Category: 492-27-3

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about Kynurenic acid protects against mastitis in mice by ameliorating inflammatory responses and enhancing blood-milk barrier integrity, the main research direction is kynurenic acid mastitis inflammation blood milk barrier; Blood-milk barrier; Kynurenic acid (KYNA); Mastitis; NF-κB; Nrf2.Reference of 4-Hydroxyquinoline-2-carboxylic Acid.

Mastitis is one of the most serious diseases in humans and animals, especially in the modern dairy industry. Seeking safe and effective mastitis prevention strategies is urgent since food safety and drug residues in milk remain an enormous concern, despite the contribution of antibiotics to control mastitis. Kynurenic acid (KYNA), derived from the kynurenine pathway of tryptophan metabolism, has been shown to exhibit anti-inflammatory and immunomodulatory effects in many diseases. Recently, it was reported that impaired KYNA levels were associated with mastitis. However, the physiol. role of KYNA in mastitis has not yet been elucidated. Therefore, the aim of this study was to investigate the protective role of KYNA in pathogen-induced mastitis in mice, as well as the underlying mechanism of this effect. We first evaluated the effects of KYNA on LPS-induced mastitis in mice. Addnl., the underlying anti-inflammatory mechanism of KYNA was investigated in mammary epithelial cells (MMECs). Furthermore, we examined the effects of KYNA on S. aureus and E. coli induced mastitis in mice. Our results demonstrated that KYNA alleviated LPS-induced mastitis by reducing inflammatory responses and enhancing blood-milk barrier integrity. The fundamental mechanisms involved the inhibition of NF-κB and activation of Nrf2/Ho-1, which is probably mediated by G protein-coupled receptor 35 but not aryl hydrocarbon receptor. Notably, KYNA also protected against S. aureus and E. coli induced mastitis in mice. In conclusion, our results highlight the role of KYNA in mastitis and serve as a basis for using endogenous metabolite as a novel preventative or therapeutic strategy for disease intervention.

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

Electric Literature of C10H7NO3. 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 Adenosine and kynurenic acid interactions: possible relevance for schizophrenia treatment?. Author is Beggiato, Sarah; Zuccarini, Mariachiara; Cassano, Tommaso; Borroto-Escuela, Dasiel Oscar; Di Iorio, Patrizia; Schwarcz, Robert; Fuxe, Kjell; Ferraro, Luca.

A review. In this article the considerations outlined indicate a possible relevance of adenosine and KYNA interactions in the pathophysiol. and treatment of schizophrenia. The present opinion paper was conceived to critically review possible interactions between adenosine and kynurenic acid (KYNA) in this context.

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

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 4-Hydroxyquinoline-2-carboxylic Acid( cas:492-27-3 ) is researched.Application of 492-27-3.Li, Hui; Cui, Lanchong; Zhang, Guolei; Zhang, Mengmeng; Jiao, Lili; Wu, Wei published the article 《[Quantitative analysis of tryptophan and its metabolites in urine by ultra performance liquid chromatography-tandem mass spectrometry].》 about this compound( cas:492-27-3 ) in Se pu = Chinese journal of chromatography. Keywords: pre-column derivation; tryptophan-kynurenine pathway; ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS); urine. Let’s learn more about this compound (cas:492-27-3).

