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Maytansinoid DM4

  CAS No.: 799840-96-3   Cat No.: BADC-00087   Purity: ≥98.0% (HPLC) 4.5  

DM4 is a cytotoxic agent. It is used as the cytotoxic component in antibody-drug conjugates.

Maytansinoid DM4

Structure of 799840-96-3

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Category
ADC Cytotoxin
Molecular Formula
C39H56ClN3O10S
Molecular Weight
780.37
Target
Microtubule/Tubulin
Shipping
Room temperature
Storage
Hygroscopic, -20°C Freezer, Under inert atmosphere

* For research and manufacturing use only. We do not sell to patients.

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Popular Publications Citing BOC Sciences Products
Synonyms
N2'-deacetyl-n2'-(4-Mercapto-4-Methyl-1-oxopentyl)-6-MethylMaytansine
IUPAC Name
[(1S,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,2,5,9,16-pentamethyl-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-[methyl-(4-methyl-4-sulfanylpentanoyl)amino]propanoate
Canonical SMILES
CC1=CC=CC(C2(CC(C(C3C(O3)(C(CC(=O)N(C4=C(C(=CC(=C4)C1)OC)Cl)C)OC(=O)C(C)N(C)C(=O)CCC(C)(C)S)C)(C)C)OC(=O)N2)O)OC
InChI
InChI=1S/C39H56ClN3O10S/c1-22-13-12-14-27(50-11)39(48)21-29(52-35(47)41-39)37(5,6)34-38(7,53-34)28(51-33(46)23(2)42(8)30(44)15-16-36(3,4)54)20-31(45)43(9)25-18-24(17-22)19-26(49-10)32(25)40/h12-14,18-19,23,27-29,34,48,54H,15-17,20-21H2,1-11H3,(H,41,47)/b14-12+,22-13+/t23-,27+,28-,29-,34-,38-,39-/m0/s1
InChIKey
SVVGCFZPFZGWRG-OTKBOCOUSA-N
Density
1.3±0.1 g/cm3
Solubility
Soluble in DMSO, chloroform (slightly), methanol (slightly)
Flash Point
522.4±34.3 °C
Index Of Refraction
1.587
Vapor Pressure
0.0±0.3 mmHg at 25°C
Appearance
White to off-white solid
Quantity
Milligrams-Grams
Shipping
Room temperature
Storage
Hygroscopic, -20°C Freezer, Under inert atmosphere
Boiling Point
940.2±65.0 °C at 760 mmHg
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT03045393Breast Cancer Triple NegativePhase 12018-07-05Duke UniversityWithdrawn (Inadequate enrollment)
NCT04606914Ovarian CancerPhase 22021-07-08University of Alabama at BirminghamRecruiting
NCT05041257Ovarian CancerPhase 22021-09-22ImmunoGen, Inc.Recruiting
NCT03455556Mesothelin PositivePhase 12020-05-15Mayo ClinicTerminated (slow accrual)
NCT00352131Non-colorectal CancerPhase 12010-03-17ImmunoGen, Inc.Completed

Maytansinoid DM4 is a semi-synthetic derivative of Maytansine and a widely used ADC cytotoxin in the development of antibody-drug conjugates. As a potent ADC payload, DM4 acts as a tubulin polymerization inhibitor, disrupting microtubule dynamics, arresting cell division, and ultimately inducing apoptosis. Its structural modifications compared to Maytansine enhance its conjugation compatibility with linker technologies, making it a versatile payload for targeted oncology therapeutics.

Within the ADC platform, Maytansinoid DM4 is commonly conjugated to antibodies through cleavable disulfide linkers. This strategy enables efficient drug release inside tumor cells where the reductive environment triggers cleavage, liberating the active cytotoxin. Such a mechanism ensures that DM4 exerts its potent cytotoxic effects selectively at the tumor site while minimizing damage to healthy tissues. The balance of stability in circulation and controlled intracellular release highlights DM4 as a reliable payload choice for next-generation ADC development.

Applications of Maytansinoid DM4 include its integration into clinical-stage ADC candidates for the treatment of various cancers, such as breast cancer, ovarian cancer, and hematologic malignancies. Its high potency allows effective therapeutic outcomes even at low drug-to-antibody ratios, which is essential for maintaining a favorable therapeutic index. Moreover, DM4’s chemical flexibility enables researchers to design customized linker-payload systems optimized for stability, pharmacokinetics, and tumor selectivity, expanding the scope of ADC drug discovery.

