Category: 492-27-3

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 492-27-3, is researched, SMILESS is O=C(C1=NC2=CC=CC=C2C(O)=C1)O, Molecular C10H7NO3Journal, Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov’t, Journal of Neuroscience called Prefrontal α7nAChR signaling differentially modulates afferent drive and trace fear conditioning behavior in adolescent and adult rats, Author is Fernandez, Anabel M. M. Miguelez; Molla, Hanna M.; Thomases, Daniel R.; Tseng, Kuei Y., the main research direction is methyllycaconitine ifenprodil alpha7nAChR neuroprotectant cognitive disorder schizophrenia adult; adolescence; amygdala; fear conditioning; prefrontal cortex; ventral hippocampus; α7nAChR.Electric Literature of C10H7NO3.

Increased level of kynurenic acid is thought to contribute to the development of cognitive deficits in schizophrenia through an α7nAChR-mediated mechanism in the prefrontal cortex (PFC). However, it remains unclear to what extent disruption of PFC α7nAChR signaling impacts afferent transmission and its modulation of behavior. Using male rats, we found that PFC infusion of methyllycaconitine (MLA; α7nAChR antagonist) shifts ventral hippocampal-induced local field potential (LFP) suppression to LFP facilitation, an effect only observed in adults. Hippocampal stimulation can also elicit a GluN2B-mediated LFP potentiation (when PFC GABAAR is blocked) that is insensitive to MLA. Conversely, PFC infusion of MLA diminished the gain of amygdalar transmission, which is already enabled by postnatal day (P)30. Behaviorally, the impact of prefrontal MLA on trace fear-conditioning and extinction was also age related. While freezing behavior during conditioning was reduced by MLA only in adults, it elicited opposite effects in adolescent and adult rats during extinction as revealed by the level of reduced and increased freezing response, resp. We next asked whether the late-adolescent onset of α7nAChR modulation of hippocampal inputs contributes to the age-dependent effect of MLA during extinction. Data revealed that the increased freezing behavior elicited by MLA in adult rats could be driven by a dysregulation of the GluN2B transmission in the PFC. Collectively, these results indicate that distinct neural circuits are recruited during the extinction of trace fear memory in adolescents and adults, likely because of the late-adolescent maturation of the ventral hippocampal-PFC functional connectivity and its modulation by α7nAChR signaling.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Formula: C10H7NO3. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about Influence of pH on radical reactions between kynurenic acid and amino acids tryptophan and tyrosine. Part I. Amino acids in free state.

In the human eye lens the endogenous chromophores of UV-A light (315-400 nm) are able to sensitize radical reactions leading to protein modifications during normal aging and the cataract progression. Kynurenic acid (KNA-) is the most photochem. active dye of the human eye lens reported to date with pKa(KNAH•2) 5.5 for its radical form. Cataract is thought to develop under oxidative stress which could be accompanied by acidosis, an acidification of the intracellular environment. Protonation of kynurenyl radicals at mildly acidic conditions may change the outcome of radical reactions leading to addnl. damage to proteins. In this work we investigated the influence of pH on the degradation of initial reagents and the formation of products in photoinduced radical reactions between KNA- and amino acids tryptophan (Trp) and tyrosine (Tyr) in free states. Our results have shown that pH variation has minor influence on kinetics of reagent decay and accumulation of products in reactions between tyrosyl and kynurenic acid radicals. However in the case of Trp a two-fold decrease of the reagent degradation without visible changes in the composition of formed products was observed with pH decrease from 7 to 3. Time-resolved measurements have shown similar acidification-induced two-fold acceleration of decay of kynurenyl and tryptophanyl radicals via Back Electron Transfer (BET) with the restoration of initial reagents. Experiments with tryptophan derivatives with different pKa values for their radical forms point out the protonation of tryptophanyl radical as the driving force for BET acceleration at low pH. Our results demonstrate that the protonation of kynurenyl radical does not change its reactivity towards amino acids radicals but the total yield of radical photodamage decreases with the protonation of tryptophanyl radicals. It could be expected that radical induced damage to proteins will depend on the pKa of tryptophanyl radicals within a protein globule.

