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Sigma-Aldrich

Mc-Val-Cit-PAB

new

≥95%

Synonym(s):

Mc-Val-Cit-PAB, 6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino]-1-oxo-5-ureidopentan-2-yl)amino]-3-methyl-1-oxobutan-2-yl)hexanamide, N-[(1S)-1-[[(1S)-4-(carbamoylamino)-1-[[4-(hydroxymethyl)phenyl]carbamoyl]butyl]carbamoyl]-2-methylpropyl]-6-(2,5-dioxopyrrol-1-yl)hexanamide, N-[6-(2,5-Dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]-L-ornithinamide (ACI), L-Ornithinamide, N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-N-[4-(hydroxymethyl)phenyl]- (9CI, ACI)

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About This Item

Empirical Formula (Hill Notation):
C28H40N6O7
Molecular Weight:
572.65
UNSPSC Code:
12352209

Quality Level

Assay

≥95%

form

powder or crystals

color

white to yellow

storage temp.

−20°C

SMILES string

[C@@H](NC([C@@H](NC(CCCCCN1C(=O)C=CC1=O)=O)[C@H](C)C)=O)(C(NC2=CC=C(CO)C=C2)=O)CCCNC(N)=O

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

Application

This is a bifunctional cathepsin cleavable linker used in the construction of antibody drug conjugates (ADC).

Features and Benefits

The maleimide functionality can be used for bioconjugation to thiols in monoclonal antibodies while the benzyl alcohol can be used for construction of carbamate linkages with amine containing payloads.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cryptophycin-52 (CR52), a tubulin inhibitor, exhibits promising antitumor activity in vitro (picomolar level) and in mouse xenograft models. However, the narrow therapeutic window in clinical trials limits its further development. Antibody-drug conjugate (ADC), formed by coupling cytotoxic compound (payload) to an
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