A double-labeled probe for molecular imaging and use thereof

A compound or a pharmaceutically acceptable salt thereof of formula (I):

• (A)-x1-(B)-x2-(C),
• wherein
• (A) is at least one motif specifically binding to cell membranes of neoplastic cells;
• (B) at least one chelator moiety of radiometals;
• (C) a dye moiety;
• x1 is a spacer covalently connecting (A) and (B);
• x2 is a spacer or a chemical single bond connecting (B) and (C);
• wherein (C) has the formula
• wherein
• X1 and X4 are independently selected from the group consisting of —N═, —N(R5)═, and —C(R6)═;
• X2 and X3 are independently selected from the group consisting of O, S, Se, N(R5), and C(R6R7);
• Y is a linker connecting the two moieties of (C) and permitting electron delocalization between said moieties, wherein Y optionally comprises a group (L-2°);
• a and b are independently selected from the group consisting of 1, 2, and 3;
• each R1 and each R2 is independently (L-)cZ, (L-)cZ0 or H;
• and two adjacent R1 and/or two adjacent R2 can also form an aromatic ring, which is optionally substituted with one or more (L-)cZ or (L-)cZ0;
• R3, R4, R5, R6, R7, R9 are independently selected from the group consisting of (L-)cZ, (L-)cZ0, and H;
• each c is independently 0, or 1;
• each L is independently T1, —OT1-, —ST1-, —C(O)T1-, —C(O)OT1-, —OC(O)T1-, —C(O)NHT1-, —NHC(O)T1, or a C1-10 alkylene group, which is optionally interrupted and/or terminated by one or more of —O—, —S—, —C(O)—, —C(O)O—, —OC(O)—, —C(O)NH—, —NHC(O)O—, and T1;
• T1 is phenyl, naphthyl, indenyl, indanyl, tetralinyl, decalinyl, adamantyl, C3-7 cycloalkyl, 3 to 7 membered heterocyclyl, or 7 to 11 membered heterobicyclyl, wherein T1 is optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C(O)R8, COORS, OR8, C(O)N(R8R8a), S(O)2N(R8R8a), S(O)N(R8R8a), S(O)2R8, N(R8)S(O)2N(R8aR8b) SR8, N(R8R8a), NO2;
• OC(O)R8, N(R8)C(O)R8a, N(R8)S(O)2R8a, N(R8)S(O)R8a, N(R8)C(O)N(R8aR8b), N(R8)C(O)OR8a, OC(O)N(R8R8a), oxo (═O), where the ring is at least partially saturated, or C1-6 alkyl, wherein C1-6 alkyl is optionally substituted with one or more halogen, which are the same or different;
• each Z is independently H, halogen, CN, C(O)R8, C(O)OR8, C(O)O− OR8, C(O)N(R8R8a), S(O)2OR8, S(O)2O−, S(O)2N(R8R8a), S(O)N(R8R8a), S(O)2R8, S(O)R8, N(R8)S(O)2N(R8aR8b), SR8, N(R8R8a), NO2;
• P(O)(OR8)2, P(O)(OR8)O−, OC(O)R8, N(R8)C(O)R8a, N(R8)S(O)2R8a, N(R8)S(O)R8a, N(R8)C(O)N(R8aR8b), N(R8)C(O)OR8a, or OC(O)N(R8R8a);
• R8, R8a, R8b are independently selected from the group consisting of H, or C1-6 alkyl, wherein C1-6 alkyl is optionally substituted with one or more halogen, which are the same or different;
• Z0 is a chemical bond connecting (C) to x2 or to (B) in case x2 is a chemical single bond;
• provided that one of R1, R2, R3, R4, R5, R6, R7, R9 is (L-)cZ0 or that Y comprises (L-)cZ0;
• wherein x1 comprises a group -AA-, wherein AA is an amino acid sequence of 4 to 8 (preferably 5 to 7, more preferably 6) naturally occurring amino acids and wherein at least two amino acids are histidine
• and wherein any remaining positive or negative charge or charges are compensated by pharmaceutically acceptable negatively or positively charged counterion or counterions.