PSMA-binding agents and uses thereof

A composition comprising a pharmaceutically acceptable carrier and a compound having the structure

• wherein
• Z is tetrazole or CO2Q;
• each Q is independently selected from hydrogen or a protecting group;
• and wherein
• m is 0, 1, 2, 3, 4, 5, or 6;
• R is a pyridine ring selected from the group consisting of
• wherein X is fluorine, iodine, a radioisotope of fluorine, a radioisotope of iodine, chlorine, bromine, a radioisotope of bromine, a radioisotope of astatine, NO2 NH2, N+(R2)3, Sn(R2)3, Si(R2)3, Hg(R2), B(OH)2, —NHNH2, —NHN═CHR3, —NHNH—CH2R3, n is 1, 2, 3, 4, or 5;
• Y is O, S, N(R′), C(O), NR′C(O), C(O)N(R′), OC(O), C(O)(O), NR′C(O)NR′, NR′C(S)NR′, NR'S(O)2, S(CH2)p, NR′(CH2)p, O(CH2)p, OC(O)CHR8NHC(O), NHC(O) CHR8NHC(O), or a covalent bond;
• wherein p is 1, 2, or 3, R′is H or C1-C6 alkyl, and R8 is hydrogen, alkyl, aryl, or heteroaryl, each of which may be substituted;
• R2 is a C1-C6 alkyl;
• and
• R3 is alkyl, alkenyl, alkynyl, aryl, or heteroaryl each of which is substituted by fluorine, iodine, a radioisotope of fluorine, a radioisotope of iodine, chlorine, bromine, a radioisotope of bromine, or a radioisotope of astatine, NO2, NH2, N+(R2)3, Sn(R2)3, Si(R2)3, Hg(R2), or B(OH)2;
• OR
• m is 0, 1, 2, 3, 4, 5, or 6;
• Y is O, S, N(R′), C(O), NR′C(O), C(O)N(R′), OC(O), C(O)(O), NR′C(O)NR′, NR′C(S)NR′, NR′, NR'S(O)2, S(CH2)P, NR′—(CH2)P, O(CH2)P, OC(O)CHR8NHC(O), NHC(O) CHR8NHC(O), or a covalent bond;
• wherein p is 1, 2, or 3,R′ is H or C1-C6 alkyl, R8 is hydrogen, alkyl, aryl, or heteroaryl, each of which may be substituted;
• R is
• X′ is selected from the group consisting of NHNH2, —NHN═CHR3, —NHNH—CH2R3;
• R3 is alkyl, alkenyl, alkynyl, aryl, or heteroaryl each of which is substituted by fluorine, iodine, a radioisotope of fluorine, a radioisotope of iodine, chlorine, bromine, a radioisotope of bromine, or a radioisotope of astatine, NO2, NH2, N+(R2)3, Sn(R2)3, Si(R2)3, Hg(R2), or B(OH)2;
• R2 is C1-C6 alkyl, n is 1, 2, 3, 4, or 5;
• OR
• m is 4,
• Y is NR′, and
• R is
• wherein
• G is O, NR′ or a covalent bond;
• R′is H or C1-C6 alkyl;
• p is 1, 2, 3, or 4, and
• R7 is selected from the group consisting of NH2, N═CHR3, NH—CH2R3, wherein R3 is alkyl, alkenyl, alkynyl, aryl, or heteroaryl each of which is substituted by fluorine, iodine, a radioisotope of fluorine, a radioisotope of iodine, chlorine, bromine, a radioisotope of bromine, or a radioisotope of astatine, NO2, NH2, N+(R2)3, Sn(R2)3, Si(R2)3, Hg(R2), or B(OH)2;
• and R2 is C1-C6 alkyl.