Name: Maytansine
Brand: BOC Sciences
Price: 629 USD
Availability: MadeToOrder

Synonyms

NSC153858; NSC-153858; 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;

IUPAC 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

Canonical 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)C)C)\C)OC)(NC(=O)O2)O

InChI

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

InChIKey

WKPWGQKGSOKKOO-RSFHAFMBSA-N

Melting Point

>165°C (dec.)

Appearance

Soild powder

Quantity

Milligrams-Grams

Shipping

-20°C (International: -20°C)

In Vitro

At the low concentrations of 0.5 to 2 microM, maytansine inhibited Tau-catalyzed tubulin assembly more effectively than it did MAP2-catalyzed assembly. This effect differed markedly from that of vinblastine, although both drugs bind competitively to tubulin. At the same low concentrations, vinblastine almost completely inhibited Tau- and MAP2-mediated tubulin assembly. At higher concentrations of 10 to 40 microM, a more striking difference was observed between the actions of the two drugs. Maytansine very effectively inhibited tubulin assembly promoted by either Tau or MAP2. Vinblastine also had this effect on MAP2-mediated tubulin assembly but in the presence of Tau induced extensive tubulin aggregation into spirals. In addition maytansine strongly inhibited vinblastine-induced Tau-dependent tubulin aggregation into spiral polymers. Even at very low concentrations, maytansine completely inhibited the effect of very high concentrations of vinblastine.

In Vivo

Maytansine, a potent clinically evaluated plant-derived anti-tumor drug, and its microbial counterpart, ansamitocin P-3, showed a substantially higher cytoxicity than many other anti-tumor drugs. The in vitro metabolism of maytansine and ansamitocin P-3 was studied after incubation with rat and human liver microsomes in the presence of NADPH, and with rat and human plasma and whole blood, using liquid chromatography/multi-stage mass spectrometry. There were no differences in maytansine metabolism between rat and human liver microsomes; however, the rate of metabolism of ansamitocin P-3 was different in rat and human liver microsomes. About 20% of ansamitocin P-3 was converted to its metabolites in rat liver microsomes and about 70% in human liver microsomes under the same conditions. Additionally, 10-O-demethylated ansamitocin P-3 was also detected in the urine after i.v. bolus administration of ansamitocin P-3 to Sprague-Dawley male rats. No metabolites were detected following incubation of maytansine and ansamitocin P-3 with human and rat whole blood and plasma.

NCT Number	Condition Or Disease	Phase	Start Date	Sponsor	Status
NCT01472887	Diffuse Large B-cell Lymphoma	Phase 2	2018-01-25	Sanofi	Completed
NCT02221505	cKIT-positive Solid Tumors	Phase 1	2016-04-05	Novartis Pharmaceuticals	Terminated
NCT04596150	Neoplasms	Phase 2	2021-10-28	CytomX Therapeutics	Recruiting
NCT02947152	Epithelial Ovarian Cancer	Phase 1	2020-12-08	Novartis Pharmaceuticals	Terminated
NCT01440179	Acute Lymphocytic Leukaemia	Phase 2	2014-08-27	Sanofi	Terminated (The study is stopped due to very modest activity compared to competitors)

Maytansine is a highly potent ADC cytotoxin and one of the most extensively studied ADC payloads in the development of antibody-drug conjugates. Belonging to the maytansinoid family, Maytansine acts as a tubulin inhibitor, binding at the vinca site of tubulin and preventing microtubule assembly. This disruption of microtubule dynamics leads to mitotic arrest and subsequent programmed cell death, making Maytansine an ideal cytotoxic agent for targeted cancer therapies.

Within the framework of antibody-drug conjugates, Maytansine is usually conjugated to monoclonal antibodies via cleavable or non-cleavable linkers. By combining the selective targeting ability of antibodies with the extreme potency of Maytansine, ADCs deliver lethal effects directly to tumor cells while sparing healthy tissue. The unique mechanism of Maytansine allows ADC platforms to achieve a therapeutic window that traditional chemotherapeutics cannot provide, establishing it as a benchmark payload in oncology research.

Applications of Maytansine as an ADC payload include both preclinical and clinical settings. It serves as the cytotoxic core of the well-known approved ADC trastuzumab emtansine (T-DM1), used in the treatment of HER2-positive breast cancer. Beyond this clinical success, Maytansine continues to inspire the development of novel maytansinoid derivatives such as DM1 and DM4, which further expand the toolbox of ADC payloads. Researchers also employ Maytansine in experimental ADC constructs targeting a broad spectrum of solid tumors and hematological malignancies, where precise delivery of a microtubule-disrupting agent is required.

1.Preclinical Efficacy and Safety Assessment of an Antibody-Drug Conjugate Targeting the c-RET Proto-Oncogene for Breast Carcinoma.

