Anthranilic Acid Research Articles

Nickel Metal-Organic Framework-Based Surfaces for Effective Supercapacitor Application

Abstract Metal–organic frameworks (MOFs), characterized by strong bonds between organic ligands and metal ions, exhibit high porosity, large surface area, and exceptional chemical stability when carefully designed. In this study, a novel MOF comprising lead ions and ligands derived from 2-carboxybenzaldehyde and 4-aminobenzoic acid was synthesized using a sonochemical approach. This innovative method enabled the rapid formation of highly porous crystals with a BET surface area of 1181.45 m2 g1 and a total pore volume of 2.27 cm3 g−1 at P/P₀ = 0.3023. Comprehensive characterization techniques, including thermal analysis, SEM, EDX, PXRD, and FT-IR, confirmed the successful formation of the MOF structure. The synthesized MOF was utilized to fabricate an enhanced Ni-MOF electrode, demonstrating superior electrochemical performance for capacitor applications. The electrode achieved a specific capacitance of 402 F g−1 at 1 mA cm−2 and maintained excellent cycling stability, with 87.9% capacitance retention over 4000 cycles at 5 A g−1. These results underline the potential of the synthesized MOF in advancing energy storage technologies, particularly in developing high-performance and durable electrochemical capacitors.

Aminobenzoic Acid Covalently Modified Polyoxotungstates Based on {XW6} Clusters with Proton Conductivity Property.

Three cases of aminobenzoic acid hybrid polyoxotungstates, Na3(H3O)2[(HPW6O21) (O2CC6H4NH2)3]·7H2O (1), K2(H3O)4[(AsW6O21)(O2CC6H4NH2)3]·4H2O (2), and [(H2N(CH3)2]3Na2(H3O)[(SbW6O21) (O2CC6H4NH2)3]·7H2O (3), were successfully synthesized. This is the first report of the successful assembly of the hexanuclear {XW6} (X = HPIII, AsIII, or SbIII) clusters and organic carboxylic acid (para aminobenzoic acid) ligands. All three hybrids feature a common {XW6} unit composed of a six-membered {WO6} octahedral ring capped by one {XO3} trigonal pyramid. Furthermore, these hybrids possess an extensive three-dimensional network of hydrogen bonds, which not only provide high thermal stability but also contribute to excellent proton conductive performances. Simultaneously, based on the Hirshfeld partition analysis, combined with the interaction between POMs and water molecules, the proton transport mechanisms of three hybrids were highlighted.

Benzoxazinone Derivatives as Antiplatelet: Synthesis, Molecular Docking, and Bleeding Time Evaluation

Background The recurrence of atherosclerosis is still a global problem. Unfortunately, the drugs currently being used are reported to have resistance. Purpose To prevent the recurrence of atherosclerosis disease, this study developed benzoxazinone derivatives as an antiplatelet agent: 2-phenyl-3,1-benzoxazine-4-one (BZ1) and 2-(4′-chlorophenyl)-3,1-benzoxazin-4-one (BZ2). Methods The target compounds were synthesized through acyl nucleophilic substitution from acyl chloride and anthranilic acid using a base catalyst in triethylamine. This compound was then given to mice at three different doses to perform bleeding-time and clotting-time tests, using acetosal as a comparison. In silico, the binding energy between the test compound and the cyclooxygenase 1 enzyme was tested using Molegro Virtual Docker version 5.5 (MVD 5.5). The pharmacokinetic parameters were predicted using pharmacokinetics and chemistry through space mapping (pkCSM). Results The synthesis provided 83% yield. The biological assay at a dose of 20 mg/kg body weight (BW) BZ1 showed a higher bleeding time (361 s) than acetosal (324 s), whereas BZ2 was lower (179 s). The molecular analysis revealed that the compound had higher activity than aspirin. The absorption, distribution, metabolism, excretion, and toxicity (ADMET) showed that the compound posed high intestinal absorption. Conclusion This research concluded that both of the synthesized compounds have the potential and prospective to be developed as antiplatelet agents.

New Ti/CNT/CNT-Ce-PbO2 anode synergy peroxymonosulfate activation for efficiently electrocatalytic degradation of p-aminobenzoic acid.

