Cell-permeable fluorogenic fluorophores

A compound of the general formula (10) or the general formula (10′)

• wherein
• R1 is selected from H and F;
• R2 and R3 are independently selected from H, fluoro-, amino-, hydroxyl-, SO3H— and/or carboxyl substituted or unsubstituted C1 to C4 alkyl;
• X is O;
• Y is OH or NRY1RY2, with
• RY1, and RY2 each independently selected from H, an unsubstituted or hydroxy-, amino-, halogen-, and/or carboxy-substituted hydrocarbon moiety selected from C1-C8 alkyl, C3-C8 cycloalkyl, C1-C4 acyl, C7-C12 alkylaryl, an unsubstituted phenyl or a phenyl substituted by any one or several of the following substituents:
• unsubstituted C1-C4 alkyl, halogen, C1-C4 oxyalkyl, COOH, COORYC, CONRYC2, with RYC being selected from H and unsubstituted or amino- or hydroxy-substituted C1-C8 alkyl;
• or
• RY1 and RY2 together are a C3-C6 unsubstituted or hydroxy-, amino-, halogen-, alkoxy- and/or carboxy-substituted alkyl forming a 4-7-membered ring structure with Y;
• or
• one of RY1 and RY2, or both RY1 and RY2, together with R2 and/or R3, respectively, form an unsubstituted or hydroxy-, amino-, halogen-, carboxy- and/or aryl-substituted 4-7-membered alkyl or alkylene ring;
• a) A and B together with the atoms that they are covalently coupled to form a phenyl ring or 5- or 6-membered heteroaryl ring, wherein the ring is unsubstituted or substituted by one of NRN1RN2— and OH and wherein the ring is optionally further substituted by R4, R5 and/or R6, wherein
• RN1 and RN2 have the same meanings as RY1, and RY2 above,
• R4 has the same meaning as R3, R5 has the same meaning as R1, and R6 has the same meaning as R2;
• b) A is an unsubstituted or hydroxy-, amino-, halogen-, and/or carboxy-substituted conjugated carbocycle or heterocycle having one, two or three rings;
• and
• B is selected from H (or D, F) and a moiety having a molecular weight between 15 and 250 u (g/mol);
• U and V
• together with the atoms they are covalently coupled to form an unsubstituted or substituted 5-7 membered ring,
• wherein the substitution is selected from one or several substituents independently selected from OH, SH, amine, halogen, CN, NC, CNO, NCO, CNS, NCS, unsubstituted C1-C4 O-alkyl, C1-C4 S-alkyl, O-aryl, S-aryl, NO2, CHO, CONRUV2, COORUV, COO-aryl, COO-alkylaryl, PO3H, PO3RUV, SO3H, SO3RUV and SO2RUV, with RUV being selected from H, and C1-C4 unsubstituted alkyl
• and the 5-7 membered ring is selected from
• cycloalkyl,
• aryl,
• heteroaryl, or
• U is selected from H, D and F and V is selected from H, D, F, and C1 to C4 unsubstituted or amino-, hydroxy- or halogen substituted alkyl,
• Z is selected from
• CN, CHO, CORZ, COORZ, and CONRZ2, wherein each RZ is independently selected from H, unsubstituted or hydroxy-, amino-, halogen-, and/or carboxy-substituted C1-C8 alkyl, C3-C8 cycloalkyl, C1-C4 acyl, C7-C12 alkylaryl, unsubstituted phenyl or phenyl substituted by any one or several of the following substituents:
• unsubstituted C1-C4 alkyl, halogen, C1-C4 oxyalkyl, COORC, CONRC2, with RC being selected from H, C1-C8 alkyl;
• or
• SO2RS with RS being selected from
• NH2, NHRSN, and NRSN2, with each RSN independently selected from an unsubstituted or hydroxy-, amino-, halogen-, and/or carboxy-substituted moiety selected from C1-C8 alkyl, C3-C8 cycloalkyl, C1-C4 acyl, C7-C12 alkylaryl, or from unsubstituted phenyl or phenyl substituted by any one or several of the following substituents:
• unsubstituted C1-C4 alkyl, halogen, O—C1-C4 alkyl, COOH, COORC, CONRC2, with RC being selected from H and C1-C8 alkyl;
• an unsubstituted or hydroxy-, amino-, halogen-, and/or carboxy-substituted moiety selected from C1-C8 alkyl, C3-C8 cycloalkyl, C1-C4 acyl, C7-C12 alkylaryl, unsubstituted phenyl or phenyl substituted by any one or several of the following substituents:
• unsubstituted C1-C4 alkyl, halogen, O—C1-C4 alkyl, COOH, COORSC, CONRSC2, with RSC being selected from H and C1-C8 alkyl;
• ORSO, with RSO selected from a unsubstituted or hydroxy-, amino-, halogen-, and/or carboxy-substituted moiety selected from C1-C8 alkyl, C3-C8 cycloalkyl, C1-C4 acyl, C7-C12 alkylaryl, or from unsubstituted phenyl or phenyl substituted by any one or several of the following substituents:
• unsubstituted C1-C4 alkyl, halogen, O—C1-C4 alkyl, COOH, COORC, CONRC2, with RC being selected from H and C1-C8 alkyl;
• CH2RF, CHRF2, and CRF3, with RF selected from CH2F, CHF2, CF3, CH2Cl, and CHCl2, CCl3;
• H
• CH2COORK1 or CH2CONHRK1 with RK1 selected from H, and unsubstituted or halogen-substituted C1 to C4 alkyl;
• with the proviso that the following compounds are not claimed:
• with
• R1, R2, R3, R4, R5 and G are H, and
• Y and E are NEt2 and
• Z is CONH2 or
• Z is CONHC6H5;
• or
• Z is CN or
• Z is selected from CH2CF3, CH2CHF2, and CH2CH2F, or
• Z is selected from CH2COOCH3 and CH2COOH,
• Z is H,
• or
• Y and E are NMe2 and Z is selected from CH2COOCH3 and CH2COOH or
• Y and E are NH2 and Z is selected from CH2COOH and CH2COOCH3
• or
• Y is OH and E is ═O (for formula 10) or E is OH (for formula 10′), and Z is C(═O)(CH3)C6H5;
• or
• R1, R3, R4, and R5 are H, R2 and G are methyl, Y and E are NHEt and Z is CH2COOH or CH2COOCH3
• or the compound is of formula (301), (302), (303), or (304)