MMAF (Monomethyl auristatin F)
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MedKoo CAT#: 407222

CAS#: 745017-94-1

Description: Monomethyl auristatin F (MMAF) is a synthetic antineoplastic agent. It is part of some experimental anti-cancer antibody-drug conjugates such as vorsetuzumab mafodotin and SGN-CD19A. In International Nonproprietary Names for MMAF-antibody-conjugates, the name mafodotin refers to MMAF plus its attachment structure to the antibody. MMAF is actually desmethyl-auristatin F; that is, the N-terminal amino group has only one methyl substituent instead of two as in auristatin F itself. (https://en.wikipedia.org/wiki/Monomethyl_auristatin_F).


Chemical Structure

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MMAF (Monomethyl auristatin F)
CAS# 745017-94-1

Theoretical Analysis

MedKoo Cat#: 407222
Name: MMAF (Monomethyl auristatin F)
CAS#: 745017-94-1
Chemical Formula: C39H65N5O8
Exact Mass: 731.48331
Molecular Weight: 731.98
Elemental Analysis: C, 64.00; H, 8.95; N, 9.57; O, 17.49

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5.0mg USD 190.0 Same Day
10.0mg USD 350.0 Same Day
25.0mg USD 650.0 Same Day
50.0mg USD 950.0 Same Day
100.0mg USD 1650.0 Same Day
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500.0mg USD 3450.0 Same Day
1.0g USD 4250.0 2 weeks
2.0g USD 7250.0 2 weeks
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Synonym: Monomethyl auristatin F; MMAF

IUPAC/Chemical Name: ((2R,3R)-3-((2S)-1-((3R,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoyl)-L-phenylalanine

InChi Key: MFRNYXJJRJQHNW-NARUGQRUSA-N

InChi Code: InChI=1S/C39H65N5O8/c1-12-25(6)34(43(9)38(48)33(24(4)5)42-37(47)32(40-8)23(2)3)30(51-10)22-31(45)44-20-16-19-29(44)35(52-11)26(7)36(46)41-28(39(49)50)21-27-17-14-13-15-18-27/h13-15,17-18,23-26,28-30,32-35,40H,12,16,19-22H2,1-11H3,(H,41,46)(H,42,47)(H,49,50)/t25-,26+,28-,29-,30+,32-,33-,34?,35+/m0/s1

SMILES Code: O=C([C@H](CC1=CC=CC=C1)NC([C@H](C)[C@H]([C@@H]2CCCN2C(C[C@@H](OC)C(N(C)C([C@@H](NC([C@H](C(C)C)NC)=O)C(C)C)=O)[C@@H](C)CC)=O)OC)=O)O

Appearance: 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

Preparing Stock Solutions

The following data is based on the product molecular weight 731.98 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.

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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Additional Information

Monomethyl auristatin F (MMAF) is an antitubulin agent that inhibits cell division by blocking the polymerization of tubulin. Because of MMAF is highly toxic, it cannot be used as a drug itself. MMAF induces potent antitumor effects when conjugated via protease cleavable linkers to a monoclonal antibody targeting internalizing, tumor-specific cell surface antigens. The linker to the monoclonal antibody is stable in extracellular fluid, but is cleaved by cathepsin once the conjugate has entered a tumor cell, thus activating the anti-mitotic mechanism.