129058-56-6

Five new firefly luciferin (1) analogues were synthesized and their light emission properties were examined. Modifications of the thiazoline moiety in 1 were employed to produce analogues containing acyclic amino acid side chains (2–4) and heterocyclic rings derived from amino acids (5 and 6) linked to the benzothiazole moiety. Although methyl esters of all of the synthetic derivatives exhibited chemiluminescence activity, only carboluciferin (6), possessing a pyrroline-substituted benzothiazole structure, had bioluminescence (BL) activity (λmax=547 nm). Results of bioluminescence studies with AMP-carboluciferin (AMP=adenosine monophosphate) and AMP-firefly luciferin showed that the nature of the thiazoline mimicking moiety affected the adenylation step of the luciferin–luciferase reaction required for production of potent BL. In addition, BL of 6 in living mice differed from that of 1 in that its luminescence decay rate was slower.

PROBLEM TO BE SOLVED: To provide a method of producing a cyclized compound, and a method of causing a solution containing the cyclized compound to emit light.SOLUTION: A method of producing a cyclized compound represented by the chemical formula (II) comprises bringing an acid into contact with a compound represented by the general formula (I). (In the formula, R, Rand Rare each independently H or a substituent that becomes H upon the contact with the acid, and Ris OH or a substituent that becomes OH upon the contact with the acid.)

(4-Benzylpiperidine-1-yl)-(6-hydroxy-1H-indole-2-yl)-methanone (6a) derived from (E)-1 -(4-benzylpiperidin-1-yl)-3-(4-hydroxy-phenyl)-propenone (5) was identified as a potent NR2B subunit-selective antagonist of the NMDA receptor. To establish the structu

Compounds useful for detecting a source of hydrogen peroxide are disclosed wherein a signalling compound of the formula: is reacted with peroxide. Sig is an aromatic or heteroaromatic ring group, B is a boron atom, and R5 and R6 are independently selected from hydrogen and lower alkyl groups and can be joined together as a straight or branched alkylene chain forming a five or six-membered ring. A detectable product compound of the formula Sig-OH Is produced and detected by measuring color, fluorescence, chemiluminescence, or bioluminescence. The signalling compound itself does not possess the detectable property or does so only to a very weak degree. The compounds can be used for detection in assays for peroxide or peroxide-producing enzymes and in assays employing enzyme-labeled specific binding pairs.

Compounds useful for detecting a source of hydrogen peroxide are disclosed wherein a signalling compound of the formula: is reacted with peroxide. Sig is an aromatic or heteroaromatic ring group, B is a boron atom, and R5 and R6 are independently selected from hydrogen and lower alkyl groups and can be joined together as a straight or branched alkylene chain forming a five or six-membered ring. A detectable product compound of the formula Sig-OH Is produced and detected by measuring color, fluorescence, chemiluminescence, or bioluminescence. The signalling compound itself does not possess the detectable property or does so only to a very weak degree. The compounds can be used for detection in assays for peroxide or peroxide-producing enzymes and in assays employing enzyme-labeled specific binding pairs.

The synthesis of 6-hydroxybenzothiazole-2-carboxylic acid (1) is presented. The benzothiazole ring was obtained by ring contraction of a remarkably stable 2-alkoxy-7-hydroxy-2H-benzo[1,4]thiazine intermediate that could be isolated. 6-Hydroxybenzothiazole