Search Results (14)

Chronic Obstructive Pulmonary Disease (COPD) is a complex inflammatory lung condition characterized by oxidative stress, changes in airway structure, and gradually worsening airflow blockage. Existing treatments offer only symptomatic management, emphasizing the need for multi-target therapeutic interventions. This study employed a combined approach of network pharmacology and molecular docking to investigate the therapeutic effects of bioactive compounds derived from Cladophora glomerata on COPD. Disease-associated genes were collected from GeneCards, Online Mendelian Inheritance in Man (OMIM), and National Center for Biotechnology Information (NCBI), while compounds from C. glomerata and their predicted molecular targets were obtained from SwissTargetPrediction. A cross-comparison of targets related to compounds and diseases revealed nine common genes, among which three central genes TP53, CASP8, and EGFR were identified using protein–protein interaction (PPI) network analysis. Analysis of gene–disease interactions highlighted Tumor Protein p53 (TP53) and Epidermal Growth Factor Receptor (EGFR) as major regulatory targets. GeneMANIA-based functional and co-expression analysis revealed predominant physical interactions (77.64%) and co-expression relationships (8.01%), highlighting strong functional connectivity among the identified genes. Molecular docking further confirmed that C. glomerata derived compounds, particularly Quinoline, 1,2,3,4-tetrahydro-1-((2-phenylcyclopropyl)sulfonyl)-, trans- (Pubchem ID: 91709903) (−7.5 kcal/mol) and1,2,4-Oxadiazole, 3-(1,3-benzodioxol-5-yl)-5-[(4-iodo-1H-pyrazol-1-yl)methyl]- (Pubchem ID: 5301194) (−7.3 kcal/mol), exhibit favorable predicted binding affinities toward EGFR and TP53 in molecular docking analysis. Overall, these insights suggest that Cladophora glomerata compounds may modulate key COPD-related pathways through multi-target interactions, providing a scientific basis for future experimental studies and the development of marine-derived therapeutic agents for COPD management. Full article

Background/Objectives: Iodine plays a key role in thyroid hormone synthesis and metabolic regulation in vertebrates. This study aimed to evaluate the in vivo bioavailability of iodine and assess selected biochemical parameters and thyroid-related gene expression in male Wistar rats fed lettuce (Lactuca sativa L.) biofortified with iodoquinolines (8-hydroxy-7-iodo-5-quinolinesulfonic acid or 5,7-diiodo-8-quinolinol) or potassium iodate. Methods: Two iodine intake levels were applied, a nutritionally adequate iodine level and a supranutritional level, to evaluate the nutritional safety of iodine obtained from biofortified vegetables. Results: A diet containing lettuce biofortified with iodoquinolines at the adequate level had no significant effect on thyroid hormone concentrations, the expression of Dio1, Dio2, Slc5a5, and Tpo genes, or thyroid morphology. While supranutritional iodine intake led to increased levels of T4, fT4, T3, and fT3, all hormone concentrations remained within the physiological range. No elevation in liver enzyme activity (ALT, AST, ALP) was observed, indicating the absence of hepatotoxic effects from high-iodine diets based on biofortified lettuce. Compared to potassium iodate, iodoquinolines demonstrated superior bioavailability, as evidenced by enhanced iodine accumulation in tissues and more efficient thyroid hormone synthesis. Conclusions: To the best of our knowledge, this is the first in vivo nutritional study assessing the physiological effects of supranutritional iodine intake from a biofortified plant source. These findings confirm the nutritional safety and efficacy of iodine biofortification using iodoquinolines and highlight the need for further research, including human nutritional clinical trials. Full article

