CAS 863971-24-8|Mc-MMAE

Introduction:Basic information about CAS 863971-24-8|Mc-MMAE, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common NameMc-MMAE
CAS Number863971-24-8Molecular Weight911.17800
Density1.144±0.06 g/cm3(Predicted)Boiling Point1025.2±65.0 °C(Predicted)
Molecular FormulaC49H78N6O10Melting Point/
MSDS/Flash Point/

Names

NameMaleimidocaproyl-monomethylauristatin E
SynonymMore Synonyms

Mc-MMAE BiologicalActivity

DescriptionMc-MMAE is a protective group (maleimidocaproyl)-conjugated monomethyl auristatin E (MMAE), which is a potent tubulin inhibitor, is a toxin payload in antibody drug conjugate (ADC).
Related CatalogSignaling Pathways >>Antibody-drug Conjugate >>Drug-Linker Conjugates for ADCSignaling Pathways >>Cell Cycle/DNA Damage >>Microtubule/TubulinSignaling Pathways >>Cytoskeleton >>Microtubule/TubulinResearch Areas >>Cancer
Target

Tubulin, Antibody-drug conjugates (ADC)[1]

In VitroSynthesis of maleimidocaproyl-MMAE (mc-MMAE) requires the addition of maleimidocaproic acid to a solution of MMAE in dichloromethane followed by the addition of diethyl cyanophosphonate and diisopropylethylamine[1].
Kinase AssayHorseradish peroxidase (HRP) is thiolated with 2-iminothiolane and conjugated to mc-MMAE to generate the HRP-MMAE reporter enzyme-drug conjugate. Briefly, a thiolation reaction mixture containing 0.2 mM HRP (8 mg/mL) and 50 mM 2-iminothiolane in 25 mM sodium borate decahydrate (Na2B4O7•10H2O) buffer (pH 9.0) is incubated for 1 hour at 37°C. Unreacted 2-iminothiolane is removed by passage through a PD-10 desalting column equilibrated in PBS (pH 7.4). Peak fractions are pooled and mc-MMAE is coupled to thiolated HRP (HRP-SH) at a molar ratio of 3:1. The final conjugation reaction mixture contained 80 μM HRP-SH (3.2 mg/mL) in sodium borate buffer [50 mM H3BO3, 50 mM NaCl (pH 8.0); 80% v/v] and 240 μM mc-MMAE in ice-cold CH3CN (20% v/v). After 30 minutes on ice, the reaction is terminated with a 20-fold molar excess of free cysteine (4.8 mM) before PD-10 chromatography. Peak fractions containing HRP-MMAE (exchanged into PBS) are pooled and evaluated for extent of modification using the thiol-reactive dye, Alexa Fluor 594 C5 maleimide[1].
References

[1]. Sanderson RJ, et al. In vivo drug-linker stability of an anti-CD30 dipeptide-linked auristatin immunoconjugate. Clin Cancer Res. 2005 Jan 15;11(2 Pt 1):843-52.

Chemical & Physical Properties

Density1.144±0.06 g/cm3(Predicted)
Boiling Point1025.2±65.0 °C(Predicted)
Molecular FormulaC49H78N6O10
Molecular Weight911.17800
Exact Mass910.57800
PSA195.20000
LogP4.91180
InChIKeyUGJOTJHSQWBROP-AXJCKIDNSA-N
SMILESCCC(C)C(C(CC(=O)N1CCCC1C(OC)C(C)C(=O)NC(C)C(O)c1ccccc1)OC)N(C)C(=O)C(NC(=O)C(C(C)C)N(C)C(=O)CCCCCN1C(=O)C=CC1=O)C(C)C
Storage condition2-8°C

Synonyms

Mc-MMAE
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