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DM1-SMCC

  CAS No.: 1228105-51-8   Cat No.: BADC-00009   Purity: 95% LCMS 4.5  

DM1 with a reactive linker SMCC, which can react with antibody to make antibody drug conjugate, as a potent EGFR inhibitor and it overcomes resistant to EGFR.

DM1-SMCC

Structure of 1228105-51-8

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Category
ADC Cytotoxin
Molecular Formula
C51H66ClN5O16S
Molecular Weight
1072.62
Shipping
Room temperature
Shipping
Store at -20°C

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

Size Price Stock Quantity
10 mg $298 In stock

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Popular Publications Citing BOC Sciences Products
Synonyms
2,5-dioxopyrrolidin-1-yl 4-((3-((3-(((2S)-1-(((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)oxy)-1-oxopropan-2-yl)(methyl)amino)-3-oxopropyl)thio)-2,5-dioxopyrrolidin-1-yl)methyl)cyclohexane-1-carboxylate; DM1 SMCC; SMCC-DM1
IUPAC Name
(2,5-dioxopyrrolidin-1-yl) 4-[[3-[3-[[(2S)-1-[[(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]oxy]-1-oxopropan-2-yl]-methylamino]-3-oxopropyl]sulfanyl-2,5-dioxopyrrolidin-1-yl]methyl]cyclohexane-1-carboxylate
Canonical SMILES
CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)CCSC5CC(=O)N(C5=O)CC6CCC(CC6)C(=O)ON7C(=O)CCC7=O)C)C)OC)(NC(=O)O2)O
InChI
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
InChIKey
IADUWZMNTKHTIN-MLSWMBHTSA-N
Density
1.4±0.1 g/cm3
Solubility
Soluble in DMSO, not in water
Index Of Refraction
1.626
PSA
282.83000
Appearance
Soild powder
Quantity
Milligrams-Grams
Quality Standard
In-house standard
Shelf Life
2 month in rt, long time
Shipping
Room temperature
Storage
Store at -20°C

DM1-SMCC, a potent cytotoxic agent, plays a vital role in the development of antibody-drug conjugates (ADCs) for targeted cancer therapy. Here are four key applications of DM1-SMCC:

Cancer Treatment: At the forefront of targeted cancer therapy, DM1-SMCC is a cornerstone in ADCs engineered to specifically seek out cancer cells. By binding to antibodies that recognize tumor-associated antigens, this cytotoxic agent is delivered directly to malignant cells, minimizing harm to healthy tissues. This precision targeting not only enhances treatment effectiveness but also reduces systemic side effects, heralding a paradigm shift in cancer care.

Pharmacokinetics Studies: In the realm of pharmacokinetics research, DM1-SMCC is a crucial tool for unraveling the behavior and distribution of ADCs in both preclinical and clinical settings. Understanding the journey of these conjugates in the body—from absorption to elimination—is paramount for optimizing dosing strategies and improving therapeutic results. These studies are instrumental in predicting clinical responses and potential adverse reactions.

Drug Development: Serving as a prototypical payload, DM1-SMCC plays a pivotal role in designing the next generation of ADCs. By manipulating linker chemistry or pairing with diverse monoclonal antibodies, scientists can craft innovative ADCs with enhanced stability, potency, and selectivity. This adaptability is key to tailoring treatments for a spectrum of cancer types.

Mechanism of Action Studies: Delving into the intricate mechanisms of ADCs’ cytotoxic effects on cancer cells, DM1-SMCC empowers researchers to explore cellular uptake, intracellular trafficking, and release within targeted cells. These investigations offer profound insights into how ADCs induce cell death, shedding light on resistance mechanisms and optimizing therapeutic approaches. This deep understanding is pivotal for refining cancer treatment strategies and overcoming therapeutic challenges.