Increased levels of p-aminobenzoic acid in aquatic environments, primarily utilized as UV filter in sunscreens, poses a serious threat to human and ecosystem health, while there is a dearth of exhaustive researches pertaining to the efficient and cost-effective elimination of p-aminobenzoic acid. Herein, a Ti/SnO2-Sb/CNT-α-PbO2/CNT-Ce-β-PbO2, referred to Ti/CNT/CNT-Ce-PbO2 electrode was constructed by incorporating CNTs into the middle layer of PbO2 electrode, and simultaneously doping CNTs and Ce in the active layer. A series of tests signify that the target electrode is successfully fabricated, which exhibits higher particle density and smaller particle size, as well as exceptional degradation performance for p-aminobenzoic acid with a degradation rate of 99.7% within 30min coupling with peroxymonosulfate activation. The optimal degradation performance was observed at a PMS dosage of 0.07g, Na2SO4 concentration of 0.05molL-1, current density of 120mAcm-2, and initial pH value of 6.94. Capture experiments, electron spin resonance test, liquid chromatography-mass spectrometry analysis, toxicity assessment and theoretical calculation were performed to clarify the main activate radicals, degradation pathways and intermediate toxicity. This study provides a new anode material, and conducted the first exploration of electrocatalysis integrating peroxymonosulfate activation for degradation p-aminobenzoic acid.

Syntheses, crystal structure, Hirshfeld Surface Analyzes of cocrystals and salt of a flexible imidazole tethered naphthalenediimide with some organic acids.

One salt and three cocrystals of 2,7-bis(3-(1H-imidazol-1-yl)propyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone (L) have been synthesized and reported. 3-Nitro benzoic acid (3NBA) forms salt with L and 4-Nitro benzoic acid (4NBA), 4-Hydroxy benzoic acid (4HBA) and 4-Amino benzoic acid (4ABA) forms cocrystals with L. L forms 1:1 salt with 3-NBA and 1:1 cocrystal with 4-NBA, 4-HBA and 4-ABA respectively. All the complexes were formed in a warm solvent condition. The solid-state structures were determined by single crystal X-ray diffraction method. Salt 1, exhibit zig zag tetrameric water cluster in the solid-state structure. Various types of supramolecular interactions such as OH…O, CH…O, π…π, and CH…π were observed in the x-ray structures and all these interactions guide the formation of 3D supramolecular architecture in the solid-state of all the complexes. Besides these, the 2D-fingerprint (2D-FP) and Hirshfeld surface analysis (HSA) computations were served to prove the 2D-network packed crystal lattice interactions.

Synthesis, Characterization, and In Vitro and In Silico Studies of Substituted‐Vanillin Hydrazones of Anthranilic Acid and Their Quinazolin‐4(3H)‐One Analogues as Anti Breast Cancer Agents

AbstractThis study synthesized a total of 18 new anthranilic acid hydrazones and quinazolin‐4(3H)‐one derivatives, evaluating their cytotoxicity against the MCF7 and HUVEC cell lines. The anticancer effects of these compounds and their interactions with estrogen receptor alpha (ERα) and HER2 through molecular docking and molecular dynamics simulations. Cytotoxicity assays revealed that most compounds exhibited higher selectivity for MCF7 cells compared to HUVEC cells, with compounds 12, 13, 14, 23, and 29 showing superior efficacy over the standard drug 5‐fluorouracil (5‐FU). Notably, compound 12 displayed the highest selectivity index (SI = 3.9) and an IC50 of 77.3 µM against MCF7 cells. Compounds 14 and 29 also demonstrated significant selectivity indices of 3.0 and 3.5, respectively, with IC50 values of 111.4 µM and 74.0 µM against MCF7 cells. Molecular docking studies identified compounds 14 and 29 as strong inhibitors of ERα and HER2, with stable interactions and favorable binding profiles in docking and MD analyses. Furthermore, ADME analysis indicated good drug like properties for most compounds, aligning with Lipinski's rule of five, supporting their potential as orally bioavailable drugs. This research highlights compounds 14, and 29 as promising candidates for targeted breast cancer therapy via inhibition of ERα and HER2

