Substituted anthraquinone dyes for cellular stains and enzyme detection
AssigneeBiotium, Inc.
InventorsFei Mao, Wai-Yee Leung, Ching-Ying Cheung, Lori Michelle Roberts
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Abstract
The invention discloses new substituted anthraquinone dyes that may be useful as cellular stains. In some aspect of the invention, the nuclear stains are useful for staining the nuclei of dead or fixed cells. Another aspect of the invention relates to substituted anthraquinone dyes comprising an enzyme substrate moiety that is transformable or cleavable by an enzyme such that the transformation or cleavage of the substrate moiety causes a detectable change in the functionality or spectral properties of the dye.
Claims7
A substituted anthraquinone dye of Formula 5:
- wherein:
- each Ra and Rb is independently H, methyl, methoxy or a halogen;
- each m and n is independently 0, 1, or 2;
- R1 and R2 are H;
- each R3 is independently H, methyl, formyl, acetyl, an alkanoyl having the formula of Formula 2, or an alkyl having the formula of Formula 3:
- -L2-X2 Formula 3
- L1 is a link comprising 2-12 atoms selected from C, N, and O;
- X1 is a substituent selected from the group consisting of a substituted or unsubstituted amino, a substituted or unsubstituted amidino, a substituted or unsubstituted guanidino, a substituted or unsubstituted aminooxy, a substituted or unsubstituted hydroxylamino, a substituted or unsubstituted hydrazino, a C3-6 trialkylammonium, a substituted or unsubstituted, natural or unnatural amino acid with a free alpha- or beta-amine where the amino acid is attached to L1 via an amide bond;
- L2 is a link comprising 2-12 atoms selected from C, N, and O;
- X2 is selected from the group consisting of a substituted or unsubstituted amidino, a substituted or unsubstituted guanidino, a substituted or unsubstituted aminooxy, a substituted or unsubstituted hydroxylamino, a substituted or unsubstituted hydrazino, a substituted or unsubstituted, natural or unnatural amino acid where the amino acid is attached to L2 via an amide bond;
- or X2 is a mono-, di- or trisubstituted amino group;
- L4 is -L2-X2′-L2′-X2″-L2″-, wherein L2, L2′, and L2″ are independently links comprising 2-12 atoms selected from C, N, and O;
- and
- X2′ and X2″ are independently selected from the group consisting of a substituted or unsubstituted amidino, a substituted or unsubstituted guanidino, a substituted or unsubstituted aminooxy, a substituted or unsubstituted hydroxylamino, a substituted or unsubstituted hydrazino, a substituted or unsubstituted, natural or unnatural amino acid with a free alpha- or beta-amine where the amino acid is attached to L2 via an amide bond;
- or X2 is a mono-, di- or trisubstituted amino group.
A substituted anthraquinone dye according to any preceding claim, wherein Ra and Rb are both H and n=m=2.
Dependencies are inferred from the claim text.