Mc-Val-Cit-PAB
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MedKoo CAT#: 555776

CAS#: 159857-80-4 (MC-Val-Cit-PAB)

Description: Mc-Val-Cit-PAB is a peptide linker molecule used in the synthesis of antibody-drug conjugates (ADCs). 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.

Chemical Structure

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Mc-Val-Cit-PAB
CAS# 159857-80-4 (MC-Val-Cit-PAB)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555776
Name: Mc-Val-Cit-PAB
CAS#: 159857-80-4 (MC-Val-Cit-PAB)
Chemical Formula: C28H40N6O7
Exact Mass: 572.30
Molecular Weight: 572.663
Elemental Analysis: C, 58.73; H, 7.04; N, 14.68; O, 19.56

Price and Availability

Size Price Availability Quantity
100mg USD 350 2 Weeks
200mg USD 600 2 Weeks
500mg USD 1250 2 Weeks
1g USD 2050 2 Weeks
2g USD 3450 2 Weeks
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Related CAS #: 159857-80-4 (MC-Val-Cit-PAB)   159857-81-5 (MC-Val-Cit-PAB-PNP)   159857-79-1 (Val-cit-PAB-OH)    

Synonym: Mc-Val-Cit-PAB

IUPAC/Chemical 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

InChi Key: UMDCMQHPXQLHGR-OFVILXPXSA-N

InChi Code: InChI=1S/C28H40N6O7/c1-18(2)25(32-22(36)8-4-3-5-16-33-23(37)13-14-24(33)38)27(40)34(20-11-9-19(17-35)10-12-20)21(26(29)39)7-6-15-31-28(30)41/h9-14,18,21,25,35H,3-8,15-17H2,1-2H3,(H2,29,39)(H,32,36)(H3,30,31,41)/t21-,25-/m0/s1

SMILES Code: O=C(N)[C@H](CCCNC(N)=O)N(C([C@H](C(C)C)NC(CCCCCN1C(C=CC1=O)=O)=O)=O)C2=CC=C(CO)C=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: MC-Val-Cit-PAB is a cathepsin cleavable ADC linker that is used for making antibody-drug conjugate.
In vitro activity: A self-immolative p-aminobenzyloxycarbonyl (PABC) spacer between the dipeptides and the DOX was required for rapid and quantitative generation of free drug. DOX release from model substrate Z-Phe-Lys-PABC-DOX 49 was 30-fold faster than from Z-Val-Cit-PABC-DOX 42 with the cysteine protease cathepsin B alone. Reference: Bioconjug Chem. 2002 Jul-Aug;13(4):855-69. https://pubmed.ncbi.nlm.nih.gov/12121142/
In vivo activity: The Mc-Val-Cit-PABOH linker (1, Fig. 2) displays high plasma stability (half-lives in mice and monkey of 6.0 and 9.6 days, respectively), and has been found to be superior over chemically labile linkers. Reference: Tetrahedron Lett. 2018 Oct 3;59(40):3594-3599. https://pubmed.ncbi.nlm.nih.gov/31156276/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 145.0 253.20

Preparing Stock Solutions

The following data is based on the product molecular weight 572.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Dubowchik GM, Firestone RA, Padilla L, Willner D, Hofstead SJ, Mosure K, Knipe JO, Lasch SJ, Trail PA. 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. 2002 Jul-Aug;13(4):855-69. doi: 10.1021/bc025536j. PMID: 12121142. 2. Mondal D, Ford J, Pinney KG. Improved Methodology for the Synthesis of a Cathepsin B Cleavable Dipeptide Linker, Widely Used in Antibody-Drug Conjugate Research. Tetrahedron Lett. 2018 Oct 3;59(40):3594-3599. doi: 10.1016/j.tetlet.2018.08.021. Epub 2018 Aug 14. PMID: 31156276; PMCID: PMC6541422.
In vitro protocol: 1. Dubowchik GM, Firestone RA, Padilla L, Willner D, Hofstead SJ, Mosure K, Knipe JO, Lasch SJ, Trail PA. 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. 2002 Jul-Aug;13(4):855-69. doi: 10.1021/bc025536j. PMID: 12121142.
In vivo protocol: 1. Mondal D, Ford J, Pinney KG. Improved Methodology for the Synthesis of a Cathepsin B Cleavable Dipeptide Linker, Widely Used in Antibody-Drug Conjugate Research. Tetrahedron Lett. 2018 Oct 3;59(40):3594-3599. doi: 10.1016/j.tetlet.2018.08.021. Epub 2018 Aug 14. PMID: 31156276; PMCID: PMC6541422.

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