40662-29-1

Upstream product

• 40662-76-8 6-hydroxy-4,4,5,7,8-pentamethyl-3,4-dihydrocoumarin 
• 541-47-9 3-Methylbutenoic acid 
• 924-50-5 Methyl 3,3-dimethylacrylate 
• 700-13-0 Trimethylhydroquinone 
• 527-18-4 Durohydroquinone 
• 84945-01-7 3,4-dihydro-6-hydroxy-4,4,7,8-tetramethyl-1(2H)-benzopyran-2-one 
• 265645-66-7 (S)-3-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-[3-methyl-3-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-butyrylamino]-propionic acid methyl ester 

Downstream Products

• 265645-66-7 (S)-3-{4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-[3-methyl-3-(2,4,5-trimethyl-3,6-dioxo-cyclohexa-1,4-dienyl)-butyrylamino]-propionic acid methyl ester 
• 40662-30-4 methyl β,β,2,4,5-pentamethyl-3,6-dioxo-1,4-cyclohexadiene-1-propanoate 
• 121030-87-3 N,N-diethyl-β,β,2,4,5-pentamethyl-3,6-dioxo-1,4-cyclohexadiene-1-propanamide 
• 1426551-41-8 N-(2-cyanobenzo[d]thiazol-6-yl)-3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide 
• 1426551-42-9 N-(4-(hydroxymethyl)phenyl)-3-methyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide 
• 1426551-48-5 N-(3-hydroxypropyl)-N,3-dimethyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide 
• 1426551-51-0 quinone-trimethyllock-C₃-diamine-Boc 
• 1426551-64-5 quinone trimethyllock Boc-N,N,2,2-tetramethylpropane-1,3-diamine 
• 1609626-97-2 C₃₉H₄₁N₃O₇ 
• 1609626-96-1 C₂₈H₄₁NO₄Si 
• 1426551-45-2 N-(4-(hydroxymethyl)phenyl)-N,3-dimethyl-3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanamide 

Relevant academic research and scientific papers

Mechanistic Studies of the Photoinduced Quinone Trimethyl Lock Decaging Process

Mechanistic studies of a general reaction that decages a wide range of substrates on exposure to visible light are described. The reaction involves a photochemically initiated reduction of a quinone mediated by an appended thioether. After reduction, a trimethyl lock system incorporated into the quinone leads to thermal decaging. The reaction could be viewed as an electron-transfer initiated reduction of the quinone or as a hydrogen abstraction-Norrish Type II-reaction. Product analysis, kinetic isotope effects, stereochemical labeling, radical clock, and transient absorption studies support the electron transfer mechanism. The differing reactivities of the singlet and triplet states are determined, and the ways in which this process deviates from typical quinone photochemistry are discussed. The mechanism suggests strategies for extending the reaction to longer wavelengths that would be of interest for applications in chemical biology and in a therapeutic setting.

Detection of DT-diaphorase Enzyme with a ParaCEST MRI Contrast Agent

A responsive magnetic resonance (MRI) contrast agent has been developed that can detect the enzyme activity of DT-diaphorase. The agent produced different chemical exchange saturation transfer (CEST) MRI signals before and after incubation with the enzyme

Natural product-inspired profluorophores for imaging NQO1 activity in tumour tissues

Herein we designed a collection of trimethyl-lock quinone profluorophores as activity-based probes for imaging NAD(P)H:quinone oxidoreductase (NQO1) in cancer cells and tumour tissues. Profluorophores were prepared via synthetic routes from naturally-occu

Spatio-Temporally Reporting Dose-Dependent Chemotherapy via Uniting Dual-Modal MRI/NIR Imaging

Unpredictable in vivo therapeutic feedback of hydroxyl radical (.OH) efficiency is the major bottleneck of chemodynamic therapy. Herein, we describe novel Fenton-based nanotheranostics NQ-Cy?Fe&GOD for spatio-temporally reporting intratumor su

