41833-13-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-3-nitrobenzyl alcohol is used as a key intermediate in the preparation of monoclonal IgG4 anti-human MET antibody and drug conjugates. These conjugates play a crucial role in cancer therapy, targeting specific cancer cells and delivering potent drugs to combat the disease effectively.
Used in Biotechnology Industry:
4-Hydroxy-3-nitrobenzyl alcohol is also utilized in the development of innovative drug delivery systems, which aim to enhance the bioavailability and therapeutic outcomes of various pharmaceutical compounds. Its unique chemical properties make it a valuable asset in the design and synthesis of novel drug carriers, ultimately contributing to the advancement of cancer treatment options.

InChI:InChI=1/C7H7NO4/c9-4-5-1-2-7(10)6(3-5)8(11)12/h1-3,9-10H,4H2/p-1

Upstream product

• 6694-75-3 4-hydroxy-3-nitro-benzyl chloride 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 88-75-5 2-hydroxynitrobenzene 
• 616-82-0 3-nitro-4-hydroxybenzoic acid 
• 1188307-69-8 C₄₁H₅₀N₆O₁₇S 
• 1224886-42-3 C₃₅H₄₆N₂O₇ 
• 1353003-29-8 C₇₂H₆₉N₇O₂₉ 
• 1075719-57-1 6-{4-[(2-(4-acetylamino-benzoylamino)-phenylcarbamoyl)oxymethyl]-2-nitro-phenoxy}-tetrahydro-2H-pyran-2-carboxylic acid 
• 404387-11-7 (2S,3S,4S,5R,6S)-6-(4-{2-[(4,5-Dimethoxy-2-nitro-benzyloxycarbonyl)-methyl-amino]-benzylcarbamoyloxymethyl}-2-nitro-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid 
• 7647-01-0 hydrogenchloride 
• 50-00-0 formaldehyd 
• 7732-18-5 water 
• 3011-34-5 4-hydroxy-3-nitrobenzaldehyde 
• 290304-24-4 [6-(3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-carbamic acid 3-nitro-4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-benzyl ester 

Downstream Products

• 3011-34-5 4-hydroxy-3-nitrobenzaldehyde 
• 616-82-0 3-nitro-4-hydroxybenzoic acid 
• 52820-13-0 3-Amino-4-hydroxybenzyl alcohol 
• 177179-94-1 4-hydroxy-3-nitrobenzyl bromide 
• 6694-75-3 4-hydroxy-3-nitro-benzyl chloride 
• 41870-24-0 (4-methoxy-3-nitrophenyl)methanol 
• 534571-75-0 2-amino-(4-ethoxymethyl)phenol 
• 246218-55-3 (R)-1-[1,1-Dimethyl-2-(4-methoxyphenyl)ethylamino]-3-[(2-nitro-4-(hydroxymethyl))phenoxy]-propan-2-ol Hydrochloride Salt 
• 942215-76-1 [4-({[4-(methyloxy)phenyl]methyl}oxy)-3-nitrophenyl]methanol 
• 1429632-44-9 2-amino-4-[(tetrahydropyran-2-yloxy)methyl]phenol 
• 132627-73-7 Exfoliazone 
• 1429632-43-8 2-nitro-4-[(tetrahydropyran-2-yloxy)methyl]phenol 

Relevant academic research and scientific papers

Chemoselective bioconjugation of triazole phosphonites in aqueous media

Readily accessible and versatile phosphonite building blocks with improved stability against hydrolysis were used for the efficient metal-free functionalization of peptides and proteins in aqueous buffers at low micromolar concentrations. The application of this protocol to the immobilization of a Rasa1-SH2 domain revealed high binding affinity to the human T-cell protein ADAP and supports the applicability of triazole phosphonites for protein modifications without harming their function.

