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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

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

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Popular Publications Citing BOC Sciences Products
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.

What is MAC glucuronide linker used for in ADCs?

MAC glucuronide linker is a cleavable linker that releases payloads in response to β-glucuronidase enzymes. It provides stability in circulation and selective activation within tumor microenvironments or lysosomes containing high glucuronidase activity.

22/4/2019

We would like to know how the glucuronide unit enhances ADC specificity.

The glucuronide moiety is specifically cleaved by β-glucuronidase, an enzyme overexpressed in tumor tissues. This selective cleavage ensures payload release predominantly at the target site, reducing systemic toxicity.

2/6/2019

Dear team, can MAC glucuronide linker improve solubility of hydrophobic payloads?

Yes, the glucuronide unit is hydrophilic, which increases the solubility of hydrophobic payloads and reduces aggregation of ADCs. This contributes to improved pharmacokinetics and manufacturability.

27/8/2020

Dear BOC Sciences, what payloads are suitable for conjugation with MAC glucuronide linker?

MAC glucuronide linker is compatible with diverse cytotoxic payloads, including auristatins and maytansinoids. Conjugation strategies typically involve reactive groups on the payload for stable linker attachment.

26/8/2019

Dear team, which supporting documents and analytical data are provided with MAC glucuronide linker?

MAC glucuronide linker is supplied with a certificate of analysis (CoA) confirming identity, structural characterization, and recommended handling. Typical analytical data include NMR, MS, and HPLC to verify the chemical structure and suitability for conjugation applications in antibody-drug conjugates.

22/3/2019

— Dr. Michael Brown, Protein Chemist (USA)

MAC glucuronide linker showed excellent solubility and consistent purity, which streamlined our conjugation workflow.

27/8/2020

— Prof. Isabelle Dupont, Biochemist (France)

BOC Sciences’ MAC glucuronide linker delivered high-quality material on time. It was critical for our ADC program.

22/3/2019

— Dr. Thomas Keller, ADC Developer (Germany)

Batch-to-batch reproducibility of MAC glucuronide linker was exceptional, ensuring smooth scale-up.

26/8/2019

— Ms. Rachel Evans, Research Scientist (UK)

The linker’s hydrophilic profile enhanced ADC solubility and reduced aggregation. Very satisfied.

22/4/2019

— Dr. Sofia Lindberg, Medicinal Chemist (Sweden)

Using MAC glucuronide linker improved payload stability and conjugation efficiency.

— Mr. Alex Johnson, Bioconjugation Analyst (Canada)

MAC glucuronide linker quality and delivery timeline were excellent, enabling timely project milestones.

2/6/2019

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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