MMAF sodium

• CAT Number: I018279
• CAS Number: 1799706-65-2
• Molecular Formula: C₃₉H₆₄N₅NaO₈
• Molecular Weight: 753.94
• Purity: ≥95%
• IUPAC Name: sodium;(2S)-2-[[(2R,3R)-3-methoxy-3-[(2S)-1-[(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl-[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(methylamino)butanoyl]amino]butanoyl]amino]heptanoyl]pyrrolidin-2-yl]-2-methylpropanoyl]amino]-3-phenylpropanoate
• InChI: InChI=1S/C39H65N5O8.Na/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);/q;+1/p-1/t25-,26+,28-,29-,30+,32-,33-,34-,35+;/m0./s1
• InChIKey: LGMDBXMBHWLORJ-KMYLZLQDSA-M
• SMILES: CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)[O-])OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC.[Na+]

MMAF sodium（Cat No.:I018279）, or monomethyl auristatin F sodium, is a potent cytotoxic agent used in antibody-drug conjugates (ADCs) for targeted cancer therapy. It is derived from the natural product auristatin and works by inhibiting microtubule polymerization, leading to cell cycle arrest and apoptosis in rapidly dividing cancer cells. The sodium salt form enhances its solubility and stability for formulation in therapeutic applications. MMAF sodium is particularly effective against various hematological malignancies and solid tumors, making it a key component in the development of innovative cancer treatments that aim to minimize systemic toxicity while maximizing therapeutic efficacy.

Reference

[1]. Lee JW, et al. EphA2 targeted chemotherapy using an antibody drug conjugate in endometrial carcinoma. Clin Cancer Res. 2010 May 1;16(9):2562-70.[2]. Lee JJ, et al. Enzymatic prenylation and oxime ligation for the synthesis of stable and homogeneous protein-drug conjugates for targeted therapy. Angew Chem Int Ed Engl. 2015 Oct 5;54(41):12020-4.[3]. Kim EG, et al. Strategies and Advancement in Antibody-Drug Conjugate Optimization for Targeted CancerTherapeutics.[4]. Doronina SO, et al. Enhanced activity of monomethylauristatin F through monoclonal antibody delivery: effects of linker technology on efficacy and toxicity. Bioconjug Chem. 2006 Jan-Feb;17(1):114-24.