Functionalizable red emitting calcium sensor bearing a 1,4-triazole chelating moiety

被引：9

作者：

Collot, Mayeul ^{[1
]}

Wilms, Christian ^{[2
,3
]}

Mallet, Jean-Maurice ^{[4
,5
,6
]}

机构：

[1] Univ Strasbourg, UMR CNRS 7213, Lab Biophoton & Pharmacol, Fac Pharm, F-67401 Illkirch Graffenstaden, France

[2] UCL, Wolfson Inst Biomed Res, London WC1E 6BT, England

[3] UCL, Dept Neurosci Physiol & Pharmacol, London WC1E 6BT, England

[4] Univ Paris 06, Lab Biomol LBM, F-75005 Paris, France

[5] ENS, F-75005 Paris, France

[6] CNRS, UMR 7203, F-75005 Paris, France

来源：

RSC ADVANCES | 2015年 / 5卷 / 09期

关键词：

FLUORESCENT; ION; MICROINJECTION; PROBE; CHEMOSENSORS; INDICATORS; SYSTEM;

D O I：

10.1039/c4ra12858c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we developed a functionalizable OFF-ON red emitting fluorescent calcium probe based on a new chelating system formed by CuAAC click chemistry (Huisgen cycloaddition). The pro-sensor 7 which is not sensitive to Ca2+, contains an alkyne moiety that, upon the click reaction, forms a chelating group involving the 1,4-triazole. Probe 10 exhibited good sensitivity towards calcium (K-d = 5.8 mu M) and zinc (5.6 mu M) with a high dynamic range (65 fold fluorescence increase), high quantum yield (0.59) and showed very low fluorescence enhancement in the presence of a high concentration of Mg2+. We extended this method and generated two dextran conjugates in order to compare their sensing properties with those of the molecular form of 10.

引用

收藏

页码：6993 / 7000

页数：8

相关论文

共 32 条

[1] PERFORMANCE OF AN AUTOMATED-SYSTEM FOR CAPILLARY MICROINJECTION INTO LIVING CELLS [J].

ANSORGE, W ;

PEPPERKOK, R .

JOURNAL OF BIOCHEMICAL AND BIOPHYSICAL METHODS, 1988, 16 (04) :283-292

[2] Selective calcium ion sensing with a bichromophoric squaraine foldamer [J].

Arunkumar, E ;

Ajayaghosh, A ;

Daub, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (09) :3156-3164

[3] Specific Ca2+ Fluorescent Sensor: Signaling by Conformationally Induced PET Suppression in a Bichromophoric Acridinedione [J].

Ashokkumar, Pichandi ;

Ramakrishnan, Vayalakkavoor T. ;

Ramamurthy, Perumal .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (34) :5941-5947

[4] Indo-1 Derivatives for Local Calcium Sensing [J].

Bannwarth, Michael ;

Correa, Ivan R., Jr. ;

Sztretye, Monika ;

Pouvreau, Sandrine ;

Fellay, Cindy ;

Aebischer, Annina ;

Royer, Leandro ;

Ríos, Eduardo ;

Johnsson, Kai .

ACS CHEMICAL BIOLOGY, 2009, 4 (03) :179-190

[5] CA2+ TRANSIENTS IN CARDIAC MYOCYTES MEASURED WITH HIGH AND LOW-AFFINITY CA2+ INDICATORS [J].

BERLIN, JR ;

KONISHI, M .

BIOPHYSICAL JOURNAL, 1993, 65 (04) :1632-1647

[6] Ruthenium-catalyzed azide-alkyne cycloaddition: Scope and mechanism [J].

Boren, Brant C. ;

Narayan, Sridhar ;

Rasmussen, Lars K. ;

Zhang, Li ;

Zhao, Haitao ;

Lin, Zhenyang ;

Jia, Guochen ;

Fokin, Valery V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (28) :8923-8930

[7] Synthesis of 3-substituted and 2,3-disubstituted-4H-1,4-benzoxazines [J].

Buon, C ;

Chacun-Lefèvre, L ;

Rabot, R ;

Bouyssou, P ;

Coudert, G .

TETRAHEDRON, 2000, 56 (04) :605-614

[8] The btp [2,6-bis(1,2,3-triazol-4-yl[pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry [J].

Byrne, Joseph P. ;

Kitchen, Jonathan A. ;

Gunnlaugsson, Thorfinnur .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (15) :5302-5325

[9] 2-(1,2,3-Triazol-4-yl)pyridine-containing ethynylarenes as selective 'turn-on' fluorescent chemosensors for Ni(II) [J].

Christensen, Joseph A. ;

Fletcher, James T. .

TETRAHEDRON LETTERS, 2014, 55 (33) :4612-4615

[10] Unexpected remote effect in red fluorescent sensors based on extended APTRA [J].

Collot, Mayeul ;

Lasoroski, Aurelie ;

Zamaleeva, Alsu I. ;

Feltz, Anne ;

Vuilleumier, Rodolphe ;

Mallet, Jean-Maurice .

TETRAHEDRON, 2013, 69 (48) :10482-10487

← 1 2 3 4 →