Biotinylated chemiluminescent labels and their conjugates, assays and assay kits
AssigneeNichols Institute Diagnostics
InventorKastooriranganathan Ramakrishnan
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Abstract
A unique class of chemiluminescent labels containing biotin substitution that are suitable for chemiluminescent assays using inter alia a streptavidin and/or avidin conjugate. The chemiluminescent labels of the invention have the ability to bind to streptavidin and/or avidin per se or to streptavidin and/or avidin conjugated with an analyte. Label structures are disclosed that have hydrolytic stability to meet the most demanding commercial assay conditions. The invention encompasses conjugates containing associated versions of the labeling compounds, assays and kits for performing such assay utilizing the conjugates.
Claims29
A chemiluminescent label compound containing a biotin substituent that forms a streptavidin or avidin complex, having the formula:
- ##STR17## in which R.sup.1 is a divalent organic group;
- and R.sup.2 is an optional substituent of the biotin and when present it is a divalent moiety containing at least 1 carbon atom;
- and R.sup.0 is a heterocyclic structure directly bonded to the biotin or substituted biotin, that has the capacity of exhibiting chemiluminescence when reacted with hydrogen peroxide in the presence of a base.
The chemiluminescent label compound of claim 10 wherein R.sup.2 comprises heteroatoms.
A chemiluminescent label compound having the biotinylated heterocyclic structure:
- ##STR18## wherein A is a biotin moiety, B is R.sup.1 and an optional R.sup.2, R.sup.1 is a divalent organic group;
- and R.sup.2 is an optional substituent of the biotin and when present it is a divalent moiety containing at least 1 carbon atom;
- and C is a heterocyclic fused ring that has the capacity of exhibiting chemiluminescence when reacted with hydrogen peroxide in the presence of a base, each R.sup.v, R.sup.w and R.sup.x is hydrogen, carbon bonded amino, carbon bonded carboxy, carbon bonded halogen, carbon bonded sulfonyl, carbon bonded hydroxyl, carbon bonded amido, carbon bonded thiol, or monovalent organo bonded directly to carbon or nitrogen, as the case may be, R.sup.y is either an aryl substituted oxy, aryl substituted sulfide moiety, or an organosubstituted sulfonimino moiety bonded to the adjacent carbonyl by an oxygen, sulfur or nitrogen bond, as the case may be, one of the Z's is nitrogen, and the remainder are carbon, provided that one of R.sup.v, R.sup.w, R.sup.x and R.sup.y is directly bonded to R.sup.2, if present, or to R.sup.1, thereby linking A to C and the R.sup.v that is bonded to a Z that is nitrogen is bonded to that nitrogen by a carbon to nitrogen bond and, optionally, the R.sup.V that are bonded to carbon join to form an aromatic fused ring structure.
Dependencies are inferred from the claim text.