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MonoMethyl auristatin E

MonoMethyl auristatin E Structure
MonoMethyl auristatin E structure
CAS No.
474645-27-7
Chemical Name:
MonoMethyl auristatin E
Synonyms
MMAE;Vedotin;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-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-L-valinamide Monomethyl;MonoMethyl auristatin E (MMAE);(S)-N-((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1R,2R)-1-Hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxohe;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-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-L-valinamide;CS-835;SGD-1010;HM-297C-22;[3H]-Vedotin
CBNumber:
CB02624235
Molecular Formula:
C39H67N5O7
Molecular Weight:
717.98
MDL Number:
MFCD22124498
MOL File:
474645-27-7.mol
Last updated:2024-02-19 08:42:31
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MonoMethyl auristatin E Properties

Melting point >90°C (dec.)
Boiling point 873.5±65.0 °C(Predicted)
Density 1.088±0.06 g/cm3(Predicted)
storage temp. -20°C Freezer
solubility DMSO (Slightly), Methanol (Slightly, Sonicated)
pka 13.66±0.20(Predicted)
form Solid
color White to Off-White
InChIKey RJACXSRFJLSJEZ-UIJRFTGLSA-N
SMILES C(NC(=O)[C@H](C(C)C)NC)(=O)[C@H](C(C)C)N([C@@H]([C@@H](C)CC)[C@H](OC)CC(N1CCC[C@H]1[C@H](OC)[C@@H](C)C(N[C@H](C)[C@@H](O)C1=CC=CC=C1)=O)=O)C
CAS DataBase Reference 474645-27-7
FDA UNII V7I58RC5EJ

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
NFPA 704
0
2 0

MonoMethyl auristatin E price More Price(24)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 16267 Monomethyl Auristatin E ≥95% 474645-27-7 500μg $81 2024-03-01 Buy
Cayman Chemical 16267 Monomethyl Auristatin E ≥95% 474645-27-7 1mg $152 2024-03-01 Buy
Cayman Chemical 16267 Monomethyl Auristatin E ≥95% 474645-27-7 5mg $356 2024-03-01 Buy
Cayman Chemical 16267 Monomethyl Auristatin E ≥95% 474645-27-7 10mg $553 2024-03-01 Buy
TRC M425410 MMAE 474645-27-7 100mg $910 2021-12-16 Buy
Product number Packaging Price Buy
16267 500μg $81 Buy
16267 1mg $152 Buy
16267 5mg $356 Buy
16267 10mg $553 Buy
M425410 100mg $910 Buy

MonoMethyl auristatin E Chemical Properties,Uses,Production

Description

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. Monomethyl auristatin E or MMAE is 100-1000 times more potent than doxorubicin. It is a very potent antimitotic agent that inhibits cell division by blocking the polymerization of tubulin.

Chemical Properties

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.
MMAE is actually desmethyl-auristatin E; that is, the N-terminal amino group has only one methyl substituent instead of two as in auristatin E itself.

Uses

Dolastatin 10 is a natural antimitotic and antineoplastic agent that binds to tubulin and inhibits tubulin polymerization. Monomethyl Auristatin E (MMAE) is a synthetic analog of dolastatin 10 that similarly inhibits tubulin polymerization and exhibits potent cytotoxicity. It is commonly conjugated with monoclonal antibodies directed at antigens specific to cancer cells for tumor-directed cytotoxicity. MMAE is typically coupled to the antibody via a protease-cleavable linker, allowing separation of the drug from the antibody following intracellular localization.[Cayman Chemical]

Uses

MMAE is an effective and synthetic cytotoxic analog of Dolastatin 10 which is a potent antimitotic polypeptide isolated from a marine animal.

Biological Activity

monomethyl auristatin e(mmae) is a potent antimitotic agent by blocking the polymerisation of tubulin.microtubules play essential role in the function of the cell. microtubules are also reported to be involved in migration, transport and reorganization and have numerous dynamic roles including movement through motor proteins such as dynein and kinesin and the separation and segregation ofchromosomes during cell division.

Biochem/physiol Actions

Monomethyl Auristatin E (MMAE) is a highly potent peptidyl antimitotic agent that blocks the polymerization of tubulin. Monomethyl Auristatin E is a component of a clinically approved antibodydirected conjugates Brentuximab vedotin, Glembatumumab vedotin, Enfortumab vedotin and Polatuzumab vedotin.

in vitro

the cytotoxic effects of the mmae conjugates on h3396 cells were determined using both pulsed and long-term drug exposure assays. it was found that under both exposure conditions, high degrees of immunological specificity were obtained with the val-cit conjugates. cbr96-val-cit-mmae was highly active at <1/100th of the concentration required for antigen saturation [1].

in vivo

in vivo therapy tests were undertaken in athymic mice with subcutaneous l2987 human lung adenocarcinoma xenografts. mmae conjugates were administered at 3 mg mab component/kg/dose. all of the tested mmae conjugates were highly efficacious, leading to long-term regressions of established tumors, whereas the nonbinding control conjugates had no effect on tumor growth. in addition, there were no apparent toxicities associated with conjugate treatment [1].

