An inhibitor of PSMA
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DUPA

Item No. 19501

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N,N′-carbonylbis-L-glutamic acid
CAS Number
302941-52-2
Molecular Formula
C11H16N2O9
Formula Weight
320.3
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mlEthanol: Sparingly soluble: 1-10 mg/mlPBS (pH 7.2): Sparingly soluble: 1-10 mg/ml
SMILES
O=C(O)[C@@H](NC(N[C@H](C(O)=O)CCC(O)=O)=O)CCC(O)=O
InChi Code
InChI=1S/C11H16N2O9/c14-7(15)3-1-5(9(18)19)12-11(22)13-6(10(20)21)2-4-8(16)17/h5-6H,1-4H2,(H,14,15)(H,16,17)(H,18,19)(H,20,21)(H2,12,13,22)/t5-,6-/m0/s1
InChi Key
SOAPXKSPJAZNGO-WDSKDSINSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $61

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    10 mg

    $109

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    25 mg

    $242

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    50 mg

    $394

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    Cayman Chemical
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    Product Description

    DUPA is an inhibitor of prostate-specific membrane antigen (PSMA; IC50 = 47 nM for the glutamate carboxypeptidase activity).1 It has been used as a ligand to target radiolabels, cytotoxic agents, and antibody-drug conjugates to cancer cells.2,3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kozikowski, A.P., Nan, F., Conti, P., et al. Design of remarkably simple, yet potent urea-based inhibitors of glutamate carboxypeptidase II (NAALADase). J. Med. Chem. 44(3), 298-301 (2001).

    2. Kularatne, S.A., Wang, K., Santhapuram, H.-K.R., et al. Prostate-specific membrane antigen targeted imaging and therapy of prostate cancer using a PSMA inhibitor as a homing ligand. Mol. Pharm. 6(3), 780-789 (2009).

    3. Kularatne, S.A., Venkatesh, C., Santhapuram, H.-K.R., et al. Synthesis and biological analysis of prostate-specific membrane antigen-targeted anticancer prodrugs. J. Med. Chem. 53(21), 7767-7777 (2010).

    4. Kim, C.H., Axup, J.Y., Lawson, B.R., et al. Bispecific small molecule-antibody conjugate targeting prostate cancer. Proc. Natl. Acad. Sci. USA 110(44), 17796-17801 (2013).