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Literature summary for 3.4.17.21 extracted from

  • Maresca, K.; Hillier, S.; Femia, F.; Keith, D.; Barone, C.; Joyal, J.; Zimmerman, C.; Kozikowski, A.; Barrett, J.; Eckelman, W.; Babich, J.
    A series of halogenated heterodimeric inhibitors of prostate specific membrane antigen (PSMA) as radiolabeled probes for targeting prostate cancer (2009), J. Med. Chem., 52, 347-357.
    View publication on PubMed
Search for more literature for 3.4.17.21

Application

Application Comment Organism
diagnostics PSMA is a validated molecular marker for prostate cancer Homo sapiens
drug development PSMA is a target for drug design Homo sapiens

Inhibitors

Inhibitors Comment Organism Structure
(9S,13S)-1-(3-iodophenyl)-3,11-dioxo-2,4,10,12-tetraazapentadecane-9,13,15-tricarboxylic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(2-chlorobenzylamino)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(2-iodobenzylamino)pentyl)ureido)-pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(3-(4-bromophenyl)ureido)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(3-(4-chlorophenyl)ureido)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(3-(4-fluorophenyl)ureido)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(3-(4-iodophenyl)ureido)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(3-chlorobenzylamino)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(3-iodobenzylamino)pentyl)ureido)-pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(3-phenylureido)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(4-bromobenzylamino)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(4-chlorobenzylamino)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(4-fluorobenzylamino)pentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(4-iodobenzylamino)pentyl)ureido)-pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(4-iodophenylsulfonamido)pentyl)-ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-1-carboxy-5-(naphthalen-1-ylmethylamino)pentyl)-ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-5-(benzylamino)-1-carboxypentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-((S)-5-amino-1-carboxypentyl)ureido)pentanedioic acid
-
 Homo sapiens
(S)-2-(3-(4-iodobenzyl)ureido)pentanedioic acid
-
 Homo sapiens
additional information design and synthesis of a series of glutamate-urea-X heterodimeric inhibitors of PSMA, where X is epsilon-N-(o-I, m-I, p-I, p-Br, o-Cl, m-Cl, p-Cl, p-F, H)-benzyl-Lys and epsilon-(p-I, p-Br, p-Cl, p-F, H)-phenylureido-Lys, overview. PSMA binding of the benzyllysine series is significantly affected by the nature of the halogen substituent. The halogen atom has little affect on the binding affinity in the para-substituted phenylureido-Lys series Homo sapiens

Localization

Localization Comment Organism GeneOntology No. Textmining
membrane PSMA Homo sapiens 16020
-

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information Homo sapiens PSMA is highly homologous to N-acetylated alpha-linked acidic dipeptidase, NAALADase ?
-
 ?
N-acetyl-L-aspartyl-L-glutamate + H2O Homo sapiens NAALADase, a neuropeptidase that produces the neurotransmitter glutamate and N-acetyl-Laspartate throught hydrolysis of N-acetyl-L-aspartyl-L-glutamate L-glutamate + N-acetyl-L-aspartate
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
LNCaP cell
-
 Homo sapiens
-
additional information no activity in PC-3 cells Homo sapiens
-
prostate cancer cell
-
 Homo sapiens
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information PSMA is highly homologous to N-acetylated alpha-linked acidic dipeptidase, NAALADase Homo sapiens ?
-
 ?
N-acetyl-L-aspartyl-L-glutamate + H2O
-
 Homo sapiens L-glutamate + N-acetyl-L-aspartate
-
 ?
N-acetyl-L-aspartyl-L-glutamate + H2O NAALADase, a neuropeptidase that produces the neurotransmitter glutamate and N-acetyl-Laspartate throught hydrolysis of N-acetyl-L-aspartyl-L-glutamate Homo sapiens L-glutamate + N-acetyl-L-aspartate
-
 ?

Synonyms

Synonyms Comment Organism
N-Acetylated alpha-linked acidic dipeptidase
-
 Homo sapiens
NAALADase
-
 Homo sapiens
Prostate-specific membrane antigen
-
 Homo sapiens
PSMA
-
 Homo sapiens

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000002
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(4-chlorobenzylamino)pentyl)ureido)pentanedioic acid
0.000002
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(3-(4-bromophenyl)ureido)pentyl)ureido)pentanedioic acid
0.000003
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(3-(4-fluorophenyl)ureido)pentyl)ureido)pentanedioic acid
0.000004
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(3-(4-chlorophenyl)ureido)pentyl)ureido)pentanedioic acid
0.00001
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(3-(4-iodophenyl)ureido)pentyl)ureido)pentanedioic acid
0.00001
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(4-iodophenylsulfonamido)pentyl)-ureido)pentanedioic acid
0.000012
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(3-phenylureido)pentyl)ureido)pentanedioic acid
0.000018
-
-
 Homo sapiens (9S,13S)-1-(3-iodophenyl)-3,11-dioxo-2,4,10,12-tetraazapentadecane-9,13,15-tricarboxylic acid
0.000022
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(4-iodobenzylamino)pentyl)ureido)-pentanedioic acid
0.000037
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(2-iodobenzylamino)pentyl)ureido)-pentanedioic acid
0.000043
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(4-bromobenzylamino)pentyl)ureido)pentanedioic acid
0.000154
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(naphthalen-1-ylmethylamino)pentyl)-ureido)pentanedioic acid
0.000245
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(2-chlorobenzylamino)pentyl)ureido)pentanedioic acid
0.000277
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(3-chlorobenzylamino)pentyl)ureido)pentanedioic acid
0.000443
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(3-iodobenzylamino)pentyl)ureido)-pentanedioic acid
0.000498
-
-
 Homo sapiens (S)-2-(3-((S)-5-amino-1-carboxypentyl)ureido)pentanedioic acid
0.0012
-
-
 Homo sapiens (S)-2-(3-((S)-1-carboxy-5-(4-fluorobenzylamino)pentyl)ureido)pentanedioic acid
0.00296
-
-
 Homo sapiens (S)-2-(3-((S)-5-(benzylamino)-1-carboxypentyl)ureido)pentanedioic acid
0.003
-
-
 Homo sapiens (S)-2-(3-(4-iodobenzyl)ureido)pentanedioic acid