PSMA-11 free base

• CAT Number: I035163
• CAS Number: 1366302-52-4
• Molecular Formula: C44H62N6O17
• Molecular Weight: 947.005
• Purity: 98%
• Synonyms: DKFZ-​PSMA-​11; Psma-hbed-CC; PSMA-11; PSMA11; PSMA 11; HBED-CC-PSMA; PSMA-11 TFA; Psma-hbed-CC
• Solubility: To be determined
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (3S,7S)-22-(3-(((2-((5-(2-Carboxyethyl)-2-hydroxybenzyl)(carboxymethyl)amino)ethyl)(carboxymethyl)amino)methyl)-4-hydroxyphenyl)-5,13,20-trioxo-4,6,12,19-tetraazadocosane-1,3,7-tricarboxylic acid
• InChI: InChI=1S/C44H62N6O17/c51-34-13-8-28(22-30(34)24-49(26-40(59)60)20-21-50(27-41(61)62)25-31-23-29(9-14-35(31)52)11-16-38(55)56)10-15-37(54)46-18-4-1-2-7-36(53)45-19-5-3-6-32(42(63)64)47-44(67)48-33(43(65)66)12-17-39(57)58/h8-9,13-14,22-23,32-33,51-52H,1-7,10-12,15-21,24-27H2,(H,45,53)(H,46,54)(H,55,56)(H,57,58)(H,59,60)(H,61,62)(H,63,64)(H,65,66)(H2,47,48,67)/t32-,33-/m0/s1
• InChIKey: QJUIUFGOTBRHKP-LQJZCPKCSA-N
• SMILES: O=C(O)CC[C@H](NC(N[C@@H](CCCCNC(CCCCCNC(CCC1=CC=C(O)C(CN(CC(O)=O)CCN(CC2=CC(CCC(O)=O)=CC=C2O)CC(O)=O)=C1)=O)=O)C(O)=O)=O)C(O)=O

PSMA-11 free base(CAT: I035163), also known as DKFZ-PSMA-11 or HBED-CC-PSMA, is a ligand used for gallium Ga 68-labeled PSMA-11, a radiotracer for PET imaging of PSMA-expressing tumors. PSMA-11 targets PSMA, a membrane protein expressed on prostatic epithelial and prostate tumor cells. Upon intravenous administration of the radiotracer, PSMA-expressing tumor cells can be detected during PET imaging. PSMA-11 enables the diagnosis, staging, and monitoring of prostate cancer due to its high specificity for PSMA-expressing cells.