Synthesis of bioreductive esters from fungal compounds

Four new bioreductive esters (7-10) have been synthesized. Their structures composed of trimethyl lock containing quinone propionic acid with an ester linkage to the fungal cytotoxic compounds; preussomerin G (1), preussomerin I (2), phaseolinone (3) and phomenone (4). The synthesized esters are aimed to act via reductive activation specifically at the cancer cells, resulting from hypoxia and overexpression of reductases. Hence, the toxicity will be lessened during distribution across the normal cells. The anticancer activity was determined in cancer cell lines with reported reductase i.e., BC-1 cells and NCI-H187 as well as in non-reductase containing cancer cells; KB cells. When considering each cell lines, result showed that structure modification giving to 7-10 led to less cytotoxicity than their parent compounds (1-4). Both 7 and 8 were strongly cytotoxic (IC50≤5 μg/ml) to NCI-H187, whereas 9 and 10 were moderately cytotoxic (IC50=6-10 μg/ml) to BC-1 cells. Additional study of stability of represented phenolic ester (8) and an alcoholic ester (9) were performed. Result illustrated that both 8 and 9 were stable in the presence of esterase. Therefore, the cytotoxicity of the synthesized compounds (8-10) might be due to partial bioreductive activation in the cancer cells.

NQO1-Selective Activated Prodrug of Triptolide: Synthesis and Antihepatocellular Carcinoma Activity Evaluation

Hepatocellular carcinoma (HCC) is the leading cause of death in patients with cirrhosis. Due to its poor response to conventional chemotherapy drugs, the prognosis for its survival is the worst. NAD(P)H:quinone oxidoreductase 1 (NQO1) is an attractive ant

Pyroptosis drug prodrug, preparation method thereof and pyroptosis drug

The invention discloses a pyroptosis drug prodrug, a preparation method thereof and a pyroptosis drug. The pyroptosis drug prodrug provided by the invention can cause mitochondria damage, release cytochrome c and activate Caspase3 to shear GSDME by targeting mitochondria, so that pyroptosis of cells occurs. The prodrug (NCyNH2) has selectivity to tumor cells, damage to normal cells is reduced, and the activation condition of the prodrug (NCyNH2) can be detected through recovery of self-fluorescence. After intratumor administration, the prodrug can effectively regulate the tumor immune microenvironment and activate T cell mediated anti-tumor immune response. The molecule has huge application prospects in the aspects of mitochondrial targeting, cell respiration inhibition, pyroptosis induction, tumor immune microenvironment improvement, T cell mediated anti-tumor immune response activation and the like.

Rational designed highly sensitive NQO1-activated near-infrared fluorescent probe combined with NQO1 substrates in vivo: An innovative strategy for NQO1-overexpressing cancer theranostics

Since NQO1 is overexpressed in many cancer cells, it can be used as a biomarker for cancer diagnosis and targeted therapy. NQO1 substrates show potent anticancer activity through the redox cycle mediated by NQO1, while the NQO1 probes can monitor NQO1 levels in cancers. High sensitivity of probes is needed for diagnostic imaging in clinic. In this study, based on the analysis of NQO1 catalytic pocket, the naphthoquinone trigger group 13 rationally designed by expanding the aromatic plane of the benzoquinone trigger group 10 shows significantly increased sensitivity to NQO1. The sensitivity of the naphthoquinone trigger group-based probe A was eight times higher than that of benzoquinone trigger group-based probe B in vivo. Probe A was selectively and efficiently sensitive to NQO1 with good safety profile and plasma stability, enabling its combination with NQO1 substrates in vivo for NQO1-overexpressing cancer theranostics for the first time.

HNQO1-ACTIVATABLE FLUORESCENT PROBE FOR IMAGING CANCER CELLS IN-VITRO AND IN-VIVO

The present invention includes a probe, an assay, a method of detecting, a human NAD(P)H quinone oxidoreductase-1 (hNQO1) enzyme activity with a fluorescent probe comprising a quinone propionic acid (QPA) conjugated to dicyanoisophorone (DCP), wherein the

NQO1-activated 6 -diazyl -5 - oxo - L -n-leucine prodrug and preparation method and application thereof

The invention discloses NQO1-activated 6 -diazyl -5 - oxo - L - n-leucine prodrug and a preparation method and application thereof. Due to the high expression NQO1 in most tumor cells, the introduced NQO1 activated quinic acid group can achieve the tumor