Chemiluminescence molecular probe with intrinsic auto-inductive amplification: incorporation of chemiexcitation in a quinone-methide elimination

被引:22
作者
Gnaim, Samer [1 ]
Shabat, Doron [1 ]
机构
[1] Tel Aviv Univ, Raymond & Beverly Sackler Fac Exact Sci, Sch Chem, IL-69978 Tel Aviv, Israel
基金
以色列科学基金会;
关键词
SELF-IMMOLATIVE DENDRIMERS; SIGNAL AMPLIFICATION; DIAGNOSTIC PROBE; FLUORIDE IONS; DIOXETANE; DESIGN; LUCIFERIN; REAGENTS; MECHANISM; POLYMERS;
D O I
10.1039/c8cc00521d
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new signal amplification system with an auto-inductive mode of action and distinct chemiluminescence output was developed. The system is composed of a unique structural motif that combines a chemiexcitation mechanism with a quinone-methide elimination into a signal building block. As demonstrated with a probe designed to detect fluoride, an auto-inductive chemiluminescence signal amplification was obtained through self-immolative disassembly and light emission mechanisms.
引用
收藏
页码:2655 / 2658
页数:4
相关论文
共 40 条
[1]   Solvent-cage effect (viscosity dependence) as a diagnostic probe for the mechanism of the intramolecular chemically initiated electron-exchange luminescence (CIEEL) triggered from a spiroadamantyl-substituted dioxetane [J].
Adam, W ;
Bronstein, I ;
Trofimov, AV ;
Vasil'ev, RF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :958-961
[2]   Self-immolative dendrimers [J].
Amir, RJ ;
Pessah, N ;
Shamis, M ;
Shabat, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (37) :4494-4499
[3]   Detection of Enzyme Activity through Catalytic Signal Amplification with Functionalized Gold Nanoparticles [J].
Bonomi, Renato ;
Cazzolaro, Alessandro ;
Sansone, Anna ;
Scrimin, Paolo ;
Prins, Leonard J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (10) :2307-2312
[4]   1,2-DIOXETANES - NOVEL CHEMI-LUMINESCENT ENZYME SUBSTRATES - APPLICATIONS TO IMMUNOASSAYS [J].
BRONSTEIN, I ;
EDWARDS, B ;
VOYTA, JC .
JOURNAL OF BIOLUMINESCENCE AND CHEMILUMINESCENCE, 1989, 4 (01) :99-111
[5]   Design, Synthesis, and Characterization of Small-Molecule Reagents That Cooperatively Provide Dual Readouts for Triaging and, When Necessary, Quantifying Point-of-Need Enzyme Assays [J].
Brooks, Adam D. ;
Mohapatra, Hemakesh ;
Phillips, Scott T. .
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (21) :10437-10445
[6]   End-capped poly(4,5-dichlorophthalaldehyde): a stable self-immolative poly(aldehyde) for translating specific inputs into amplified outputs, both in solution and the solid state [J].
DiLauro, Anthony M. ;
Phillips, Scott T. .
POLYMER CHEMISTRY, 2015, 6 (17) :3252-3258
[7]   Signal amplification and detection via a supramolecular allosteric catalyst [J].
Gianneschi, NC ;
Nguyen, ST ;
Mirkin, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (06) :1644-1645
[8]   Self-Immolative Chemiluminescence Polymers: Innate Assimilation of Chemiexcitation in a Domino-like Depolymerization [J].
Gnaim, Samer ;
Shabat, Doron .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (29) :10002-10008
[9]   Quinone-Methide Species, A Gateway to Functional Molecular Systems: From Self-Immolative Dendrimers to Long-Wavelength Fluorescent Dyes [J].
Gnaim, Samer ;
Shabat, Doron .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (10) :2970-2984
[10]   Approaches towards molecular amplification for sensing [J].
Goggins, Sean ;
Frost, Christopher G. .
ANALYST, 2016, 141 (11) :3157-3218