ]
Schepers, Ute [2 ]
Komarov, Igor, V [4 ,6 ]
Ulrich, Anne S. [1 ,3 ]
机构
[1] KIT, IOC, Fritz Haber Weg 6, D-76131 Karlsruhe, Germany
[2] KIT, Inst Funct Interfaces IFG, POB 3640, D-76021 Karlsruhe, Germany
[3] KIT, Inst Biol Interfaces IBG 2, POB 3640, D-76021 Karlsruhe, Germany
[4] Taras Shevchenko Natl Univ Kyiv, Vul Volodymyrska 60, UA-01601 Kiev, Ukraine
[5] Enamine Ltd, Vul Chervonotkatska 78, UA-02094 Kiev, Ukraine
[6] Lumobiotics GmbH, Auerstr 2, D-76227 Karlsruhe, Germany
基金
欧盟地平线“2020”;
关键词
cell-penetrating peptides; cell uptake; diarylethenes; photopharmacology; photoswitches; PROTEIN-PROTEIN INTERACTIONS; IN-VIVO; DRUG-DELIVERY; DESIGN; PHOTOCONTROL; CYCLOTIDES; DRIVEN;
D O I
10.1002/cptc.201900019
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
We report on diarylethene (DAE)-containing photoswitchable cell-penetrating peptides (CPPs) capable of photocontrolled cell entry. We demonstrate in vitro that reversible photoisomerization of a DAE fragment in the backbones of non-cytotoxic cyclic peptides influences their binding to cell membranes and subsequent CPP-mediated cargo internalization. Benign red light can be used to activate cell entry of our compounds. We suggest that the observed differences in cell uptake of the two photoisomers are due to changes in the molecular flexibility achieved upon DAE photoisomerization.
引用
收藏
页码:384 / 391
页数:8
相关论文
共 95 条
[1]  
[Anonymous], 2012, Angew. Chem
[2]  
[Anonymous], ANGEW CHEM
[3]  
Babii O., 2016, Angewandte Chemie, V128, P5583, DOI [DOI 10.1002/ANGE.201600506, 10.1002/ange.201600506]
[4]  
Babii O., 2014, Angew. Chem, V126, P3460, DOI DOI 10.1002/ANGE.201310019
[5]   Structure-Activity Relationships of Photoswitchable Diarylethene-Based β-Hairpin Peptides as Membranolytic Antimicrobial and Anticancer Agents [J].
Babii, Oleg ;
Afonin, Sergii ;
Ishchenko, Aleksandr Yu. ;
Schober, Tim ;
Negelia, Anatoliy O. ;
Tolstanova, Ganna M. ;
Garmanchuk, Liudmyla V. ;
Ostapchenko, Liudmyla I. ;
Komarov, Igor V. ;
Ulrich, Anne S. .
JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (23) :10793-10813
[6]   Direct Photocontrol of Peptidomimetics: An Alternative to Oxygen-Dependent Photodynamic Cancer Therapy [J].
Babii, Oleg ;
Afonin, Sergii ;
Garmanchuk, Liudmyla V. ;
Nikulina, Viktoria V. ;
Nikolaienko, Tetiana V. ;
Storozhuk, Olha V. ;
Shelest, Dmytro V. ;
Dasyukevich, Olga I. ;
Ostapchenko, Liudmyla I. ;
Iurchenko, Volodymyr ;
Zozulya, Sergey ;
Ulrich, Anne S. ;
Komarov, Igor V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (18) :5493-5496
[7]   Controlling Biological Activity with Light: Diarylethene- Containing Cyclic Peptidomimetics [J].
Babii, Oleg ;
Afonin, Sergii ;
Berditsch, Marina ;
Reisser, Sabine ;
Mykhailiuk, Pavel K. ;
Kubyshkin, Vladimir S. ;
Steinbrecher, Thomas ;
Ulrich, Anne S. ;
Komarov, Igor V. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (13) :3392-3395
[8]   Cell-penetrating peptides: 20 years later, where do we stand? [J].
Bechara, Cherine ;
Sagan, Sandrine .
FEBS LETTERS, 2013, 587 (12) :1693-1702
[9]   Delivering quantum dots to cells: bioconjugated quantum dots for targeted and nonspecific extracellular and intracellular imaging [J].
Biju, Vasudevanpillai ;
Itoh, Tamitake ;
Ishikawa, Mitsuru .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (08) :3031-3056
[10]   Fluorophore labeling of a cell-penetrating peptide induces differential effects on its cellular distribution and affects cell viability [J].
Birch, Ditlev ;
Christensen, Malene Vinther ;
Staerk, Dan ;
Franzyk, Henrik ;
Nielsen, Hanne Morck .
BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES, 2017, 1859 (12) :2483-2494