203849-91-6

Basic information

• Product Name: MonoMethyl Dolastatin 10
• Synonyms: DeMethyldolastatin 10;MMAD;MonoMethyl Dolastatin 10;MonoMethylauristatin D;(S)-N-((3R,4S,5S)-3-methoxy-1-((S)-2-((1R,2R)-1-methoxy-2-methyl-3-oxo-3-(((S)-2-phenyl-1-(thiazol-2-yl)ethyl)amino)propyl)pyrrolidin-1-yl)-5-methyl-1-oxoheptan-4-yl)-N,3-dimethyl-2-((S)-3-methyl-2-(methylamino)butanamido)butanamide;N-Methyl-L-valyl-N-[(1S,2R)-2-methoxy-4-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]amino]propyl]-1-pyrrolidinyl]-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-L-valinamide;EOS-60620;MMAD (Demethyldolastatin 10
• CAS NO: 203849-91-6
• Molecular Formula: C41H66N6O6S
• Molecular Weight: 771.06434
• Mol File: 203849-91-6.mol

Chemical Properties

• Boiling Point: 906.1±65.0 °C(Predicted)
• Appearance: /
• Density: 1.119±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Soluble in DMSO
• PKA: 13.81±0.46(Predicted)
• CAS DataBase Reference: MonoMethyl Dolastatin 10(CAS DataBase Reference)
• NIST Chemistry Reference: MonoMethyl Dolastatin 10(203849-91-6)
• EPA Substance Registry System: MonoMethyl Dolastatin 10(203849-91-6)

Safety Data

• Hazardous Substances Data: 203849-91-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
MonoMethyl Dolastatin 10 is used as a tubulin inhibitor for the development of site-specific antibody-drug conjugates (ADCs). These ADCs are designed to selectively target and deliver the potent anti-cancer agent to cancer cells, minimizing damage to healthy cells and reducing side effects. The conjugation of MMAD to monoclonal antibodies allows for the precise targeting of specific cancer cells, enhancing the therapeutic efficacy and selectivity of the treatment.

Biological Activity

mmad is a highly potent inhibitor of tubulin [1].mmad is one of the auristatins, which are used as the drugs of antibody drug conjugates (adcs). in adcs, the therapeutic compounds and the high selectivity of antibodies are combined by the linkers. by taking advantage of antigen-selectivity of mabs, it can deliver these cytotoxic drugs to antigen-expressing tumor cells, thus increasing both the efficacy and safety of therapy. as a payload of adcs, mmad is used to target the tubulin of the tumor cells. it can interfere with tubulin polymerization and induce rapid cell death at low picomolar concentrations [1].additionally, mmad is reported to be used in the production of site-specific antibody drug conjugates (ndcs). in the ndcs, mmad is combined with anti-5t4 antibody or anti-her2 antibody. it is shown that the ndcs demonstrate better efficacy and pharmacokinetics [2].

references

[1] puja sapra, andrea t hooper, christopher j, o’donnell & hans-peter gerber. investigational antibody drug conjugates for solid tumors. expert opin. investig. drugs. 2011, 20(8):1131-1149. [2] feng tiana, yingchun lu, anthony manibusan, aaron sellers et al. a general approach to site-specific antibody drug conjugates. pnas. 2014, february, 111(5): 1766-1771.

Upstream product

• 173441-25-3 Z-N-Me-Val-Val-Dil-Dap-Doe 
• 120205-50-7 N-Boc-(2R,3R,4S)-dolaproine 
• 135383-56-1 (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid 
• 120205-52-9 tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(benzyloxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate 
• 163768-51-2 benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoate 
• 149606-97-3 benzyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate 
• 149664-79-9 (3R,4S,5S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxy-5-methyl-heptanoic acid methyl ester 
• 177423-00-6 (3R,4S,5S)-4-[(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate 
• 173441-13-9 Cbz-MeVal-Val-Dil-OtBu 
• 920017-22-7 (5S,8S,11S,12R)-11-((S)-sec-butyl)-5,8-diisopropyl-12-methoxy-4,10-dimethyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazatetradecan-14-oic acid 
• 474645-22-2 tert-Butyl (3R,4S,5S)-3-methoxy-4-(N-methylamino)-5-methylheptanoate 
• 120205-54-1 tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidine-1-carboxylate 
• 120205-58-5 tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate 
• 69610-41-9 Boc-L-Pro-H 

Downstream Products

• 1615234-92-8 C₇₁H₁₁₁N₁₃O₁₄S 

Relevant articles and documents

Synthesis and antitumor activity of novel dolastatin 10 analogs

Dolastatin 10 (1) is a potent antineoplastic pentapeptide. Novel dolastatin 10 analogs each modified at one of the constituent amino acid derivatives, were synthesized and their antitumor activity was evaluated against P388 leukemia in mice. The structural requirements for antitumor activity are discussed. Some of the analogs, 31c, 35c, 38b, and 50c showed excellent activity in vivo. Highly active 50c, which lacks the thiazole group of 1, was selected for further development as an antitumor agent.