Tryptophan (Trp), also known as α-amino β-indolepropionic acid, is an essential amino acid, which is involved in various physiological processes. Studies have shown that tumors, infectious diseases, and neurological diseases are accompanied by Trp-related metabolic disorders. Understanding the excretion of Trp and its metabolites in normal individuals is of great significance for treating Trp-related diseases and monitoring the health. A rapid quantitative method was developed based on ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS). Further, this method was applied to the simultaneous determination of Trp and its metabolites, including kynurenine (Kyn), kynurenic acid (KA), 3-hydroxykynurenine (3-OH-Kyn), 3-hydroxyanthranilic acid (3-OH-AA), xanthurenic acid (XA), 5-hydroxytryptamine (5-HT), and 5-hydroxyindoleacetic acid (5-HIAA). The excretion and amount of target compounds in random urine samples collected from healthy participants were studied using this method. Urine samples were collected from healthy male volunteers (between 20-22 years old) without any diet and exercise restrictions. Urine samples were collected between 11∶00-13∶00 daily for 10 d. Thereafter, the urine samples were diluted, centrifuged, and subjected to pre-column derivatization with dansyl chloride (DNS-Cl). Caffeic acid (CA) was used as the internal control. Later, the derivatives were detected using triple quadrupole mass spectrometry with electron pray ionization (ESI) in positive and multi reaction monitoring (MRM) modes. The samples were separated using a Thermo C18 column (50 mm×3 mm, 2.7 μm) with 0.1% aqueous formic acid aqueous solution and methanol as mobile phases at a flow rate of 0.2 mL/min. The three most abundant ions for each derivative were selected for downstream analysis, and the internal control was used for quantification. The polarity and molecular weight of the compounds were found to be altered effectively after DNS-Cl derivatization treatment. The dansyl group effectively altered the polarities of the derivatives, such that their retention behaviors in the reverse elution system were similar and they were well separated. The interference due to impurities was effectively eliminated using the MRM mode. The results showed significant linear correlation, since the correlation coefficients were greater than 0.9740. The recoveries were between 93.24%-107.65%, and the LODs were 0.005-0.5 ng/mL for the eight compounds. Trp prototype and the seven target metabolites, including 3-OH-Kyn, 3-OH-AA, XA, Kyn, KA, 5-HIAA, and 5-HT generated through Trp-5-HT and Trp-Kyn pathways were detected in the urine samples. These results indicated that Trp was excreted in a prototypic form or after being metabolized. The level of the target compounds in random urine samples of individuals were 0.99-3.72 (3-OH-Kyn), 2.51-21.11 (3-OH-AA), 0.25-1.12 (XA), 0.15-1.53 (Kyn), 0.24-2.58 (KA), 0-0.31 (5-HT), and 2.2-17.94 (5-HIAA) μg/mL. For the same individual, in the state of physical health, the fluctuations of Trp and its metabolites in urine were large. Due to these large fluctuations in the absolute content, the difference between individuals was not significant. The data generated using 70 urine samples revealed that the amount of excreted Trp being metabolized was 124%-268% of prototype, which further indicated that the excretion after metabolism was the major underlying mechanism. Upon comparing the levels of metabolites in the Trp-5-HT and Trp-Kyn pathways, the results indicated that the levels of 3-OH-AA and 3-OH-Kyn generated upon Trp degradation through the Kyn pathway was higher than those of the other products. Trp was degraded via Kyn pathway to produce 3-OH-AA, which was the main metabolite of Trp found to be present in the body. This manuscript detected the levels of Trp and its metabolites, as well as summarized the characteristics of excretion using random urine samples, which could provide valuable information for clinical practice.

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

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 4-Hydroxyquinoline-2-carboxylic Acid, is researched, Molecular C10H7NO3, CAS is 492-27-3, about Maternal protein restriction affects cardiovascular, but not respiratory response to L-glutamate microinjection into the NTS of conscious rats, the main research direction is glutamate microinjection protein cardiovascular respiratory maternal rat; L-glutamate microinjection; Maternal protein malnutrition; acid kinurenic microinjection; cardiac variability; glutamatergic system; hypertension; nucleus of the solitary tract; respiratory variability.Synthetic Route of C10H7NO3.

