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US 5,859,259 AGranted
Activated esters of 1-phenylpyrazolin-5-one for labeling amine-functionalized molecules
AssigneePerSeptive Biosystems, Inc.
InventorsNanda D. Sinha, Jonathan N. Kremsky
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Abstract
The disclosed invention is drawn to pyrazolinone derivatives, and methods of use thereof, for non-radioactive labeling of amine-functionalized molecules, especially biomolecules such as DNA, RNA, PNA, oligomers, carbohydrates, amino acids and peptides. Carboxyl-containing reporter groups such as biotin and fluorescein may be activated for nucleophilic addition to a primary or secondary amine moiety. Representative compounds of the invention include Dimethoxytritylbiotin-XPP, biotin-XPP, and fluorescein-XPP.
Claims6
A pyrazolinone derivative having the formula:
- ##STR4## wherein R.sub.1 is selected from the group consisting of H, methyl, ethyl, isopropyl, phenyl, nitrophenyl, chlorophenyl and benzyl;
- R.sub.2 is selected from the group consisting of H, methyl, ethyl, isopropyl, phenyl nitrophenyl, chlorophenyl, benzyl, halogen and NO.sub.2 ;
- a b, c, d and e are selected from the group consisting of H, NO.sub.2, halogen and SO.sub.3 H, provided that at least one of a, b, c, d, and e is NO.sub.2 or SO.sub.3 H;
- and
- X is selected from the group consisting of anthracene, acridine, benzofuran, BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) and its derivatives, coumarin and its derivatives, digoxigenin, eosin, Lucifer Yellow, rhodamine and its derivatives, a steroid, a sulphonated aminonaphthalene, 1-anilinonaphthalene-8-sulfonic acid, 2-anilinonaphthalene-6-sulfonic acid, 8-aminonaphthalene-1,3,6-trisulfonic acid (ANTS), 8-aminonaphthalene-1,3-disulfonic acid, 8-anilinonaphthalene-1,6-disulfonic acid, and 8-aminonaphthalene-3,6-disulfonic acid.
2 more elements
A pyrazolinone derivative having the formula:
- ##STR5## wherein R.sub.1 is selected from the group consisting of H, methyl, ethyl, isopropyl, phenyl, nitrophenyl, chlorophenyl and benzyl;
- R.sub.2 is selected from the group consisting of H, methyl, ethyl, isopropyl, phenyl nitrophenyl, chlorophenyl, benzyl, halogen and NO.sub.2 ;
- a, b, c, d and e are selected from the group consisting of H, NO.sub.2, halogen and SO.sub.3 H, provided that at least one of a, b, c, d, and e is NO.sub.2 or SO.sub.3 H;
- and
- X--CO.sub.2 -- is a moiety selected from the group consisting of biotin, dimethoxytritylbiotin, fluorescein and dipivaloylcarboxyfluorescein.
2 more elements
Dependencies are inferred from the claim text.