Tricarbocyanine-cyclodextrin(s) conjugates and use thereof

A fluorescent compound of formula (I)

• F-Ln-CDn (I)
• wherein
• F is a tricarbocyanine residue of formula (II)
• wherein
• R1 and R2 are independently selected from H, SO3H, CO2H, SO2NH2, CH2COOH, NH2, NHCOCH2I, NO2, Br, Cl, CH3;
• R3 and R4 are independently selected from C1-4 alkyl, (CH2)3C≡CH, (CH2)4C≡CH (CH2)5COOH, (CH2)3SO3H, (CH2)4SO3H, (CH2)3NH2, (CH2)4NH2, (CH2)3N+(CH3)3, (CH2)5N+(CH3)3, (CH2)3N3, (CH2)4N3, (CH2)3NHCOCH2I, (CH2)4NHCOCH2I, (CH2CH2O)2CH3, (CH2CH2O)3CH3, (CH2CH2O)4CH3;
• R5 is selected from
• wherein
• CD is a cyclodextrin residue of formula (III)
• wherein
• m is and integer equal to 6, 7 or 8,
• R′, R″, R′″ are independently selected from OH, OCH3, OCH2CH3, OCH2CHOHCH3, OCHOHCH3, OCH2COOH, O(CH2)4SO3H, N3, NH2, NHCOCH3, OCH2C≡CH, SH;
• L is a linker group resulting from the coupling of the tricarbocyanine of formula (II) to the cyclodextrin(s) of formula (III) according to the following Table:
• Functional group of
• Functional group
• the tricarbocyanine
• of the cyclodextrin
• (F) in any of the
• (CD) in any of the
• groups R3, R4 or R5
• groups R′, R″ or R′′′
• Linker group (L)
• COOH
• OH
• —C(O)O—
• COOH
• NH2
• —C(O)NH—
• NH2
• COOH
• —NHC(O)—
• NHCOCH2I
• SH
• NHC(O)CH2S—
• C≡CH
• N3
• N3
• C≡CH
• n is an integer from 1 to 4,
• and salts thereof, and
• wherein the fluorescent compound is a compound of formula (XII):
• wherein CD1 and CD2 are, independently, 2-hydroxypropyl-β-cyclodextrin (HβCD) or 2-hydroxypropyl-γ-cyclodextrin (HγCD) and the linkers L of Formula (I) are ester bonds formed in the coupling reaction of a carboxyl group of the tricarbocyanine with a residue group R′″═OH of CD1 and CD2, respectively.