Dual specificity tyrosine-phosphorylation regulated kinase 1A (DYRK1A), a phosphorylation kinase, is localized within the central nervous system and is linked to hyperphosphorylation of Tau. Imaging of DYRK1A may provide an earlier biomarker for Tauopathies, including Alzheimer’s disease (AD). We have used Chimera-Autodock to evaluate potential molecules for binding to the binding site of DYRK1A. Five molecules, 10-bromo-2-iodo-11H-indolo[3,2-c]quinoline-6-carboxylic acid (4E3), 10-iodo-11H-indolo[3,2-c]quinoline-6-carboxylic acid (KuFal184), harmine, 6-(fluoro-3-(1H-pyrrolo[2,3-c]pyridin-1-yl)isoquinolin-5-amine (MK-6240), and 6-iodo-3-(1H-pyrrolo[2,3-c]pyridine-1-yl)isoquinoline (IPPI), were found to have binding energies of −10.4, −10.1, −9.0, −9.1, and −9.4 kcal/mole, respectively. Two molecules, 4E3 and KuFal184, were selective for DYRK1A, while harmine also had a monoamine oxidase A affinity, and MK-6240 and IPPI had affinity for Tau. Tau present in the brain slices of AD subject were labeled with [¹²⁵I]IPPI. KuFal184 had no effect on the binding of [¹²⁵I]IPPI, suggesting the absence of binding overlap of the two molecules. MK-6240, a known Tau agent was, however, able to compete with [¹²⁵I]IPPI. The binding energies of harmine, MK-6240, and IPPI for the DYRK1A site suggest affinities of approximately 80–100 nM, which is insufficient to serve as an imaging agent. The higher affinity of KuFal184 (6 nM for DYRK1A) suggested that [¹²⁵I]KuFal184 may be a potential imaging agent. Electrophilic radioiodination was used to synthesize [¹²⁵I]KuFal184 in modest yields (25%) and high radiochemical purity (>95%). Preliminary binding studies with [¹²⁵I]KuFal184 in AD brain slices showed some selectivity for cortical grey matter regions containing Tau. Full article

Background: Iodine is one of the essential trace elements for human life. The main objective of the biofortification of plants with iodine is to obtain food with a higher content of this element compared to conventional food. Biofortification of plants with iodine can increase the intake of this trace element by different populations. In addition, it may reduce the risk of iodine deficiency diseases. Objectives: The aim of the study was to investigate the effect of kale biofortified with 8-hydroxy-7-iodo-5-quinolinesulfonic acid (8-OH-7-I-5QSA) on iodine bioavailability and biochemical effects in Wistar rats. Methods: Kale biofortified with (8-OH-7-I-5QSA) was tested for iodine levels in urine, feces, and selected tissues using the ICP-MS/MS technique. The feeding experiment was designed to investigate potential changes in selected thyroid-regulated biochemical parameters in blood serum of Wistar rats. Results: The dietary intake of Wistar rats fed kale biofortified with (8-OH-7-I-5QSA) from both the “Oldenbor F₁” and “Redbor F₁” cultivars for 8 weeks resulted in significantly (p ≤ 0.05) higher iodine concentrations in the urine and kidneys of rats, which proves iodine bioavailability. Rats’ diets with “Oldenbor F₁” and “Redbor F₁” kale non- and -biofortified with 8-OH-7-I-5QSA had a significantly (p ≤ 0.05) lower or a tendency for lower concentration of TSH, triglyceride, total and direct bilirubin, TBARs, uric acid, aspartate aminotransferase (AST) and alanine aminotransferase (ALT) concentrations in serum. Dietary intake of “Oldenbor F₁” and “Redbor F₁” kale biofortified with 8-OH-7-I-5QSA significantly (p ≤ 0.05) increased the total antioxidant status (TAS). Conclusions: Our study confirms that kale biofortified with iodine in organic form iodoquinoline 8-OH-7-I-5QSA is bioavailable and well absorbed by the Wistar rat and has a positive effect on selected biochemical parameters. The results obtained in this study may be highly predictive for further studies in humans. Full article

The quinoline ring is found in many biologically active natural alkaloids and is still being highly exploited by researchers due to its numerous potential applications in fields ranging from pharmacology to material science. During our synthetic attempts for new quinoline-4-carboxylic acids, using an extended version of the Doebner reaction, a new puzzling compound emerged when para-iodine aniline was reacted with salicylaldehyde and pyruvic acid in acetic acid as a reaction medium. The chemical structure of this new compound was established based on the information obtained from 1D and 2D NMR experiments (¹H-, ¹³C-, and ¹⁵N-NMR), corroborated with MS spectrometry and IR spectroscopy. The photophysical properties (UV–vis and fluorescence) were also investigated. The proposed structure contains as the main elements a 1,4-dioxane-2,5-dione core symmetrically substituted with a propylidene chain that has attached to it a salicylaldehyde fragment and a pyrrole-2-one ring containing two 4-iodophenyl fragments. The isolation of this compound, reported here for the first time, is direct evidence that unexpected compounds can emerge from “classical” synthetic pathways when the right components are combined. Full article

