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Mitotic inhibitor
Monomethyl auristatin F
Другие языки:

Monomethyl auristatin F

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Monomethyl auristatin F
Monomethylauristatin F.svg
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
3D model (JSmol)
Abbreviations MMAF
ChemSpider
PubChem CID
UNII
  • 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
    Key: MFRNYXJJRJQHNW-DEMKXPNLSA-N
  • InChI=1/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
    Key: MFRNYXJJRJQHNW-DEMKXPNLBL
  • O=C(N2[C@H]([C@H](OC)[C@H](C(=O)N[C@H](C(=O)O)Cc1ccccc1)C)CCC2)C[C@@H](OC)[C@@H](N(C(=O)[C@@H](NC(=O)[C@@H](NC)C(C)C)C(C)C)C)[C@@H](C)CC
Properties
C39H65N5O8
Molar mass 731.976 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Monomethyl auristatin F (MMAF) is a synthetic antineoplastic agent. It is part of the approved drug belantamab mafodotin in multiple myeloma and 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.

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.

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.

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.

See also


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