Quenching dye for labeling biomolecules and method for preparing the same
AssigneeDkc Corporation
InventorsJin Woo Park, Kiwon Kim
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Abstract
The present disclosure provides a quenching dye with an anthraquinone structure, which has a broad and high absorption spectrum in the visible and near-infrared wavelength regions and exhibits high stability and superior solubility in aqueous conditions. A quenching dye composition containing the anthraquinone compound according to the present disclosure as an active ingredient can be widely used in the field of optical molecular imaging to observe the movement of a biomolecule because it can easily label a biomolecule manipulated in an aqueous buffer.
Claims12
An anthraquinone compound represented by [Chemical Formula 1]:
- where
- each of R1, R2, R3 and R4, which are identical to or different from each other, is independently selected from hydrogen, a hydroxyl group, an amine group, a nitro group, a C1-C6 alkyl group, a C7-C10 alkyl group, a C1-C6 alkoxy group, a sulfonic acid group and a sulfonate group,
- R5 is selected from a C1-C6 alkyl group and a C7-C10 alkyl group,
- R6 is selected from a hydroxyl group, a hydrazinyl group, NH(CH2)pNH2, a N-hydroxysuccinimide group, NH—(CH2)q—N(CO)2C2H2, a 2,4-dihalo-6-hydrazino-1,3,5-triazine group and NH—A—SO2CH═CH2,
- A is selected from (CH2)m, para-(C6H4) and meta-(C6H4),
- each of m, p and q, which are identical to or different from each other, is independently an integer from 1 to 10, and
- n is an integer from 1 to 23.
A method for preparing an anthraquinone compound represented by [Chemical Formula 1], comprising:
- preparing a compound of [Chemical Formula 2] into a diazonium salt;
- and
- obtaining a compound of [Chemical Formula 1] by reacting the diazonium salt with a compound of [Chemical Formula 3]:
- wherein
- each of R1, R2, R3 and R4, which are identical to or different from each other, is independently selected from hydrogen, a hydroxyl group, an amine group, a nitro group, a C1-C6 alkyl group, a C7-C10 alkyl group, a C1-C6 alkoxy group, a sulfonic acid group and a sulfonate group,
- R5 is selected from a C1-C6 alkyl group and a C7-C10 alkyl group,
- R6 is selected from a hydroxyl group, a hydrazinyl group, NH(CH2)pNH2, a N-hydroxysuccinimide group, NH—(CH2)q—N(CO)2C2H2, a 2,4-dihalo-6-hydrazino-1,3,5-triazine group and NH—A—SO2CH═CH2,
- A is selected from (CH2)m, para-(C6H4) and meta-(C6H4),
- each of m, p and q, which are identical to or different from each other, is independently an integer from 1 to 10, and
- n is an integer from 1 to 23.
Dependencies are inferred from the claim text.