MMAE | Monomethyl auristatin E | CAS#474645-27-7 | mitotic inhibitor

MMAE (Monomethyl auristatin E)
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WARNING: This product is for research use only, not for human or veterinary use.

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

MMAE (Monomethyl auristatin E)

CAS# 474645-27-7

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 120202
Name: MMAE (Monomethyl auristatin E)
CAS#: 474645-27-7
Chemical Formula: C39H67N5O7
Exact Mass: 717.50
Molecular Weight: 717.979
Elemental Analysis: C, 65.24; H, 9.41; N, 9.75; O, 15.60

Price and Availability

Size	Price	Availability
5mg	USD 90	Ready to ship
10mg	USD 150	Ready to ship
25mg	USD 300	Ready to ship
50mg	USD 500	Ready to ship
100mg	USD 850	Ready to ship
200mg	USD 1450	Ready to ship
500mg	USD 2950	Ready to Ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

More Info: 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.

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot# T20D04P14

QC Data:

View QC data: current batch, Lot#T20D04P14

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Monomethyl auristatin E (MMAE; SGD-1010) is a synthetic derivative of dolastatin 10 and functions as a potent mitotic inhibitor by inhibiting tubulin polymerization.
In vitro activity:	RC68 recognized EGFR on tumor cells, particularly for higher EGFR expressing H125, A431, HCC827 and H1975 cells. The RC68 was conjugated with an average of 4 MMAE molecules to generate RC68-MC-VC-PAB-MMAE and RC68-PY-VC-PAB-MMAE, respectively. The RC68-MC-VC-PAB-MMAE, RC68-PY-VC-PAB-MMAE and RC68 displayed similar binding affinity to EGFR on tumor cells, and RC68-MC-VC-PAB-MMAE and RC68-PY-VC-PAB-MMAE were effectively internalized by H125 cells. The RC68-MC-VC-PAB-MMAE and RC68-PY-VC-PAB-MMAE inhibited the growth of H125 cells in vitro with an IC50 7.37-8.04 ng/mL. Reference: Cancer Chemother Pharmacol. 2019 Jul;84(1):61-72. https://dx.doi.org/10.1007/s00280-019-03848-9
In vivo activity:	In SCID mouse xenograft models of anaplastic large cell lymphoma or Hodgkin disease, cAC10-vcMMAE (an anti-CD30-monomethyl auristatin E conjugate) was efficacious at doses as low as 1 mg/kg. Mice treated at 30 mg/kg cAC10-vcMMAE showed no signs of toxicity. These data indicate that cAC10-vcMMAE may be a highly effective and selective therapy for the treatment of CD30+ neoplasias. Reference: Blood. 2003 Aug 15;102(4):1458-65. https://ashpublications.org/blood/article/102/4/1458/17083/cAC10-vcMMAE-an-anti-CD30-monomethyl-auristatin-E

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	45.0	62.67
	Ethanol	50.0	69.64

Preparing Stock Solutions

The following data is based on the product molecular weight 717.98 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.

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

Formulation protocol:	1. Li Z, Wang M, Yu D, Luo W, Fang J, Huang C, Yao X. Monomethyl auristatin E-conjugated anti-EGFR antibody inhibits the growth of human EGFR-positive non-small cell lung cancer. Cancer Chemother Pharmacol. 2019 Jul;84(1):61-72. doi: 10.1007/s00280-019-03848-9. Epub 2019 Apr 29. PMID: 31037333. 2. Okeley NM, Miyamoto JB, Zhang X, Sanderson RJ, Benjamin DR, Sievers EL, Senter PD, Alley SC. Intracellular activation of SGN-35, a potent anti-CD30 antibody-drug conjugate. Clin Cancer Res. 2010 Feb 1;16(3):888-97. doi: 10.1158/1078-0432.CCR-09-2069. Epub 2010 Jan 19. Erratum in: Clin Cancer Res. 2011 Aug 15;17(16):5524. PMID: 20086002. 3. Li Z, Wang M, Yu D, Luo W, Fang J, Huang C, Yao X. Monomethyl auristatin E-conjugated anti-EGFR antibody inhibits the growth of human EGFR-positive non-small cell lung cancer. Cancer Chemother Pharmacol. 2019 Jul;84(1):61-72. doi: 10.1007/s00280-019-03848-9. Epub 2019 Apr 29. PMID: 31037333. 4. Buckel L, Savariar EN, Crisp JL, Jones KA, Hicks AM, Scanderbeg DJ, Nguyen QT, Sicklick JK, Lowy AM, Tsien RY, Advani SJ. Tumor radiosensitization by monomethyl auristatin E: mechanism of action and targeted delivery. Cancer Res. 2015 Apr 1;75(7):1376-1387. doi: 10.1158/0008-5472.CAN-14-1931. Epub 2015 Feb 13. PMID: 25681274; PMCID: PMC4458508.
In vitro protocol:	1. Li Z, Wang M, Yu D, Luo W, Fang J, Huang C, Yao X. Monomethyl auristatin E-conjugated anti-EGFR antibody inhibits the growth of human EGFR-positive non-small cell lung cancer. Cancer Chemother Pharmacol. 2019 Jul;84(1):61-72. doi: 10.1007/s00280-019-03848-9. Epub 2019 Apr 29. PMID: 31037333. 2. Okeley NM, Miyamoto JB, Zhang X, Sanderson RJ, Benjamin DR, Sievers EL, Senter PD, Alley SC. Intracellular activation of SGN-35, a potent anti-CD30 antibody-drug conjugate. Clin Cancer Res. 2010 Feb 1;16(3):888-97. doi: 10.1158/1078-0432.CCR-09-2069. Epub 2010 Jan 19. Erratum in: Clin Cancer Res. 2011 Aug 15;17(16):5524. PMID: 20086002.
In vivo protocol:	1. Li Z, Wang M, Yu D, Luo W, Fang J, Huang C, Yao X. Monomethyl auristatin E-conjugated anti-EGFR antibody inhibits the growth of human EGFR-positive non-small cell lung cancer. Cancer Chemother Pharmacol. 2019 Jul;84(1):61-72. doi: 10.1007/s00280-019-03848-9. Epub 2019 Apr 29. PMID: 31037333. 2. Buckel L, Savariar EN, Crisp JL, Jones KA, Hicks AM, Scanderbeg DJ, Nguyen QT, Sicklick JK, Lowy AM, Tsien RY, Advani SJ. Tumor radiosensitization by monomethyl auristatin E: mechanism of action and targeted delivery. Cancer Res. 2015 Apr 1;75(7):1376-1387. doi: 10.1158/0008-5472.CAN-14-1931. Epub 2015 Feb 13. PMID: 25681274; PMCID: PMC4458508.

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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.

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MMAE (Monomethyl auristatin E) featured