IC 50

less than 1 nm for various cancer cell lines

References

[1] doronina so,toki be,torgov my,mendelsohn ba,cerveny cg,chace df,deblanc rl,gearing rp,bovee td,siegall cb,francisco ja,wahl af,meyer dl,senter pd. development of potent monoclonal antibody auristatin conjugates for cancer therapy. nat biotechnol.2003 jul;21(7):778-84.
[2] jian xu*, priya agarwal, ola saad, et al. clinical pharmacokinetics (pk) of anti-muc16 antibody-drug conjugates (adcs), dmuc5754a, in patients with platinum-resistant ovarian cancer: results from phase i study. this poster was presented at world adc summit 2014.

MonoMethyl auristatin E synthesis

120205-50-7
474645-27-7
Synthesis of MonoMethyl auristatin E from N-Boc-(2R,3R,4S)-dolaproine

MonoMethyl auristatin E Preparation Products And Raw materials

Raw materials

4-HYDROXY-3-NITROBENZYL ALCOHOL

Preparation Products

McMMAE

MonoMethyl auristatin E Suppliers

Global( 283)Suppliers
Supplier Tel Email Country ProdList Advantage
ChemExpress
+86-021-58950125 info@chemexpress.com China 557 58
Anhui Ruihan Technology Co., Ltd 		+8617756083858 daisy@anhuiruihan.com China 994 58
Alpha Biopharmaceuticals Co., Ltd 		+86-411-39042497 +8613921981412 sales@alphabiopharm.com China 886 58
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806 sales@capotchem.com China 29797 60
Henan Tianfu Chemical Co.,Ltd. 		+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21691 55
Nanjing Finetech Chemical Co., Ltd. 		025-85710122 17714198479 sales@fine-chemtech.com CHINA 885 55
ATK CHEMICAL COMPANY LIMITED 		+undefined-21-51877795 ivan@atkchemical.com China 32480 60
career henan chemical co 		+86-0371-86658258 sales@coreychem.com China 29914 58
Biochempartner 		0086-13720134139 candy@biochempartner.com CHINA 967 58
Jinan Carbotang Biotech Co.,Ltd. 		+8615866703830 figo.gao@foxmail.com China 6992 58
Supplier Advantage
ChemExpress
58
Anhui Ruihan Technology Co., Ltd 		58
Alpha Biopharmaceuticals Co., Ltd 		58
Capot Chemical Co.,Ltd. 		60
Henan Tianfu Chemical Co.,Ltd. 		55
Nanjing Finetech Chemical Co., Ltd. 		55
ATK CHEMICAL COMPANY LIMITED 		60
career henan chemical co 		58
Biochempartner 		58
Jinan Carbotang Biotech Co.,Ltd. 		58

Related articles

View Lastest Price from MonoMethyl auristatin E manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
MonoMethyl auristatin E pictures 2023-09-07 MonoMethyl auristatin E
474645-27-7
 US $30.00 / kg 1kg 99% 1000t/year Anhui Ruihan Technology Co., Ltd
MonoMethyl auristatin E pictures 2023-05-20 MonoMethyl auristatin E
474645-27-7
 US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
MMAE;[3H]-Vedotin pictures 2021-07-13 MMAE;[3H]-Vedotin
474645-27-7
 US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • MMAE;[3H]-Vedotin pictures
  • MMAE;[3H]-Vedotin
    474645-27-7
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

MonoMethyl auristatin E Spectrum

MonoMethyl auristatin E(474645-27-7)1HNMR

474645-27-7(MonoMethyl auristatin E)Related Search:

Ethanol Ozone Acrylic acid Feed Mould inhibitor Polyethylene
L-Threonine Potassium pyrophosphate FARNESENE MonoMethylauristatin F (2R,3R)-N-((1S,2R)-1-hydroxy-1-phenylpropan-2-yl)-3-Methoxy-2-Methyl-3-((S)-pyrrolidin-2-yl)propanaMide (hydrochloride)
VcMMAE 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 (3R,4S,5S)-tert-butyl 3-Methoxy-5-Methyl-4-(MethylaMino)heptanoate hydroc hloride Valine
Ethylene glycol Organic acid

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MonoMethyl auristatin E(MMAE, vedotin) HM-297C-22 MonoMethyl auristatin E Monomethyl auristatin E, >=98% MMAE(Monomethyl auristatin E) (2S)-N-[(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]-3-methyl-2-(methylamino)butanamide [3H]-Vedotin (S)-N-((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1R,2R)-1-Hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy best price 99% Monomethyl Auristatin E, MMAE factory in stock CAS NO.474645-27-7 CS-835 MMAE; VEDOTIN;?MONOMETHYL AURISTATIN E L-Valinamide, 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-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl- Monomethyl auristatin E (vedotin) L-Valinamide, 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-methoxy-1-[(1S)-1-methylpropyl]-4-oxob MMAE Vedotin 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-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-L-valinamide Monomethyl (S)-N-((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1R,2R)-1-Hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxohe MonoMethyl auristatin E (MMAE) 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-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-L-valinamide Ethanol,2,2'-[1,5-naphthalenediylbis(oxy-2,3-ethanediyloxy)]bis- (2S)-N-[(2S)-1-[[(3R,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]-3-methyl-2-(methylamino)butanamide 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-pyrrolidine] -2-methoxy-1- [(1S) -1-methylpropyl] -4-oxobutyl] - N-methyl-L Valamide SGD-1010 474645-27-7 474645-27-8 74645-27-7 C39H67N5O7 intermediates Pharmaceutical ADCs