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.


Chemical Structure

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Mafodotin
CAS# 863971-19-1

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

Price and Availability

Size Price Availability Quantity
25.0mg USD 2750.0 Ask
50.0mg USD 4450.0 Ask
100.0mg USD 5950.0 Ask
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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

Appearance: Light yellow waxy solid

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 925.178 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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1: Sedlik C, Heitzmann A, Viel S, Ait Sarkouh R, Batisse C, Schmidt F, De La Rochere P, Amzallag N, Osinaga E, Oppezzo P, Pritsch O, Sastre-Garau X, Hubert P, Amigorena S, Piaggio E. Effective antitumor therapy based on a novel antibody-drug conjugate targeting the Tn carbohydrate antigen. Oncoimmunology. 2016 Apr 22;5(7):e1171434. doi: 10.1080/2162402X.2016.1171434. eCollection 2016 Jul. PubMed PMID: 27622021; PubMed Central PMCID: PMC5006918.

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8: Breij EC, de Goeij BE, Verploegen S, Schuurhuis DH, Amirkhosravi A, Francis J, Miller VB, Houtkamp M, Bleeker WK, Satijn D, Parren PW. An antibody-drug conjugate that targets tissue factor exhibits potent therapeutic activity against a broad range of solid tumors. Cancer Res. 2014 Feb 15;74(4):1214-26. doi: 10.1158/0008-5472.CAN-13-2440. Epub 2013 Dec 26. PubMed PMID: 24371232.

9: Simon M, Frey R, Zangemeister-Wittke U, Plückthun A. Orthogonal assembly of a designed ankyrin repeat protein-cytotoxin conjugate with a clickable serum albumin module for half-life extension. Bioconjug Chem. 2013 Nov 20;24(11):1955-66. doi: 10.1021/bc4004102. Epub 2013 Nov 11. PubMed PMID: 24168270.

10: Sapra P, Damelin M, Dijoseph J, Marquette K, Geles KG, Golas J, Dougher M, Narayanan B, Giannakou A, Khandke K, Dushin R, Ernstoff E, Lucas J, Leal M, Hu G, O'Donnell CJ, Tchistiakova L, Abraham RT, Gerber HP. Long-term tumor regression induced by an antibody-drug conjugate that targets 5T4, an oncofetal antigen expressed on tumor-initiating cells. Mol Cancer Ther. 2013 Jan;12(1):38-47. doi: 10.1158/1535-7163.MCT-12-0603. Epub 2012 Dec 5. PubMed PMID: 23223830.

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12: Nilsson R, Mårtensson L, Eriksson SE, Sjögren HO, Tennvall J. Toxicity-reducing potential of extracorporeal affinity adsorption treatment in combination with the auristatin-conjugated monoclonal antibody BR96 in a syngeneic rat tumor model. Cancer. 2010 Feb 15;116(4 Suppl):1033-42. doi: 10.1002/cncr.24790. PubMed PMID: 20127954.

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18: Smith LM, Nesterova A, Ryan MC, Duniho S, Jonas M, Anderson M, Zabinski RF, Sutherland MK, Gerber HP, Van Orden KL, Moore PA, Ruben SM, Carter PJ. CD133/prominin-1 is a potential therapeutic target for antibody-drug conjugates in hepatocellular and gastric cancers. Br J Cancer. 2008 Jul 8;99(1):100-9. doi: 10.1038/sj.bjc.6604437. Epub 2008 Jun 10. PubMed PMID: 18542072; PubMed Central PMCID: PMC2453027.

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Mafodotin

25.0mg / USD 2750.0


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)