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4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate is a complex organic compound that serves as an essential intermediate in the synthesis of various pharmaceutical agents. It is characterized by its unique chemical structure, which includes a nitrophenyl group, a glucopyranosiduronic acid moiety, and a methyl ester functional group. The compound's structure allows it to be a versatile building block in the development of novel therapeutics, particularly in the field of cancer treatment.

148579-93-5

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  • 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate

    Cas No: 148579-93-5

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148579-93-5 Usage

Uses

Used in Pharmaceutical Industry:
4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate is used as a key intermediate in the synthesis of Camptothecin-based anticancer therapy. Camptothecin is a potent chemotherapeutic agent that has demonstrated significant efficacy against various types of cancer, including colorectal, ovarian, and lung cancer. The compound's unique structure enables the development of Camptothecin analogs with improved pharmacological properties, such as enhanced solubility, stability, and bioavailability.
In the synthesis of Camptothecin-based anticancer therapy, 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate plays a crucial role in the formation of the final therapeutic agent. Its chemical reactivity allows for the introduction of various functional groups and modifications, which can lead to the development of more effective and targeted cancer treatments. By utilizing 4-ForMyl-2-nitrophenyl β-D-Glucopyranosiduronic Acid Methyl Ester 2,3,4-Triacetate as a starting material, researchers can explore new strategies for the design and synthesis of novel anticancer drugs, potentially improving patient outcomes and overall survival rates.

Check Digit Verification of cas no

The CAS Registry Mumber 148579-93-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,8,5,7 and 9 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 148579-93:
(8*1)+(7*4)+(6*8)+(5*5)+(4*7)+(3*9)+(2*9)+(1*3)=185
185 % 10 = 5
So 148579-93-5 is a valid CAS Registry Number.

148579-93-5Downstream Products

148579-93-5Relevant articles and documents

Design, synthesis and in vitro evaluation of β-glucuronidase-sensitive prodrug of 5-aminolevulinic acid for photodiagnosis of breast cancer cells

Herceg,Adriouach,Janikowska,Allémann,Lange,Babi?

, p. 372 - 380 (2018)

Treatment of cancer cells by clinically approved hexyl ester of 5-aminolevulinic acid (ALA-Hex) induces accumulation of fluorescent porphyrins in tumors. This allows fluorescence photodiagnosis (PD) of bladder cancer by blue light illumination. However, PD of other cancers is hampered by acute toxicity of the compound limiting its use to local applications. We have designed and synthesized a new prodrug of ALA-Hex that tackles the stability-activity paradox of amino-modified 5-ALA prodrugs. The glucuronide prodrug Glu-ALA-Hex demonstrates excellent stability under physiological conditions and activation in the presence of the target enzyme. β-glucuronidase-triggered release of 5-ALA is programmed to yield fluorescence in tumor environment with elevated β-glucuronidase activity, a characteristic of many solid tumors. Glu-ALA-Hex produces similar levels of fluorescence as ALA-Hex in breast cancer MCF7 cells in vitro but with much lower non-specific cell toxicity.

β-Glucuronidase triggers extracellular MMAE release from an integrin-targeted conjugate

López Rivas, Paula,Müller, Christoph,Breunig, Christian,Hechler, Torsten,Pahl, Andreas,Arosio, Daniela,Belvisi, Laura,Pignataro, Luca,Dal Corso, Alberto,Gennari, Cesare

, p. 4705 - 4710 (2019)

A non-internalizing αvβ3 integrin ligand was conjugated to the anticancer drug MMAE through a β-glucuronidase-responsive linker. In the presence of β-glucuronidase, only the conjugate bearing a PEG4 spacer inhibited the proliferation

Real-Time Multi-Photon Tracking and Bioimaging of Glycosylated Theranostic Prodrugs upon Specific Enzyme Triggered Release

Calatrava-Pérez, Elena,Elmes, Robert B. P.,Gunnlaugsson, Thorfinnur,Lynch, Dylan M.,Marchetti, Luke A.,McManus, Gavin J.,Scanlan, Eoin M.,Williams, D. Clive

, (2021/12/09)

Real-time tracking of prodrug uptake, delivery and activation in vivo represents a major challenge for prodrug development. Herein, we demonstrate the use of novel glycosylated theranostics of the cancer pharmacophore Amonafide in highly-selective, enzyma

A class of intestinal lysis type co-drugs and their preparation and use

-

Paragraph 0150-0155, (2022/01/20)

The present invention relates to a class of intestinal cleavage type co-drugs (Codrug) and preparation and use thereof, in particular, the present invention provides a co-drug compound as shown in formula I. The present invention further provides a method