Nguyen M1, Miyakawa S1, Kato J1, Mori T2, Arai T2, Armanini M1, Gelmon K3, Yerushalmi R3, Leung S3, Gao D3, Landes G1, Haak-Frendscho M1, Elias K1, Simmons AD4. Clin Cancer Res. 2015 Dec 15;21(24):5552-62. doi: 10.1158/1078-0432.CCR-15-0468. Epub 2015 Aug 3.

PURPOSE: The RET proto-oncogene has been implicated in breast cancer, and the studies herein describe the preclinical and safety assessment of an anti-RET antibody-drug conjugate (ADC) being developed for the treatment of breast cancer.

2.Preclinical Efficacy of Ado-trastuzumab Emtansine in the Brain Microenvironment.

Askoxylakis V1, Ferraro GB1, Kodack DP1, Badeaux M1, Shankaraiah RC1, Seano G1, Kloepper J1, Vardam T1, Martin JD1, Naxerova K1, Bezwada D1, Qi X1, Selig MK1, Brachtel E1, Duda DG1, Huang P1, Fukumura D1, Engelman JA1, Jain RK2. J Natl Cancer Inst. 2015 Nov 7;108(2). pii: djv313. doi: 10.1093/jnci/djv313. Print 2016 Feb.

BACKGROUND: Central nervous system (CNS) metastases represent a major problem in the treatment of human epidermal growth factor receptor 2 (HER2)-positive breast cancer because of the disappointing efficacy of HER2-targeted therapies against brain lesions. The antibody-drug conjugate ado-trastuzumab emtansine (T-DM1) has shown efficacy in trastuzumab-resistant systemic breast cancer. Here, we tested the hypothesis that T-DM1 could overcome trastuzumab resistance in murine models of brain metastases.

3.Taxanes-induced cutaneous eruption: another histopathologic mimicker of malignancy.

Prieto-Torres L1, Llamas-Velasco M2, Machan S3, Haro R3, de Asis S4, Carmo M5, Loredo A6, Del Puerto C7, Fried I8, Kempf W9, Cerroni L8, Requena L3. J Eur Acad Dermatol Venereol. 2016 Apr;30(4):638-44. doi: 10.1111/jdv.13475. Epub 2015 Nov 11.

BACKGROUND: Paclitaxel and docetaxel are antineoplastic drugs that bind the microtubules, producing the arrest of mitoses, which may be seen histopathologically. These histopathologic changes may simulate an intraepidermal keratinocytic malignant neoplasm, and an accurate diagnosis may be only established by clinicopathological correlation.

HNMR

HPLC

What is Maytansine?

Maytansine is a potent microtubule inhibitor isolated from the Maytenus plant. As a cytotoxic payload in ADCs, it disrupts microtubule dynamics, inducing cell cycle arrest and apoptosis, enabling precise targeting of cancer cells when linked to monoclonal antibodies.

29/7/2016

We would like to know how Maytansine is used in antibody-drug conjugates.

Maytansine is covalently attached to antibodies via stable or cleavable linkers, facilitating selective delivery to tumor cells. This targeted approach enhances therapeutic efficacy while reducing off-target effects in preclinical and clinical studies.

19/8/2020

Dear team, we are interested in understanding why Maytansine is significant in oncology research. Could you advise?

Maytansine is widely used in oncology research to study ADC mechanisms, evaluate cytotoxic potency, and optimize linker-payload designs. Its application aids in the development of novel targeted therapies and preclinical drug evaluation.

4/9/2019

Could you let me know if BOC Sciences can assist with custom Maytansine ADC synthesis?

BOC Sciences provides custom ADC synthesis services with Maytansine, including payload conjugation, linker selection, and analytical support. This service ensures researchers can efficiently produce ADC candidates for experimental or preclinical studies.

12/9/2022

Good morning! What support does BOC Sciences provide for Maytansine handling and ADC integration?

BOC Sciences offers guidance on safe handling, storage, and integration of Maytansine into ADC projects. Expert consultation includes optimizing conjugation conditions and troubleshooting analytical challenges to maintain payload integrity.

24/7/2018

— Dr. Michael Green, Senior Scientist (USA)

BOC Sciences’ Maytansine enabled our ADC development with high purity and reproducibility. Shipment was timely and documentation complete.

4/9/2019

— Dr. Charlotte Wilson, Chemist (UK)

Excellent compound stability and batch-to-batch consistency. Their support team is very knowledgeable.

24/7/2018

— Dr. Andreas Schmidt, ADC Researcher (Germany)

Fast delivery and high-quality Maytansine made our cytotoxicity assays efficient and reproducible.

12/9/2022

— Dr. Laura Thompson, Biochemist (Canada)

BOC Sciences provides compounds that perfectly meet analytical standards. Reliable partner for ADC projects.