Radiolabeled compounds targeting the prostate-specific membrane antigen

A compound of Formula I:

• or a salt or a solvate thereof, wherein:
• R0 is O or S;
• R1a is —CO2H, —SO2H, —SO3H, —PO2H, —PO3H2, —OPO3H2, —OSO3H, —B(OH)2, or
• R1b is —CO2H, —SO2H, —SO3H, —PO2H, —PO3H2, —B(OH)2, or
• R1c is —CO2H, —SO2H, —SO3H, —PO2H, —PO3H2, —B(OH)2, or
• R2 is —CH2—, —CH(OH)—, —CHF—, —CF2—, —CH(CH3)—, —C(CH3)2—, —(CH2)2—, —CH2CH(OH)—, —CH2CHF—, —CHFCH2—, —CF2CH2—, —CH2CF2—, —CH(OH)CH2—, —CH(CH3)CH2—, —CH2CH(CH3)—, —C(CH3)2CH2—, —CH2C(CH3)2—, —CH2CH(OH)CH2—, —CH2CHFCH2—, —(CH2)2CH(OH)—, —(CH2)2CHF—, —(CH2)3—, —CH2OCH2—, —CH2SCH2—, —CHFCH2CH2—, —CH(OH)CH2CH2—, —CH(CH3)CH2CH2—, —CH2CH(CH3)CH2—, —CH2CH2CH(CH3)—, —C(CH3)2CH2CH2—, —CH2C(CH3)2CH2—, —CH2CH2C(CH3)2—, —CH(CH3)—O—CH2—, —C(CH3)2O—CH2—, —CH2—O—CH(CH3)—, —CH2—O—C(CH3)2—, —CH2—S(O)—CH2—, —CH2—S(O)2—CH2—, —CH(CH3)—S—CH2—, —C(CH3)2—S—CH2—, —CH2—S—CH(CH3)—, —CH2—S—C(CH3)2—, —CH(CH3)—S(O)—CH2—, —C(CH3)2—S(O)—CH2—, —CH2—S(O)—CH(CH3)—, —CH2—S(O)—C(CH3)2—, —CH(CH3)—S(O)2—CH2—, —C(CH3)2—S(O)2—CH2—, —CH2—S(O)2—CH(CH3)—, —CH2—S(O)2—C(CH3)2—, —CH2—NH—C(O)—, —C(O)—NH—CH2—, —C(O)—NH—CH(CH3)—, or —C(O)—NH—C(CH3)2—;
• R3 is a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C1-C20 alkylenyl, alkenylenyl, or alkynylenyl, or a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C2-C20 heteroalkylenyl, heteroalkenylenyl, or heteroalkynylenyl;
• R4 is —O—, —S—, —Se—, —S(O)—, —S(O)2—, —NHC(O)—, —C(O)NH—,
• —C(O)—(NH)2—C(O)—, —OC(O)NH—, —NHC(O)O—, —NHC(O)NH—, —OC(S)NH—, —NHC(S)O—, —NHC(S)NH—, —NHC(O)C(O)NH—, —S—S—, —S—CH2—S—, —NH—NH—C(O)—, or —C(O)—NH—NH—;
• R5 is a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C1-C30 alkylenyl, alkenylenyl or alkynylenyl, or is a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C2-C30 heteroalkylenyl, heteroalkenylenyl or heteroalkynylenyl;
• R6 is hydrogen, methyl or ethyl;
• Xaa1 is an amino acid of formula —N(R8)R9C(O)—;
• each R8 is independently hydrogen or methyl;
• each R9 is independently:
• a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C1-C20 alkylenyl, alkenylenyl or alkynylenyl;
• or a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C2-C20 heteroalkylenyl, heteroalkenylenyl or heteroalkynylenyl;
• wherein at least one R9 or R5 is —(CH2)0-3CH(R10)(CH2)0-3—;
• R10 is:
• a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C2-C19 alkyl, alkenyl or alkynyl;
• a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C2-C19 heteroalkyl, heteroalkenyl or heteroalkynyl having only 1-3 heteroatoms;
• —CH2R23, in which R23 is an optionally substituted C4-C16 aromatic ring or partially or fully aromatic fused ring system, wherein 0-3 carbons in the aromatic ring or the partially or fully aromatic fused ring system are replaced with N, S and/or O heteroatoms, and wherein the optional substitutions are selected from OH, NH2, NO2, halogen, C1-C6 alkyl, and/or C1-C6 alkoxyl groups;
• or
• selected from:
• optionally modified with one, more than one, or a combination of:
• halogen, OMe, SMe, NH2, NO2, CN, OH, or additional endocyclic ring nitrogen atoms;
• R7 is
• Xaa2 is —N(R13)R14C(O)—;
• each R13 is independently hydrogen or methyl;
• each R14 is independently:
• a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C1-C20 alkylenyl, alkenylenyl or alkynylenyl;
• or a linear or branched, cyclic or acyclic, and/or aromatic or non-aromatic C2-C20 heteroalkylenyl, heteroalkenylenyl or heteroalkynylenyl;
• wherein each R14 is optionally substituted;
• wherein each R14 is optionally substituted with a carboxylic acid, a sulfonic acid, a sulfinic acid, or a phosphoric acid;
• wherein each R14 is optionally substituted with one RX;
• and wherein at least one R14 is substituted with one RX;
• and
• RX is
• —(C(O))p—(CH2)q-(radiolabeling group), or —(N(R)C(O))p—(CH2)q-(radiolabeling group), wherein the radiolabeling group independently selected from:
• an aryl or heteroaryl substituted with a radioisotope or a prosthetic group comprising a trifluoroborate;
• R is hydrogen or methyl;
• wherein at least one RX is
• and at least one other RX is —(C(O))p—(CH2)q-(radiolabeling group) or —(N(R)C(O))p—(CH2)q-(radiolabeling group);
• r is 0 or 1;
• n is 1, 2, 3, or 4;
• m is 1, 2, 3, or 4;
• p is 0 or 1;
• q is 0, 1, 2, 3, 4, or 5;
• and
• m1, m2, m3, and m4 are each independently 1, 2, 3, or 4.