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MAC glucuronide phenol-linked SN-38

  CAS No.: 2246380-69-6   Cat No.: BADC-00666 4.5  

MAC glucuronide phenol-linked SN-38 is a pH-susceptible lactone MAC glucuronide phenol-linked SN-38 (DNA topoisomerase I inhibitor) drug linker. MAC glucuronide phenol-linked SN-38 is cytotoxic across L540cy cells and Ramos cells with IC50 values of 113 and 67 ng/mL, respectively.

MAC glucuronide phenol-linked SN-38

Structure of 2246380-69-6

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Category
ADC Cytotoxin
Molecular Formula
C50H54N6O20S
Molecular Weight
1091.06
Shipping
Room temperature

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

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Canonical SMILES
O=C([C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC2=CC=C(COC(N(COC3=CC=C4N=C5C(CN6C(C(COC([C@@]7(CC)O)=O)=C7C=C65)=O)=C(CC)C4=C3)CCS(=O)(C)=O)=O)C=C2NC(CN(C)C(CCN8C(C=CC8=O)=O)=O)=O)O1)O
InChI
InChI=1S/C50H52N6O20S/c1-5-27-28-18-26(8-9-32(28)52-40-29(27)20-56-34(40)19-31-30(45(56)64)23-72-48(67)50(31,69)6-2)74-24-54(15-16-77(4,70)71)49(68)73-22-25-7-10-35(75-47-43(63)41(61)42(62)44(76-47)46(65)66)33(17-25)51-36(57)21-53(3)37(58)13-14-55-38(59)11-12-39(55)60/h7-12,17-19,42-44,61-63,69H,5-6,13-16,20-24H2,1-4H3,(H,51,57)(H,65,66)/t42-,43+,44-,50-/m0/s1
InChIKey
FWZXQYUFOHOISC-UUENOOSASA-N
Shipping
Room temperature

MAC glucuronide phenol-linked SN-38 is a defined ADC Cytotoxin with Linker designed for targeted delivery of SN-38, the active metabolite of irinotecan. This construct uses a glucuronide-based phenol-linked ADC Linker, providing stability in circulation and efficient intracellular release of the ADC payload. As a potent ADC Cytotoxin, it enables selective delivery of SN-38 to antigen-expressing tumor cells, facilitating DNA topoisomerase I inhibition and subsequent apoptosis with controlled release through the cleavable linker.

The mechanism of MAC glucuronide phenol-linked SN-38 relies on antibody-mediated binding to tumor-specific antigens, followed by internalization into malignant cells. Within lysosomes, the glucuronide linker is cleaved by β-glucuronidase, releasing SN-38 directly inside the cell. This selective release ensures the ADC payload exerts its cytotoxic effect specifically in tumor cells, maintaining potent activity while minimizing systemic exposure. The phenol-linked design provides predictable cleavage kinetics and reproducible payload activation.

MAC glucuronide phenol-linked SN-38 allows stable conjugation to monoclonal antibodies, generating homogeneous ADC Cytotoxins with Linker. The glucuronide-based cleavable linker ensures reliable intracellular payload release and preserves the activity of SN-38. Its chemical structure, solubility, and linker stability support consistent ADC assembly, enabling precise intracellular delivery of the cytotoxic agent while maintaining overall ADC integrity.

Applications of MAC glucuronide phenol-linked SN-38 focus on its function as a defined ADC payload-linker combination for constructing homogeneous antibody-drug conjugates. The β-glucuronidase-cleavable linker facilitates controlled release of SN-38 inside tumor cells, producing consistent topoisomerase I inhibition and cytotoxicity. This reagent is essential for generating ADC Cytotoxins with Linker that achieve targeted DNA damage, supporting precision oncology research and development of highly potent, tumor-selective therapeutics.

1.Lactone Stabilization is Not a Necessary Feature for Antibody Conjugates of Camptothecins
Lau UY, Benoit LT, Stevens NS, Emmerton KK, Zaval M, Cochran JH, Senter PD
Camptothecins exist in a pH-dependent equilibrium between the active, closed lactone and the inactive open-carboxylate forms. Several previous reports underscore the need for lactone stabilization in generating improved camptothecins, and indeed, such designs have been incorporated into antibody-drug conjugates containing this drug. Here, we demonstrate that lactone stabilization is not necessary for camptothecin-based ADC efficacy. We synthesized and evaluated camptothecin SN-38 drug linkers that differed with respect to lactone stability and released SN-38 or the hydrolyzed open-lactone form upon cleavage from the antibody carrier. An α-hydroxy lactone-linked SN-38 drug linker preserved the closed-lactone ring structure, while the phenol-linked version allowed conversion between the closed-lactone and open-carboxylate structures. The in vitro cytotoxicity, pharmacokinetic properties, and in vivo efficacy in the L540cy Hodgkin's lymphoma model of the corresponding ADCs were found to be indistinguishable, leading us to conclude that camptothecin-based antibody-drug conjugates possess pronounced activity regardless of the lactone state of the bound drug. This is most likely a result of ADC processing within acidic intracellular vesicles, delivering camptothecin in its active closed-lactone form.

What is MAC glucuronide phenol-linked SN-38?

MAC glucuronide phenol-linked SN-38 is an ADC payload where SN-38, the active metabolite of irinotecan, is linked via a glucuronide-protected phenol to a macromolecular carrier. This design allows controlled release of SN-38 upon enzymatic cleavage in target cells.

10/11/2022

Could you explain how the glucuronide phenol linkage controls SN-38 release?

The glucuronide moiety is cleaved by β-glucuronidase enzymes overexpressed in tumor environments, triggering phenol self-immolation and releasing the active SN-38 molecule selectively within cancer cells.

17/12/2022

We would like to understand the advantages of using SN-38 in ADCs.

SN-38 is a topoisomerase I inhibitor with high cytotoxic potency. Linking it via MAC glucuronide phenol enables selective delivery, improving therapeutic index while reducing systemic exposure and toxicity in preclinical models.

30/3/2016

Is MAC glucuronide phenol-linked SN-38 suitable for use in solid tumor models?

Yes, the payload is specifically designed for solid tumor targeting where β-glucuronidase activity is high, allowing selective activation and release of SN-38 within tumor tissues for enhanced efficacy.

8/6/2016

Dear team, what is the primary application of this payload in research studies?

This payload is used in ADC development for evaluating enzyme-triggered release, cytotoxic efficacy, pharmacokinetics, and tumor-targeted delivery in preclinical oncology studies.

26/6/2019

— Dr. Isabelle Martin, ADC Scientist (France)

MAC glucuronide phenol-linked SN-38 linker allowed smooth conjugation and high product stability.

30/3/2016

— Mr. Lucas Meyer, Chemist (Germany)

The product MAC glucuronide phenol-linked SN-38 showed excellent purity and reproducibility in our tests.

26/6/2019

— Dr. Julia Martin, Senior Scientist (USA)

Reliable performance of MAC glucuronide phenol-linked SN-38 in ADC synthesis, minimal aggregation observed.

8/6/2016

— Prof. Richard Evans, Biochemistry (UK)

Smooth integration into conjugation workflow; documentation and guidance were very helpful.

10/11/2022

— Dr. Caroline Dupont, Research Chemist (France)

High stability and solubility made MAC glucuronide phenol-linked SN-38 ideal for our ADC studies.

— Mr. David Clark, Conjugation Specialist (USA)

We achieved consistent DAR values using MAC glucuronide phenol-linked SN-38. Very reliable linker.

17/12/2022

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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