The role of kynurenine and kynurenine metabolites in psoriasis

Abstract Objectives Psoriasis is a widespread immunological disease characterised by inflammation and primarily associated with skin and joint symptoms. The kynurenine pathway significantly influences inflammation and immune system activity. The aim of this study is to determine serum concentrations of kynurenine metabolites in patients with psoriasis and investigate their correlation with disease severity. Methods This study included 30 participants with psoriasis and 30 individuals without the disease as healthy controls. Serum levels of tryptophan, kynurenine, 3-OH anthranilic acid, quinolinic acid, 3-OH kynurenine, and kynurenic acid were determined by liquid chromatography-mass spectrometry (LC-MS/MS). Results Serum levels of kynurenic acid (p<0.001), tryptophan (p<0.001) and the tryptophan/kynurenine ratio (TKR) (p<0.001) were statistically significantly lower in psoriasis patients than in healthy controls, while levels of quinolinic acid (p=0.007) and kynurenine (p=0.001) were significantly higher. The Psoriasis Area Severity Index (PASI) correlated positively with 3-hydroxykynurenine and kynurenic acid. Conclusions Kynurenine metabolites are associated with the pathophysiology of psoriasis and could serve as valuable candidate markers for monitoring inflammation.

Constructing Lewis Acid-Base Pairs to Boost Electrocatalytic Hydrogenation of p-Nitrobenzoic Acid to Valuable p-Aminobenzoic Acid Using Water as the Hydrogen Source.

Electrocatalytic hydrogenation of toxic nitrobenzene to value-added aniline is of great significance in addressing the issues of energy crisis and environmental pollution. However, it is a considerable challenging and crucial to develop highly efficient and earth-abundant transition metal-based electrocatalysts with superior durability for the electro-hydrogenation of nitrobenzene due to the competitive hydrogen evolution reaction (HER). In this work, a facile approach is designed and introduced to constructing an integrated self-supported heterostructured Co1- xNix(OH)(CO3)/Al(OH)3 nanoarrays (CoNiCH/Al(OH)3) for the electrocatalytic reduction of nitrobenzoic acid (PNBA) to p-aminobenzoic acid (PABA) and its electrocatalytic mechanism for PNBA reduction is investigated. This unique Lewis acid-base pairs with abundant oxygen vacancies (OVs) can effectively regulate the adsorption energy of PNBA and active hydrogen intermediates, facilitate the proton-coupled electrocatalytic reduction process, leading to the high activity and selectivity for PNBA to PABA. The optimal CoNiCH/Al(OH)3-0.5 exhibits outstanding performance for the electrocatalytic hydrogenation of PNBA to PABA with a yield of 92%, selectivity of 95% and Faraday efficiency (FE) of 92% at -0.545V (vs reversible hydrogen electrode, RHE) under 0.1m phosphate buffered solution (PBS) neutral electrolyte. Besides, it can maintain a high electrocatalytic activity for at least eight electrocatalytic cycle-test.

Synthesis and Degradation of the Phytohormone Indole-3-Acetic Acid by the Versatile Bacterium Paraburkholderia xenovorans LB400 and Its Growth Promotion of Nicotiana tabacum Plant.

Plant growth-promoting bacteria (PGPB) play a role in stimulating plant growth through mechanisms such as the synthesis of the phytohormone indole-3-acetic acid (IAA). The aims of this study were the characterization of IAA synthesis and degradation by the model aromatic-degrading bacterium Paraburkholderia xenovorans LB400, and its growth promotion of the Nicotiana tabacum plant. Strain LB400 was able to synthesize IAA (measured by HPLC) during growth in the presence of tryptophan and at least one additional carbon source; synthesis of anthranilic acid was also observed. RT-PCR analysis indicates that under these conditions, strain LB400 expressed the ipdC gene, which encodes indole-3-pyruvate decarboxylase, suggesting that IAA biosynthesis proceeds through the indole-3-pyruvate pathway. In addition, strain LB400 degraded IAA and grew on IAA as a sole carbon and energy source. Strain LB400 expressed the iacC and catA genes, which encode the α subunit of the aromatic-ring-hydroxylating dioxygenase in the IAA catabolic pathway and the catechol 1,2-dioxygenase, respectively, which may suggest a peripheral IAA pathway leading to the central catechol pathway. Notably, P. xenovorans LB400 promoted the growth of tobacco seedlings, increasing the number and the length of the roots. In conclusion, this study indicates that the versatile bacterium P. xenovorans LB400 is a PGPB.

