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139504-50-0,MFCD28398157
Catalog No.:AA001B2A

139504-50-0 | DM1

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1mg
99%
in stock  
$32.00   $22.00
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2mg
99%
in stock  
$45.00   $32.00
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5mg
99%
in stock  
$76.00   $54.00
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100mg
99%
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$583.00   $408.00
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250mg
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$1,176.00   $823.00
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1g
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$2,940.00   $2,058.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA001B2A
Chemical Name:
DM1
CAS Number:
139504-50-0
Molecular Formula:
C35H48ClN3O10S
Molecular Weight:
738.2877
MDL Number:
MFCD28398157
SMILES:
SCCC(=O)N([C@H](C(=O)O[C@@H]1CC(=O)N(C)c2cc(C/C(=C/C=C\[C@H]([C@]3(C[C@@H]([C@H](C4[C@@]1(C)O4)C)OC(=O)N3)O)OC)/C)cc(c2Cl)OC)C)C
Properties
Properties
 
Form:
Solid  
MP:
>168°C (dec.)  
Storage:
Keep in dry area;2-8℃;  

Computed Properties
 
Complexity:
1340  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
50  
Hydrogen Bond Acceptor Count:
11  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
8  
XLogP3:
2.2  

Upstream Synthesis Route

[1]JournalofMedicinalChemistry,2006,vol.49,#14,p.4392-4408

[2]JournalofMedicinalChemistry,2014,vol.57,#16,p.6949-6964

[1]JournalofMedicinalChemistry,2006,vol.49,#14,p.4392-4408

[1]JournalofMedicinalChemistry,2006,vol.49,#14,p.4392-4408

[1]JournalofMedicinalChemistry,2014,vol.57,#16,p.6949-6964

Downstream Synthesis Route
452072-22-9    139504-50-0   
N2'-deacetyl-N2'-3-(3-carboxy-1-methyl-propyldithio)-1-oxopropylmaytansine 

[1]JournalofMedicinalChemistry,2006,vol.49,p.4392-4408

139504-50-0   
N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)maytansinedimer 

[1]JournalofMedicinalChemistry,2006,vol.49,p.4392-4408

[1]JournalofMedicinalChemistry,2006,vol.49,p.4392-4408

[2]JournalofMedicinalChemistry,2014,vol.57,p.6949-6964

[1]JournalofMedicinalChemistry,2006,vol.49,p.4392-4408

[1]JournalofMedicinalChemistry,2006,vol.49,p.4392-4408

Literature

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Journal: Toxicology and applied pharmacology 20131201

Title: A phase II study of trastuzumab emtansine in patients with human epidermal growth factor receptor 2-positive metastatic breast cancer who were previously treated with trastuzumab, lapatinib, an anthracycline, a taxane, and capecitabine.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20120910

Title: Drug interaction potential of trastuzumab emtansine (T-DM1) combined with pertuzumab in patients with HER2-positive metastatic breast cancer.

Journal: Current drug metabolism 20120901

Title: Phase I multidose-escalation study of the anti-CD19 maytansinoid immunoconjugate SAR3419 administered by intravenous infusion every 3 weeks to patients with relapsed/refractory B-cell lymphoma.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20120801

Title: HER2 testing in patients with breast cancer.

Journal: BMJ (Clinical research ed.) 20120611

Title: Phase I studies of AVE9633, an anti-CD33 antibody-maytansinoid conjugate, in adult patients with relapsed/refractory acute myeloid leukemia.

Journal: Investigational new drugs 20120601

Title: Clinical implications of pathophysiological and demographic covariates on the population pharmacokinetics of trastuzumab emtansine, a HER2-targeted antibody-drug conjugate, in patients with HER2-positive metastatic breast cancer.

Journal: Journal of clinical pharmacology 20120501

Title: Clinical pharmacology of trastuzumab emtansine (T-DM1): an antibody-drug conjugate in development for the treatment of HER2-positive cancer.

Journal: Cancer chemotherapy and pharmacology 20120501

Title: Combined treatment of the immunoconjugate bivatuzumab mertansine and fractionated irradiation improves local tumour control in vivo.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20120301

Title: An isolable acyclic hemiacetal of ansamitocin P-3.