1.Understanding How the Stability of the Thiol-Maleimide Linkage Impacts the Pharmacokinetics of Lysine-Linked Antibody-Maytansinoid Conjugates.
Ponte JF;Sun X;Yoder NC;Fishkin N;Laleau R;Coccia J;Lanieri L;Bogalhas M;Wang L;Wilhelm S;Widdison W;Pinkas J;Keating TA;Chari R;Erickson HK;Lambert JM Bioconjug Chem. 2016 Jul 20;27(7):1588-98. doi: 10.1021/acs.bioconjchem.6b00117. Epub 2016 Jun 20.
Antibody-drug conjugates (ADCs) have become a widely investigated modality for cancer therapy, in part due to the clinical findings with ado-trastuzumab emtansine (Kadcyla). Ado-trastuzumab emtansine utilizes the Ab-SMCC-DM1 format, in which the thiol-functionalized maytansinoid cytotoxic agent, DM1, is linked to the antibody (Ab) via the maleimide moiety of the heterobifunctional SMCC linker. The pharmacokinetic (PK) data for ado-trastuzumab emtansine point to a faster clearance for the ADC than for total antibody. Cytotoxic agent release in plasma has been reported with nonmaytansinoid, cysteine-linked ADCs via thiol-maleimide exchange, for example, brentuximab vedotin. For Ab-SMCC-DM1 ADCs, however, the main catabolite reported is lysine-SMCC-DM1, the expected product of intracellular antibody proteolysis. To understand these observations better, we conducted a series of studies to examine the stability of the thiol-maleimide linkage, utilizing the EGFR-targeting conjugate, J2898A-SMCC-DM1, and comparing it with a control ADC made with a noncleavable linker that lacked a thiol-maleimide adduct (J2898A-(CH2)3-DM). We employed radiolabeled ADCs to directly measure both the antibody and the ADC components in plasma.
2.Bystander killing effect of DS-8201a, a novel anti-human epidermal growth factor receptor 2 antibody-drug conjugate, in tumors with human epidermal growth factor receptor 2 heterogeneity.
Ogitani Y;Hagihara K;Oitate M;Naito H;Agatsuma T Cancer Sci. 2016 Jul;107(7):1039-46. doi: 10.1111/cas.12966. Epub 2016 Jun 22.
Antibody-drug conjugates deliver anticancer agents selectively and efficiently to tumor tissue and have significant antitumor efficacy with a wide therapeutic window. DS-8201a is a human epidermal growth factor receptor 2 (HER2)-targeting antibody-drug conjugate prepared using a novel linker-payload system with a potent topoisomerase I inhibitor, exatecan derivative (DX-8951 derivative, DXd). It was effective against trastuzumab emtansine (T-DM1)-insensitive patient-derived xenograft models with both high and low HER2 expression. In this study, the bystander killing effect of DS-8201a was evaluated and compared with that of T-DM1. We confirmed that the payload of DS-8201a, DXd (1), was highly membrane-permeable whereas that of T-DM1, Lys-SMCC-DM1, had a low level of permeability. Under a coculture condition of HER2-positive KPL-4 cells and negative MDA-MB-468 cells in vitro, DS-8201a killed both cells, whereas T-DM1 and an antibody-drug conjugate with a low permeable payload, anti-HER2-DXd (2), did not. In vivo evaluation was carried out using mice inoculated with a mixture of HER2-positive NCI-N87 cells and HER2-negative MDA-MB-468-Luc cells by using an in vivo imaging system. In vivo, DS-8201a reduced the luciferase signal of the mice, indicating suppression of the MDA-MB-468-Luc population; however, T-DM1 and anti-HER2-DXd (2) did not.
3.A novel anti-CD37 antibody-drug conjugate with multiple anti-tumor mechanisms for the treatment of B-cell malignancies.
Deckert J;Park PU;Chicklas S;Yi Y;Li M;Lai KC;Mayo MF;Carrigan CN;Erickson HK;Pinkas J;Lutz RJ;Chittenden T;Lambert JM Blood. 2013 Nov 14;122(20):3500-10. doi: 10.1182/blood-2013-05-505685. Epub 2013 Sep 3.
CD37 has gathered renewed interest as a therapeutic target in non-Hodgkin lymphoma (NHL) and chronic lymphocytic leukemia (CLL); however, CD37-directed antibody-drug conjugates (ADCs) have not been explored. Here, we identified a novel anti-CD37 antibody, K7153A, with potent in vitro activity against B-cell lines through multiple mechanisms including apoptosis induction, antibody-dependent cellular cytotoxicity, antibody-dependent cellular phagocytosis, and complement-dependent cytotoxicity. The antibody was conjugated to the maytansinoid, DM1, a potent antimicrotubule agent, via the thioether linker, N-succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxylate (SMCC), and the resulting ADC, IMGN529, retained the intrinsic antibody activities and showed enhanced cytotoxic activity from targeted payload delivery. In lymphoma cell lines, IMGN529 induced G2/M cell cycle arrest after internalization and lysosomal processing to lysine-N(ε)-SMCC-DM1 as the sole intracellular maytansinoid metabolite. IMGN529 was highly active against subcutaneous B-cell tumor xenografts in severe combined immunodeficient mice with comparable or better activity than rituximab, a combination of cyclophosphamide, vincristine, and prednisone, or bendamustine.

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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