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Synthesis and chemiluminescent properties of amino-acylated luminol derivatives bearing phosphonium cations

The monitoring of reactive oxygen species in living cells provides valuable information on cell function and performance. Lately, the development of chemiluminescence-based reactive oxygen species monitoring has gained increased attention due to the advantages posed by chemiluminescence, including its rapid measurement and high sensitivity. In this respect, specific organelle-targeting trackers with strong chemiluminescence performance are of high importance. We herein report the synthesis and chemiluminescence properties of eight novel phosphonium-functionalized amino-acylated luminol and isoluminol derivatives, designed as mitochondriotropic chemiluminescence reactive oxygen species trackers. Three different phosphonium cationic moieties were employed (phenyl, p-tolyl, and cyclohexyl), as well as two alkanoyl chains (hexanoyl and undecanoyl) as bridges/linkers. Synthesis is accomplished via the acylation of the corresponding phthalimides, as phthalhydrazide precursors, followed by hydrazinolysis. This method was chosen because the direct acylation of (iso)luminol was discouraging. The new derivatives? chemiluminescence was evaluated and compared with that of the parent molecules. A relatively poor chemiluminescence performance was observed for all derivatives, with the isoluminol-based ones being the poorest. This result is mainly attributed to the low yield of the fluorescence species formation during the chemiluminescence oxidation reaction.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N617 – PubChem

Archives for Chemistry Experiments of 72702-95-5

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Statil suppresses cancer cell growth and proliferation by the inhibition of tumor marker AKR1B10

Aldo-keto reductase 1B10 (AKR1B10) is an oncogenic carbonyl reductase that eliminates alpha,beta-unsaturated carbonyl compounds/lipid peroxides and mediates retinoic acid signaling. Targeted inhibition of AKR1B10 activity is a newly emerging strategy for cancer therapy. This study evaluated the inhibitory activity of a small chemical statil towards AKR1B10 and tested its antiproliferative activity in breast (BT-20) and lung (NCI-H460) cancer cells that express AKR1B10. Experimental results showed that statil inhibited AKR1B10 enzyme activity efficiently, with an IC50 at 0.21¡À0.06 mumol/l. Exposing BT-20 and NCI-H460 cells to statil and diclofenac, a selective AKR1B10 inhibitor, led to dose-dependent inhibition of cell growth and proliferation and plating efficiency. At higher doses (50 mumol/l or higher), statil induced cell death with apoptotic characteristics, such as DNA fragmentation and Annexin-V staining. Furthermore, statil enhanced the susceptibility of cells to acrolein, an active substrate of AKR1B10. Taken together, these data suggest that statil possesses potent antiproliferative activity by inhibiting AKR1B10 activity.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N852 – PubChem

Archives for Chemistry Experiments of Phthalazine

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Recent advances with 5-HT3 modulators for neuropsychiatric and gastrointestinal disorders

Serotonin (5-hydroxytryptophan [5-HT]) is a biologically active amine expressed in platelets, in gastrointestinal (GI) cells and, to a lesser extent, in the central nervous system (CNS). This biogenic compound acts through the activation of seven 5-HT receptors (5-HT1-7Rs). The 5-HT3R is a ligand-gated ion channel belonging to the Cys-loop receptor family. There is a wide variety of 5-HT3R modulators, but only receptor antagonists (known as setrons) have been used clinically for chemotherapy-induced nausea and vomiting and irritable bowel syndrome treatment. However, since the discovery of the setrons in the mid-1980s, a large number of studies have been published exploring new potential applications due their potency in the CNS and mild side effects. The results of these studies have revealed new potential applications, including the treatment of neuropsychiatric disorders such as schizophrenia, depression, anxiety, and drug abuse. In this review, we provide information related to therapeutic potential of 5-HT3R antagonists on GI and neuropsychiatric disorders. The major attention is paid to the structure, function, and pharmacology of novel 5-HT3R modulators developed over the past 10 years.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N217 – PubChem

More research is needed about Phthalazine

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Synthesis and structure of new 2-[N-(Aryl)carbamoil-methyl]phtalazinium iodides

New 2-[N-(aryl)carbamoylmethyl]phthalazinium iodides 10a-n were obtained in good yields by reaction between N-aryl-2-iodoacetamides 8a-n and phthalazine (9). The structure of the quaternary salts 10a-n was assigned by elemental analysis and NMR experiments (HH-COSY, HETCOR, NOE).

