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US 7,115,757 B2Granted
1,2-dioxetane derivatives and reagents employing them
AssigneeTosoh Corporation
InventorsMasakatsu Matsumoto, Nobuko Watanabe, Masashi Yamada
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AssigneeTosoh Corporation
InventorsMasakatsu Matsumoto, Nobuko Watanabe, Masashi Yamada
Estimating the term…
A 1,2-dioxetane derivative of the formula (I): wherein Ar is an aryl group which may have an alkyl group, an aryl group, a halogen atom, an alkoxyl group, a carboxyl group, a formyl group, an alkyl ester, an aryl ester, an alkylketone, an arylketone or a hetero ring bonded thereto, X is a substituent capable of labeling an organic compound or a biological molecule, or an ester, Y is a hydrogen atom, an acyl group or a group of the formula —Si(R4R5R6) (wherein each of R4, R5 and R6 which are independent of one another, is an alkyl group or an aryl group), Z is an alkyl group, an aryl group, an oxygen atom, a sulfur atom, a carbonyl group, —(CO)—O—, —O—(CO)—, —NH—, —NH—CO—, —CO—NH—, —OSi(R7R8)— (wherein each of R7 and R8 which are independent of each other, is an alkyl group or aryl group) or a group of the formula —(R9R10)SiO— (wherein each of R9 and R10 which are independent of each other, is an alkyl group or an aryl group), each of R1 and R2 is an alkyl group or an aryl group, and R3 is a spacer.
A chemiluminescent reagent, comprising:
An immunoassay reagent, comprising a 1,2-dioxetane derivative of formula (I) bonded via X of formula (I) to an antibody or a receptor:
An immunoassay reagent, comprising:
Dependencies are inferred from the claim text.
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From the US filing history. Foreign family members aren’t listed.
In which the condensed system contains two hetero rings: ortho-condensed systems
Heterocyclic compounds containing rings having two oxygen atoms as the only ring
Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages: compounds having Si-O-C linkages
Heterocyclic compounds
Term ended 7 Mar 2023 (estimated)
The present invention relates to 1,2-dioxetane derivatives. The 1,2-dioxetane derivatives of the present invention are compounds which are capable of inducing chemiluminescence and can be used, for example, as substrates for immunoassay.
Heretofore, various 1,2-dioxetane derivatives have been synthesized, and it is known that compounds having a spiroadamantyl group bonded at the 3-position, are useful as chemiluminescent substrates (see, for example, JP-B-5-21918, and JP-B-5-45590) Further, as produced by the present inventors, various compounds are known (see, for example, JP-A-8-245615, JP-A-8-169885, JP-A-8-165287 and JP-A-2002-338576). These 1,2-dioxetane derivatives have an enzyme recognition site such as a phosphate ester group and will be triggered by an enzyme to produce luminescence. A series of such compounds are useful for a method wherein the activities of an enzyme labeled on an antigen or antibody adsorbed on a solid phase after an immunoreaction, are detected by a chemiluminescent reaction. In such a method, a 1,2-dioxetane solution is added to the measuring system, whereby even in a case no enzyme is present, luminescence by a heat or by a non-enzymatic decomposition reaction of e.g. a trace amount of impurities, will be detected, which leads to a rise of the background. Such a rise of the background is substantially influential to the detection sensitivity and thus is problematic.
Therefore, various compounds have been synthesized (see, for example, Japanese Patent 2,572,171, JP-A-08-502968 and JP-A-2002-508654), but the low stability of such dioxetane compounds themselves has still remained as a problem to be solved.
In the accompanying drawing,
FIG. 1 is a graph showing a luminescence curve obtained in Example 38.
Now, the present invention will be described in detail with reference to the preferred embodiments.
In this specification, “an alkyl group” means a C1-20 straight chain or branched alkyl group which may have a substituent, and it may, for example, be a straight chain group such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl or icosanyl, or a group in which such an alkyl group is branched. The substituent which such an alkyl group may have, is, for example, a hydroxyl group, an alkoxyl group or an aryl group.
In this specification, “an alkoxyl group” may, for example, be one having from 1 to 5 C1-20 alkoxyl groups bonded in a straight chain form or in a branched form, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, methoxyethoxy, methoxypropoxy, ethoxyethoxy, ethoxypropoxy or methoxyethoxyethoxy. In this specification, “an aryl group” may, for example, be a C6-20 aromatic hydrocarbon group such as phenyl or naphthyl, or a heteroaryl group having from 1 to 5 nitrogen atoms, oxygen atoms or sulfur atoms in a ring, such as furyl, thienyl or pyridyl.