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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
1mg
Price
$145
Updated
2021/12/16
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
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
Levena (Suzhou) Biopharma Co., Ltd.
Tel
0512-81877925 051281877925
Email
info@levena.cn
Country
China
ProdList
48
Advantage
58
Shanghai ruichang pharmaceutical technology co., LTD
Tel
18621054990
Email
maychemicals@sina.com
Country
China
ProdList
673
Advantage
58
Shanghai Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
021-58955996
Email
info@chemexpress.com
Country
China
ProdList
774
Advantage
58
Shanghai Send Pharmaceutical Technology Co., Ltd.
Tel
+86-021-50266790 Q2816483246
Fax
021-50266790
Email
sale@shsendpharm.com
Country
China
ProdList
194
Advantage
50
Jinan Chengquan Chemical Co., Ltd
Tel
13616405505 13616405505
Email
zhulinsun1@126.com
Country
China
ProdList
121
Advantage
58
YJ Pharma
Tel
13962794339 13962794339
Email
3686954964@qq.com
Country
China
ProdList
167
Advantage
58
Xirui Biotech (Suzhou) Co., Ltd
Tel
15051451360
Email
3833346036@qq.com
Country
China
ProdList
132
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
Shanghai Topbiochem Technology Co., Ltd
Tel
021-58170097
Email
info@topbiochem.com
Country
China
ProdList
9459
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