Mertansine (DM1)
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MedKoo CAT#: 123212

CAS#: 139504-50-0

Description: Mertansine refers to the thiol-containing maytansinoid, DM1 (N2’-deacetyl-N2’-(3-mercapto-1-oxopropyl)maytansine) attached to a monoclonal antibody through reaction of the thiol group with the SPP (N-succinimidyl 4-(2-pyridyldithio)) linker to create an antibody-drug conjugate or ADC. Experimental ADCs with the SPP-DM1 design include lorvotuzumab mertansine. DM1 can also be linked to an antibody using the SMCC (4-(3-mercapto-2,5-dioxo-1-pyrrolidinylmethyl)-cylohexanecarboxylic acid) linker, in which case the International Nonproprietary Name of the conjugate formed contains the word emtansine. DM1 and its attachment via these linkers result from ImmunoGen Inc research. Trastuzumab emtansine (T-DM1) is an anti-HER2/neu antibody-drug conjugate.


Price and Availability

Size
Price

10mg
USD 150
100mg
USD 850
1g
USD 4650
Size
Price

25mg
USD 250
200mg
USD 1550
2g
USD 7950
Size
Price

50mg
USD 450
500mg
USD 3150

Mertansine, purity > 98%, is in stock. The same day shipping out after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Note: the estimated shipping out time for order > 200mg may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 123212
Name: Mertansine (DM1)
CAS#: 139504-50-0
Chemical Formula: C35H48ClN3O10S
Exact Mass: 737.27489
Molecular Weight: 738.29
Elemental Analysis: C, 56.94; H, 6.55; Cl, 4.80; N, 5.69; O, 21.67; S, 4.34


Synonym: DM1; DM-1; DM 1; DM1 Compound; DM1 [Maytansinoid]; Maytansinoid DM 1; Maytansinoid DM1; Maytansinoid DM-1; UNII-DDZ29HGH0E; maytansine, Mertansine; emtansine;

IUPAC/Chemical Name: (14S,16S,33S,2R,4R,10E,12Z,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-(3-mercaptopropanoyl)-N-methyl-L-alaninate

InChi Key: ANZJBCHSOXCCRQ-GCRZMMRQSA-N

InChi Code: InChI=1S/C35H48ClN3O10S/c1-19-10-9-11-26(46-8)35(44)18-25(47-33(43)37-35)20(2)31-34(4,49-31)27(48-32(42)21(3)38(5)28(40)12-13-50)17-29(41)39(6)23-15-22(14-19)16-24(45-7)30(23)36/h9-11,15-16,20-21,25-27,31,44,50H,12-14,17-18H2,1-8H3,(H,37,43)/b11-9-,19-10+/t20-,21+,25+,26-,27-,31?,34+,35+/m1/s1

SMILES Code: 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(C1O4)C)OC(=O)[C@H](C)N(C)C(=O)CCS)C)/C)OC)(NC(=O)O2)O


Technical Data

Appearance:
White to off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Safety Data Sheet (MSDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Koniev O, Kolodych S, Baatarkhuu Z, Stojko J, Eberova J, Bonnefoy JY, Cianférani S, Van Dorsselaer A, Wagner A. MAPN: First-in-Class Reagent for Kinetically Resolved Thiol-to-Thiol Conjugation. Bioconjug Chem. 2015 Sep 3. [Epub ahead of print] PubMed PMID: 26335849.

2: Van den Mooter T, Teuwen LA, Rutten A, Dirix L. Trastuzumab emtansine in advanced human epidermal growth factor receptor 2-positive breast cancer. Expert Opin Biol Ther. 2015 May;15(5):749-60. doi: 10.1517/14712598.2015.1036026. PubMed PMID: 25865453.

3: Loganzo F, Tan X, Sung M, Jin G, Myers JS, Melamud E, Wang F, Diesl V, Follettie MT, Musto S, Lam MH, Hu W, Charati MB, Khandke K, Kim KS, Cinque M, Lucas J, Graziani E, Maderna A, O'Donnell CJ, Arndt KT, Gerber HP. Tumor cells chronically treated with a trastuzumab-maytansinoid antibody-drug conjugate develop varied resistance mechanisms but respond to alternate treatments. Mol Cancer Ther. 2015 Apr;14(4):952-63. doi: 10.1158/1535-7163.MCT-14-0862. Epub 2015 Feb 2. PubMed PMID: 25646013.

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5: Whiteman KR, Johnson HA, Mayo MF, Audette CA, Carrigan CN, LaBelle A, Zukerberg L, Lambert JM, Lutz RJ. Lorvotuzumab mertansine, a CD56-targeting antibody-drug conjugate with potent antitumor activity against small cell lung cancer in human xenograft models. MAbs. 2014 Mar-Apr;6(2):556-66. doi: 10.4161/mabs.27756. Epub 2014 Jan 8. PubMed PMID: 24492307; PubMed Central PMCID: PMC3984343.

6: Berdeja JG. Lorvotuzumab mertansine: antibody-drug-conjugate for CD56+ multiple myeloma. Front Biosci (Landmark Ed). 2014 Jan 1;19:163-70. Review. PubMed PMID: 24389179.

