Detectable molecules, method of preparation and use

• US 4,849,505 A
• Filed: 04/28/1987
• Issued: 07/18/1989
• Est. Priority Date: 01/30/1984
• Status: Expired due to Term

• Current Assignee: Enzo Diagnostics, Inc.
• Original Assignee: Enzo Biochem Incorporated
• Inventors: Stavrianopoulos, Jannis G.
• Primary Examiner(s): Nucker, Christine M.
• Application Number:
  US07/043,572
• Time in Patent Office: 812 Days
• Field of Search: 424/1.1, 435/5, 435/6, 435/7, 435/180, 436/518, 436/531, 436/532, 530/300, 530/350, 530/402, 530/405, 536/26, 536/27, 536/55.1
• US Class Current: 530/300
• CPC Class Codes: A61K 51/0497 conjugates with a carrier being an organic compounds
• CPC Class Codes: A61K 51/1093 conjugates with carriers being antibodies
• CPC Class Codes: G01N 33/533 with fluorescent label
• CPC Class Codes: G01N 33/553 Metal or metal coated

Abstract

A detectable molecule of the formula

A.sup.3 --(--X--R.sup.1 --E--Det.sup.b).sub.m

where A³ is A² or a polymer, where A³ has at least one modifiable reactive group selected from the group consisting of amino, hydroxy, cis OH, halides, aryl, imidazoyl, carbonyl, carboxy, thiol or a residue comprising an activated carbon; --X-- is selected from the group consisting of ##STR1## --R¹ -- is ##STR2## or a C₁ -C₁₀ branched or unbranched alkyl or aralkyl, which may be substituted by --OH; --Y-- is a direct bond to --E--, or --Y-- is --E--R² -- where R² is a C₁ -C₁₀ branched or unbranched alkyl; Z_a is chlorine, bromine or iodine; E is O, NH or an acyclic divalent sulfur atom; Det^b is a chemical moiety capable of being detected, preferably comprising biotin or a metal chelator of the formula: ##STR3## or the 4-hydroxy or acyloxy derivatives thereof, where R³ is C₁ -C₄ alkyl or CH₂ COOM, M is the same or different and selected from the group consisting of hydrogen, a metal or non-metal cation or is C₁ -C₁₀ alkyl, aryl or aralkyl; and m is an integer from 1 to the total number of modified reactive groups on A³. The detectable molecules are useful in in vitro or in vivo assays or therapy.

Claims

1. A detectable molecule of the formula:

##STR53## where A⁴ is A² or a polymer, both A² and the polymer having at least one modifiable reactive group selected from the group consisting of amino, aryl, imidazoyl and a residue comprising an activated carbon;

A² is a specific binding ligand having a molecular weight of less than about 2,000;

j is an electron withdrawing group;

K is a signal generating entity or a solid matrix;

n is an integer from one to about two; and

m is an integer from one to the total number of modifiable reactive groups on A⁴.

2. The molecule of claim 1 wherein j is selected from the group consisting of chlorine, fluorine, bromine, and iodine.

3. The molecule of claim 2 wherein j is chlorine.

4. The molecule of claim 1 wherein A⁴ is a polynucleotide or a polypeptide.

5. The molecule of claim 1 wherein n is two.

6. The molecule of claim 1 having the formula:

##STR54##