Journal: Magnetic resonance in chemistry : MRC 20120301

Title: Biosynthesis of 3,5-AHBA-derived natural products.

Journal: Natural product reports 20120201

Title: Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates.

Journal: Nature biotechnology 20120122

Title: The interplay between mutasynthesis and semisynthesis: generation and evaluation of an ansamitocin library.

Journal: Angewandte Chemie (International ed. in English) 20120116

Title: Combined muta- and semisynthesis: a powerful synthetic hybrid approach to access target specific antitumor agents based on ansamitocin P3.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20120116

Title: Responses to subsequent anti-HER2 therapy after treatment with trastuzumab-DM1 in women with HER2-positive metastatic breast cancer.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20120101

Title: Dual carbamoylations on the polyketide and glycosyl moiety by asm21 result in extended ansamitocin biosynthesis.

Journal: Chemistry & biology 20111223

Title: Enhanced production of ansamitocin P-3 by addition of Mg2+ in fermentation of Actinosynnema pretiosum.

Journal: Bioresource technology 20111101

Title: Trastuzumab emtansine in human epidermal growth factor receptor 2-positive breast cancer: a review.

Journal: Current opinion in oncology 20111101

Title: Enthusiasm for antibody-drug conjugates.

Journal: Journal of the National Cancer Institute 20111019

Title: Trastuzumab emtansine: a unique antibody-drug conjugate in development for human epidermal growth factor receptor 2-positive cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20111015

Title: SAR3419: an anti-CD19-Maytansinoid Immunoconjugate for the treatment of B-cell malignancies.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20111015

Title: A novel pathway for maytansinoid release from thioether linked antibody-drug conjugates (ADCs) under oxidative conditions.

Journal: Chemical communications (Cambridge, England) 20111014

Title: Modeling the effects of drug binding on the dynamic instability of microtubules.

Journal: Physical biology 20111001

Title: Antibody-DM1 conjugates as cancer therapeutics.

Journal: Cancer letters 20110828

Title: N-methylation of the amide bond by methyltransferase asm10 in ansamitocin biosynthesis.

Journal: Chembiochem : a European journal of chemical biology 20110725

Title: Trastuzumab-DM1 (T-DM1) retains all the mechanisms of action of trastuzumab and efficiently inhibits growth of lapatinib insensitive breast cancer.

Journal: Breast cancer research and treatment 20110701

Title: Combinatorial effect of maytansinol and radiation in Drosophila and human cancer cells.

Journal: Disease models & mechanisms 20110701

Title: Synthesis and evaluation of hydrophilic linkers for antibody-maytansinoid conjugates.

Journal: Journal of medicinal chemistry 20110526

Title: Design of antibody-maytansinoid conjugates allows for efficient detoxification via liver metabolism.

Journal: Bioconjugate chemistry 20110420

Title: Disulfide-linked antibody-maytansinoid conjugates: optimization of in vivo activity by varying the steric hindrance at carbon atoms adjacent to the disulfide linkage.

Journal: Bioconjugate chemistry 20110420

Title: The microtubule as a breast cancer target.

Journal: Breast cancer (Tokyo, Japan) 20110401

Title: Mutational biosynthesis of ansamitocin antibiotics: a diversity-oriented approach to exploit biosynthetic flexibility.

Journal: Chembiochem : a European journal of chemical biology 20110307

Title: Megakaryocyte lineage-specific class VI β-tubulin suppresses microtubule dynamics, fragments microtubules, and blocks cell division.

Journal: Cytoskeleton (Hoboken, N.J.) 20110301

Title: Trastuzumab-DM1: building a chemotherapy-free road in the treatment of human epidermal growth factor receptor 2-positive breast cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20110201

Title: Phase II study of the antibody drug conjugate trastuzumab-DM1 for the treatment of human epidermal growth factor receptor 2 (HER2)-positive breast cancer after prior HER2-directed therapy.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20110201

Title: Enhanced production of ansamitocin P-3 by addition of isobutanol in fermentation of Actinosynnema pretiosum.

Journal: Bioresource technology 20110101

Title: Can cancer clinical trials be fixed?

Journal: Nature biotechnology 20110101

Title: Trastuzumab-DM1 causes tumour growth inhibition by mitotic catastrophe in trastuzumab-resistant breast cancer cells in vivo.

