Synthetic macrocyclic peptidomimetics as tunable pH probes for the fluorescence imaging of acidic organelles in live cells

被引:144
作者
Galindo, F
Burguete, MI
Vigara, L
Luis, SV
Kabir, N
Gavrilovic, J
Russell, DA
机构
[1] Univ Jaume 1, Dept Quim Inorgan & Organ, Castellon de La Plana 12071, Spain
[2] Univ E Anglia, Sch Chem Sci & Pharm, Norwich NR4 7TJ, Norfolk, England
[3] Univ E Anglia, Sch Biol Sci, Norwich NR4 7TJ, Norfolk, England
基金
英国惠康基金;
关键词
biosensors; fluorescent probes; macrocycles; peptidomimetics; protonation;
D O I
10.1002/anie.200501920
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) Acid test: Macrocyclic compounds that comprise a 9,10-anthracene subunit linked by a C2-symmetric peptidomimetic chain (see formula) are useful as fluorescent probes in a pH range of biomedical interest. Changes in the size of the macrocycle (n = 3,4,6,8) produce a shift in the pKa values. Experiments with live mouse macrophage cells show the selective localization of the probe in the acidic organelles (see differential interference contrast image). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6504 / 6508
页数:5
相关论文
共 37 条
[1]  
*ACS S SER, 1993, FLUOR CHEM ION MOL R, V538
[2]   Self-assembly of small peptidomimetic cyclophanes [J].
Becerril, J ;
Burguete, MI ;
Escuder, B ;
Galindo, F ;
Gavara, R ;
Miravet, JF ;
Luis, SV ;
Peris, G .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (16) :3879-3890
[3]   Efficient macrocyclization of U-turn preorganized peptidomimetics:: The role of intramolecular H-bond and solvophobic effects [J].
Becerril, J ;
Bolte, M ;
Burguete, MI ;
Galindo, F ;
García-España, E ;
Luis, SV ;
Miravet, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6677-6686
[4]  
Beer PD, 2001, ANGEW CHEM INT EDIT, V40, P486, DOI 10.1002/1521-3773(20010202)40:3<486::AID-ANIE486>3.3.CO
[5]  
2-G
[6]  
BEER PD, 2001, ANGEW CHEM, V113, P502
[7]   LUMINESCENCE AND CHARGE-TRANSFER .2. AMINOMETHYL ANTHRACENE-DERIVATIVES AS FLUORESCENT PET (PHOTOINDUCED ELECTRON-TRANSFER) SENSORS FOR PROTONS [J].
BISSELL, RA ;
CALLE, E ;
DE SILVA, AP ;
DESILVA, SA ;
GUNARATNE, HQN ;
HABIBJIWAN, JL ;
PEIRIS, SLA ;
RUPASINGHE, RADD ;
SAMARASINGHE, TKSD ;
SANDANAYAKE, KRAS ;
SOUMILLION, JP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (09) :1559-1564
[8]   Regulation and modulation of pH in the brain [J].
Chesler, M .
PHYSIOLOGICAL REVIEWS, 2003, 83 (04) :1183-1221
[9]   CHEMICAL COMMUNICATION IN WATER USING FLUORESCENT CHEMOSENSORS [J].
CZARNIK, AW .
ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (10) :302-308
[10]   A NEW CLASS OF FLUORESCENT PH INDICATORS BASED ON PHOTOINDUCED ELECTRON-TRANSFER [J].
DE SILVA, AP ;
RUPASINGHE, RADD .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (23) :1669-1670