A peptide linker molecule
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Mc-Val-Cit-PAB

Item No. 28285

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide
CAS Number
159857-80-4
Molecular Formula
C28H40N6O7
Formula Weight
572.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
O=C(N[C@@H](C(C)C)C(N[C@@H](CCCNC(N)=O)C(NC1=CC=C(CO)C=C1)=O)=O)CCCCCN2C(C=CC2=O)=O
InChi Code
InChI=1S/C28H40N6O7/c1-18(2)25(33-22(36)8-4-3-5-16-34-23(37)13-14-24(34)38)27(40)32-21(7-6-15-30-28(29)41)26(39)31-20-11-9-19(17-35)10-12-20/h9-14,18,21,25,35H,3-8,15-17H2,1-2H3,(H,31,39)(H,32,40)(H,33,36)(H3,29,30,41)/t21-,25-/m0/s1
InChi Key
AMKBTTRWLGVRER-OFVILXPXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    50 mg

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    Product Description

    Mc-Val-Cit-PAB is a peptide linker molecule used in the synthesis of antibody-drug conjugates (ADCs).1 It contains a maleimidocaproyl (Mc) group that can be conjugated to an antibody and a p-aminobenzyl (PAB) spacer that allows the peptide to be linked to active compounds, such as anticancer agents. Mc-Val-Cit-PAB is cleaved in vivo by cathepsin B, a protease highly expressed in cancer cells, which confers specificity of the ADC to cancer cells. Upon cleavage by cathepsin B, the active compound is released at the target site. Mc-Val-Cit-PAB has been used in the synthesis of an ADC containing the tubulin polymerization inhibitor KGP05. It has also been used as a precursor in the synthesis of Mc-Val-Cit-PABC-PNP (Item No. 23881).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mondal, D., Ford, J., and Pinney, K.G. Improved methodology for the synthesis of a cathepsin B cleavable dipeptide linker, widely used in antibody-drug conjugate research. Tetrahedron Lett. 59(40), 3594-3599 (2018).

    2. Dubowchik, G.M., Firestone, R.A., Padilla, L., et al. Cathepsin B-labile dipeptide linkers for lysosomal release of doxorubicin from internalizing immunoconjugates: Model studies of enzymatic drug release and antigen-specific in vitro anticancer activity. Bioconjug. Chem. 13(4), 855-869 (2002).