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| 5mg |
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| 10mg |
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Maytansine (maitansine; NSC153858) is a cytotoxic antitubulin agent and an ansamycin antibiotic originally isolated from the Ethiopian shrub Maytenus serrata. Because it binds to tubulin at the rhizoxin binding site, it prevents microtubule formation. The plant genus Maytenus yields this macrolide, which belongs to the ansamycin type. Originally derived from the Ethiopian shrub Maytenus serrata, this antibiotic was originally called anansamycin. Maytansine is able to bind to tubulin at the site where rhizoxin binds, which causes microtubule disassembly, assembly inhibition, and disruption of mitosis. It is possible that maytansine will prevent tumor growth in vivo because it is cytotoxic to a variety of tumor cell lines.
| ln Vitro |
Maytansine, at 6x10-8 M, irreversibly inhibits the division of cells in sea urchin and clam eggs. If added too early, maytansine causes a mitotic apparatus to disappear or stops one from forming. Maytansine prevents tubulin from polymerizing in vitro[2].
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| References | |
| Additional Infomation |
Maytansine is an organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumour cell lines. It has a role as a plant metabolite, an antimicrobial agent, an antineoplastic agent, a tubulin modulator and an antimitotic. It is an epoxide, a carbamate ester, an organochlorine compound, an alpha-amino acid ester, an organic heterotetracyclic compound and a maytansinoid.
Maytansine has been reported in Putterlickia verrucosa and Gymnosporia diversifolia with data available. Maytansine is an ansamycin antibiotic originally isolated from the Ethiopian shrub Maytenus serrata. Maytansine binds to tubulin at the rhizoxin binding site, thereby inhibiting microtubule assembly, inducing microtubule disassembly, and disrupting mitosis. Maytansine exhibits cytotoxicity against many tumor cell lines and may inhibit tumor growth in vivo. (NCI04) An ansa macrolide isolated from the MAYTENUS genus of East African shrubs. |
| Molecular Formula |
C34H46CLN3O10
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|---|---|
| Molecular Weight |
692.2
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| Exact Mass |
691.287
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| Elemental Analysis |
C, 59.00; H, 6.70; Cl, 5.12; N, 6.07; O, 23.11
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| CAS # |
35846-53-8
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| Related CAS # |
35846-53-8
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| PubChem CID |
5281828
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| Appearance |
White to off-white solid powder
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| Density |
1.32g/cm3
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| Boiling Point |
895.1ºC at 760mmHg
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| Flash Point |
495.1ºC
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| Index of Refraction |
1.59
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| LogP |
3.928
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
48
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| Complexity |
1300
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| Defined Atom Stereocenter Count |
8
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| SMILES |
C[C@@]12[C@@H](O2)[C@H](C)[C@]([H])(C[C@](N3)(O)[C@]([H])(OC)/C=C/C=C(CC4=CC(N(C(C[C@@]1(OC([C@@H](N(C(C)=O)C)C)=O)[H])=O)C)=C(Cl)C(OC)=C4)\C)OC3=O
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| InChi Key |
WKPWGQKGSOKKOO-RSFHAFMBSA-N
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| InChi Code |
InChI=1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10+,18-11+/t19-,20+,25+,26-,27+,30+,33+,34+/m1/s1
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| Chemical Name |
[(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] (2S)-2-[acetyl(methyl)amino]propanoate
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| Synonyms |
NSC 153858; NSC-153858; NSC153858; maytansine; Maitansinum; Maitansina; DM-1; Maitansine; Mertansine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~100 mg/mL (144.5 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.61 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (3.61 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (3.61 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.4447 mL | 7.2233 mL | 14.4467 mL | |
| 5 mM | 0.2889 mL | 1.4447 mL | 2.8893 mL | |
| 10 mM | 0.1445 mL | 0.7223 mL | 1.4447 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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