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 | |
| 745017-94-1 | |
| Abbreviations | MMAF |
| ChemSpider | 8570614 |
| Jmol interactive 3D | Image |
| PubChem | 10395173 |
| |
| |
| Properties | |
| 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]
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]
See also
References
- ↑ Tai, Y. T.; Mayes, P. A.; Acharya, C; Zhong, M. Y.; Cea, M; Cagnetta, A; Craigen, J; Yates, J; Gliddon, L; Fieles, W; Hoang, B; Tunstead, J; Christie, A. L.; Kung, A. L.; Richardson, P; Munshi, N. C.; Anderson, K. C. (2014). "Novel afucosylated anti-B cell maturation antigen-monomethyl auristatin F antibody-drug conjugate (GSK2857916) induces potent and selective anti-multiple myeloma activity". Blood 123 (20): 3128–38. doi:10.1182/blood-2013-10-535088. PMID 24569262.
- ↑ Statement on a nonproprietary name adopted by the USAN Council: Mafodotin
- 1 2 3 Dosio, F.; Brusa, P.; Cattel, L. (2011). "Immunotoxins and Anticancer Drug Conjugate Assemblies: The Role of the Linkage between Components". Toxins 3 (12): 848. doi:10.3390/toxins3070848.
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