In addition to the literature in the link below, there is a lot of literature about this compound(4-Hydroxyquinoline-2-carboxylic Acid)Formula: C10H7NO3, illustrating the importance and wide applicability of this compound(492-27-3).

Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Formula: C10H7NO3. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about Clinical relevance of depressed kynurenine pathway in episodic migraine patients: potential prognostic markers in the peripheral plasma during the interictal period. Author is Tuka, Bernadett; Nyari, Aliz; Cseh, Edina Katalin; Kortesi, Tamas; Vereb, Daniel; Tomosi, Ferenc; Kecskemeti, Gabor; Janaky, Tamas; Tajti, Janos; Vecsei, Laszlo.

Altered glutamatergic neurotransmission and neuropeptide levels play a central role in migraine pathomechanism. Previously, we confirmed that kynurenic acid, an endogenous glutamatergic antagonist, was able to decrease the expression of pituitary adenylate cyclase-activating polypeptide 1-38, a neuropeptide with known migraine-inducing properties. Hence, our aim was to reveal the role of the peripheral kynurenine pathway in episodic migraineurs. We focused on the complete tryptophan catabolism, which comprises the serotonin and melatonin routes in addition to kynurenine metabolites. We investigated the relationship between metabolic alterations and clin. characteristics of migraine patients. Female migraine patients aged between 25 and 50 years (n = 50) and healthy control subjects (n = 34) participated in this study. Blood samples were collected from the cubital veins of subjects (during both the interictalictal periods in migraineurs, n = 47/12, resp.). 12 metabolites of Trp pathway were determined by neurochem. measurements (UHPLC-MS/MS). Plasma concentrations of the most Trp metabolites were remarkably decreased in the interictal period of migraineurs compared to healthy control subjects, especially in the migraine without aura subgroup Trp (p 〈 0.025), L-kynurenine (p /0.001), kynurenic acid (p / 0.016), anthranilic acid (p / 0.007), picolinic acid (p / 0.03), 5-hydroxy-indoleaceticacid (p / 0.025) and melatonin (p / 0.023). Several metabolites showed a tendency to elevate during the ictal phase, but this was significant only in the cases of anthranilic acid, 5-hydroxy-indoleaceticacid and melatonin in MWoA patients. In the same subgroup, higher interictal kynurenic acid levels were identified in patients whose headache was severe and not related to their menstruation cycle. Neg. linear correlation was detected between the interictal levels of xanthurenic acid/melatonin and attack frequency. Pos. associations were found between the ictal 3-hydroxykynurenine levels and the beginning of attacks, just as between ictal picolinic acid levels and last attack before ictal sampling. Our results suggest that there is a widespread metabolic imbalance in migraineurs, which manifests in a completely depressed peripheral Trp catabolism during the interictal period. It might act as trigger for the migraine attack, contributing to glutamate excess induced neurotoxicity and generalised hyperexcitability. This data can draw attention to the clin. relevance of KP in migraine.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 492-27-3, is researched, Molecular C10H7NO3, about Phase 1 study to access safety, tolerability, pharmacokinetics, and pharmacodynamics of kynurenine in healthy volunteers, the main research direction is human nervous system kynurenine safety tolerability pharmacokinetics pharmacodynamics; epilepsy; glutamat; kynurenic acid; migraine; stroke.COA of Formula: C10H7NO3.