Dysregulation of glutamatergic neurotransmission (GN) is linked to sympathetic-respiratory overactivity and hypertension. We investigated whether maternal protein restriction is able to alter GN into the nucleus of the solitary tract (NTS) in adult offspring. Wistar rat dams were fed with control (NP; 17% protein) or low-protein (LP; 8% protein) diet during pregnancy and lactation, and their offspring were evaluated at 70-90d old. Direct measurements of mean arterial pressure (MAP), heart rate (HR), respiratory frequency (RF) and respiratory (RV) and cardiac (CV) variabilities were assessed in consciousness. The evaluation of GN into NTS over cardiovascular system were assessed by microinjections of unilateral glutamate (L-glu 0.5 nmol/100nL) and bilateral kynurenic acid (Kyn 2.5 nmol/50nL). The NP and LP groups were compared using unpaired Student′s t-test where p < 0.05 was considered significant. The LP exhibited higher MAP at rest (p = 0.03) and after L-glu microinjection (p = 0.04), as well as an increase over HR after Kyn microinjection when compared to the NP (p = 0.049). In the RV, the LP group showed an increase of the component-standard deviation 1 (p = 0.037) at rest. In the CV, the LP presented an increase of the low frequency (LF) component of the pulse interval (PI) (p = 0.034), a decrease of high frequency (HF) of the PI (p = 0.034), beyond an increased LF/HF ratio of the PI (p = 0.027) when compared to the NP. The kynurenic acid microinjection did not produce changes in RV or CV (p > 0.05). Altered GN into the NTS may contribute to augmented blood pressure in protein-restricted offspring.

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

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, Metabolites called Effects of Tryptophan Supplementation and Exercise on the Fate of Kynurenine Metabolites in Mice and Humans, Author is Valente-Silva, Paula; Cervenka, Igor; Ferreira, Duarte M. S.; Correia, Jorge C.; Edman, Sebastian; Horwath, Oscar; Heng, Benjamin; Chow, Sharron; Jacobs, Kelly R.; Guillemin, Gilles J.; Blomstrand, Eva; Ruas, Jorge L., the main research direction is tryptophan supplementation kynurenine metabolite exercise; behavior; dietary supplements; energy metabolism; exercise; kynurenine metabolites; skeletal muscle; tryptophan.Electric Literature of C10H7NO3.

The kynurenine pathway of tryptophan (TRP) degradation (KP) generates metabolites with effects on metabolism, immunity, and mental health. Endurance exercise training can change KP metabolites by changing the levels of KP enzymes in skeletal muscle. This leads to a metabolite pattern that favors energy expenditure and an anti-inflammatory immune cell profile and reduces neurotoxic metabolites. Here, we aimed to understand if TRP supplementation in untrained vs. trained subjects affects KP metabolite levels and biol. effects. Our data show that chronic TRP supplementation in mice increases all KP metabolites in circulation, and that exercise reduces the neurotoxic branch of the pathway. However, in addition to increasing wheel running, we did not observe other effects of TRP supplementation on training adaptations, energy metabolism or behavior in mice. A similar increase in KP metabolites was seen in trained vs. untrained human volunteers that took a TRP drink while performing a bout of aerobic exercise. With this acute TRP administration, TRP and KYN were higher in the trained vs. the untrained group. Considering the many biol. effects of the KP, which can lead to beneficial or deleterious effects to health, our data encourage future studies of the crosstalk between TRP supplementation and phys. exercise.

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

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called KYNA/Ahr Signaling Suppresses Neural Stem Cell Plasticity and Neurogenesis in Adult Zebrafish Model of Alzheimer’s Disease, published in 2021, which mentions a compound: 492-27-3, Name is 4-Hydroxyquinoline-2-carboxylic Acid, Molecular C10H7NO3, COA of Formula: C10H7NO3.

