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MAC glucuronide linker

  CAS No.: 2260960-07-2   Cat No.: BADC-00672 4.5  

MAC glucuronide linker is a vital tool used in the biomedical industry for drug discovery and targeted therapy. It enables the conjugation of drugs with glucuronide, facilitating their delivery and activation in specific organs or tissues. This linker plays a significant role in treating various diseases, including cancer, inflammation, and metabolic disorders.

MAC glucuronide linker

Structure of 2260960-07-2

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Category
ADC Linker
Molecular Formula
C43H48BrN3O17S
Molecular Weight
990.82
Shipping
Room temperature

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IUPAC Name
methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[4-[[bromomethyl(2-methylsulfonylethyl)carbamoyl]oxymethyl]-2-[[2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]acetyl]amino]phenoxy]oxane-2-carboxylate
Canonical SMILES
CC(=O)OC1C(C(OC(C1OC(=O)C)OC2=C(C=C(C=C2)COC(=O)N(CCS(=O)(=O)C)CBr)NC(=O)CN(C)C(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)C(=O)OC)OC(=O)C
InChI
InChI=1S/C43H48BrN3O17S/c1-24(48)60-36-37(61-25(2)49)39(62-26(3)50)41(64-38(36)40(52)57-5)63-34-16-15-27(21-58-43(54)47(23-44)17-18-65(6,55)56)19-33(34)45-35(51)20-46(4)42(53)59-22-32-30-13-9-7-11-28(30)29-12-8-10-14-31(29)32/h7-16,19,32,36-39,41H,17-18,20-23H2,1-6H3,(H,45,51)/t36-,37-,38-,39+,41+/m0/s1
Shipping
Room temperature
In Vitro
A series of MAC β-glucuronide model constructs were prepared to evaluate stability and enzymatic release, and the results demonstrated high stability at physiological pH in a substitution-dependent manner. All the MAC model compounds efficiently released alcohol drug surrogates under the action of β-glucuronidase. To assess the MAC technology for ADCs, the potent microtubule-disrupting agent auristatin E (AE) was incorporated through the norephedrine alcohol. Conjugation of the MAC β-glucuronide AE drug linker to the anti-CD30 antibody cAC10, and an IgG control antibody, gave potent and immunologically specific activities in vitro and in vivo.

MAC glucuronide linker is a specialized chemical linker used in the development of targeted drug delivery systems, particularly in antibody-drug conjugates (ADCs). The linker features a glucuronide moiety, which is a biologically stable group that can be cleaved under specific conditions, such as in the presence of β-glucuronidase enzymes commonly found in the tumor microenvironment. This cleavable linker allows for the selective release of the attached cytotoxic drug at the site of the tumor, minimizing off-target effects and enhancing the therapeutic efficacy of the ADC. By taking advantage of the differential enzyme activity in tumors versus normal tissues, MAC glucuronide linker enables precise drug delivery to cancer cells.

One of the primary applications of MAC glucuronide linker is in the development of ADCs for the treatment of various cancers. The linker facilitates the conjugation of potent cytotoxic agents, such as chemotherapeutic drugs or toxins, to monoclonal antibodies that target tumor-specific antigens. Once the ADC binds to the tumor cell, the glucuronide group is cleaved by β-glucuronidase, releasing the cytotoxic drug directly inside the tumor cell. This approach significantly improves the selectivity of cancer treatment, reducing the systemic toxicity often associated with traditional chemotherapy. By targeting the tumor microenvironment, MAC glucuronide linkers contribute to more effective and safer therapies for cancers like breast, ovarian, and colorectal cancers.

In addition to its use in ADCs, MAC glucuronide linker is being explored for its application in prodrug strategies, where the drug remains inactive until it is cleaved by specific enzymes. This feature makes it valuable for developing drugs that can be activated only in the targeted tissue, such as tumor cells, reducing the risk of side effects and increasing the specificity of treatment. Prodrugs that incorporate the MAC glucuronide linker could offer better control over the pharmacokinetics and pharmacodynamics of the drug, leading to improved clinical outcomes, particularly in the context of cancer therapy.

MAC glucuronide linker is also being studied for its potential in combination therapies, where it could be used in conjunction with other targeting strategies, such as immune checkpoint inhibitors or targeted small molecules. These combinations aim to enhance the anti-tumor efficacy by addressing multiple pathways involved in tumor growth and resistance mechanisms. Early-stage research suggests that combining MAC glucuronide linker-based ADCs with other treatments could offer synergistic effects, potentially leading to better therapeutic responses and reduced relapse rates in cancer patients.

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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