1. Ado-Trastuzumab Emtansine for Patients With HER2-Mutant Lung Cancers: Results From a Phase II Basket Trial
Bob T Li, Jose Baselga, Michael Offin, Fabiola Cecchi, David M Hyman, Daniel Feldman, Michelle S Ginsberg, Nick Pavlakis, Maurizio Scaltriti, Mark G Kris, Michael F Berger, Stephen Clarke, Maria E Arcila, Darren Buonocore, Sarit Schwartz, Gregory J Riely, Helen H Won, Alexander Drilon, Edyta B Brzostowski, Ronglai Shen, Todd Hembrough, Charles M Rudin, Zachary T Olah, David B Solit, Ai Ni, Gary A Ulaner J Clin Oncol . 2018 Aug 20;36(24):2532-2537. doi: 10.1200/JCO.2018.77.9777.
Purpose Human epidermal growth factor receptor 2 ( HER2, ERBB2)-activating mutations occur in 2% of lung cancers. We assessed the activity of ado-trastuzumab emtansine, a HER2-targeted antibody-drug conjugate, in a cohort of patients with HER2-mutant lung cancers as part of a phase II basket trial. Patients and Methods Patients received ado-trastuzumab emtansine at 3.6 mg/kg intravenously every 3 weeks until progression. The primary end point was overall response rate using Response Evaluation Criteria in Solid Tumors (RECIST) version 1.1. A Simon two-stage optimal design was used. Other end points included progression-free survival and toxicity. HER2 testing was performed on tumor tissue by next generation sequencing, fluorescence in situ hybridization, immunohistochemistry, and protein mass spectrometry. Results We treated 18 patients with advanced HER2-mutant lung adenocarcinomas. The median number of prior systemic therapies was two (range, zero to four prior therapies). The partial response rate was 44% (95% CI, 22% to 69%), meeting the primary end point. Responses were seen in patients with HER2 exon 20 insertions and point mutations in the kinase, transmembrane, and extracellular domains. Concurrent HER2 amplification was observed in two patients. HER2 immunohistochemistry ranged from 0 to 2+ and did not predict response, and responders had low HER2 protein expression measured by mass spectrometry. The median progression-free survival was 5 months (95% CI, 3 to 9 months). Toxicities included grade 1 or 2 infusion reactions, thrombocytopenia, and elevated hepatic transaminases. No patient stopped therapy as a result of toxicity or died on study. Conclusion Ado-trastuzumab emtansine is an active agent in patients with HER2-mutant lung cancers. This is the first positive trial in this molecular subset of lung cancers. Further use and study of this agent are warranted.
2. HER2-positive gastric cancer
Narikazu Boku Gastric Cancer . 2014 Jan;17(1):1-12. doi: 10.1007/s10120-013-0252-z.
Human epidermal growth factor receptor 2 (HER2) is involved in the pathogenesis and poor outcomes of several types of cancer, including advanced gastric and gastroesophageal junction cancer. Molecular-targeted drugs, such as trastuzumab, which prolong overall survival and progression-free survival in HER2-positive breast cancer, may also be beneficial in patients with HER2-positive gastric cancer. Several studies have examined this possibility, such as the Trastuzumab for Gastric Cancer trial. In this context, the first part of this review provides an update on our knowledge of HER2 in breast and gastric cancer, including the detection and prognostic relevance of HER2 in gastric cancer. The second part of the review discusses the results of pivotal clinical trials that examined the potential for using trastuzumab to treat this disease. This section also summarizes the trials that have been conducted or that are underway to determine the optimal uses of trastuzumab in gastric cancer, including its use as monotherapy and continuation beyond disease progression. The final section discusses the future prospects of other anti-HER2 drugs, including lapatinib, trastuzumab emtansine, and pertuzumab, for the treatment of HER2-positive gastric cancer. The introduction of trastuzumab led to the establishment of a new disease entity, "HER2-positive gastric cancer," similar to HER2-positive breast cancer. It is expected that more anti-HER2 drugs will be developed and introduced into clinical practice to treat HER2-positive cancers, including gastric cancer.
3. Trastuzumab emtansine: mechanisms of action and drug resistance
Mark Barok, Jorma Isola, Heikki Joensuu Breast Cancer Res . 2014 Mar 5;16(2):209. doi: 10.1186/bcr3621.
Trastuzumab emtansine (T-DM1) is an antibody-drug conjugate that is effective and generally well tolerated when administered as a single agent to treat advanced breast cancer. Efficacy has now been demonstrated in randomized trials as first line, second line, and later than the second line treatment of advanced breast cancer. T-DM1 is currently being evaluated as adjuvant treatment for early breast cancer. It has several mechanisms of action consisting of the anti-tumor effects of trastuzumab and those of DM1, a cytotoxic anti-microtubule agent released within thetarget cells upon degradation of the human epidermal growth factor receptor-2 (HER2)-T-DM1 complex in lysosomes. The cytotoxic effect of T-DM1 likely varies depending on the intracellular concentration of DM1 accumulated in cancer cells, high intracellular levels resulting in rapid apoptosis, somewhat lower levels in impaired cellular trafficking and mitotic catastrophe, while the lowest levels lead to poor response to T-DM1. Primary resistance of HER2-positive metastatic breast cancer to T-DM1 appears to be relatively infrequent, but most patients treated with T-DM1 develop acquired drug resistance. The mechanisms of resistance are incompletely understood, but mechanisms limiting the binding of trastuzumab to cancer cells may be involved. The cytotoxic effect of T-DM1 may be impaired by inefficient internalization or enhanced recycling of the HER2-T-DM1 complex in cancer cells, or impaired lysosomal degradation of trastuzumab or intracellular trafficking of HER2. The effect ofT-DM1 may also be compromised by multidrug resistance proteins that pump DM1 out of cancer cells. In this review we discuss the mechanism of action of T-DM1 and the key clinical results obtained with it, the combinations ofT-DM1 with other cytotoxic agents and anti-HER drugs, and the potential resistance mechanisms and the strategies to overcome resistance to T-DM1.