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Phthalazine – Wikipedia,
Phthalazine | C8H6N134 – PubChem

A new application about 6-Amino-2,3-dihydrophthalazine-1,4-dione

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S100B and NSE serum levels in patients with Parkinson’s disease

We evaluated S100B protein and neuron-specific enolase (NSE) serum levels in Parkinson’s disease (PD) patients and their correlation with the severity of disease. The levels of S100B (P=0.16) and NSE (P=0.39) between PD and controls were similar. However, S100B levels correlated positively with the Hoehn and Yahr scale (r=0.368; P=0.02) and negatively with the Activities of Daily Living (ADL) scale (r=-0.431; P=0.006). Therefore, S100B and NSE may not have a diagnostic role in PD, but S100B may have a potential role as a marker of disease progression. The study of S100B may also contribute to elucidate the controversial role of glial cells in PD.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N631 – PubChem

Simple exploration of 4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Application In Synthesis of 4-(4-Fluoro-3-(piperazine-1-carbonyl)benzyl)phthalazin-1(2H)-one, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 763111-47-3, in my other articles.

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Red Si-rhodamine drug conjugates enable imaging in GFP cells

Here we evaluated a series of Si-derivatized rhodamine (SiR) dyes for their ability to visualize a model drug in live cells. We show that a charge neutral SiR derivative (but not others) can indeed be used to follow the intracellular location of the model therapeutic drug in GFP cells. This journal is the Partner Organisations 2014.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N822 – PubChem

Discovery of Phthalazine

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The electrochemical reduction of diazanaphthalenes; a spectro-electrochemical investigation

The electrochemical reduction of diazanaphthalenes in dimethylformamide at first- and second-wave diffusion levels has been investigated by means of transmission spectro-electrochemical methods.It has been found that the reaction of dianions with parent meutral molecules is an essential step in the reaction mechanism.Rate constants for all non-electrochemical steps have been measured or estimated.Independent estimations of diffusion and absorbance coefficients are presented, as well as some principles of digital simulation.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N483 – PubChem

Awesome Chemistry Experiments For 253-52-1

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The literature of heterocyclic chemistry, part XVII, 2017

A systematized survey of reviews and monographs published in 2017 on all aspects of heterocyclic chemistry is given.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N70 – PubChem

A new application about 253-52-1

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Synthesis of new pyrrolo[2,1-a]phthalazine derivatives via multicomponent reaction of phthalazine with 1,1-dicyanoalkenes and alkyl isocyanides

[Figure not available: see fulltext.] Multicomponent reactions between phthalazine, alkyl isocyanides, and 1,1-dicyanoalkenes in acetonitrile?water mixture produced high yields of substituted pyrrolo[2,1-a]phthalazines, which were converted upon treatment with 10% hydrochloric acid to pyrrolo[2,1-a]-phthalazines unsubstituted at position 1. As a result, a range of new pyrrolo[2,1-a]phthalazine derivatives have been synthesized by this one-pot approach.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N288 – PubChem

A new application about 253-52-1

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Aldehyde Oxidase: Reaction Mechanism and Prediction of Site of Metabolism

Aldehyde oxidase (AO) is a molybdenum-containing enzyme involved in the clearance of drug compounds containing aldehydes and N-containing heterocyclic fragments. AO has gained considerable interest in recent years because of examples of too fast clearance of drug compounds in development. Thus, it is important to be able to predict AO-mediated drug metabolism. Therefore, we have characterized the structural and energetic aspects of different mechanisms with density functional theory using the molybdenum cofactor as a model for the reactive part of the enzyme. For a series of 6-substituted 4-quinazolinones, the trend in activation energies is the same for three tested reaction mechanisms. Using the concerted mechanism as a model for the enzymatic reaction, the transition states (TSs) for the formation of all possible metabolites for a series of known AO substrates were determined. The lowest activation energies correspond in all cases to the experimentally observed sites of metabolism (SOMs). Various molecular properties were calculated and investigated as more easily determinable markers for reactivity. The stabilities of both intermediates and products correlate to some extent with the TS energies and may be used to predict the SOM. The electrostatic-potential-derived charges are also good markers for the prediction of the experimental SOM for this set of compounds and may pave the way for the development of fast methods for the prediction of SOM for AO substrates.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N294 – PubChem