Tear Fluid-Based Metabolomics Profiling in Chronic Dacryocystitis Patients.

Chronic dacryocystitis (CD) can result in severe complications and vision impairment due to ongoing microbial infections and persistent tearing. Tear fluid, which contains essential components vital for maintaining ocular surface health, has been investigated for its potential in the noninvasive identification of ocular biomarkers through metabolomics analysis. In this study, we employed UHPLC-MS/MS to analyze the tear metabolome of CD patients. UHPLC-MS/MS analysis of tear samples from CD patients revealed significant metabolic alterations. Compared with the control group, 298 metabolites were elevated, while 142 were decreased. KEGG pathway analysis suggested that these changes primarily affected arginine and proline metabolism, biosynthesis of amino acids, and phenylalanine biosynthesis in CD. Notably, 3-dehydroquinic acid, anthranilic acid, citric acid, and l-isoleucine emerged as potential biomarker candidates of CD with high diagnostic accuracy (AUC = 0.94). These findings suggest that tear fluid metabolism, particularly amino acid biosynthesis, plays a significant role in the pathogenesis of CD. Uncovering these metabolic products and pathways provides valuable insights into the mechanisms underlying CD and paves the way for the development of diagnostic tools and targeted therapies.

Anthranilic Acid-G-Protein Coupled Receptor109A-Cytosolic Phospholipase A2-Myelin-Cognition Cascade: A New Target for the Treatment/Prevention of Cognitive Impairment in Schizophrenia, Dementia, and Aging.

Cognitive impairment is a core feature of neurodevelopmental (schizophrenia) and aging-associated (mild cognitive impairment and Alzheimer's dementia) neurodegenerative diseases. Limited efficacy of current pharmacological treatments warrants further search for new targets for nootropic interventions. The breakdown of myelin, a phospholipids axonal sheath that protects the conduction of nerve impulse between neurons, was proposed as a neuropathological abnormality that precedes and promotes the deposition of amyloid-β in neuritic plaques. The present review of the recent literature and our own pre- and clinical data suggest (for the first time) that the anthranilic acid (AA)-induced activation of microglial-expressed G-protein coupled receptor (GPR109A) inhibits cytosolic phospholipase A2 (cPLA2), an enzyme that triggers the degradation of myelin and consequently attenuates cognitive impairment. The present review suggests that the up-regulation of AA formation is a sex-specific compensatory (adaptive) reaction aimed to prevent/treat cognitive impairment. The AA-GPR109A-cPLA2-myelin-cognition cascade suggests new nootropic interventions, e.g., the administration of pegylated kynureninase, an enzyme that catalyzes AA formation from Kynurenine (Kyn), a tryptophane catabolite; pegylated interferon-alpha; central and peripheral Kyn aminotransferase inhibitors that increase availability of Kyn as a substrate for AA formation; and vagus nerve stimulation. The cascade predicts nootropic activity of exogenous GPR109A agonists that were designed and underwent clinical trials (unsuccessful) as anti-dyslipidemia agents. The proposed cascade might contribute to the pathogenesis of cognitive impairment. Data on AA in neurodegenerative disorders are scarce, and the proposed cascade needs further exploration in pre- and clinical studies.

Lack of evidence for kynurenine pathway dysfunction in Huntington's disease: Cerebrospinal fluid and plasma analyses from the HDClarity study