6-Iodo-substituted carboxy-quinolines were obtained using a one-pot, three-component method with trifluoroacetic acid as a catalyst under acidic conditions. Iodo-aniline, pyruvic acid and 22 phenyl-substituted aldehydes (we varied the type and number of radicals) or O-heterocycles, resulting in different electronic effects, were the starting components. This approach offers advantages such as rapid response times, cost-effective catalysts, high product yields and efficient purification procedures. A comprehensive investigation was conducted to examine the impact of aldehyde structure on the synthesis pathway. A library of compounds was obtained and characterized by FT-IR, MS, ¹H NMR and ¹³C NMR spectroscopy and single-ray crystal diffractometry. Their antimicrobial activity against S. epidermidis, K. pneumonie and C. parapsilosis was tested in vitro. The effect of iodo-quinoline derivatives on microbial adhesion, the initial stage of microbial biofilm development, was also investigated. This study suggests that carboxy-quinoline derivatives bearing an iodine atom are interesting scaffolds for the development of novel antimicrobial agents. Full article

Many disorders are a result of an inadequate supply of macronutrients and micronutrients in the diet. One such element is iodine. This study used curly kale (Brassica oleracea var. Sabellica L.) biofortified with the 5,7-diiodo-8-quinolinol iodine compound. The effect of the heat treatment on the chemical composition of the curly kale was studied. In addition, iodine bioavailability was evaluated in in vivo studies. Our investigation showed that iodine loss depends on the type of heat treatment as well as on the variety of kale. Curly kale biofortified with iodoquinoline had significantly higher iodine levels after thermal processing (steaming, blanching, boiling) than the vegetable biofortified with KIO₃. Generally, steaming was the best thermal processing method, as it contributed to the lowest iodine loss in curly kale. The red variety of kale, ‘Redbor F₁’, showed a better iodine stability during the heat treatment than the green variety, ‘Oldenbor F₁’. The thermal treatment also significantly affected the dry matter content and the basic chemical composition of the tested varieties of the 5,7-diI-8-Q biofortified kale. The steaming process caused a significant increase in total carbohydrates, fiber, protein and crude fat content (‘Oldenbor F₁’, ‘Redbor F₁’), and antioxidant activity (‘Oldenbor F₁’). On the other hand, boiling caused a significant decrease, while steaming caused a significant increase, in protein and dry matter content (‘Oldenbor F₁’, ‘Redbor F₁’). The blanching process caused the smallest significant decrease in ash compared to the other thermal processes used (‘Oldenbor F₁’). A feeding experiment using Wistar rats showed that iodine from the 5,7-diI-8-Q biofortified kale has a higher bioavailability than that from the AIN-93G diet. A number of promising results have been obtained, which could form the basis for further research. Full article

Iodine deficiency impacts on the development of thyroid disease. Vegetables and fruits usually have a low iodine content; hence, it makes sense to increase their iodine content. Potato is consumed daily by millions of consumers and would, therefore, be a good target for biofortification with iodine programs. The aim of this study was to determine the effects of biofortification via the application of soil solutions of two iodoquinolines [8-hydroxy-7-iodo-5-quinolinic acid (8-OH-7-I-5QSA) and 5-chloro-7-iodo-8-quinoline (5-Cl-7-I-8-Q)] and KIO₃ (as an iodine positive control) on the iodine content and basic chemical composition, macro and micronutrient content, nitrogen compounds, vitamin C, and antioxidant potential of potato tubers Solanum tuberosum L. The biofortification process had no significant effect on the tuber weight in yield. The application of I in forms of KIO₃, 8-OH-7-I-5QSA, 5-Cl-7-I-8-Q resulted in an increase in the I content of tubers (1400.15; 693.65; 502.79, respectively, compared with control, 24.96 µg·kg⁻¹ d.w.). This also resulted in a decrease in elements that are harmful to consumers, such as: Al, Ni, Cr, Ag, Pb and Tl. The enrichment of tubers with 8-OH-7-I-5QSA and 5-Cl-7-I-8-Q resulted in a significant reduction in the content of ammonium ions (from 19.16 to 14.96; 13.52 mg∙kg⁻¹ f.w.) and chlorides (from 423.59 to 264.92; 265.31 mg∙kg⁻¹ f.w.). Biofortification with 8-OH-7-I-5QSA improved the polyphenolic profile of the potato tuber from 197.31 to 233.33 mg GAE·100 g⁻¹ f.w. A significant reduction in the carotenoid content of tubers after the enrichment of the plant with iodine in KIO₃, 8-OH-7-I-5QSA and 5-Cl-7-I-8-Q (from 3.46 to 2.96, 2.45, and 1.47 mg∙100 g⁻¹ d.w., respectively) was observed. It can be postulated that the production of potatoes enriched with iodoquinolines and/or KIO₃ is worthwhile, as it can provide a good source of I in the diet and simultaneously reduce the risk of developing deficiencies. Full article