Journal: Breast cancer research : BCR 20110101

Title: World Antibody Drug Conjugate Summit Europe: February 21-23, 2011; Frankfurt, Germany.

Journal: mAbs 20110101

Title: [Antibody-drug conjugate--a new age for personalized cancer treatment].

Journal: Chimia 20110101

Title: Cyclization of synthetic seco-proansamitocins to ansamitocin macrolactams by Actinosynnema pretiosum as biocatalyst.

Journal: Chembiochem : a European journal of chemical biology 20101210

Title: Engineered thio-trastuzumab-DM1 conjugate with an improved therapeutic index to target human epidermal growth factor receptor 2-positive breast cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20101001

Title: Maytansine and cellular metabolites of antibody-maytansinoid conjugates strongly suppress microtubule dynamics by binding to microtubules.

Journal: Molecular cancer therapeutics 20101001

Title: Maytansinoid-antibody conjugates induce mitotic arrest by suppressing microtubule dynamic instability.

Journal: Molecular cancer therapeutics 20101001

Title: Physicochemical stability of the antibody-drug conjugate Trastuzumab-DM1: changes due to modification and conjugation processes.

Journal: Bioconjugate chemistry 20100915

Title: Biological considerations and clinical applications of new HER2-targeted agents.

Journal: Expert review of anticancer therapy 20100901

Title: A new antitumour ansamitocin from Actinosynnema pretiosum.

Journal: Natural product research 20100701

Title: [Current impact of natural products in the discovery of anticancer drugs].

Journal: Annales pharmaceutiques francaises 20100701

Title: Phase I study of trastuzumab-DM1, an HER2 antibody-drug conjugate, given every 3 weeks to patients with HER2-positive metastatic breast cancer.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20100601

Title: Modeling the efficacy of trastuzumab-DM1, an antibody drug conjugate, in mice.

Journal: Journal of pharmacokinetics and pharmacodynamics 20100601

Title: Trastuzumab emtansine, an antibody-drug conjugate for the treatment of HER2+ metastatic breast cancer.

Journal: Current opinion in molecular therapeutics 20100601

Title: Preparative isolation and purification of anti-tumor agent ansamitocin P-3 from fermentation broth of Actinosynnema pretiosum using high-performance counter-current chromatography.

Journal: Journal of separation science 20100501

Title: Antibody-maytansinoid conjugates designed to bypass multidrug resistance.

Journal: Cancer research 20100315

Title: Tumor delivery and in vivo processing of disulfide-linked and thioether-linked antibody-maytansinoid conjugates.

Journal: Bioconjugate chemistry 20100101

Title: Tau overexpression inhibits cell apoptosis with the mechanisms involving multiple viability-related factors.

Journal: Journal of Alzheimer's disease : JAD 20100101

Title: [Immunoconjugates, drug-armed antibodies to fight against cancer].

Journal: Medecine sciences : M/S 20091201

Title: Constitutive overexpression of asm2 and asm39 increases AP-3 production in the actinomycete Actinosynnema pretiosum.

Journal: Journal of industrial microbiology & biotechnology 20091101

Title: In vivo effects of targeting CD79b with antibodies and antibody-drug conjugates.

Journal: Molecular cancer therapeutics 20091001

Title: The monoclonal antibody nBT062 conjugated to cytotoxic Maytansinoids has selective cytotoxicity against CD138-positive multiple myeloma cells in vitro and in vivo.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090615

Title: Superior antitumor activity of SAR3419 to rituximab in xenograft models for non-Hodgkin's lymphoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20090615

Title: Formal total synthesis of N-methylmaysenine.

Journal: Organic letters 20090416

Title: Timing of the Delta(10,12)-Delta(11,13) double bond migration during ansamitocin biosynthesis in Actinosynnema pretiosum.

Journal: Journal of the American Chemical Society 20090325

Title: Antibody-drug conjugates for the treatment of non-Hodgkin's lymphoma: target and linker-drug selection.

Journal: Cancer research 20090315

Title: P-gp activity is a critical resistance factor against AVE9633 and DM4 cytotoxicity in leukaemia cell lines, but not a major mechanism of chemoresistance in cells from acute myeloid leukaemia patients.