Background Evidence from animal studies and post-mortem studies of brains from people with Huntington's disease (PwHD) has suggested that the kynurenine pathway (KP) may be dysregulated in Huntington's disease (HD). Objective To determine whether there are differences in KP metabolites in the cerebrospinal fluid (CSF) and plasma of PwHD vs. healthy controls enrolled in the HDClarity study. Methods CSF and plasma samples from 141 PwHD with mild and moderate manifest disease and 75 healthy controls were analyzed for 3-hydroxykynurenine (3-OH-KYN), quinolinic acid, kynurenine, anthranilic acid, kynurenic acid, and tryptophan concentrations using validated high-performance liquid chromatography with tandem mass spectrometry methods. The primary and secondary endpoints compared metabolite concentrations between groups, and an exploratory analysis (PwHD only) evaluated the association between the metabolite levels and severity of disease. Results No significant differences in CSF or plasma concentrations of any of the six KP metabolites were observed between PwHD and controls, and there were no strong associations between the concentration of any KP metabolite and disease severity. A principal component analysis of the combined CSF and plasma measures showed a substantial positive correlation among all metabolites except for tryptophan in plasma. Conclusions We found no evidence to support the hypothesis of dysregulation of KP metabolites in HD based on CSF and plasma metabolite levels. The monitoring of KP metabolites in CSF or plasma is unlikely to serve as a pharmacodynamic biomarker for disease progression or therapeutic intervention in HD.

Synthesis, Characterisation, Computational ADME studies, Pharmacological screening and In-vitro Hydrolysis studies of potential novel mutual prodrugs of N-(2,3-xylyl anthranillic acid)

In the present work we report Synthesis, Computational ADME study, Pharmacological evaluation and In-vitro hydrolysis study of new mutual prodrugs of N-(2,3-xylyl anthranillic acid) prepared with and without spacer using Dicyclohexylcarbodiimide (DCC) as coupling agent. The structures of mutual prodrugs formed were confirmed by advanced spectroscopic techniques. The title compounds were tested for analgesic activity by Eddy’s hot plate and tail-flick method; for anti-inflammatory activity by carrageenan induced rat paw edema method and for ulcerogenicity and acute oral toxicity. Title compounds exhibited promising analgesic and anti-inflammatory activity. The compounds were found to be devoid of ulcerogenicity at the test dose level and presented significant values of the ADME properties studied, obeying Lipinski Rule of five violations, good oral absorption and lipophilicity. Hydrolysis studies revealed that the compounds were sufficiently stable at pH 1.2, indicating that no appreciable hydrolysis to the free acids might occur in the stomach. The amount of free drug released on hydrolysis in 80% human plasma (pH 7.4) was greater than that released in aqueous buffers, suggesting that the rate of hydrolysis of compounds in 80% human plasma was markedly accelerated compared with that in aqueous buffers.

Synthesis and Pharmacological Evaluation of 3-alkyl/aryl–2- methylquinazolin-4-one Derivatives

Quinazolin-4-ones with 2, 3-disubstitution is reported to possess significant analgesic, anti-inflammatory and anticonvulsant activities. We have developed an efficient method for the synthesis of 3-substituted-2-methylquinazolin-4-one by the condensation reaction of Anthranilic acid, acetic anhydride with various amines. The synthesized compounds were evaluated for anxiolytic activity by Elevated plus Maze Test and Light and Dark Test. It is observed that the aliphatic and aromatic substitution at 3-position of 2-methylquinazolin-4-one gives potent anxiolytic activity. In particular, ENA showed highest anxiolytic activity in Elevated plus Maze Test and EMQ and AMQ showed highest anxiolytic activity in Light and dark test model

Exploring enhanced gas-phase toluene adsorption by engineered a novel magnetic nanoadsorbent modified with p-aminobenzoic acid: Insights on characterization, performance, kinetics, isotherm, mechanism and reusability

In this study, a novel magnetic nanoadsorbent (MNA), Fe3O4@SiO2 functionalized with p-aminobenzoic acid (p-AMBA), was prepared, characterized, and assessed for its efficiency in removing gas-phase toluene, a volatile organic compound (VOC). The Fe3O4, Fe3O4@SiO2, and Fe3O4@SiO2@p-AMBA MNAs were prepared and subjected to comprehensive analysis using techniques such as FTIR, SEM, EDX, VSM, XRD, TGA and BET to clearly reveal their properties through detailed characterization. Adsorption studies revealed that the Fe3O4@SiO2@p-AMBA exhibited the highest capacity, with an adsorption value of 555 mg/g for toluene, compared to 188 mg/g for Fe3O4 and 321 mg/g for Fe3O4@SiO2. The modification with p-AMBA significantly improved the adsorption performance of the material. Kinetic and isotherm models indicated that the adsorption process is best described by the pseudo-2nd-order kinetic model and by the Dubinin-Radushkevich isotherm model, suggesting both physical and chemical adsorption mechanisms. Furthermore, the reusability and adsorption stability performance of the MNAs was evaluated. The MNAs continued exhibiting excellent adsorption, with reuse efficiencies of 83 % (corresponding to 158 mg/g) for Fe3O4, 86 % (corresponding to 279 mg/g) for Fe3O4@SiO2, and 87 % (corresponding to 486 mg/g) for Fe3O4@SiO2@p-AMBA after five consecutive cycles, indicating superior structural and regeneration abilities. The results highlight the significant effect of surface modification on adsorption efficiency, positioning Fe3O4@SiO2@p-AMBA as a promising material for VOC removal and air pollution control. This work highlights the importance of developing sustainable materials to address environmental challenges.