Neurogenesis decreases in Alzheimer’s disease (AD) patients, suggesting that restoring the normal neurogenic response could be a disease modifying intervention. To study the mechanisms of pathol.-induced neuro-regeneration in vertebrate brains, zebrafish is an excellent model due to its extensive neural regeneration capacity. Here, we report that Kynurenic acid (KYNA), a metabolite of the amino acid tryptophan, neg. regulates neural stem cell (NSC) plasticity in adult zebrafish brain through its receptor, aryl hydrocarbon receptor 2 (Ahr2). The production of KYNA is suppressed after amyloid-toxicity through reduction of the levels of Kynurenine amino transferase 2 (KAT2), the key enzyme producing KYNA. NSC proliferation is enhanced by an antagonist for Ahr2 and is reduced with Ahr2 agonists or KYNA. A subset of Ahr2-expressing zebrafish NSCs do not express other regulatory receptors such as il4r or ngfra, indicating that ahr2-pos. NSCs constitute a new subset of neural progenitors that are responsive to amyloid-toxicity. By performing transcriptome-wide association studies (TWAS) in three late onset Alzheimer disease (LOAD) brain autopsy cohorts, we also found that several genes that are components of KYNA metabolism or AHR signaling are differentially expressed in LOAD, suggesting a strong link between KYNA/Ahr2 signaling axis to neurogenesis in LOAD.

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

Computed Properties of 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 Kynurenic acid in neurodegenerative disorders-unique neuroprotection or double-edged sword?. Author is Ostapiuk, Aleksandra; Urbanska, Ewa M..

A review. The family of kynurenine pathway (KP) metabolites includes compounds produced along two arms of the path and acting in clearly opposite ways. The equilibrium between neurotoxic kynurenines, such as 3-hydroxykynurenine (3-HK) or quinolinic acid (QUIN), and neuroprotective kynurenic acid (KYNA) profoundly impacts the function and survival of neurons. This comprehensive review summarizes accumulated evidence on the role of KYNA in Alzheimer′s, Parkinson′s and Huntington′s diseases, and discusses future directions of potential pharmacol. manipulations aimed to modulate brain KYNA. The synthesis of specific KP metabolites is tightly regulated and may considerably vary under physiol. and pathol. conditions. Exptl. data consistently imply that shift of the KP to neurotoxic branch producing 3-HK and QUIN formation, with a relative or absolute deficiency of KYNA, is an important factor contributing to neurodegeneration. Targeting specific brain regions to maintain adequate KYNA levels seems vital; however, it requires the development of precise pharmacol. tools, allowing to avoid the potential cognitive adverse effects. Boosting KYNA levels, through interference with the KP enzymes or through application of prodrugs/analogs with high bioavailability and potency, is a promising clin. approach. The use of KYNA, alone or in combination with other compounds precisely influencing specific populations of neurons, is awaiting to become a significant therapy for neurodegenerative disorders.

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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 Vitamin C and E Treatment Blocks Changes in Kynurenine Metabolism Triggered by Three Weeks of Sprint Interval Training in Recreationally Active Elderly Humans. Author is Wyckelsma, Victoria L.; Trepci, Ada; Schwieler, Lilly; Venckunas, Tomas; Brazaitis, Marius; Kamandulis, Sigitas; Paulauskas, Henrikas; Gapeyeva, Helena; Paeaesuke, Mati; Gastaldello, Stefano; Imbeault, Sophie; Westerblad, Haakan; Erhardt, Sophie; Andersson, Daniel C..

The kynurenine pathway (KP) is gaining attention in several clin. fields. Recent studies show that phys. exercise offers a therapeutic way to improve ratios of neurotoxic to neuroprotective KP metabolites. Antioxidant supplementation can blunt beneficial responses to phys. exercise. We here studied the effects of endurance training in the form of sprint interval training (SIT; three sessions of 4-6 x 30 s cycling sprints per wk for three weeks) in elderly (~65 years) men exposed to either placebo (n = 9) or the antioxidants vitamin C (1 g/day) and E (235 mg/day) (n = 11). Blood samples and muscle biopsies were taken under resting conditions in association with the first (untrained state) and last (trained state) SIT sessions. In the placebo group, the blood plasma level of the neurotoxic quinolinic acid was lower (~30%) and the neuroprotective kynurenic acid to quinolinic acid ratio was higher (~50%) in the trained than in the untrained state. Moreover, muscle biopsies showed a training-induced increase in kynurenine aminotransferase (KAT) III in the placebo group. All these training effects were absent in the vitamin-treated group. In conclusion, KP metabolism was shifted towards neuroprotection after three weeks of SIT in elderly men and this shift was blocked by antioxidant treatment.

