For research use only. Not for therapeutic Use.
DUPA(OtBu)-OH is a DUPA precursor. DUPA is used as the targeting moiety to actively deliver Docetaxel (DTX) for treatment of Prostate-Specific Membrane Antigen (PSMA) expressing prostate cancer.
DUPA(OtBu)-OH (DUPA precursor 17) is a 2-[3-(1,3-dicarboxypropyl)ureido]pentanedioic acid (DUPA) reagent[1]. The targeting ligand DUPA enhances the transport capability and selectivity of Paclitaxel (PTX) to tumor cells via prostate-specific membrane antigen (PSMA) mediated endocytosis. Besides, DUPA is conjugated with PTX via a disulfide bond, which facilitates the rapid and differential drug release in tumor cells[2].
DUPA-targeted Docetaxel (DTX) conjugate with longer spacer has no toxicity in major organs of treated mice[3].
| Catalog Number | I019955 |
| CAS Number | 1026987-94-9 |
| Synonyms | (4S)-4-[[(2S)-1,5-bis[(2-methylpropan-2-yl)oxy]-1,5-dioxopentan-2-yl]carbamoylamino]-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid |
| Molecular Formula | C23H40N2O9 |
| Purity | ≥95% |
| InChI | InChI=1S/C23H40N2O9/c1-21(2,3)32-17(28)13-11-15(19(30)34-23(7,8)9)25-20(31)24-14(10-12-16(26)27)18(29)33-22(4,5)6/h14-15H,10-13H2,1-9H3,(H,26,27)(H2,24,25,31)/t14-,15-/m0/s1 |
| InChIKey | KBDDHSXZOLZZGF-GJZGRUSLSA-N |
| SMILES | CC(C)(C)OC(=O)CCC(C(=O)OC(C)(C)C)NC(=O)NC(CCC(=O)O)C(=O)OC(C)(C)C |
| Reference | [1]. Roy J, et al. DUPA conjugation of a cytotoxic indenoisoquinoline topoisomerase I inhibitor for selectiveprostate cancer cell targeting. J Med Chem. 2015 Apr 9;58(7):3094-103. [2]. Lv Q, et al. Prostate-Specific Membrane Antigen Targeted Therapy of Prostate Cancer Using a DUPA-Paclitaxel Conjugate. Mol Pharm. 2018 May 7;15(5):1842-1852. [3]. Peng ZH, et al. Spacer length impacts the efficacy of targeted docetaxel conjugates in prostate-specificmembrane antigen expressing prostate cancer. J Drug Target. 2013 Dec;21(10):968-80. |
