DUPA(OtBu)-OH - CAS 1026987-94-9
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DUPA(OtBu)-OH - CAS 1026987-94-9 Catalog number: BADC-00511

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DUPA(OtBu)-OH is a PEG linker for antibody-drug-conjugation (ADC). 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.

Category
ADCs Linker
Product Name
DUPA(OtBu)-OH
CAS
1026987-94-9
Catalog Number
BADC-00511
Molecular Formula
C23H40N2O9
Molecular Weight
488.57
DUPA(OtBu)-OH

Ordering Information

Catalog Number Size Price Quantity
BADC-00511 500 mg $1099
BADC-00511 1 g $1573
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Description
DUPA(OtBu)-OH is a PEG linker for antibody-drug-conjugation (ADC). 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.
Synonyms
(S)-5-tert-Butoxy-4-(3-((s)-1,5-di-tert-butoxy-1,5-dioxopentan-2-yl)ureido)-5-oxopentanoic Acid; L-Glutamic acid, N-[[[(1S)-3-carboxy-1-[(1,1-dimethylethoxy)carbonyl]propyl]amino]carbonyl]-, 1,5-bis(1,1-dimethylethyl) ester; 2-[3-(1,3-bis-tert-butoxycarbonylpropyl)ureido]pentanedioic acid 1-tert-butyl ester
IUPAC Name
(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
Canonical 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
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
Solubility
Sparingly soluble in chloroform, soluble in methanol
Melting Point
120-123 °C
Appearance
White to Off-white Solid
Purity
95%
Shipping
Room temperature
Storage
2-8 °C

DUPA(OtBu)-OH, also known as 23-dehydro-2-deoxy-N-trifluoroacetylneuraminic acid, is a versatile chemical intermediate with a multitude of applications in bioscience. Here are four key applications of DUPA(OtBu)-OH:

Cancer Research: Playing a pivotal role in the realm of cancer research, DUPA(OtBu)-OH is indispensably utilized in the synthesis of targeted therapeutic agents tailored for prostate cancer. By binding to specific ligands, it facilitates the development of compounds capable of selectively attaching to cancer cells expressing the Prostate-Specific Membrane Antigen (PSMA). This targeted strategy not only enhances the effectiveness of cancer treatments but also diminishes the adverse effects associated with traditional therapies.

Drug Delivery Systems: Embracing the potential of DUPA(OtBu)-OH, researchers are harnessing its properties in the creation of drug conjugates designed to revolutionize drug delivery systems. Through precise binding to receptors on target cells, it ensures the accurate delivery of therapeutics to specific tissues, thereby amplifying treatment efficiency. This innovative method plays a crucial role in minimizing systemic toxicity while enhancing therapeutic outcomes, marking a significant advancement in the field of drug delivery.

Molecular Imaging: At the forefront of molecular imaging, DUPA(OtBu)-OH emerges as a key component in the development of imaging agents for diagnostic purposes. By conjugating with radioactive isotopes or fluorescent markers, it facilitates the visualization of PSMA-expressing tumors using cutting-edge techniques such as Positron Emission Tomography (PET) or fluorescence imaging. This application represents a substantial leap in cancer detection and monitoring, offering heightened precision and accuracy in diagnostic imaging.

Receptor Binding Studies: Serving as an invaluable tool in the exploration of receptor-ligand interactions, DUPA(OtBu)-OH enables researchers to delve into the intricacies of binding affinities and specificities between different ligands and PSMA. By synthesizing analogs of DUPA(OtBu)-OH, scientists can unravel the complex web of molecular interactions crucial for designing more potent therapeutic agents and diagnostics with enhanced efficacy. This comprehensive understanding of receptor binding dynamics propels forward the development of advanced bioactive compounds.