Journal: BMC cancer 20090101

Title: Antibody-maytansinoid conjugates for the treatment of myeloma.

Journal: mAbs 20090101

Title: Targeting HER2-positive breast cancer with trastuzumab-DM1, an antibody-cytotoxic drug conjugate.

Journal: Cancer research 20081115

Title: Hedgehog/GLI-mediated transcriptional inhibitors from Zizyphus cambodiana.

Journal: Bioorganic & medicinal chemistry 20081101

Title: Cantuzumab mertansine in a three-times a week schedule: a phase I and pharmacokinetic study.

Journal: Cancer chemotherapy and pharmacology 20081001

Title: Phase I trial with the CD44v6-targeting immunoconjugate bivatuzumab mertansine in head and neck squamous cell carcinoma.

Journal: Oral oncology 20080901

Title: Amide N-glycosylation by Asm25, an N-glycosyltransferase of ansamitocins.

Journal: Chemistry & biology 20080825

Title: Anti-CD22-MCC-DM1 and MC-MMAF conjugates: impact of assay format on pharmacokinetic parameters determination.

Journal: Bioconjugate chemistry 20080801

Title: Effective immunoconjugate therapy in cancer models targeting a serine protease of tumor fibroblasts.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080715

Title: Highly active ansamitocin derivatives: mutasynthesis using an AHBA-blocked mutant.

Journal: Chembiochem : a European journal of chemical biology 20080505

Title: Targeted cancer therapy: conferring specificity to cytotoxic drugs.

Journal: Accounts of chemical research 20080101

Title: The ansacarbamitocins: polar ansamitocin derivatives.

Journal: Journal of natural products 20071001

Title: Folate receptor-specific antitumor activity of EC131, a folate-maytansinoid conjugate.

Journal: Cancer research 20070701

Title: New amide N-glycosides of ansamitocins identified from Actinosynnema pretiosum.

Journal: Archives of pharmacal research 20070601

Title: Chemoenzymatic approaches toward dechloroansamitocin P-3.

Journal: Organic letters 20070412

Title: Pharmacokinetics, immunogenicity and safety of bivatuzumab mertansine, a novel CD44v6-targeting immunoconjugate, in patients with squamous cell carcinoma of the head and neck.

Journal: International journal of oncology 20070401

Title: An integrative expression vector for Actinosynnema pretiosum.

Journal: BMC biotechnology 20070101

Title: On the biosynthetic origin of methoxymalonyl-acyl carrier protein, the substrate for incorporation of 'glycolate' units into ansamitocin and soraphen A.

Journal: Journal of the American Chemical Society 20061108

Title: A phase I dose escalation study with anti-CD44v6 bivatuzumab mertansine in patients with incurable squamous cell carcinoma of the head and neck or esophagus.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20061015

Title: Determination of the cryptic stereochemistry of the first PKS chain-extension step in ansamitocin biosynthesis by Actinosynnema pretiosum.

Journal: Chembiochem : a European journal of chemical biology 20060801

Title: Semisynthetic maytansine analogues for the targeted treatment of cancer.

Journal: Journal of medicinal chemistry 20060713

Title: Combinatorial biosynthesis--potential and problems.

Journal: Journal of biotechnology 20060625

Title: Antibody-maytansinoid conjugates are activated in targeted cancer cells by lysosomal degradation and linker-dependent intracellular processing.

Journal: Cancer research 20060415

Title: Antibody-drug conjugates designed to eradicate tumors with homogeneous and heterogeneous expression of the target antigen.

Journal: Cancer research 20060315

Title: Synthesis of the N-acetylcysteamine thioester of seco-proansamitocin.

Journal: Organic letters 20060105

Title: Structural characterization of the maytansinoid-monoclonal antibody immunoconjugate, huN901-DM1, by mass spectrometry.

Journal: Protein science : a publication of the Protein Society 20050901

Title: A reversed-phase high-performance liquid chromatography method for analysis of monoclonal antibody-maytansinoid immunoconjugates.

Journal: Analytical biochemistry 20050515

Title: Mass spectral analyses of labile DOTA-NHS and heterogeneity determination of DOTA or DM1 conjugated anti-PSMA antibody for prostate cancer therapy.

