| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Tubulin, specifically at the rhizoxin binding site (vinca site).
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| 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].
Maytansine is highly cytotoxic to a variety of tumor cell lines. IC50 values: 0.26 ± 0.06 nM for IOMM-Lee cells and 0.31 ± 0.01 nM for CH157 cells; 54.255 μM, 5.193 μM, and 0.647 μM at 24, 48, and 72 h in thyroid cancer C643 cells. It inhibits proliferation, migration, and invasion, and induces apoptosis and autophagy. |
| ln Vivo |
Maytansine inhibits tumor growth in vivo and augments the therapeutic efficacy of radiotherapy in meningioma models. It induces G2/M phase cell cycle arrest and enhances DNA double-strand break damage. However, clinical trials showed a small therapeutic window due to neurotoxicity and gastrointestinal toxicity.
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| Enzyme Assay |
Tubulin binding is measured using tubulin polymerization assays. Purified tubulin is incubated with varying concentrations of Maytansine, and microtubule assembly is monitored by turbidity at 340 nm. Binding affinity is assessed by competition assays with radiolabeled vinca alkaloids.
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| Cell Assay |
Cancer cell lines (e.g., IOMM-Lee, CH157, C643, HCT-15, A431) are treated with Maytansine at various concentrations. Cell viability is assessed by CCK-8 or MTT assays. Cell cycle analysis is performed by flow cytometry. Apoptosis is evaluated by Annexin V/PI staining. Migration and invasion are assessed by scratch and transwell assays.
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| Animal Protocol |
Maytansine is evaluated in mouse xenograft models of various cancers. Tumor-bearing mice are treated with Maytansine via intravenous administration. Tumor growth inhibition, survival, and toxicity are monitored. In meningioma models, Maytansine augments radiotherapy efficacy. Pharmacodynamic studies assess mitotic arrest and DNA damage.
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| ADME/Pharmacokinetics |
Maytansine is a heterocyclic organic compound with molecular weight 692.2 and formula C34H46ClN3O10. It is a solid powder with ≥95% purity. As a potent tubulin inhibitor, it is used as a cytotoxic payload in ADCs. Clinical development was limited by a narrow therapeutic window.
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| Toxicity/Toxicokinetics |
In human clinical trials, Maytansine showed a small therapeutic window due to neurotoxicity and harmful effects on the gastrointestinal tract. These toxicities limited its clinical development as a standalone therapeutic agent, leading to its use as a payload in ADCs for targeted delivery.
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| References | |
| Additional Infomation |
Maytansine is an organoheterocyclic compound and a 19-membered macrocyclic lactam antibiotic, initially isolated from the Ethiopian shrub Maytenus serrata, but also found in other Maytenus species. It exhibits cytotoxicity against various tumor cell lines. Maytansine functions as a plant metabolite, antibacterial agent, antitumor agent, microtubule regulator, and antimitotic agent. It is an epoxide, carbamate, organochlorine compound, α-amino acid ester, organoheterocyclic compound, and maytansine class compound. Maytansine has also been reported in Putterlickia verrucosa and Gymnosporia diversifolia, with relevant data available. Maytansine is an ansarcomon antibiotic, initially isolated from the Ethiopian shrub Maytenus serrata. Maytansin binds to the rhizomycin binding site of tubulin, thereby inhibiting microtubule assembly, inducing microtubule depolymerization, and disrupting mitosis. Maytansin exhibits cytotoxicity against various tumor cell lines and may inhibit tumor growth in vivo. (NCI04)
An anesine macrolide isolated from East African shrubs of the genus Maytansin. Maytansine is the first ansa macrolide shown to contain carbinolamine and demonstrates significant in vivo tumor inhibitory activity. It is used as the cytotoxic component in antibody-drug conjugates (ADCs). Its mechanism involves binding to tubulin at the rhizoxin/vinca site, inhibiting microtubule assembly, and disrupting mitosis. No standalone therapeutic indications are approved; maytansine derivatives (DM1, DM4) are used in FDA-approved ADCs. |
| 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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