The kynurenine pathway (KP) is the main path for tryptophan metabolism, and it represents a multitude of potential sites for drug discovery in neuroscience, including pain, stroke, and epilepsy. L-kynurenine (LKYN), the first active metabolite in the pathway, emerges to be a prodrug targeting glutamate receptors. The safety, tolerability, pharmacokinetics, and pharmacodynamics of LKYN in humans have not been previously investigated. In an open-label, single ascending dose study, six participants received an i.v. infusion of 50, 100, and 150μg/kg LKYN and new six participants received an i.v. infusion of 0.3, 0.5, 1, and 5 mg/kg LKYN. To compare the pharmacol. effects between species, we investigated in vivo the vascular effects of LKYN in rats. In humans, LKYN was safe and well-tolerated at all dose levels examined After infusion, LKYN plasma concentration increased significantly over time 3.23 ± 1.12μg/mL (after 50μg/kg), 4.04 ± 1.1μg/mL (after 100μg/kg), and 5.25 ± 1.01μg/mL (after 150μg/kg) (p < 0.001). We observed no vascular changes after infusion compared with baseline. In rats, LKYN had no effect on HR and MAP and caused no dilation of dural and pial arteries. This first-in-human study of LKYN showed that LKYN was safe and well-tolerated after i.v. infusion up to 5 mg/kg over 20 min. The lack of change in LKYN metabolites in plasma suggests a relatively slow metabolism of LKYN and no or little feed-back effect of LKYN on its synthesis. The therapeutic potential of LKYN in stroke and epilepsy should be explored in future studies in humans. There are many compounds similar to this compound(492-27-3)COA of Formula: C10H7NO3. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, General Review, Article, Review, Trends in Molecular Medicine called The kynurenine pathway in chronic diseases: a compensatory mechanism or a driving force, Author is Joisten, Niklas; Ruas, Jorge L.; Braidy, Nady; Guillemin, Gilles J.; Zimmer, Philipp, which mentions a compound: 492-27-3, SMILESS is O=C(C1=NC2=CC=CC=C2C(O)=C1)O, Molecular C10H7NO3, Quality Control of 4-Hydroxyquinoline-2-carboxylic Acid.

A review. A Review. The kynurenine (KYN) pathway (KP) of tryptophan (TRP) metabolism is dysregulated in inflammation-driven pathologies including oncol. and brain diseases [e.g., multiple sclerosis (MS), depression] and thus is a promising therapeutic target. Both pathol. and compensatory mechanisms underlie disease-associated KP activation. There is growing evidence for bioenergetic roles of certain KP metabolites such as kynurenic acid (KA), or quinolinic acid (QA) as an NAD+ precursor, which may explain its frequently observed ′pathol.′ overactivation. Disease- and tissue-specific aspects, neg. feedback on inflammatory signals, and the balance of downstream metabolites are likely to be decisive factors in the interpretation of an imbalanced KP. Therapeutic strategies should consider the compensatory actions and bioenergetic roles of KP metabolites to successfully design future theragnostic approaches aimed at attenuating disease progression.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

HPLC of Formula: 492-27-3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about A new insight into the potential role of tryptophan-derived AhR ligands in skin physiological and pathological processes. Author is Szelest, Monika; Walczak, Katarzyna; Plech, Tomasz.

A review. The aryl hydrocarbon receptor (AhR) plays a crucial role in environmental responses and xenobiotic metabolism, as it controls the transcription profiles of several genes in a ligandspecific and cell-type-specific manner. Various barrier tissues, including skin, display the expression of AhR. Recent studies revealed multiple roles of AhR in skin physiol. and disease, including melanogenesis, inflammation and cancer. Tryptophan metabolites are distinguished among the groups of natural and synthetic AhR ligands, and these include kynurenine, kynurenic acid and 6-formylindolo[3,2-b]carbazole (FICZ). Tryptophan derivatives can affect and regulate a variety of signaling pathways. Thus, the interest in how these substances influence physiol. and pathol. processes in the skin is expanding rapidly. The widespread presence of these substances and potential continuous exposure of the skin to their biol. effects indicate the important role of AhR and its ligands in the prevention, pathogenesis and progression of skin diseases. In this review, we summarize the current knowledge of AhR in skin physiol. Moreover, we discuss the role of AhR in skin pathol. processes, including inflammatory skin diseases, pigmentation disorders and cancer. Finally, the impact of FICZ, kynurenic acid, and kynurenine on physiol. and pathol. processes in the skin is considered. However, the mechanisms of how AhR regulates skin function require further investigation.