7: Patel TA, Dave B, Rodriguez AA, Chang JC, Perez EA, Colon-Otero G. Dual HER2 blockade: preclinical and clinical data. Breast Cancer Res. 2014 Aug 1;16(4):419. doi: 10.1186/s13058-014-0419-5. Erratum in: Breast Cancer Res. 2014;16(6):468. PubMed PMID: 25928889; PubMed Central PMCID: PMC4429364.

8: Wood AC, Maris JM, Gorlick R, Kolb EA, Keir ST, Reynolds CP, Kang MH, Wu J, Kurmasheva RT, Whiteman K, Houghton PJ, Smith MA. Initial testing (Stage 1) of the antibody-maytansinoid conjugate, IMGN901 (Lorvotuzumab mertansine), by the pediatric preclinical testing program. Pediatr Blood Cancer. 2013 Nov;60(11):1860-7. doi: 10.1002/pbc.24647. Epub 2013 Jun 24. PubMed PMID: 23798344; PubMed Central PMCID: PMC4260400.

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10: Ballantyne A, Dhillon S. Trastuzumab emtansine: first global approval. Drugs. 2013 May;73(7):755-65. doi: 10.1007/s40265-013-0050-2. Review. PubMed PMID: 23620199.

11: Pode-Shakked N, Shukrun R, Mark-Danieli M, Tsvetkov P, Bahar S, Pri-Chen S, Goldstein RS, Rom-Gross E, Mor Y, Fridman E, Meir K, Simon A, Magister M, Kaminski N, Goldmacher VS, Harari-Steinberg O, Dekel B. The isolation and characterization of renal cancer initiating cells from human Wilms' tumour xenografts unveils new therapeutic targets. EMBO Mol Med. 2013 Jan;5(1):18-37. doi: 10.1002/emmm.201201516. Epub 2012 Dec 13. PubMed PMID: 23239665; PubMed Central PMCID: PMC3569651.

12: Lambert JM. Drug-conjugated antibodies for the treatment of cancer. Br J Clin Pharmacol. 2013 Aug;76(2):248-62. doi: 10.1111/bcp.12044. Review. PubMed PMID: 23173552; PubMed Central PMCID: PMC3731599.

13: Beck A, Lambert J, Sun M, Lin K. Fourth World Antibody-Drug Conjugate Summit: February 29-March 1, 2012, Frankfurt, Germany. MAbs. 2012 Nov-Dec;4(6):637-47. doi: 10.4161/mabs.21697. Epub 2012 Aug 22. PubMed PMID: 22909934; PubMed Central PMCID: PMC3502230.

14: Erickson HK, Lambert JM. ADME of antibody-maytansinoid conjugates. AAPS J. 2012 Dec;14(4):799-805. doi: 10.1208/s12248-012-9386-x. Epub 2012 Aug 9. Review. PubMed PMID: 22875610; PubMed Central PMCID: PMC3475867.

15: Gurtner K, Hessel F, Eicheler W, Dörfler A, Zips D, Heider KH, Krause M, Baumann M. Combined treatment of the immunoconjugate bivatuzumab mertansine and fractionated irradiation improves local tumour control in vivo. Radiother Oncol. 2012 Mar;102(3):444-9. doi: 10.1016/j.radonc.2011.10.013. Epub 2011 Nov 17. PubMed PMID: 22100655.

16: Ricart AD. Immunoconjugates against solid tumors: mind the gap. Clin Pharmacol Ther. 2011 Apr;89(4):513-23. doi: 10.1038/clpt.2011.8. Epub 2011 Mar 2. Review. PubMed PMID: 21368753.

17: Platt VM, Szoka FC Jr. Anticancer therapeutics: targeting macromolecules and nanocarriers to hyaluronan or CD44, a hyaluronan receptor. Mol Pharm. 2008 Jul-Aug;5(4):474-86. doi: 10.1021/mp800024g. Epub 2008 Jun 3. Review. PubMed PMID: 18547053; PubMed Central PMCID: PMC2772999.

18: Rodon J, Garrison M, Hammond LA, de Bono J, Smith L, Forero L, Hao D, Takimoto C, Lambert JM, Pandite L, Howard M, Xie H, Tolcher AW. Cantuzumab mertansine in a three-times a week schedule: a phase I and pharmacokinetic study. Cancer Chemother Pharmacol. 2008 Oct;62(5):911-9. doi: 10.1007/s00280-007-0672-8. Epub 2008 Feb 27. PubMed PMID: 18301896.

19: Riechelmann H, Sauter A, Golze W, Hanft G, Schroen C, Hoermann K, Erhardt T, Gronau S. Phase I trial with the CD44v6-targeting immunoconjugate bivatuzumab mertansine in head and neck squamous cell carcinoma. Oral Oncol. 2008 Sep;44(9):823-9. doi: 10.1016/j.oraloncology.2007.10.009. Epub 2008 Jan 18. PubMed PMID: 18203652.

20: Rupp U, Schoendorf-Holland E, Eichbaum M, Schuetz F, Lauschner I, Schmidt P, Staab A, Hanft G, Huober J, Sinn HP, Sohn C, Schneeweiss A. Safety and pharmacokinetics of bivatuzumab mertansine in patients with CD44v6-positive metastatic breast cancer: final results of a phase I study. Anticancer Drugs. 2007 Apr;18(4):477-85. PubMed PMID: 17351401.