MMAE (Monomethyl auristatin E)
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MedKoo CAT#: 120202

CAS#: 474645-27-7

Description: MMAE, also known as Monomethyl auristatin E, 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. MMAE 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. MMAE show potency of up to 200 times that of vinblastine, another antimitotic drug used for Hodgkin lymphoma as well as other types of cancer.


Chemical Structure

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MMAE (Monomethyl auristatin E)
CAS# 474645-27-7

Theoretical Analysis

MedKoo Cat#: 120202
Name: MMAE (Monomethyl auristatin E)
CAS#: 474645-27-7
Chemical Formula: C39H67N5O7
Exact Mass: 717.50405
Molecular Weight: 717.97858
Elemental Analysis: C, 65.24; H, 9.41; N, 9.75; O, 15.60

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1.0g USD 2950.0 Same day
2.0g USD 4950.0 Same day
5.0g USD 8950.0 2 weeks
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Synonym: MMAE; Vedotin; Monomethyl auristatin E.

IUPAC/Chemical Name: (S)-N-((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)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamide

InChi Key: DASWEROEPLKSEI-UIJRFTGLSA-N

InChi Code: InChI=1S/C39H67N5O7/c1-13-25(6)34(43(10)39(49)33(24(4)5)42-38(48)32(40-9)23(2)3)30(50-11)22-31(45)44-21-17-20-29(44)36(51-12)26(7)37(47)41-27(8)35(46)28-18-15-14-16-19-28/h14-16,18-19,23-27,29-30,32-36,40,46H,13,17,20-22H2,1-12H3,(H,41,47)(H,42,48)/t25-,26+,27+,29-,30+,32-,33-,34-,35+,36+/m0/s1

SMILES Code: CC(C)[C@H](NC([C@@H](NC)C(C)C)=O)C(N([C@@H]([C@@H](C)CC)[C@H](OC)CC(N1[C@H]([C@H](OC)[C@@H](C)C(N[C@H](C)[C@@H](O)C2=CC=CC=C2)=O)CCC1)=O)C)=O

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 45.0 62.67

Preparing Stock Solutions

The following data is based on the product molecular weight 717.97858 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Pan LQ, Wang HB, Xie ZM, Li ZH, Tang XJ, Xu YC, Zhang C, Naranmandura H, Chen SQ. Novel conjugation of tumor-necrosis-factor-related apoptosis-inducing ligand (TRAIL) with monomethyl auristatin E for efficient antitumor drug delivery. Adv Mater. 2013 Sep 14;25(34):4718-22. doi: 10.1002/adma.201301385. Epub 2013 Jul 12. PubMed PMID: 23847045.

2: Li D, Poon KA, Yu SF, Dere R, Go M, Lau J, Zheng B, Elkins K, Danilenko D, Kozak KR, Chan P, Chuh J, Shi X, Nazzal D, Fuh F, McBride J, Ramakrishnan V, de Tute R, Rawstron A, Jack AS, Deng R, Chu YW, Dornan D, Williams M, Ho W, Ebens A, Prabhu S, Polson AG. DCDT2980S, an anti-CD22-monomethyl auristatin E antibody-drug conjugate, is a potential treatment for non-Hodgkin lymphoma. Mol Cancer Ther. 2013 Jul;12(7):1255-65. doi: 10.1158/1535-7163.MCT-12-1173. Epub 2013 Apr 18. PubMed PMID: 23598530.

3: Valliere-Douglass JF, McFee WA, Salas-Solano O. Native intact mass determination of antibodies conjugated with monomethyl Auristatin E and F at interchain cysteine residues. Anal Chem. 2012 Mar 20;84(6):2843-9. doi: 10.1021/ac203346c. Epub 2012 Mar 2. PubMed PMID: 22384990.

4: Naumovski L, Junutula JR. Glembatumumab vedotin, a conjugate of an anti-glycoprotein non-metastatic melanoma protein B mAb and monomethyl auristatin E for the treatment of melanoma and breast cancer. Curr Opin Mol Ther. 2010 Apr;12(2):248-57. PubMed PMID: 20373269.

5: Francisco JA, Cerveny CG, Meyer DL, Mixan BJ, Klussman K, Chace DF, Rejniak SX, Gordon KA, DeBlanc R, Toki BE, Law CL, Doronina SO, Siegall CB, Senter PD, Wahl AF. cAC10-vcMMAE, an anti-CD30-monomethyl auristatin E conjugate with potent and selective antitumor activity. Blood. 2003 Aug 15;102(4):1458-65. Epub 2003 Apr 24. PubMed PMID: 12714494.



Additional Information

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. (http://en.wikipedia.org/wiki/Monomethyl_auristatin_E).

Brentuximab Vedotin (ADCETRIS®) was approved in 2011; Glembatumumab vedotin (also known as CDX-011 and CR011-vcMMAE) is currently under clinical trials.