Mafodotin
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MedKoo CAT#: 206584

CAS#: 863971-19-1

Description: Mafodotin, also known as mc-MMAF and SGD-1269 or Maleimidocaproyl monomethylauristatin F, is a MMAF derivative having a Maleimidocaproyl linker (MC linker), which is ready to conjugate to antibody or other proteins or biopolymers. Mafodotin is a useful agent for make antibody drug conjugate (ADC) for targeted drug delivery. MMAF is a potent antimitotic and antitublin auristatin derivative with a charged C-terminal phenylalanine residue that attenuates its cytotoxic activity compared to its uncharged counterpart, MMAE.


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1g
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2g
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5g
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Mafodotin is not stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206584
Name: Mafodotin
CAS#: 863971-19-1
Chemical Formula: C49H76N6O11
Exact Mass: 924.5572
Molecular Weight: 925.178
Elemental Analysis: C, 63.61; H, 8.28; N, 9.08; O, 19.02


Synonym: SGD-1269; SGD 1269; SGD1269; mc-MMAF; mcMMAF; L4-MMAF; Maleimidocaproyl-MMAF; Maleimidocaproyl monomethylauristatin F; Mafodotin.

IUPAC/Chemical Name: ((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-methylhexanamido)-3-methylbutanamido)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoyl)-L-phenylalanine

InChi Key: ORFNVPGICPYLJV-YTVPMEHESA-N

InChi Code: InChI=1S/C49H76N6O11/c1-12-32(6)44(37(65-10)29-41(59)54-27-19-22-36(54)45(66-11)33(7)46(60)50-35(49(63)64)28-34-20-15-13-16-21-34)53(9)48(62)42(30(2)3)51-47(61)43(31(4)5)52(8)38(56)23-17-14-18-26-55-39(57)24-25-40(55)58/h13,15-16,20-21,24-25,30-33,35-37,42-45H,12,14,17-19,22-23,26-29H2,1-11H3,(H,50,60)(H,51,61)(H,63,64)/t32-,33+,35-,36-,37+,42-,43-,44-,45+/m0/s1

SMILES Code: O=C(O)[C@H](CC1=CC=CC=C1)NC([C@H](C)[C@H]([C@H]2N(C(C[C@@H](OC)[C@@H](N(C)C([C@@H](NC([C@@H](N(C)C(CCCCCN3C(C=CC3=O)=O)=O)C(C)C)=O)C(C)C)=O)[C@@H](C)CC)=O)CCC2)OC)=O


Technical Data

Appearance:
Light yellow waxy solid

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


Additional Information

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. 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. 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)


References

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