Maytansine

ChemicalBook > CAS DataBase List > Maytansine

Product Name: Maytansine
CAS No.: 35846-53-8
Chemical Name: Maytansine
Synonyms: NSC 153858;Maytansine;maitansine;Maitansina;Microtubule/Tubulin,tumor,mitotic,microtubule-targeted,arrest,Inhibitor,potent,subnanomolar,Maytansine,inhibit;(14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-Chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl N-acetyl-N-methyl-L-alaninate
CBNumber: CB8903295
Molecular Formula: C34H46ClN3O10
Formula Weight: 692.2
MOL File: 35846-53-8.mol

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Maytansine Property

Melting point:: 183.5-184℃
alpha: D26 -145° (c = 0.055 in chloroform)
Boiling point:: 895.1±65.0 °C(Predicted)
Density: 1.1049 (rough estimate)
refractive index: 1.6000 (estimate)
storage temp.: Store at -20°C
solubility: DMF: 1 mg/ml; DMSO: 10 mg/ml; Ethanol: 2 mg/ml; PBS (pH 7.2): insol
form: A solid
pka: 9.82±0.70(Predicted)
Stability:: Light Sensitive
InChIKey: WKPWGQKGSOKKOO-YHBUUTGONA-N

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Safety

Toxicity: LD50 in rats (mg/kg): 0.48 s.c. (Mugera, Ward)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H331Toxic if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P311Call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML3451
Product name: Maytansine
Purity: ≥95% (HPLC)
Packaging: 5MG
Price: $89.4
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML3451
Product name: Maytansine
Purity: ≥95% (HPLC)
Packaging: 25MG
Price: $360
Updated: 2024/03/01

TRC

Product number: M197940
Product name: Maytansine
Packaging: 1mg
Price: $245
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: API0010073
Product name: MAITANSINE
Purity: 95.00%
Packaging: 5MG
Price: $505.8
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 52062
Product name: Maytansine
Packaging: 10mg
Price: $2600
Updated: 2021/12/16

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Maytansine Chemical Properties,Usage,Production

Description

This novel ansa macrolide alkaloid occurs in a number of May tan us species. The structure given has been elucidated from chemical and spectroscopic data. In low doses (25-50 mcg/kg), maytansine prolonged the survival of mice bearing vincristine-sensitive P388 leukemia but not those bearing vincristine-resistant tumour lines. In vitro, it suppressed the growth of U21 0, LSl78Y and P388 leukemia cells with ED₅₀ of 2 X 10^-9 , 1.5 X 10^-9 and 6 X 10^-10M respectively and elevated the mitotic index in L 121 0 cells. From labelling studies it was shown that the alkaloid inhibited DNA formation by P388 cells to a greater extent than RNA and protein synthesis. Maytensine did not inhibit RNA polymerase from Escherichia coli at levels as high as 1 X 10^-4M.

Uses

Antineoplastic.

Definition

ChEBI: 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 tumo r cell lines.

Biological Functions

Maytansine is a potent microtubule-targeted compound that inhibits proliferation of cells at mitosis. Antibody-maytansinoid conjugates consisting of maytansinoids (DM1 and DM4) attached to tumor-specific antibodies have shown promising clinical results The microtubule-targeting maytansinoids accumulate in cells and induce mitotic arrest at 250- to 1000-fold lower concentrations than those required for their association with tubulin or microtubules.

Toxicology

Maytansine, an ansa macrolide isolated from African plants of the genera Maytenus and Putterlickia was first described almost two decades ago. It had been reported to be active against several forms of cancer, but a later phase II evaluation suggested no major role for this drug in tumor treatment. Although the toxic side effects were moderate, the antitumor activity was also not impressive.
Maytansine binds to tubulin rapidly and reversibly. Competitive inhibition of binding between maytansine and the vinca alkaloids has been observed, suggesting that maytansine must occupy at least one of vinblastine's binding sites on the tubulin molecule. The number of the maytansine binding sites is not known. Assembly of MT is inhibited at maytansine concentrations below 1μM. This suggests a substoichiometric poisoning mechanism as in the cases of colchicine, vinblastine and podophyllotoxin, but the details are not known. In contrast to many other MT-interacting toxins，maytansine does not promote the formation of aberrant tubulin polymers, even at millimolar concentrations. In fact, low concentrations of maytansine even inhibit vinblastine-induced formation of aberrant polymers.

Mode of action

Maytansine is a new drug undergoing clinical investigation. It has functional similarities to vincristine.
Maytansine, an ansa macrolide of considerable antitumor potency, is obtained from plants of the genera Maytenus and Putterlickia. Maytansine binds rapidly and reversibly to tubulin, and is a competitive inhibitor of vinca alkaloid binding. Colchicine has no effect on maytansine binding. Maytansine and the vinca alkaloids have comparable binding constants, share a common binding site, although an additional site or attachment position specific for maytansine appears to be present. Maytansine may inhibit tubulin polymerization by interfering with certain critical-SH groups necessary for assembly. Like the vincas, it inhibits assembly substroichiometric. Unlike the vincas, as well as colchicine and podophyllotoxin, maytansine appears capable of inducing rapid microtubule disassembly in vitro when added to microtubules at end state. Furthermore, maytansine enhances alkylation by iodoacetamide，an effect opposite to that obtained with V BL, suggesting that maytansine may have different conformation effects on tubulin.

References

Walpert-Defillipes et al., Biochem. Pharmacol., 24, 751 (1975)

Maytansine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Maytansine manufacturers

Wuhan Monad Medicine Tech Co.,LTD

Product: Maytansine 35846-53-8
Price: US $10.00/Kg/Bag
Min. Order: 1Kg/Bag
Purity: 99%min
Supply Ability: 2000
Release date: 2020-12-22

Zhuozhou Wenxi import and Export Co., Ltd

Product: maytansine 35846-53-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-11

35846-53-8, MaytansineRelated Search:

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maitansine

Maytansine

NSC 153858

(14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-Chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl N-acetyl-N-methyl-L-alaninate

Maitansina

Microtubule/Tubulin,tumor,mitotic,microtubule-targeted,arrest,Inhibitor,potent,subnanomolar,Maytansine,inhibit

35846-53-8

35845-53-8

C34H46ClN3O10