Chemiluminescent enhancers

C - Chemistry – Metallurgy – 12 – Q

Patent

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C12Q 1/28 (2006.01) G01N 21/76 (2006.01) G01N 33/52 (2006.01) G01N 33/53 (2006.01) G01N 33/58 (2006.01)

Patent

CA 2125866

2125866 9316195 PCTABS00025 A method of increasing the light output and/or signal: background ratio of light output from a chemiluminescent reaction of a dihydrophthalazinedione (DPD), a peroxidase enzyme catalyst and an oxidant, by carrying out this reaction in the presence of an enhancer, "signal" being in the presence of the peroxidase, "background" in its absence, characterised in that the enhancer includes compounds of formula (I) in which R, W, X, Y and Z have the following meanings: R is selected from hydrogen, n-butyl, O,O-propylene (a cyclic ether), 4'-chlorophenyl and 3',5'-dichlorophenyl, W is selected from hydrogen, hydroxy, methyl, methoxy and chloro, X is selected from hydrogen, methyl, chloro, amino and nitro, Y is selected from hydrogen, methyl, carboxy, chloro, bromo, iodo, phenyl, phenoxy, 4'-chloroanilino, 4'-boronylphenyl, 4'-bromophenyl, 2'-carboxyethenyl and trimethylsilyl, Z is selected from hydrogen, 5-chloro, 5-bromo, 5-(3'-trifluoromethyl)phenylazo, or 6-chloro, W and X together may represent a fused benzene ring and X and Y together may represent a fused benzene ring substituted by hydroxy in the 6-position of the naphthalene ring numbering, provided that when R is hydrogen, W, X, Y, Z are each separately hydrogen; when R, W, X and Z are each hydrogen Y is selected from iodo, bromo, chloro, trimethylsilyl, phenoxy, phenyl, 4'-chloroanilino, methyl, 4'-boronylphenyl, 2'-carboxyethenyl; when Y is hydrogen and the Rs together represent O,O-propylene (a cyclic ether), X is hydrogen; when R, W and Z are each hydrogen, X and Y together represent a fused benzene ring substituted by hydroxy in the 6-position of the naphthalene ring numbering; when W, X and Z are each hydrogen, R is n-butyl and Y is bromo or 4'-bromophenyl; when W, X and Z are each hydrogen, R is 4'-chlorophenyl and Y is chloro; when W and Y are each hydrogen, R is 3', 5'-dichlorophenyl, Y is chloro and Z is 5-chloro; when W is methoxy, Z is 5-bromo; when W is hydroxy, Z is 5-(3'-trifluoromethyl)phenylazo; when W is chloro, X is chloro when Y is chloro, X is nitro or chloro; when Y is carboxy, X is nitro; when W and Y are each chloro and X is amino, Z is 6-chloro; and the compounds bis(catechol)borate, boroglycine, pentaerythritol borate, 4-(3'-borono-4'-hydroxyphenylazo)benzoic acid, diphenylisobutoxyborane, diphenylboronic anhydride, dimethylphenylboronic acid (substitution pattern not established) and the sodium salt of 3-nitrophenylboronic acid.

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