Mc-Val-Cit-PAB | CAS#159857-80-4 | peptide linker molecule

MedKoo Cat#: 555776 | Name: Mc-Val-Cit-PAB

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Mc-Val-Cit-PAB

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

Theoretical Analysis

MedKoo Cat#: 555776

Name: Mc-Val-Cit-PAB

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

Chemical Formula: C28H40N6O7

Exact Mass: 572.2958

Molecular Weight: 572.66

Elemental Analysis: C, 58.73; H, 7.04; N, 14.68; O, 19.56

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
200mg	USD 600.00	2 Weeks
500mg	USD 1,250.00	2 Weeks
1g	USD 2,050.00	2 Weeks
2g	USD 3,450.00	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; Mc-Val-Cit PAB; Mc-Val-Cit PAB; 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/

	Solvent	mg/mL	mM
Solubility
	DMSO	145.0	253.20

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

[1]. Anti-cd70 antibody-drug conjugates and their use for the treatment of cancer and immune disorders https://patents.google.com/patent/US20080025989