Cell permeable, fluorescent dye

摘要

The invention pertains to a near-infrared fluorescent dye that is cell permeable and can be attached to selected proteins in living cells. The dye has the general formula;
or its corresponding spirolactone
;
wherein
Y is chosen from the group consisting of Si, Ge and Sn;R0 is —COO− or COOH;R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15 and R16 are substituents, including hydrogen, independently from each other.;The dye (i) absorbs and emits light at wavelengths above 600 nm; (ii) possesses high photostability; (iii) has high extinction coefficients and high quantum yields; (iv) can be derivatized with different molecules; and (v) is membrane-permeable and shows minimal background binding to biomolecules and biomolecular structures.

主权项

1. A compound chosen from the group consisting of: a corresponding spirolactone of each of (VI), (VII) and (VIII); and alternative protonation stages of (VI), (VII) and (VIII), comprising negatively or positively charged counterions; wherein for each of (VI), (VII) and (VIII), the corresponding spirolactones of (VI), (VII) and (VIII), and the alternative protonation stages of (VI), (VII) and (VIII): each of R13, R14, R15 and R16 are independently, respectively, one of:
H, F, Cl, Br, I, SO3X, a carboxylic acid, a salt of a carboxylic acid, an ester of a carboxylic acid, an amide, CN, nitro, hydroxyl, azido, amino, hydrazino;C1-C18 alkyl, alkoxy, C1-C18 alkylthio, alkanoylamino, C1-C18 alkylaminocarbonyl, C2-C36 dialkylaminocarbonyl, C1-C18 alkyloxycarbonyl, C6-C18 arylcarboxamido, and the alkyl portion(s) of each of the aforementioned are:
optionally substituted one or more times with F, Cl, Br, I, hydroxy, a carboxylic acid, a salt of a carboxylic acid, a carboxylic ester of a C1-C6 alcohol, —SO3X, amino, C1-C6 alkylamino, C2-C12 dialkylamino, C1-C6 alkoxy; and/oroptionally comprise one or more alkenyl and/or alkynyl moieties; orat least one pair of adjacent substituents R13 and R14, or R14 and R15, when taken in combination with carbons with which they are attached, forms a fused six-membered aromatic substructure that is optionally further substituted by a carboxylic acid or a salt of a carboxylic acid;each of R2, R3, R4 and R5 being independently, respectively one of: H, F, CI, Br, and C1-C6 alkyl; andat least one of R13, R14 and R15 is a second acyl functional group.