Derivatives, immunogens, and antibodies for detecting ecstasy-class drugs
View Patent ↗Compounds including haptens, intermediates, and immunogens that are useful in the production of antibodies specific for the methylenedioxy class of amphetamine derivatives are described. Antibodies specific for the methylenedioxy class of amphetamine derivatives, reagent kits containing antibodies specific for the methylenedioxy class of amphetamine derivatives, methods of producing antibodies specific for the methylenedioxy class of amphetamine derivatives, and methods of detecting analytes including members of the methylenedioxy class of amphetamine derivatives are also described.
1. A compound having a structure
wherein:
R 1 is —J—M—T;
R 2 is a protecting group; and
R 3 is an optionally substituted alkyl group; wherein
J is a straight or branched chain comprising 1–15 carbon atoms and 0–6 heteroatoms;
M is—CO—, and
T is selected from the group consisting of a hydroxyl and a leaving group.
2. The compound of claim 1 wherein J comprises 1–11 carbon atoms.
3. The compound of claim 2 wherein J is —(CH 2 ) k —and k is 1, 2, 3, 4, 5, or 6.
4. The compound of claim 3 wherein R 3 is selected from the group consisting of methyl, ethyl, n-propyl, and n-butyl.
5. The compound of claim 4 wherein k is 3.
6. The compound of claim 5 wherein T is a leaving group.
7. The compound of claim 5 wherein R 2 is a protecting group, and R 3 is methyl.
8. The compound of claim 5 wherein T is a leaving group comprising N-oxysuccinimide.
9. The compound of claim 8 wherein R 3 is methyl.
10. The compound of claim 7 wherein R 2 is trifluoroacetyl and T is N-oxysuccinimide.
11. The compound of claim 7 wherein R 2 is trifluoroacetyl and T is hydroxyl.
12. A compound having a structure
wherein:
R 1 is —J—M—T;
R 2 is a protecting group; and
R 3 is an optionally substituted alkyl group; wherein
J is a straight or branched chain comprising 1–15 carbon atoms and 0–6 heteroatoms;
M is selected from the group consisting of —O—, —CO—, —NR 4 —, —S—, —C(═NH)O—,
—NH(CO)—, —NH(CO)NH—, —NH(CS)—, —NH(CS)NH—, —O(CO)NH—, and
—NH(C═NH)—, wherein R 4 is selected from the group consisting of hydrogen and an alkyl
group; and
T is a macromolecular carrier.
13. The compound of claim 12 wherein J is a straight chain comprising 3 carbon atoms and M is —CO—.
14. The compound of claim 12 wherein the macromolecular carrier is selected from the group consisting of a protein, a polypeptide, and a polysaccharide.
15. The compound of claim 14 wherein the protein is selected from the group consisting of keyhole limpet hemocyanin, bovine serum albumin, and bovine thyroglobulin.
16. The compound of claim 12 wherein T is a macromolecular carrier selected from the group consisting of a hemocyanin, a globulin, and an albumin.
17. The compound of claim 16 wherein R 3 is methyl.
18. A compound having a structure
wherein:
R 1 is —J—M—T;
R 2 is a protecting group; and
R 3 is an optionally substituted alkyl group; wherein
J is a straight or branched chain comprising 1–15 carbon atoms and 0–6 heteroatoms;
M is selected from the group consisting of —O—, —CO—, —NR 4 —, —S—, —C(═NH)O—,
—NH(CO)—, —NH(CO)NH—, —NH(CS)—, —NH(CS)NH—, —O(CO)NH—, and
—NH(C═NH)—, wherein R 4 is selected from the group consisting of hydrogen and an alkyl
group; and
T is a label.