A reactive drug-linker molecule containing DM1
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Product Type

Biochemicals

Research Area

Cancer
Immunology

DM1-SMCC

Item No. 23926

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N2'-deacetyl-N2'-[3-[[1-[[4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]cyclohexyl]methyl]-2,5-dioxo-3-pyrrolidinyl]thio]-1-oxopropyl]-maytansine
CAS Number
1228105-51-8
Synonyms
  • SMCC-DM1
Molecular Formula
C51H66ClN5O16S
Formula Weight
1072.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mlDMF:PBS (pH 7.2) (1:5): 0.16 mg/mlDMSO: 12 mg/ml
SMILES
C/C(C1)=C\C=C\[C@](OC)([H])[C@](C[C@@](O2)([H])[C@@H](C)[C@H]3[C@](O3)(C)[C@](OC([C@H](C)N(C)C(CCSC4C(N(CC5CCC(C(ON6C(CCC6=O)=O)=O)CC5)C(C4)=O)=O)=O)=O)([H])CC(N(C)C7=CC1=CC(OC)=C7Cl)=O)(O)NC2=O
InChi Code
InChI=1S/C51H66ClN5O16S/c1-27-10-9-11-37(69-8)51(67)25-35(70-49(66)53-51)28(2)45-50(4,72-45)38(24-42(61)55(6)33-21-31(20-27)22-34(68-7)44(33)52)71-47(64)29(3)54(5)39(58)18-19-74-36-23-43(62)56(46(36)63)26-30-12-14-32(15-13-30)48(65)73-57-40(59)16-17-41(57)60/h9-11,21-22,28-30,32,35-38,45,67H,12-20,23-26H2,1-8H3,(H,53,66)/b11-9+,27-10+/t28-,29+,30?,32?,35+,36?,37-,38+,45+,50+,51+/m1/s1
InChi Key
IADUWZMNTKHTIN-MLSWMBHTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $54

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    5 mg

    $203

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    10 mg

    $324

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    25 mg

    $742

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    Cayman Chemical
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    Product Description

    DM1-SMCC is a reactive drug-linker molecule containing the maytansinoid DM1 (mertansine; Item No. 22483) and the crosslinker SMCC.1,2 It inhibits the proliferation of HER2-positive HCC1954 and HER2-negative MDA-MB-468 breast cancer cells (IC50s = 17.2 and 49.9 nM, respectively).3 DM1-SMCC has been linked to B38.1, a chimeric antibody for the tumor antigen epithelial cell adhesion molecule (EpCAM), as an antibody-drug conjugate (ADC) to target DM1 to tumor sites.4 DM1-SMCC linked to B38.1 inhibits the proliferation of MCF-7 breast cancer cells (IC50 = 11 nM).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Luo, Q., Chung, H.H., Borths, C., et al. Structural characterization of a monoclonal antibody-maytansinoid immunoconjugate. Anal. Chem. 88(1), 695-702 (2016).

    2. Hamblett, K.J., Jacob, A.P., Gurgel, J.L., et al. SLC46A3 is required to transport catabolites of noncleavable antibody maytansine conjugates from the lusosome to the cytoplasm. Cancer Res. 75(24), 5329-5340 (2015).

    3. Shao, S., Tsai, M.-H., Lu, J., et al. Site-specific and hydrophilic ADCs through disulfide-bridged linker and branched PEG. Bioorg. Med. Chem. Lett. 28(8), 1363-1370 (2018).

    4. Oroudjev, E., Lopus, M., Wilson, L., et al. Maytansinoid-antibody conjugates induce mitotic arrest by suppressing microtubule dynamic instability. Mol. Cancer Ther. 9(10), 2700-2713 (2010).