Reference

1: Verma P, Malhotra G, Meshram V, Chandak A, Sonavane S, Lila AR, Bandgar TR, Asopa RV. Prostate-Specific Membrane Antigen Expression in Patients With Differentiated Thyroid Cancer With Thyroglobulin Elevation and Negative Iodine Scintigraphy Using 68Ga-PSMA-HBED-CC PET/CT. Clin Nucl Med. 2021 Aug 1;46(8):e406-e409. doi: 10.1097/RLU.0000000000003655. PMID: 33883490.
2: Guglielmo P, Gasparro D, Scarlattei M, Baldari G, Bola S, Migliari S, Sammartano A, Maestroni U, Ruffini L. [68Ga]Ga-PSMA-HBED-CC PET/CT demonstrates to be superior to ceCT in detecting early treatment response in metastatic clear cell renal cell carcinoma. Eur J Nucl Med Mol Imaging. 2021 Mar 22. doi: 10.1007/s00259-021-05250-1. Epub ahead of print. PMID: 33754194.
3: Malhotra G, Aute PP, Awasare S, Asopa RV. 68Ga-PSMA-HBED-CC PET/CT Findings in a Patient of Polyostotic Fibrous Dysplasia. Clin Nucl Med. 2021 Jul 1;46(7):e349-e352. doi: 10.1097/RLU.0000000000003492. PMID: 33417342.
4: Yip JWL, Hilliar L, Le K, Loh H, Mansberg R. 68Ga-Prostate-Specific Membrane Antigen Solitary Base of Skull Prostate Adenocarcinoma Metastasis. Clin Nucl Med. 2021 Jan;46(1):63-65. doi: 10.1097/RLU.0000000000003390. PMID: 33181755.
5: Grubmüller B, Jahrreiss V, Huebner N, Mitterhauser M, Stangl-Kremser J, Grubmüller KH, Baltzer P, Hacker M, Goldner G, Shariat SF, Rasul S. Differential impact of radiation therapy after radical prostatectomy on recurrence patterns: an assessment using [68Ga]Ga-PSMA ligand PET/CT(MRI). Prostate Cancer Prostatic Dis. 2021 Jun;24(2):439-447. doi: 10.1038/s41391-020-00294-0. Epub 2020 Sep 29. PMID: 32994534.
6: Golan H, Esa M, Moshkoviz K, Feldhaim A, Hoch B, Shalom E. Enhancing capacity and synthesis of [68Ga]68-Ga-PSMA-HBED-CC with the lyophilized ready-to-use kit for nuclear pharmacy applications. Nucl Med Commun. 2020 Sep;41(9):986-990. doi: 10.1097/MNM.0000000000001232. PMID: 32796488.
7: Sørensen MA, Andersen VL, Hendel HW, Vriamont C, Warnier C, Masset J, Huynh THV. Automated synthesis of 68 Ga/177 Lu-PSMA on the Trasis miniAllinOne. J Labelled Comp Radiopharm. 2020 Jun 30;63(8):393-403. doi: 10.1002/jlcr.3846. Epub 2020 Jun 1. PMID: 32374450.
8: Wong VCK, Yip JWL, Stevanovic A, Le K, Mansberg R. 68Ga-Prostate-Specific Membrane Antigen Uptake in Dissecting Abdominal Aortic Aneurysm. Clin Nucl Med. 2020 Jun;45(6):455-458. doi: 10.1097/RLU.0000000000002972. PMID: 32149812.
9: Sood A, Vadi SK, Kumar R, Singh H, Mittal BR. Incidental Detection of Hypothyroidism on 68Ga-PSMA-HBED-CC PET/CT Imaging. Clin Nucl Med. 2020 Apr;45(4):e217-e218. doi: 10.1097/RLU.0000000000002965. PMID: 32108699.
10: van Boxtel W, Lütje S, van Engen-van Grunsven ICH, Verhaegh GW, Schalken JA, Jonker MA, Nagarajah J, Gotthardt M, van Herpen CML. 68Ga-PSMA-HBED- CC PET/CT imaging for adenoid cystic carcinoma and salivary duct carcinoma: a phase 2 imaging study. Theranostics. 2020 Jan 12;10(5):2273-2283. doi: 10.7150/thno.38501. PMID: 32089741; PMCID: PMC7019174.
11: Sakthivel P, Thakar A, Prashanth A, Bhalla AS, Kakkar A, Sikka K, Singh CA, Kumar R, Sharma SC, Kumar R. Prostate-Specific Membrane Antigen Expression in Primary Juvenile Nasal Angiofibroma-A Pilot Study. Clin Nucl Med. 2020 Mar;45(3):195-199. doi: 10.1097/RLU.0000000000002928. PMID: 31977481.
12: Wong VCK, Shen L, Nasser E, Adams DN, Mansberg R. 68Ga-Prostate-Specific Membrane Antigen Uptake in Cerebral Tuberculosis. Clin Nucl Med. 2020 Mar;45(3):238-240. doi: 10.1097/RLU.0000000000002910. PMID: 31977467.
13: Pollard JH, Raman C, Zakharia Y, Tracy CR, Nepple KG, Ginader T, Breheny P, Sunderland JJ. Quantitative Test-Retest Measurement of 68Ga-PSMA- HBED-CC in Tumor and Normal Tissue. J Nucl Med. 2020 Aug;61(8):1145-1152. doi: 10.2967/jnumed.119.236083. Epub 2019 Dec 5. PMID: 31806776.
14: Yadav MP, Ballal S, Bal C, Sahoo RK, Damle NA, Tripathi M, Seth A. Efficacy and Safety of 177Lu-PSMA-617 Radioligand Therapy in Metastatic Castration- Resistant Prostate Cancer Patients. Clin Nucl Med. 2020 Jan;45(1):19-31. doi: 10.1097/RLU.0000000000002833. PMID: 31789908.
15: Parihar AS, Sood A, Mittal BR, Kumar R, Singh H, Dhatt SS. 68Ga-PSMA-HBED-CC PET/CT and 18F-FDG PET/CT in Ewing Sarcoma. Clin Nucl Med. 2020 Jan;45(1):e57-e58. doi: 10.1097/RLU.0000000000002764. PMID: 31524682.
16: Schmidkonz C, Cordes M, Goetz TI, Prante O, Kuwert T, Ritt P, Uder M, Wullich B, Goebell P, Bäuerle T. 68Ga-PSMA-11 PET/CT derived quantitative volumetric tumor parameters for classification and evaluation of therapeutic response of bone metastases in prostate cancer patients. Ann Nucl Med. 2019 Oct;33(10):766-775. doi: 10.1007/s12149-019-01387-0. Epub 2019 Jul 23. PMID: 31338731.
17: Wo S, Matesan MC. 18F-Fluciclovine Uptake in Celiac Ganglia: A Pitfall in Prostate Cancer PET Imaging. Clin Nucl Med. 2019 Sep;44(9):743-745. doi: 10.1097/RLU.0000000000002693. PMID: 31283598.
18: Sheng K, Le K, Bui C, Mansberg R. Incidental Detection of Splenic Hemangioma on 68Ga-PSMA PET/CT. Clin Nucl Med. 2019 Oct;44(10):821-823. doi: 10.1097/RLU.0000000000002662. PMID: 31162264.
19: McCarthy M, Francis R, Tang C, Watts J, Campbell A. A Multicenter Prospective Clinical Trial of 68Gallium PSMA HBED-CC PET-CT Restaging in Biochemically Relapsed Prostate Carcinoma: Oligometastatic Rate and Distribution Compared With Standard Imaging. Int J Radiat Oncol Biol Phys. 2019 Jul 15;104(4):801-808. doi: 10.1016/j.ijrobp.2019.03.014. Epub 2019 Mar 16. PMID: 30890448.
20: Verma P, Malhotra G, Goel A, Rakshit S, Chandak A, Chedda R, Banerjee S, Asopa RV. Differential Uptake of 68Ga-PSMA-HBED-CC (PSMA-11) in Low-Grade Versus High-Grade Gliomas in Treatment-Naive Patients. Clin Nucl Med. 2019 May;44(5):e318-e322. doi: 10.1097/RLU.0000000000002520. PMID: 30829867.