Monomethyl auristatin F

Monomethyl auristatin F

Names
IUPAC name (S)-2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoic acid
Identifiers
CAS Registry Number	745017-94-1
Abbreviations	MMAF
InChI[show]
Jmol-3D images	Image
PubChem	56841603
SMILES[show]
Properties
Chemical formula	C39H65N5O8
Molar mass	731.98 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Monomethyl auristatin F (MMAF) is a synthetic antineoplastic agent.^[1] 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.^[2]

Contents

• 1 Mechanism of action
• 2 Chemistry
• 3 See also
• 4 References

Mechanism of action

Monomethyl auristatin F is an antimitotic agent which inhibits cell division by blocking the polymerisation of tubulin. It is linked to an antibody with high affinity to structures on cancer cells, causing MMAF to accumulate in such cells.^[3]

Chemistry

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.^[3]

Structure of conjugate of MMAF with a monoclonal antibody (MAB). The attachment group consists of maleimide and caproic acid. About eight such structures are bound to a single antibody molecule.^[3]