MonoMethyl auristatin E
- 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
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) | GHS07 |
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Signal word | Warning | |||||||||
Hazard statements | H302-H315-H319-H335 | |||||||||
Precautionary statements | P261-P305+P351+P338 | |||||||||
NFPA 704 |
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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 |
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 Preparation Products And Raw materials
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
ChemExpress | +86-021-58950125 +86-021-58950125; | info@chemexpress.com | China | 598 | 58 |
Anhui Ruihan Technology Co., Ltd | +8617756083858 | daisy@anhuiruihan.com | China | 994 | 58 |
Alpha Biopharmaceuticals Co., Ltd | +86-15542445688 | sales@alabiochem.com | China | 888 | 58 |
Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29798 | 60 |
Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21667 | 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 | 32836 | 60 |
career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29888 | 58 |
Biochempartner | 0086-13720134139 | candy@biochempartner.com | CHINA | 967 | 58 |
Jinan Carbotang Biotech Co.,Ltd. | +8615866703830 | figo.gao@foxmail.com | China | 7621 | 58 |
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View Lastest Price from MonoMethyl auristatin E manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
---|---|---|---|---|---|---|---|---|
2023-09-07 | MonoMethyl auristatin E
474645-27-7
|
US $30.00 / kg | 1kg | 99% | 1000t/year | Anhui Ruihan Technology Co., Ltd | ||
2023-05-20 | MonoMethyl auristatin E
474645-27-7
|
US $0.00 / KG | 1KG | 99% | 50000KG/month | Hebei Mojin Biotechnology Co., Ltd | ||
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 |
- MonoMethyl auristatin E
474645-27-7
- US $30.00 / kg
- 99%
- Anhui Ruihan Technology Co., Ltd
- MonoMethyl auristatin E
474645-27-7
- US $0.00 / KG
- 99%
- Hebei Mojin Biotechnology Co., Ltd
- MMAE;[3H]-Vedotin
474645-27-7
- US $15.00-10.00 / KG
- 99%+ HPLC
- Zhuozhou Wenxi import and Export Co., Ltd
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