Left Ventricular Remodeling Predictors in Chronic Heart Failure of Ischemic Etiology.

Aim To identify metabolomic and structure and function markers of remote left ventricular (LV) remodeling in patients with chronic heart failure (CHF) of ischemic etiology and LV ejection fraction (EF) <50%.Material and methods This prospective study included 56 patients with 3-4 NYHA functional class CHF of ischemic etiology (mean age, 66±7 years) and 50 patients with ischemic heart disease (IHD) without signs of CHF (69 [64; 73.7] years). Concentration of 19 amino acids, 11 products of kynurenine catabolism of tryptophan, 30 acylcarnitines with different chain lengths were measured in all participants. The metabolites that showed statistical differences between the comparison groups were then used for the analysis. Echocardiography was used to assess LV cavity remodeling at the time of the CHF patient inclusion in the study and after 6 months of follow-up. Predictors of long-term LV cavity remodeling were assessed for this cohort taking into account statistically significant echocardiographic parameters and metabolites.Results Patients with CHF of ischemic etiology, predominantly (81%) had pathological calculated types of LV remodeling (concentric and eccentric hypertrophy, 46 and 35%, respectively). However, this classification had limitations in describing this cohort. In addition, in this group, the concentrations of alanine, proline, asparagine, glycine, arginine, histidine, lysine, valine, indolyl-3-acetic acid, indolyl-3-propionic acid, C16-1-OH, and C16-OH were significantly (p<0.05) lower, and the concentrations of most medium- and long-chain acylcarnitines were higher than in patients with IHD without signs of CHF. The long-term (6 months) reverse remodeling of the LV cavity in CHF of ischemic etiology was influenced by changes in the interventricular septum thickness (hazard ratio, HR, 19.07; 95% confidence interval, CI, 1.76-206.8; p=0.006) and concentrations of anthranilic acid (HR 19.8; 95% CI 1.01-387.8; p=0.019) and asparagine (HR 8.76; 95% CI 1.07-71.4; p=0.031).Conclusion The presence of an interventricular septum thickness of more than 13.5 mm, anthranilic acid concentrations of higher than 0.235 μM/l, or an asparagine concentration of less than 135.2 μM/l in patients with CHF of ischemic etiology after 6 months of follow-up affects their achievement of LV cavity reverse remodeling.

Microviridae bacteriophages influence behavioural hallmarks of food addiction via tryptophan and tyrosine signalling pathways.

Food addiction contributes to the obesity pandemic, but the connection between how the gut microbiome is linked to food addiction remains largely unclear. Here we show that Microviridae bacteriophages, particularly Gokushovirus WZ-2015a, are associated with food addiction and obesity across multiple human cohorts. Further analyses reveal that food addiction and Gokushovirus are linked to serotonin and dopamine metabolism. Mice receiving faecal microbiota and viral transplantation from human donors with the highest Gokushovirus load exhibit increased food addiction along with changes in tryptophan, serotonin and dopamine metabolism in different regions of the brain, together with alterations in dopamine receptors. Mechanistically, targeted tryptophan analysis shows lower anthranilic acid (AA) concentrations associated with Gokushovirus. AA supplementation in mice decreases food addiction and alters pathways related to the cycle of neurotransmitter synthesis release. In Drosophila, AA regulates feeding behaviour and addiction-like ethanol preference. In summary, this study proposes that bacteriophages in the gut microbiome contribute to regulating food addiction by modulating tryptophan and tyrosine metabolism.

