Mertansine

Base Information

• Chemical Name: Mertansine
• CAS No.: 139504-50-0
• Deprecated CAS: 1194029-14-5
• Molecular Formula: C35H48ClN3O10S
• Molecular Weight: 738.299
• European Community (EC) Number: 641-051-4
• UNII: DDZ29HGH0E
• ChEMBL ID: CHEMBL4802230
• Nikkaji Number: J3.653.420F
• Wikidata: Q4515649
• Wikipedia: Mertansine
• Mol file: 139504-50-0.mol

Synonyms:DM1, Maytansinoid;DM4, Maytansinoid;DMMO Maytansine;DMMO-maytansine;emtansine;Maitansine;Maytansine;Maytansinoid DM1;Maytansinoid DM4;Mertansine;N2'-deacetyl-N2'-(4-mercapto-4-methyl-1-oxopentyl)maytansine;Ravtansine;Soravtansine

Chemical Property of Mertansine

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 190-192 oC (decomp)**
• Boiling Point: 937.1±65.0 °C(Predicted)
• PKA: 9.82±0.70(Predicted)
• PSA: 195.27000
• Density: 1.33±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• LogP: 4.22820
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 737.2748936
• Heavy Atom Count: 50
• Complexity: 1340

Purity/Quality:

97%, ^*data from raw suppliers

Mertansine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)CCS)C)C)OC)(NC(=O)O2)O
• Isomeric SMILES: C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)CCS)C)\C)OC)(NC(=O)O2)O
• Description: Maytansine, a natural alkaloid, was first isolated from Maydens ovale in 1972 and exists in the genus Maydens of the family Weedaceae and its relatives. The mechanism of action of maytansine, acting on microtubules and tubulin, blocks the formation of spindles in the process of cell mitosis by inhibiting the depolymerization of cell microtubules, and has a strong ability to inhibit tumor cell proliferation.
• Uses: Mertansine (DM1) is a microtubulin inhibitor which binds at the tips of microtubules and suppresses the dynamicity of microtubules.. Mertansine is an antibody-conjugatable maytansinoid that was developed to overcome systemic toxicity associated with maytansine and to enhance tumor-specific delivery. It can be attached to a monoclonal antibody with a linker to create an antibody-drug conjugate (ADC).

Technology Process of Mertansine

There total 6 articles about Mertansine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

N2'-deacetyl-N2'-[3-(methyldithio)-1-oxopropyl]maytansine (138148-68-2) → N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)maytansine (139504-50-0)

Guidance literature:

With ethylenediaminetetraacetic acid; diothiothreitol; In methanol; phosphate buffer; ethyl acetate; for 3h; pH=7.5;

DOI:10.1021/jm060319f

Reference yield:

maytansinol (57103-68-1) → N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)maytansine (139504-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / dicyclohexylcarbodiimide; ZnCl₂ / CH₂Cl₂; diethyl ether / 2 h / 20 °C

2: 76 percent / dithiothreitol; EDTA / methanol; ethyl acetate; aq. phosphate buffer / 3 h / pH 7.5

With ethylenediaminetetraacetic acid; dicyclohexyl-carbodiimide; zinc(II) chloride; diothiothreitol; In methanol; phosphate buffer; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/jm060319f

Reference yield:

N-methyl-N-[(3-methyldithio)-1-oxopropyl]-L-alanine (138148-62-6) → N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)maytansine (139504-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / dicyclohexylcarbodiimide; ZnCl₂ / CH₂Cl₂; diethyl ether / 2 h / 20 °C

2: 76 percent / dithiothreitol; EDTA / methanol; ethyl acetate; aq. phosphate buffer / 3 h / pH 7.5

With ethylenediaminetetraacetic acid; dicyclohexyl-carbodiimide; zinc(II) chloride; diothiothreitol; In methanol; phosphate buffer; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/jm060319f

upstream raw materials:

N^2'-deacetyl-N^2'-[3-(methyldithio)-1-oxopropyl]maytansine

N-methyl-N-[(3-methyldithio)-1-oxopropyl]-L-alanine

maytansinol

ansamitocin P-3

Downstream raw materials:

N²'-deacetyl-N²'-[3-[[1-[[4-[[[(1S)-5-amino-1-carboxypentyl]amino]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-1-oxopropyl]maytansine

N^2'-deacetyl-N^2'-(3-mercapto-1-oxopropyl)maytansine dimer

Refernces

• 1、 Lambert, John M.,Chari, Ravi V. J.. "Ado-trastuzumab emtansine (T-DM1): An antibody-drug conjugate (ADC) for HER2-positive breast cancer". . p. 6949 - 6964. Retrieved 2014.
• 2、 Widdison, Wayne C.,Wilhelm, Sharon D.,Cavanagh, Emily E.,Whiteman, Kathleen R.,Leece, Barbara A.,Kovtun, Yelena,Goldmacher, Victor S.,Xie, Hongsheng,Steeves, Rita M.,Lutz, Robert J.,Zhao, Robert,Wang, Lintao,Bl?ttler, Walter A.,Chari, Ravi V. J.. "Semisynthetic Maytansine analogues for the targeted treatment of cancer". . p. 4392 - 4408. Retrieved 2007/10/03.