Linker Hydrophilicity Modulates the Anticancer Activity of RGD–Cryptophycin Conjugates

Anselmi, Michele,Borbély, Adina,Figueras, Eduard,Michalek, Carmela,Kemker, Isabell,Gentilucci, Luca,Sewald, Norbert

supporting information, p. 1015 - 1022 (2020/12/11)

Most anticancer agents are hydrophobic and can easily penetrate the tumor cell membrane by passive diffusion. This may impede the development of highly effective and tumor-selective treatment options. A hydrophilic β-glucuronidase-cleavable linker was used to connect the highly potent antimitotic agent cryptophycin-55 glycinate with the αvβ3 integrin ligand c(RGDfK). Incorporation of the self-immolative linker containing glucuronic acid results in lower cytotoxicity than that of the free payload, suggesting that hydrophilic sugar linkers can preclude passive cellular uptake. In vitro drug-release studies and cytotoxicity assays demonstrated the potential of this small molecule–drug conjugate, providing guidance for the development of therapeutics containing hydrophobic anticancer drugs.

NEODEGRADER CONJUGATES

-

Paragraph 0525; 0527; 0554, (2021/10/11)

The present disclosure provides neoDegraders and neoDegraders conjugated to binding moieties. Also provided are compositions comprising the conjugates. The compounds and compositions are useful for treating a disease or condition, e.g., cancer, in a subject in need thereof.

BIO-ACTIVATED REPORTERS TO VISUALIZE, IN REAL TIME, SPECIFIC GENE THERAPY PRODUCTS

-

Paragraph 0022; 0139, (2021/02/05)

Provided herein are MRI contrast agents that are conditionally activated by an enzyme from a reporter gene coupled to a gene of interest. In some embodiments, provided herein is a platform where a substrate (blocking access of water to a Gd(III) ion) is r

Molecular, Macromolecular, and Supramolecular Glucuronide Prodrugs: Lead Identified for Anticancer Prodrug Monotherapy

Dagn?s-Hansen, Frederik,Jarlstad Olesen, Morten T.,Poier, Pier Paolo,Walther, Raoul,Zelikin, Alexander N.

supporting information, p. 7390 - 7396 (2020/03/13)

In this work, a tumor growth intervention by localized drug synthesis within the tumor volume, using the enzymatic repertoire of the tumor itself, is presented. Towards the overall success, molecular, macromolecular, and supramolecular glucuronide prodrug

COMPOUNDS, COMPOSITIONS, METHODS, AND USES FOR TREATING CANCER AND IMMUNOLOGICAL DISORDERS

-

, (2020/02/06)

The present disclosure provides novel polypeptide-therapeutic compound or hormone-therapeutic compound conjugates using cleavable or non-cleavable linkers, whereby the polypeptide or hormone serves to target specific cells using receptor expression on the targeted cell to bind the ligand (polypeptide or hormone) carrying the therapeutic compound unlike antibody drug conjugates. Upon binding, the ligand and the therapeutic compound (multiples of the therapeutic compound in some embodiments) enter the cell by receptor-mediated endocytosis, and release drugs conjugated to the ligand by linkers, to interact with intracellular components to enhance, restore, or block a signal transduction process. The ligands for the polypeptide-therapeutic compound or hormone-therapeutic compound conjugates include, but are not limited to: cytokines, growth factors and hormones among other proteins with corresponding cell surface specific receptors. The disorders targeted by such polypeptide-therapeutic compound or hormone-therapeutic compound conjugates include, but are not limited to: immunological disorders (e.g., allergy and autoimmune disorders) and cancer.

PRO-CYCLIC DINUCLEOTIDES AND PRO-CYCLIC DINUCLEOTIDE CONJUGATES FOR CYTOKINE INDUCTION

-

, (2019/07/17)

The present invention provides a Pro-cyclic dinucleotide (Pro-CDN) comprising a STING agonist cyclic dinucleotide which is coupled to a linker system. The Pro-CDNs of the present invention can be metabolized at a targeted site into CDNs and exert their full immunomodulatory effects at said targeted site. The present invention also provides conjugates wherein a Pro-CDN is conjugated to a Biologically Active Molecule (BAM) such as e.g. a cytotoxic molecule, a lipid, a protein, a peptide, a nucleic acid, a sugar or a PRR ligand. The invention provides also methods related to the use of such compounds to perform their activities at their targeted sites, to exert cytotoxic, cytostatic or immunomodulatory effects, to treat or to prevent diseases such as cancers, immunological disorders or infections.

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