What is Maytansinoid DM4?

Maytansinoid DM4 is a potent microtubule-disrupting cytotoxin commonly used in the construction of antibody-drug conjugates (ADCs). It binds to tubulin and inhibits microtubule assembly, making it highly effective for targeted delivery in cancer therapy research.

3/9/2018

Dear team, how does Maytansinoid DM4 function in ADCs?

In ADCs, Maytansinoid DM4 serves as the payload that exerts cytotoxic activity upon internalization by target cells. Once released intracellularly, it disrupts microtubules, leading to cell cycle arrest and apoptosis. This mechanism ensures selective action on targeted cells.

12/9/2016

Good afternoon! What types of linkers are compatible with Maytansinoid DM4?

Maytansinoid DM4 is compatible with a variety of cleavable and non-cleavable linkers, including disulfide and thioether-based linkers. The choice of linker influences drug release kinetics, stability, and overall efficacy of the resulting ADC.

9/12/2019

Dear Sir, I would like to know if BOC Sciences can provide custom Maytansinoid DM4 ADC synthesis.

BOC Sciences offers custom ADC synthesis incorporating Maytansinoid DM4. Our services include linker selection, conjugation optimization, and analytical characterization to support research and preclinical development.

9/3/2019

Good afternoon! How is Maytansinoid DM4 supplied for research purposes?

Maytansinoid DM4 is provided in formats suitable for laboratory use, including solid or solution forms, along with handling guidelines to ensure safe storage, accurate dosing, and compatibility with ADC development workflows.

4/7/2022

— Dr. David Miller, Senior ADC Researcher (USA)

Maytansinoid DM4 delivered by BOC Sciences met all our purity and stability requirements. Technical support was very helpful.

9/12/2019

— Dr. Alice Johnson, Medicinal Chemist (UK)

Excellent consistency between Maytansinoid DM4 batches enabled smooth ADC conjugation and in vivo studies.

4/7/2022

— Dr. Felix Schneider, Biochemist (Germany)

Fast delivery and professional support. Maytansinoid DM4 quality was outstanding.

9/3/2019

— Dr. Sophie Wilson, Senior Scientist (Canada)

Detailed QC reports ensured confidence in every batch of Maytansinoid DM4.

3/9/2018

— Dr. Robert Hughes, Research Fellow (USA)

BOC Sciences’ Maytansinoid DM4 helped accelerate our ADC pipeline efficiently.

— Dr. Emma Laurent, Pharmacology Scientist (France)

Excellent technical guidance and consistent Maytansinoid DM4 quality. Crucial for our projects.

12/9/2016

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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