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VcMMAE

Product Name
VcMMAE
CAS No.
646502-53-6
Chemical Name
VcMMAE
Synonyms
MC-VC-PAB-MMAE;MC-Val-Cit-PAB-MMAE;VcMMAE;VeMMAE;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
Formula Weight
1316.63
MOL File
646502-53-6.mol
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VcMMAE Property

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
InChI
InChI=1/C68H105N11O15/c1-15-43(8)59(51(92-13)38-55(83)78-37-23-27-50(78)61(93-14)44(9)62(85)71-45(10)60(84)47-24-18-16-19-25-47)76(11)66(89)57(41(4)5)75-65(88)58(42(6)7)77(12)68(91)94-39-46-29-31-48(32-30-46)72-63(86)49(26-22-35-70-67(69)90)73-64(87)56(40(2)3)74-52(80)28-20-17-21-36-79-53(81)33-34-54(79)82/h16,18-19,24-25,29-34,40-45,49-51,56-61,84H,15,17,20-23,26-28,35-39H2,1-14H3,(H,71,85)(H,72,86)(H,73,87)(H,74,80)(H,75,88)(H3,69,70,90)/t43-,44+,45+,49-,50-,51+,56-,57-,58-,59-,60+,61+/s3
InChIKey
NLMBVBUNULOTNS-NNNQBTKHNA-N
SMILES
[C@@H](C(=O)N[C@H](C(=O)N(C)[C@@H]([C@@H](C)CC)[C@@H](CC(N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C)[C@@H](O)C1C=CC=CC=1)=O)OC)C(C)C)(C(C)C)N(C)C(=O)OCC1C=CC(NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(CCCCCN2C(=O)C=CC2=O)=O)CCCNC(=O)N)=CC=1 |&1:0,4,9,10,14,21,22,25,30,32,62,66,r|
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

BroadPharm
Product number
BP-23969
Product name
MC-Val-Cit-PAB-MMAE
Purity
98%
Packaging
5mg
Price
$265
Updated
2021/12/16
BroadPharm
Product number
BP-23969
Product name
MC-Val-Cit-PAB-MMAE
Purity
98%
Packaging
10mg
Price
$410
Updated
2021/12/16
BroadPharm
Product number
BP-23969
Product name
MC-Val-Cit-PAB-MMAE
Purity
98%
Packaging
1mg
Price
$145
Updated
2021/12/16
ChemScene
Product number
CS-1242
Product name
VcMMAE
Purity
99.89%
Packaging
250mg
Price
$1580
Updated
2021/12/16
Biorbyt Ltd
Product number
orb573074
Product name
VcMMAE
Purity
>99.11%
Packaging
100mg
Price
$1949.9
Updated
2021/12/16
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VcMMAE Chemical Properties,Usage,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.

in vitro

MMAE is efficiently released from SGN-35 within CD30 cancer cells and, due to its membrane permeability, is able to exert cytotoxic activity on bystander cells+. MMAE sensitized colorectal and pancreatic cancer cells to IR in a schedule and dose dependent manner correlating with mitotic arrest. Radiosensitization is evidenced by decreased clonogenic survival and increased DNA double strand breaks in irradiated cells.

in vivo

MMAE in combination with IR results in tumor growth delay, tumor-targeted ACPP-cRGD-MMAE with IR produces a more robust and significantly prolonged tumor regression in xenograft models.

target

Auristatin

VcMMAE Preparation Products And Raw materials

Raw materials

Preparation Products

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VcMMAE Suppliers

China 184 China Hong Kong 1 United States 10 Global 195
ALB Technology Limited
Tel
702-983-3769
Fax
702-983-3769
Email
sales@albtechnology.com
Country
United States
ProdList
2993
Advantage
55
Musechem
Tel
+1-800-259-7612
Fax
+1-800-259-7612
Email
info@musechem.com
Country
United States
ProdList
4660
Advantage
60
TargetMol Chemicals Inc.
Tel
+1-781-999-5354 +1-00000000000
Email
marketing@targetmol.com
Country
United States
ProdList
32165
Advantage
58
BOC Sciences
Tel
16314854226; +16314854226
Email
inquiry@bocsci.com
Country
United States
ProdList
19741
Advantage
58
InvivoChem
Tel
+1-708-310-1919 +1-13798911105
Fax
708-557-7486
Email
sales@invivochem.cn
Country
United States
ProdList
6391
Advantage
58
Protheragen-ING
Tel
+16313385890
Email
info@protheragen-ing.com
Country
United States
ProdList
3868
Advantage
58
Aladdin Scientific
Tel
+1-+1(833)-552-7181
Email
sales@aladdinsci.com
Country
United States
ProdList
57505
Advantage
58
TargetMol Chemicals Inc.
Tel
Email
support@targetmol.com
Country
United States
ProdList
38632
Advantage
58
Cayman Chemical Company
Tel
--
Fax
--
Email
cayman@caymanchem.com
Country
United States
ProdList
6213
Advantage
81
MedChemExpress
Tel
--
Fax
--
Email
sales@medchemexpress.com
Country
United States
ProdList
6398
Advantage
58
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View Lastest Price from VcMMAE manufacturers

Xian confluore Biological Technology Co., Ltd.
Product
MC-Val-Cit-PAB-MMAE 646502-53-6
Price
US $0.00/mg
Min. Order
100mg
Purity
>98.00%
Supply Ability
100mg
Release date
2024-03-29
Zhuozhou Wenxi import and Export Co., Ltd
Product
VCMMAE 646502-53-6
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-11
HONG KONG IPURE BIOLOGY CO.,LIMITED
Product
Fmoc-Val-Cit-PAB-MMAE 646502-53-6
Price
US $1.00/BOU/Drum
Min. Order
1KG
Purity
98%
Supply Ability
1kg
Release date
2020-11-24

646502-53-6, VcMMAERelated Search:

MonoMethylauristatin F (2R,3R)-N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-3-Methoxy-2-Methyl-3-((S)-pyrrolidin-2-yl)propanaMide (hydrochloride) N-Boc-(2R,3R,4S)-dolaproine (9H-fluoren-9-yl)Methyl ((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-Met MonoMethyl auristatin E (3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydroc hloride

  • VcMMAE
  • MC-Val-Cit-PAB-MMAE
  • 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-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
  • Maleimidocaproyl-valine-citrulline-p-aminobenzyloxycarbonyl monomethylauristatin E
  • VcMMAE (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