1.DUPA conjugation of a cytotoxic indenoisoquinoline topoisomerase I inhibitor for selective prostate cancer cell targeting
Roy J, Nguyen TX, Kanduluru AK, Venkatesh C, Lv W, Reddy PV, Low PS, Cushman M.
Prostate-specific membrane antigen (PSMA) is overexpressed in most prostate cancer cells while being present at low or undetectable levels in normal cells. This difference provides an opportunity to selectively deliver cytotoxic drugs to prostate cancer cells while sparing normal cells that lack PSMA, thus improving potencies and reducing toxicities. PSMA has high affinity for 2-[3-(1,3-dicarboxypropyl)ureido]pentanedioic acid (DUPA) (Ki = 8 nM). After binding to a DUPA-drug conjugate, PSMA internalizes, unloads the conjugate, and returns to the surface. In the present studies, an indenoisoquinoline topoisomerase I inhibitor was conjugated to DUPA via a peptide linker and a drug-release segment that facilitates intracellular cleavage to liberate the drug cargo. The DUPA-indenoisoquinoline conjugate exhibited an IC50 in the low nanomolar range in 22RV1 cell cultures and induced a complete cessation of tumor growth with no toxicity, as determined by loss of body weight and death of treated mice.
2.Prostate-Specific Membrane Antigen Targeted Therapy of Prostate Cancer Using a DUPA-Paclitaxel Conjugate
Lv Q, Yang J, Zhang R, Yang Z, Yang Z, Wang Y, Xu Y, He Z.
Prostate cancer (PCa) is the most prevalent cancer among men in the United States and remains the second-leading cause of cancer mortality in men. Paclitaxel (PTX) is the first line chemotherapy for PCa treatment, but its therapeutic efficacy is greatly restricted by the nonspecific distribution in vivo. Prostate-specific membrane antigen (PSMA) is overexpressed on the surface of most PCa cells, and its expression level increases with cancer aggressiveness, while being present at low levels in normal cells. The high expression level of PSMA in PCa cells offers an opportunity for target delivery of nonspecific cytotoxic drugs to PCa cells, thus improving therapeutic efficacy and reducing toxicity. PSMA has high affinity for DUPA, a glutamate urea ligand. Herein, a novel DUPA-PTX conjugate is developed using DUPA as the targeting ligand to deliver PTX specifically for treatment of PSMA expressing PCa. The targeting ligand DUPA enhances the transport capability and selectivity of PTX to tumor cells via PSMA mediated endocytosis. Besides, DUPA is conjugated with PTX via a disulfide bond, which facilitates the rapid and differential drug release in tumor cells. The DUPA-PTX conjugate exhibits potent cytotoxicity in PSMA expressing cell lines and induces a complete cessation of tumor growth with no obvious toxicity. Our findings give new insight into the PSMA-targeted delivery of chemotherapeutics and provide an opportunity for the development of novel active targeting drug delivery systems for PCa therapy.
3.Spacer length impacts the efficacy of targeted docetaxel conjugates in prostate-specific membrane antigen expressing prostate cancer
Peng ZH, Sima M, Salama ME, Kopečková P, Kopeček J.
Combination of targeted delivery and controlled release is a powerful technique for cancer treatment. In this paper, we describe the design, synthesis, structure validation and biological properties of targeted and non-targeted N-(2-hydroxypropyl)methacrylamide (HPMA) copolymer-docetaxel conjugates. Docetaxel (DTX) was conjugated to HPMA copolymer via a tetrapeptide spacer (-GFLG-). 3-(1,3-dicarboxypropyl)-ureido]pentanedioic acid (DUPA) was used as the targeting moiety to actively deliver DTX for treatment of Prostate-Specific Membrane Antigen (PSMA) expressing prostate cancer. Short and long spacer DUPA monomers were prepared, and four HPMA copolymer--DTX conjugates (non-targeted, two targeted with short spacer of different molecular weight and targeted with long spacer) were prepared via Reversible Addition-Fragmentation Chain Transfer (RAFT) copolymerization. Following confirmation of PSMA expression on C4-2 cell line, the DTX conjugates' in vitro cytotoxicity was tested against C4-2 tumor cells and their anticancer efficacies were assessed in nude mice bearing s.c. human prostate adenocarcinoma C4-2 xenografts. The in vivo results show that the spacer length between targeting moieties and HPMA copolymer backbone can significantly affect the treatment efficacy of DTX conjugates against C4-2 tumor bearing nu/nu mice. Moreover, histological analysis indicated that the DUPA-targeted DTX conjugate with longer spacer had no toxicity in major organs of treated mice.
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