Design and synthesis of chemiluminescent substrates with high luminescent efficiency in an aqueous system: 5-tert-butyl-4,4-dimethyl-2,6,7-trioxabicyclo[3.2.0]heptanes bearing a 3-hydroxy-4-(1-iminoethyl)phenyl moiety at the 1-position

Luminescence

Volumn 16, Issue 4, 2001, Pages 275-280

  Matsumoto, Masakatsu ^a   Sakuma, Toshimitsu ^a   Watanabe, Nobuko ^a  

^a KANAGAWA UNIVERSITY   (Japan)

Author keywords

Aqueous system; CIEEL active 1,2 dioxetanes; Oxime; Oxime O alkyl ether; Semicarbazone

Indexed keywords

CHEMILUMINESCENCE; DECAY (ORGANIC); EFFICIENCY;

ALKYL ETHERS; AQUEOUS SYSTEM; CIEEL-ACTIVE 1,2-DIOXETANE; DECAY RATE; DIOXETANES; LUMINESCENT EFFICIENCY; METHYL ETHERS; OXIME; OXIME O-ALKYL ETHER; SEMICARBAZONES;

ETHERS;

1,2 DIOXETANE; 1,2-DIOXETANE; ACETONITRILE; ACETONITRILE DERIVATIVE; DIAGNOSTIC AGENT; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; SEMICARBAZONE DERIVATIVE; WATER;

ARTICLE; CHEMISTRY; CHEMOLUMINESCENCE; DRUG DESIGN; ENZYME SPECIFICITY; METABOLISM; SENSITIVITY AND SPECIFICITY; STRUCTURE ACTIVITY RELATION;

ACETONITRILES; BICYCLO COMPOUNDS, HETEROCYCLIC; CHEMILUMINESCENT MEASUREMENTS; DRUG DESIGN; HETEROCYCLIC COMPOUNDS; SEMICARBAZONES; SENSITIVITY AND SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; WATER;

EID: 0035406551     PISSN: 15227235     EISSN: None     Source Type: Journal    
DOI: 10.1002/bio.650     Document Type: Article

References (5)

1. Schaap AP, Chen T-S, Handley RS, Desilva R, Giri BP. Chemical and enzymatic triggering of 1,2-dioxetanes. 2: Fluonde-induced chemiluminescence from tert-butyldimethylsiloxy-substituted dioxetanes. Tetrahedron Lett. 1997; 28: 1155-1158.
2. Adam W, Bronstein I, Edwards B et al. Electron exchange luminescence of spiroadaniantane-substituted dioxetanes triggered by akaline phosphatase. Kinetics and elucidation of pH effects. J. Am. Chem. Soc. 1996; 118: 10400-10407.
3. Bronstein I, Juo RR, Voyta JC, Edwards B. Novel chemiluminescent adamantyl 1,2-dioxetane enzyme substrates In Bioluminescence and Chemiluminescence, Stanley PE, Kricka LJ Wiley: Chichester, 1991; 74-82.
4. Matsumoto M, Arai N, Watanabe N. 3-(4-Acyl-3-hydroxyphenyl)-1,2-dioxetanes as a chemiluminescent substrate with high efficiency in aqueous system. Tetrahedron Lett. 1996; 37: 8535-8538.
5. Matsumoto M, Watanabe N, Ishikawa A, Murakami H. Base-induced cyclization of 1-benzyloxy-2,2,4,4-tetramethylpentan-3-ones: intramolecular nucleophilic addition of an anion of a benzyl ether to the carbonyl moiety without the Wittig rearrangement or protophilic decomposition. J. Chem. Soc. Chem. Commun. 1997; 2395-2396.