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VcMMAE

VcMMAE Structure
CAS No.
646502-53-6
Chemical Name:
VcMMAE
Synonyms
MC-VC-PAB-MMAE;MC-Val-Cit-PAB-MMAE;VeMMAE;VcMMAE;EOS-60990;VC-MMAE;VC MMAE;MC-VC-PABC-MMAE;MC-VAL-CIT-PABC-MMAE;VcMMAE (mc-vc-PAB-MMAE);Brentuximab Impurity 1 (Vedotin)
CBNumber:
CB22666699
Molecular Formula:
C68H105N11O15
Molecular Weight:
1316.63
MOL File:
646502-53-6.mol
Modify Date:
2024/7/2 8:55:03

VcMMAE Properties

Boiling point 1347.6±65.0 °C(Predicted)
Density 1.196±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
solubility Soluble in DMSO, DCM, DMF
form A solid
pka 13.29±0.70(Predicted)
color White to off-white
InChIKey NLMBVBUNULOTNS-NNNQBTKHNA-N

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P280-P305+P351+P338
NFPA 704
0
4 0

VcMMAE Chemical Properties,Uses,Production

Description

MC-Val-Cit-PAB-MMAE is a precursor of antibody drug conjugate. It contains a thio reactive maleimidocaproyl (MC) group, a protease-sensitive Val-Cit dipeptide, a PABC linker and a MMAE payload. The MMAE is a synthetic antineoplastic agent. It can be attached to a monoclonal antibody (MAB) which directs it toward cancer cells.

Uses

Vedotin is an ultra-high-affinity small organic ligand of fibroblast activation protein used for tumor-targeting applications

Application

VcMMAE is a MMAE derivative with valine-citrulline (Vc) linker. VcMMAE can be used to make antibody drug conjugate. VcMMAE is a anti-mitotic agent, monomethyl auristatin E (MMAE), linked via the lysosomally cleavable dipeptide, valine-citrulline (vc). Monomethyl auristatin E (MMAE) is a synthetic antineoplastic agent. Because of its toxicity, it cannot be used as a drug itself; instead, it is linked to a monoclonal antibody (MAB) which directs it to the cancer cells. In International Nonproprietary Names for MMAE-MAB-conjugates, the name vedotin refers to MMAE plus its linking structure to the antibody. It is a potent antimitotic drug derived from peptides occurring in marine shell-less mollusc Dolabella auricularia called dolastatins which show potent activity in preclinical studies, both in vitro and in vivo, against a range of lymphomas, leukemia and solid tumors. These drugs show potency of up to 200 times that of vinblastine, another antimitotic drug used for Hodgkin lymphoma as well as other types of cancer?

Biological Activity

VcMMAE is an antibody-drug conjugate (ADC) with potent antitumor activity by using the anti-mitotic agent, monomethyl auristatin E (MMAE), linked via the lysosomally cleavable dipeptide, valine-citrulline (vc). As a monoclonal antibody, it acts by binding to the extracellular domain of epidermal growth factor receptor (EGFR) and blocking its interaction with the ligands, thereby inhibiting cellular proliferation.

VcMMAE Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 188)Suppliers
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BOC Sciences 16314854226; +16314854226 United States 19743 58 Inquiry
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Hubei Ipure Biology Co., Ltd +8613367258412 China 10326 58 Inquiry
ANHUI WITOP BIOTECH CO., LTD +8615255079626 China 23556 58 Inquiry
Xi'an MC Biotech, Co., Ltd. 029-89275612 +8618991951683 China 2255 58 Inquiry
VcMMAE Maleimidocaproyl-valine-citrulline-p-aminobenzoyloxycarbonyl-monomethyl auristatin E 4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-y MC-VC-PAB-MMAE,MC-Val-Cit-PAB-MMAE maleimido-caproyl-val-Cit-PAB-MMAE VeMMAE EOS-60990 4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-Uriedidopenamiamido)benzyl((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S),2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-y VC-MMAE;VC MMAE 4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl ((S)-1-((S)-2-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-y 4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl ((S)-1-((S)-2-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methylbutanamido)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate L-Valinamide, N-[[[4-[[N-[6-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxohexyl]-L-valyl-N5-(aminocarbonyl)-L-ornithyl]amino]phenyl]methoxy]carbonyl]-N-methyl-L-valyl-N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl]-2-met... MC-VAL-CIT-PABC-MMAE Brentuximab Impurity 1 (Vedotin) [4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl N-[(2S)-1-[[(2S)-1-[[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]-N-methylcarbamate VcMMAE (mc-vc-PAB-MMAE) Maleimidocaproyl-valine-citrulline-p-aminobenzyloxycarbonyl monomethylauristatin E MC-Val-Cit-PAB-MMAE MC-VC-PAB-MMAE 4-((S)-2-((S)-2-(6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl ((S)-1-(((S)-1-(((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxoheptan-4-yl)(methyl)amino)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)(methyl)carbamate VcMMAE(Synonyms: mc-vc-PAB-MMAE) [4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[6-(2,5-dioxopyrrol-1-yl)hexanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl N-[(2S)-1-[[(2S)-1-[[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-o MC-VC-PABC-MMAE 646502-53-6 645602-53-6 646502-53-7 64650-53-6 C68H105N11O15 ADCs ADC ADC LINKER 646502-53-6