There are many compounds similar to this compound(492-27-3)HPLC of Formula: 492-27-3. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Related Products of 492-27-3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about Kynurenic acid and its chromophoric core 4-hydroxyquinoline react with tryptophan via proton-coupled electron transfer, and with tyrosine via H-transfer. Author is Morozova, Olga B.; Yurkovskaya, Alexandra V.; Sherin, Peter S..

Kynurenic acid (KNA) and 4-hydroxyquinoline (4HQN) are photochem. active products of tryptophan catabolism that readily react with tryptophan (Trp) and tyrosine (Tyr) after optical excitation. Recently, transient absorption experiments have shown that at neutral pH Trp reacts with triplet KNA via proton-coupled electron transfer (PCET), and not via electron transfer (ET) as it was suggested before. PCET includes the stepwise transition of both electrons and protons from Trp to triplet KNA. In this work, we confirmed that PCET is the reaction mechanism by the alternative method of time-resolved chem. induced dynamic nuclear polarization (TR-CIDNP). Further studies by TR-CIDNP revealed hydrogen transfer as the mechanism of the reaction between triplet KNA and Tyr in neutral solutions and a transition of both PCET and H-transfer mechanisms to ET under acidic conditions. 4HQN, being the chromophoric core of KNA, exhibits different spectral and photophys. properties from KNA but employs the same mechanisms for the reactions of its triplet state with Trp and Tyr at neutral and acidic pH.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Related Products of 492-27-3. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about Tryptophan levels associate with incident cardiovascular disease in chronic kidney disease.

Background. Non-traditional risk factors like inflammation and oxidative stress play an essential role in the increased cardiovascular disease (CVD) risk prevalent in chronic kidney disease (CKD). Tryptophan catabolism by the kynurenine pathway (KP) is linked to systemic inflammation and CVD in the general and dialysis population. However, the relationship of KP to incident CVD in the CKD population is unknown. Methods. We measured tryptophan metabolites using targeted mass spectrometry in 92 patients with a history of CVD (old CVD); 46 patients with no history of CVD and new CVD during follow-up (no CVD); and 46 patients with no CVD history who developed CVD in the median follow-up period of 2 years (incident CVD). Results. The three groups are well-matched in age, gender, race, diabetes status and CKD stage, and only differed in total cholesterol and proteinuria. Tryptophan and kynurenine levels significantly decreased in patients with ′Incident CVD′ compared with the no CVD or old CVD groups (P=5.2E-7; P=0.003 resp.). Kynurenic acid, 3-hydroxykynurenine and kynurenine are all increased with worsening CKD stage (P<0.05). An increase in tryptophan levels at baseline was associated with 0.32-fold lower odds of incident CVD (P=0.000014) compared with the no CVD group even after adjustment for classic CVD risk factors. Addition of tryptophan and kynurenine levels to the receiver operating curve constructed from discriminant anal. predicting incident CVD using baseline clin. variables increased the area under the curve from 0.76 to 0.82 (P=0.04). Conclusions. In summary, our study demonstrates that low tryptophan levels are associated with incident CVD in CKD. There are many compounds similar to this compound(492-27-3)Related Products of 492-27-3. if you want to know more, you can check out my other articles. I hope it will help you，maybe you’ll find some useful information.

Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Quality Control of 4-Hydroxyquinoline-2-carboxylic Acid. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about Effect of dural inflammatory soup application on activation and sensitization markers in the caudal trigeminal nucleus of the rat and the modulatory effects of sumatriptan and kynurenic acid. Author is Spekker, Eleonora; Laborc, Klaudia Flora; Bohar, Zsuzsanna; Nagy-Grocz, Gabor; Fejes-Szabo, Annamaria; Szucs, Monika; Vecsei, Laszlo; Pardutz, Arpad.

The topical inflammatory soup can model the inflammation of the dura mater causing hypersensitivity and activation of the trigeminal system, a phenomenon present in migraineurs. We investigated the effect of inflammatory soup induced dural inflammation on the calcitonin gene-related peptide, transient receptor potential vanilloid-1 receptor, and neuronal nitric oxide synthase levels in the caudal trigeminal nucleus. We also tested whether pretreatment with a well-known antimigraine drug, such as sumatriptan and kynurenic acid, a compound with a different mechanism of action, can affect these changes and if their modulatory effects are comparable. After s.c. sumatriptan or i.p. kynurenic acid the dura mater of adult male Sprague-Dawley rats (n = 72) was treated with inflammatory soup or its vehicle (synthetic interstitial fluid). Two and a half or four hours later perfusion was performed and the caudal trigeminal nucleus was removed for immunohistochem. Inflammatory soup increased calcitonin gene-related peptide, transient receptor potential vanilloid-1 receptor, and neuronal nitric oxide synthase in the caudal trigeminal nucleus compared to placebo, which was attenuated by sumatriptan and kynurenic acid. This suggests the involvement of 5-HT1B/1D and NMDA receptors in neurogenic inflammation development of the dura and thus in migraine attacks.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

Synthetic Route of C10H7NO3. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about A randomized cross-over trial to define neurophysiological correlates of AV-101 N-methyl-D-aspartate receptor blockade in healthy veterans. Author is Murphy, Nicholas; Ramakrishnan, Nithya; Vo-Le, Bylinda; Vo-Le, Brittany; Smith, Mark A.; Iqbal, Tabish; Swann, Alan C.; Mathew, Sanjay J.; Lijffijt, Marijn.

The kynurenine pathway (KP) is a strategic metabolic system that combines regulation of neuronal excitability via glutamate receptor function and neuroinflammation via other KP metabolites. This pathway has great promise in treatment of depression and suicidality. The KP modulator AV-101 (4-chlorokynurenine, 4-Cl-KYN), an oral prodrug of 7-chlorokynurenic acid (7-Cl-KYNA), an N-methyl-D-aspartate receptor (NMDAR) glycine site antagonist, and of 4-chloro-3-hydroxyanthranilic acid (4-Cl-3-HAA), a suppressor of NMDAR agonist quinolinic acid (QUIN), is a promising potential antidepressant that targets glutamate functioning via the KP. However, a recent placebo-controlled clin. trial of AV-101 in depression found neg. results. This raises the question of whether AV-101 can penetrate the brain and engage the NMDAR and KP effectively. To address this problem, ten healthy US military veterans (mean age = 32.6 years ± 6.11; 1 female) completed a phase-1 randomized, double-blind, placebo-controlled, crossover study to examine dose-related effects of AV-101 (720 and 1440 mg) on NMDAR engagement measured by γ-frequency band auditory steady-state response (40 Hz ASSR) and resting EEG. Linear mixed models revealed that 1440 mg AV-101, but not 720 mg, increased 40 Hz ASSR and 40 Hz ASSR γ-inter-trial phase coherence relative to placebo. AV-101 also increased 4-Cl-KYN, 7-Cl-KYNA, 4-Cl-3-HAA, 3-HAA, and KYNA in a dose-dependent manner, without affecting KYN and QUIN. AV-101 was safe and well tolerated. These results corroborate brain target engagement of 1440 mg AV-101 in humans, consistent with blockade of interneuronal NMDAR blockade. Future studies should test higher doses of AV-101 in depression. Suicidal behavior, which has been associated with high QUIN and low KYNA, is also a potential target for AV-101.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”