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Lys-SMCC-DM1

  CAS No.: 1281816-04-3   Cat No.: BADC-00574 4.5  

Lys-SMCC-DM1 is an ADC cytotoxin conjugate with a lysine-reactive SMCC linker and DM1 payload, designed to improve antibody conjugation efficiency and stability in targeted cancer therapies. Keywords: SMCC linker, DM1 payload, lysine conjugation, ADC stability.

Lys-SMCC-DM1

Structure of 1281816-04-3

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Category
ADC Cytotoxin
Molecular Formula
C53H75ClN6O15S
Molecular Weight
1103.71
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Room temperature, or blue ice upon request.

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

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Synonyms
(2S)-2-amino-6-[[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]cyclohexanecarbonyl]amino]hexanoic acid
IUPAC Name
(2S)-2-amino-6-[[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]cyclohexanecarbonyl]amino]hexanoic acid
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)NCCCCC(C(=O)O)N)C)C)OC)(NC(=O)O2)O
InChI
InChI=1S/C53H75ClN6O15S/c1-29-12-11-14-40(72-8)53(70)27-38(73-51(69)57-53)30(2)46-52(4,75-46)41(26-43(62)59(6)36-23-33(22-29)24-37(71-7)45(36)54)74-50(68)31(3)58(5)42(61)19-21-76-39-25-44(63)60(48(39)65)28-32-15-17-34(18-16-32)47(64)56-20-10-9-13-35(55)49(66)67/h11-12,14,23-24,30-32,34-35,38-41,46,70H,9-10,13,15-22,25-28,55H2,1-8H3,(H,56,64)(H,57,69)(H,66,67)/b14-11+,29-12+/t30-,31+,32?,34?,35+,38+,39?,40-,41+,46+,52+,53+/m1/s1
InChIKey
UBRZDBDIKWWPEN-YCPOLOASSA-N
Shipping
Room temperature, or blue ice upon request.

Lys-SMCC-DM1 is an advanced antibody-drug conjugate (ADC) that combines the targeting capability of antibodies with the cytotoxic potency of the drug DM1, a derivative of maytansine. The compound consists of a lysine (Lys) residue, a reactive crosslinker (SMCC), and the highly potent cytotoxic agent DM1. The SMCC linker facilitates the conjugation of DM1 to the antibody, ensuring that the cytotoxic drug is delivered selectively to cancer cells. This precise targeting of tumor cells allows for the effective killing of cancerous tissue while minimizing damage to surrounding healthy tissues, a key advantage of ADCs over traditional chemotherapy. Lys-SMCC-DM1 is primarily being explored for its potential in treating a variety of cancers, including breast cancer and other solid tumors.

One of the major applications of Lys-SMCC-DM1 is in the treatment of HER2-positive breast cancer. HER2 is a receptor commonly overexpressed in certain breast cancers, and targeting this receptor with an anti-HER2 antibody conjugated to DM1 has shown promising results in clinical trials. By selectively delivering DM1 to HER2-expressing tumor cells, Lys-SMCC-DM1 provides an effective therapeutic approach for patients with advanced or metastatic breast cancer. This targeted therapy reduces systemic toxicity compared to traditional chemotherapy, improving the patient’s quality of life while still delivering potent anti-cancer effects.

In addition to breast cancer, Lys-SMCC-DM1 is being investigated for the treatment of other solid tumors, such as ovarian cancer and non-small cell lung cancer (NSCLC). The ability to target specific tumor-associated antigens, like HER2 or other cell surface markers, allows Lys-SMCC-DM1 to be potentially effective in treating a wide range of cancers. Early studies suggest that this ADC could be beneficial in cancers that are resistant to conventional treatments, offering a new therapeutic option for patients with limited choices.

Lys-SMCC-DM1 is also being explored for use in combination therapies. Researchers are investigating its potential synergistic effects when combined with immune checkpoint inhibitors, chemotherapies, or other ADCs. These combination strategies aim to enhance the efficacy of Lys-SMCC-DM1, overcome resistance mechanisms, and provide a more comprehensive treatment for aggressive cancers. By using multiple approaches to target cancer cells, combination therapies could improve overall survival rates and reduce the risk of relapse in patients with solid tumors.

1.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.
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. Furthermore, it was confirmed that DS-8201a was not effective against MDA-MB-468-Luc tumors inoculated at the opposite side of the NCI-N87 tumor, suggesting that the bystander killing effect of DS-8201a is observed only in cells neighboring HER2-positive cells, indicating low concern in terms of systemic toxicity. These results indicated that DS-8201a has a potent bystander effect due to a highly membrane-permeable payload and is beneficial in treating tumors with HER2 heterogeneity that are unresponsive to T-DM1.

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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