A molecular approach to rationally constructing specific fluorogenic substrates for the detection of acetylcholinesterase activity in live cells, mice brains and tissues

Acetylcholinesterase (AChE) is an extremely critical hydrolase tightly associated with neurological diseases. Currently, developing specific substrates for imaging AChE activity still remains a great challenge due to the interference from butyrylcholinesterase (BChE) and carboxylesterase (CE). Herein, we propose an approach to designing specific substrates for AChE detection by combining dimethylcarbamate choline with a self-immolative scaffold. The representative P10 can effectively eliminate the interference from CE and BChE. The high specificity of P10 has been proved via imaging AChE activity in cells. Moreover, P10 can also be used to successfully map AChE activity in different regions of a normal mouse brain, which may provide important data for AChE evaluation in clinical studies. Such a rational and effective approach can also provide a solid basis for designing probes with different properties to study AChE in biosystems and another way to design specific substrates for other enzymes. This journal is

Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation

The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.

Increased Potency and Selectivity for Group III Metabotropic Glutamate Receptor Agonists Binding at Dual sites

A group III metabotropic glutamate (mGlu) receptor agonist (PCEP) was identified by virtual HTS. This orthosteric ligand is composed by an l-AP4-derived fragment that mimics glutamate and a chain that binds into a neighboring pocket, offering possibilities to improve affinity and selectivity. Herein we describe a series of derivatives where the distal chain is replaced by an aromatic or heteroaromatic group. Potent agonists were identified, including some with a mGlu4 subtype preference, e.g., 17m (LSP1-2111) and 16g (LSP4-2022). Molecular modeling suggests that aromatic functional groups may bind at either one of the two chloride regulatory sites. These agonists may thus be considered as particular bitopic/dualsteric ligands. 17m was shown to reduce GABAergic synaptic transmission at striatopallidal synapses. We now demonstrate its inhibitory effect at glutamatergic parallel fiber-Purkinje cell synapses in the cerebellar cortex. Although these ligands have physicochemical properties that are markedly different from typical CNS drugs, they hold significant therapeutic potential.

CONJUGATES COMPRISING SELF-IMMOLATIVE GROUPS AND METHODS RELATED THERETO

In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self- immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

CONJUGATES COMPRISING PEPTIDE GROUPS AND METHODS RELATED THERETO

In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and at least two active agents. In preferred embodiments, the linker comprises a peptide sequence of a plurality of amino acids, and at least two of the active agents are covalently coupled to side chains of the amino acids. The antibody-drug conjugate may comprise a self-immolative group, preferably two-self-immolative groups. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

COMPOSITIONS AND METHODS RELATED TO ANTI-CD19 ANTIBODY DRUG CONJUGATES

In some aspects, the invention relates to an antibody-drug conjugate, comprising an anti-CD 19 antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self-immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

COMPOSITIONS AND METHODS RELATED TO ANTI-EGFR ANTIBODY DRUG CONJUGATES

In some aspects, the invention relates to an antibody-drug conjugate, comprising an anti-epidermal growth factor receptor ("EGFR") antibody; a linker; and an active agent. The antibody-drug conjugate may comprise a self-immolative group. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the drug; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

COMPOUNDS COMPRISING SELF-IMMOLATIVE GROUP

Provided are compounds comprising a self-immolative group, and the compounds comprising a self-immolative group according to the present invention may include a protein (for example, an oligopeptide, a polypeptide, an antibody, or the like) having substrate-specificity for a target and an active agent (for example, a drug, a toxin, a ligand, a detection probe, or the like) having a specific function or activity.

Synthesis and biological evaluations of a monomethylauristatin E glucuronide prodrug for selective cancer chemotherapy

We developed a glucuronide prodrug of the potent monomethylauristatin E (MMAE). This prodrug is signi ficantly less toxic than the parent drug. However, in the presence of b-glucuronidase the prodrug leads to the efficient release of MMAE thereby triggering a subnanomolar cytotoxic activity against several cancer cell lines. Preliminary in vivo experiments conducted in C57BL/6 mice bearing a subcutaneous murine Lewis Lung Carcinoma (LLC) demonstrated the potential of this targeting system for the selective treatment of solid tumors.