Symmetry Breaking of Electronic Structure upon the π→π* Excitation in Anthranilic Acid Homodimer.

The main purpose of this study is to characterize the nature of the low-energy singlet excited states of the anthranilic acid homodimer (AA2) and their changes (symmetry breaking) caused by deformation of the centrosymmetric, ground state structure of AA2 towards the geometry of the S1 state. We employ both the correlated ab initio methods (approximate Coupled Clusters Singles and Doubles-CC2 and CASSCF/NEVPT2) as well as the DFT/TDDFT calculations with two exchange-correlation functionals, i.e., B3LYP and CAM-B3LYP. The composition of the wavefunctions is investigated using the one-electron transition density matrix and difference density maps. We demonstrate that in the case of AA2, small asymmetric distortions of geometry bring about unproportionally large changes in the excited state wavefunctions. We further provide comprehensive characterization of the AA2 electronic structure, showing that the excitation is nearly completely localized on one of the monomers, which stands in agreement with the experimental evidence. The excitation increases the π-electronic coupling of the substituents and the aromatic ring, but only in the excited monomer, while the changes in the electronic structure of the unexcited monomer are negligible (after geometry relaxation). The increased electronic density strengthens both intra- and intermolecular hydrogen bonds formed by the carbonyl oxygen atom of the excited monomer, making them significantly stronger than in the ground state. Although the overall pattern of changes remains qualitatively consistent across all methods employed, CC2 predicts more pronounced excitation-induced modifications of the electronic structure compared to the more routinely used TDDFT approach. The most important deficiency of the B3LYP functional in the present context is locating two charge-transfer states at erroneously low energies, in close proximity of the S1 and S2 states. The range-corrected CAM-B3LYP exchange-correlation functional gives a considerably improved description of the CT states at the price of overshot excitation energies.

Bio-computational modeling, POM analysis and molecular dynamic simulation for novel synthetic quinolone and benzo[d][1,3]oxazine candidates as antimicrobial inhibitors

The current study offers a metal-free, direct, and successful synthesis technique for a new series of quinolinone and benzo[d][1,3]oxazine, along with an assessment of their biological activities. Heteroannulation of anthranilic acid with carbonyl-containing chemicals (aroyl pyruvate, ethyl acetoacetatete, maleic anhydride, and ethyl cyanoacetate) resulted in the desired quinolones and benzo[d][1,3]oxazines. This technique introduces a number of fundamental breakthroughs in organic synthesis, including metal-free catalysts, smart reaction conditions with column purification, and a wide functional scope. Furthermore, the structure of the newly synthesized chemical series was investigated and validated using spectroscopic techniques. The synthesized series were evaluated for antibacterial (against gram-positive and gram-negative bacterial strains) and antifungal activity. The quinolone and benzo[d][1,3]oxazine candidates had remarkable antibacterial action. Furthermore, molecular docking investigations corroborated the biological studies using the Molecular Operating Environment and Petro Osiris Molinspiration (POM) experiments, which confirmed the activity of compounds 8, 15, and 17. Our studies on the cytotoxic activity of various chemicals have demonstrated that these compounds exhibit minimal toxicity. Specifically, when comparing the cytotoxic effects on human lung fibroblast (WI38) cells to those of Doxorubicin, a well-known chemotherapy agent, compounds 8, 15, and 17 showed weak cytotoxic effects on the normal WI38 cells. This indicates that these compounds may possess some level of selectivity and reduced toxicity towards normal cells, suggesting potential for further exploration as antibacterial agents with a safer profile for normal cells.

Amino-Based Probe for Natural Products with Covalent Binding Ability to Lysine and Mechanism of Action of Medermycin.

A chemoselective amino-based probe was designed for discovering natural products with covalent binding potential to lysine. Using this reactivity-based technique, a marine-derived Streptomyces strain was identified, which could produce medermycin as the major metabolite. A new compound, mederpyrrole A, derived from medermycin and anthranilic acid through nonenzymatic reaction was isolated. Medermycin can react with primary amines under mild conditions to generate chimeric products possessing a naphthoquinone-pyrrole skeleton. It can also covalently bind to proteins.