Molecular analytical release tags and their use in chemical analysis
First Claim
1. A release tag compound for labeling substances for analytical purposes, said compound being represented by the formula
wherein;
each Sg is a signal group, each CO is a carbonyl group to which an Sg is bonded, each Rx is a reactivity group, L is a linking group to which each SgCO group and each Rx group are bonded, and each COL portion is a release group which is cleavable to release an Sg-containing compound; and
wherein;
each Sg is a C-linked organic moiety containing from 1 to 20 carbon atoms, the carbon atom of Sg which is bonded to the carbonyl carbon adjacent to linking group L being denominated as the α
-position, and Sg comprises a radical selected from the group consisting of substituted alkyl, substituted keto-alkyl, substituted alkenyl, and substituted alkynyl radicals;
said substituted alkyl, substituted keto-alkyl, and substituted alkenyl radicals bearing at least two electronegative substituents, and said substituted alkynyl radicals bearing at least one electronegative substituent;
said electronegative substituents being selected from the group consisting of halogens, cyano, dihalomethyl and trihalomethyl; and
further,1) when Sg is keto-alkyl, alkenyl, or alkynyl, Sg comprises at least one moiety selected from the group consisting of;
β
-E-alkynyl, α
-E-α
-alkynyl, β
-E-α
-keto (provided that the carbonyl carbon adjacent to linking group L is connected to a nitrogen or oxygen atom of L), α
-E-alkenyl, and α
-E-α
-alkenyl, wherein E is an electronegative substituent selected from the group consisting of halogens, cyano, dihalomethyl, and trihalomethyl;
2) when Sg is alkyl, the α
-carbon atom bears at least two of said electronegative substituents but no more than one fluorine atom;
each Sg being further selected such that upon cleavage of said release tag compound at said COL portion, signal group Sg is released in a volatile form suitable for electron capture determination in the gas phase;
L is oxy or amino; and
Rx comprises a phenylene moiety which is connected to L and which contains a reactive, functional group.
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Accused Products
Abstract
Analytical reagents designated "release tags", for labeling molecular species with a highly detectable signal group which can be released in the form of a volatile compound at a desired point in an analytical procedure. In one embodiment, the release tags have the formula
(SgCo).sub.x L(Rx).sub.r
wherein each Sg is a signal group bearing one or more electronegative substituents, L is any of a wide variety of groups which when attached to a carbonyl group form a readily cleaved linkage, each COL moiety is a release group which upon scission releases signal group Sg in the form of a volative compound, and each Rx is a reactivity group for attaching the release tag compound to a molecular species to be labeled. In a second embodiment, the release tags have the formula
SgReRx
wherein Sg and Rx are defined as above and Re is a release group which is an olefin, α-hydroxy ketone or vicinal diol. Conjugates of the release tag compounds and assay methods employing them are also disclosed.
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Citations
11 Claims
- 1. A release tag compound for labeling substances for analytical purposes, said compound being represented by the formula
- space="preserve" listing-type="equation">Sg--CO--L--Rx
wherein; each Sg is a signal group, each CO is a carbonyl group to which an Sg is bonded, each Rx is a reactivity group, L is a linking group to which each SgCO group and each Rx group are bonded, and each COL portion is a release group which is cleavable to release an Sg-containing compound; and
wherein;each Sg is a C-linked organic moiety containing from 1 to 20 carbon atoms, the carbon atom of Sg which is bonded to the carbonyl carbon adjacent to linking group L being denominated as the α
-position, and Sg comprises a radical selected from the group consisting of substituted alkyl, substituted keto-alkyl, substituted alkenyl, and substituted alkynyl radicals;
said substituted alkyl, substituted keto-alkyl, and substituted alkenyl radicals bearing at least two electronegative substituents, and said substituted alkynyl radicals bearing at least one electronegative substituent;
said electronegative substituents being selected from the group consisting of halogens, cyano, dihalomethyl and trihalomethyl; and
further,1) when Sg is keto-alkyl, alkenyl, or alkynyl, Sg comprises at least one moiety selected from the group consisting of; β
-E-alkynyl, α
-E-α
-alkynyl, β
-E-α
-keto (provided that the carbonyl carbon adjacent to linking group L is connected to a nitrogen or oxygen atom of L), α
-E-alkenyl, and α
-E-α
-alkenyl, wherein E is an electronegative substituent selected from the group consisting of halogens, cyano, dihalomethyl, and trihalomethyl;2) when Sg is alkyl, the α
-carbon atom bears at least two of said electronegative substituents but no more than one fluorine atom;each Sg being further selected such that upon cleavage of said release tag compound at said COL portion, signal group Sg is released in a volatile form suitable for electron capture determination in the gas phase; L is oxy or amino; and Rx comprises a phenylene moiety which is connected to L and which contains a reactive, functional group. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
Specification
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- Resources
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Current AssigneeNortheastern University
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Original AssigneeNortheastern University
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InventorsAbdel-Baky, Samy, Allam, Kariman, Giese, Roger W.
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Primary Examiner(s)Higel, Floyd D.
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Application NumberUS07/496,251Time in Patent Office2,681 DaysField of Search548/542, 548/342, 548/339.1, 435/7, 435/188, 435/175, 435/181, 435/183, 435/12, 435/424, 435/280, 435/6, 435/7.2, 530/389, 530/390, 530/391, 536/27, 436/2, 436/536, 436/521, 436/547, 436/544US Class Current435/6.12CPC Class CodesG01N 33/532 Production of labelled immu...