Journal: Journal of pharmaceutical sciences 20050401

Title: Metabolism studies of the anti-tumor agent maytansine and its analog ansamitocin P-3 using liquid chromatography/tandem mass spectrometry.

Journal: Journal of mass spectrometry : JMS 20050301

Title: Analysis of the composition of immunoconjugates using size-exclusion chromatography coupled to mass spectrometry.

Journal: Rapid communications in mass spectrometry : RCM 20050101

Title: Cytotoxic activity of the maytansinoid immunoconjugate B-B4-DM1 against CD138+ multiple myeloma cells.

Journal: Blood 20041201

Title: Technology evaluation: cantuzumab mertansine, ImmunoGen.

Journal: Current opinion in molecular therapeutics 20041201

Title: An API LC/MS/MS quantitation method for ansamitocin P-3 (AP3) and its preclinical pharmacokinetics.

Journal: Journal of pharmaceutical and biomedical analysis 20041119

Title: A prostate-specific membrane antigen-targeted monoclonal antibody-chemotherapeutic conjugate designed for the treatment of prostate cancer.

Journal: Cancer research 20041101

Title: Cytotoxic activity of maytanprine isolated from Maytenus diversifolia in human leukemia K562 cells.

Journal: Biological & pharmaceutical bulletin 20040801

Title: In vitro and in vivo activity of the maytansinoid immunoconjugate huN901-N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)-maytansine against CD56+ multiple myeloma cells.

Journal: Cancer research 20040701

Title: A phase I study of cantuzumab mertansine administered as a single intravenous infusion once weekly in patients with advanced solid tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040701

Title: A novel amide N-glycoside of ansamitocins from Actinosynnema pretiosum.

Journal: The Journal of antibiotics 20040501

Title: Pharmacokinetics and biodistribution of the antitumor immunoconjugate, cantuzumab mertansine (huC242-DM1), and its two components in mice.

Journal: The Journal of pharmacology and experimental therapeutics 20040301

Title: Recent developments in the maytansinoid antitumor agents.

Journal: Chemical & pharmaceutical bulletin 20040101

Title: The post-polyketide synthase modification steps in the biosynthesis of the antitumor agent ansamitocin by Actinosynnema pretiosum.

Journal: Journal of the American Chemical Society 20031126

Title: Dolastatin 15 binds in the vinca domain of tubulin as demonstrated by Hummel-Dreyer chromatography.

Journal: European journal of biochemistry 20030901

Title: Occurrence and non-detectability of maytansinoids in individual plants of the genera Maytenus and Putterlickia.

Journal: Phytochemistry 20030201

Title: Cantuzumab mertansine, a maytansinoid immunoconjugate directed to the CanAg antigen: a phase I, pharmacokinetic, and biologic correlative study.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20030115

Title: Identification of asm19 as an acyltransferase attaching the biologically essential ester side chain of ansamitocins using N-desmethyl-4,5-desepoxymaytansinol, not maytansinol, as its substrate.

Journal: Journal of the American Chemical Society 20020612

Title: Prostate stem cell antigen as therapy target: tissue expression and in vivo efficacy of an immunoconjugate.

Journal: Cancer research 20020501

Title: Identification of a set of genes involved in the formation of the substrate for the incorporation of the unusual 'glycolate' chain extension unit in ansamitocin biosynthesis.

Journal: Journal of the American Chemical Society 20020424

Title: Perspectives on anti-HER monoclonal antibodies.

Journal: Oncology 20020101

Title: Technology evaluation: C242-DM1, ImmunoGen Inc.

Journal: Current opinion in molecular therapeutics 20010401

Title: Binding of dolastatin 10 to tubulin at a distinct site for peptide antimitotic agents near the exchangeable nucleotide and vinca alkaloid sites.

Journal: The Journal of biological chemistry 19901005

Title: Rhizoxin, a macrocyclic lactone antibiotic, as a new antitumor agent against human and murine tumor cells and their vincristine-resistant sublines.

Journal: Cancer research 19860101

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Tags:139504-50-0 Molecular Formula|139504-50-0 MDL|139504-50-0 SMILES|139504-50-0 DM1