Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 - CAS 148579-93-5

Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 - CAS 148579-93-5 Catalog number: BADC-00957

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Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs).

Category
ADCs Linker
Product Name
Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2
CAS
148579-93-5
Catalog Number
BADC-00957
Molecular Formula
C20H21NO13
Molecular Weight
483.38
Purity
>98.0%
Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2

Ordering Information

Catalog Number Size Price Quantity
BADC-00957 -- $-- Inquiry
Description
Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 is a cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs).
Synonyms
Me-triacetyl-beta-D-glucopyranuronate-Ph-ald-NO2; methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-formyl-2-nitrophenoxy)oxane-2-carboxylate; 4-Formyl-2-nitrophenyl -D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate
IUPAC Name
methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-formyl-2-nitrophenoxy)oxane-2-carboxylate
Canonical SMILES
CC(=O)OC1C(C(OC(C1OC(=O)C)OC2=C(C=C(C=C2)C=O)[N+](=O)[O-])C(=O)OC)OC(=O)C
InChI
InChI=1S/C20H21NO13/c1-9(23)30-15-16(31-10(2)24)18(32-11(3)25)20(34-17(15)19(26)29-4)33-14-6-5-12(8-22)7-13(14)21(27)28/h5-8,15-18,20H,1-4H3/t15-,16-,17-,18+,20+/m0/s1
InChIKey
MHAQOFAFDHVKQE-KVIJGQROSA-N
Density
1.4±0.1 g/cm3
Solubility
Soluble in DMSO (10 mm)
Flash Point
219.6±32.1 °C
Index Of Refraction
1.550
LogP
2.62
Vapor Pressure
0.0±1.6 mmHg at 25°C
Shelf Life
-20°C 3 years powder; -80°C 2 years in solvent
Shipping
Room temperature
Storage
Store at -20 °C, keep in dry and avoid sunlight.
Boiling Point
582.6±50.0 °C at 760 mmHg

Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 is an essential cleavable linker in the design and synthesis of antibody-drug conjugates (ADCs), a class of targeted cancer therapeutics. These linkers play a pivotal role in determining the efficacy and safety of ADCs by controlling the release of the cytotoxic drug once the antibody component has specifically bound to a target cancer cell. The Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 linker is designed to be cleaved within the tumor microenvironment, leveraging changes in conditions such as pH, the presence of specific enzymes, or other biochemical stimuli. This site-specific cleavage ensures that the cytotoxic payload is released primarily within the cancer cells, minimizing collateral damage to healthy cells and thereby reducing systemic toxicity.

One of the critical advantages of using Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 as a cleavable linker is its stability in circulation coupled with its responsive cleavage once inside the targeted cancer cells. This dual functionality is achieved by incorporating a β-D-glucopyranuronate moiety, which can be selectively cleaved by enzymes such as beta-glucuronidase that are often overexpressed in certain tumor environments. This enzymatic specificity allows the conjugate to remain stable as it circulates through the body, reducing premature drug release and enhancing the ADC's therapeutic index. This specificity is crucial in enhancing the therapeutic window of ADCs, thus maximizing tumor cell kill while sparing normal tissues.

In addition to its enzymatic cleavability, the Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 linker integrates a pH-sensitive component. Many solid tumors exhibit a slightly acidic microenvironment compared to normal tissues. The pH-responsiveness of this linker ensures that it remains intact in the neutral pH of the bloodstream and primarily releases the drug under the acidic conditions encountered within tumor cells or late endosomal/lysosomal compartments. This pH-sensitive property further improves the specificity of the drug release, contributing to a more precise and controlled therapeutic action.

Beyond enhancing the specificity and efficacy of ADCs, Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 also supports the modular design of ADC platforms. Its inclusion can facilitate the conjugation of various payloads, ranging from small chemotherapy drugs to biologically active peptides. This versatility enables researchers to explore a wide range of therapeutic payloads, optimizing ADCs for different types of cancer and possibly other diseases where targeted delivery is beneficial. By tailoring the cleavable linkers to the biological characteristics of specific tumors, significant advancements can be made in personalized medicine approaches, offering the potential for more effective treatments with fewer side effects. Overall, Me-triacetyl-β-D-glucopyranuronate-Ph-ald-NO2 is indispensable in modern drug development, providing critical functionality that drives the therapeutic success of antibody-drug conjugates.

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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