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

Application In Synthesis of 4-Hydroxyquinoline-2-carboxylic Acid. 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 The Mechanism of the Neuroprotective Effect of Kynurenic Acid in the Experimental Model of Neonatal Hypoxia-Ischemia: The Link to Oxidative Stress.

The over-activation of NMDA receptors and oxidative stress are important components of neonatal hypoxia-ischemia (HI). Kynurenic acid (KYNA) acts as an NMDA receptor antagonist and is known as a reactive oxygen species (ROS) scavenger, which makes it a potential therapeutic compound This study aimed to establish the neuroprotective and antioxidant potential of KYNA in an exptl. model of HI. HI on seven-day-old rats was used as an exptl. model. The animals were injected i.p. with different doses of KYNA 1 h or 6 h after HI. The neuroprotective effect of KYNA was determined by the measurement of brain damage and elements of oxidative stress (ROS and glutathione (GSH) level, SOD, GPx, and catalase activity). KYNA applied 1 h after HI significantly reduced weight loss of the ischemic hemisphere, and prevented neuronal loss in the hippocampus and cortex. KYNA significantly reduced HI-increased ROS, GSH level, and antioxidant enzyme activity. Only the highest used concentration of KYNA showed neuroprotection when applied 6 h after HI. The presented results indicate induction of neuroprotection at the ROS formation stage. However, based on the presented data, it is not possible to pinpoint whether NMDA receptor inhibition or the scavenging abilities are the dominant KYNA-mediated neuroprotective mechanisms.

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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 The role of the kynurenine pathway and quinolinic acid in adolescent major depressive disorder, the main research direction is kynurenine signaling quinolinic acid major depressive disorder adolescent.Formula: C10H7NO3.

The biol. mechanisms underlying major depressive disorder (MDD) are not yet sufficiently understood. The kynurenine pathway has been proposed to play a key role between peripheral inflammation and alterations in the central nervous system. This is because of reduced usability of tryptophan (TRP) and production of oxygen radicals and highly potent neurotoxic agents in this pathway. In this study, we aimed to compare the metabolites of the serum kynurenine pathway (tryptophan, kynurenine, quinolinic acid and kynurenic acid) and IFN-γ, IL-6, IL-1β and high-sensitivity C-reactive protein (hsCRP) levels in patients with major depressive disorder and in healthy controls and to evaluate the relationship between cytokine levels and the functioning of the kynurenine pathway. Clin. and biochem. data from the patients were obtained and assessed in a cross-sectional design. Serum samples were analyzed for IL-6, IL-1β, interferon (IFN)-γ, tryptophan (TRP), quinolinic acid (QUIN), kynurenic acid (KYNA) and kynurenine (Kyn) levels by the ELISA. hsCRP test was analyzed by the immunoturbidimetric method. In total, 48 adolescent patients with major depressive disorder (no drug use) and 31 healthy controls were included in the study. TRP levels were observed to be significantly lower in patients with MDD than in healthy controls (P = .046); the Kyn/TRP ratio was significantly higher in patients with MDD than in healthy controls (P = .032); the levels of QUIN were significantly higher in patients with MDD than in healthy controls (P = .003). No significant difference was found between the groups in terms of other kynurenine metabolites and cytokines levels. These results suggest that the Kyn and related mol. pathways may play a role in the pathophysiol. of MDD. The most important finding was the increased level of QUIN, which has a neurotoxic effect, in the kynurenine pathway.

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