The aminocarbonylation of 6-iodoquinoline has been investigated in the presence of large series of amine nucleophiles, providing an efficient synthetic route for producing various quinoline-6-carboxamide and quinoline-6-glyoxylamide derivatives. It was shown, after detailed optimization study, that the formation of amides and ketoamides is strongly influenced by the reaction conditions. Performing the reactions at 40 bar of carbon monoxide pressure in the presence of Pd(OAc)₂/2 PPh₃, the corresponding 2-ketocarboxamides were formed as major products (up to 63%). When the monodentate triphenylphosphine was replaced by the bidentate XantPhos, the quinoline-6-carboxamide derivatives were synthesized almost exclusively under atmospheric conditions (up to 98%). The isolation and characterization of the new carbonylated products of various structures were also accomplished. Furthermore, the structure of three new mono- and double-carbonylated compounds were unambiguously established by using a single-crystal XRD study. Full article

The search to replace conventional cancer treatment therapies, such as chemotherapy, radiotherapy and surgery has led over the last ten years, to a substantial effort in the development of several classes of photodynamic therapy photosensitizers with desired photophysicochemical and photobiological properties. Herein we report the synthesis of 6-iodoquinoline- and benzothiazole-based unsymmetrical squaraine cyanine dyes functionalized with amine groups located in the four-membered central ring. Their photodegradation and singlet oxygen production ability, as well as their in vitro photocytotoxicity against Caco-2 and HepG2 cell lines using a 630.8 ± 0.8 nm centered light-emitting diode system, were also investigated. All photosensitizer candidates displayed strong absorption within the tissue transparency spectral region (650–850 nm). The synthesized dyes were found to have moderate light stability. The potential of these compounds is evidenced by their cytotoxic activity against both tumor cell lines, highlighting the zwitterionic unsubstituted dye, which showed more intense photodynamic activity. Although the singlet oxygen quantum yields of these iodinated derivatives are considered low, it could be concluded that their introduction into the quinoline heterocycle was highly advantageous as it played a role in increasing selective cytotoxicity in the presence of light. Thus, the novel synthesized dyes present photophysicochemical and in vitro photobiological properties that make them excellent photosensitizer candidates for photodynamic therapy. Full article

Buchwald-Hartwig-Migita cross-coupling of 1-thiosugars with α- or β-3-iodo-N-glycosylquinolin-2-ones has been accomplished under mild and operationally simple reaction conditions through the use of a Pd-G3 XantPhos palladacycle precatalyst. This new methodology has been successfully applied to a variety of α- or β-mono-, di-, and poly-thiosugar derivatives to efficiently synthesize a series of α- or β-N,S-bis-glycosyl quinolin-2-ones, which are difficult to synthesize by classical methods. Full article

Dual-specificity tyrosine phosphorylation-regulated kinase 1A (DYRK1A) is a potential drug target because of its role in the development of Down syndrome and Alzheimer’s disease. The selective DYRK1A inhibitor 10-iodo-11H-indolo[3,2-c]quinoline-6-carboxylic acid (KuFal194), a large, flat and lipophilic molecule, suffers from poor water solubility, limiting its use as chemical probe in cellular assays and animal models. Based on the structure of KuFal194, 7-chloro-1H-indole-3-carbonitrile was selected as fragment template for the development of smaller and less lipophilic DYRK1A inhibitors. By modification of this fragment, a series of indole-3-carbonitriles was designed and evaluated as potential DYRK1A ligands by molecular docking studies. Synthesis and in vitro assays on DYRK1A and related protein kinases identified novel double-digit nanomolar inhibitors with submicromolar activity in cell culture assays. Full article

Palladium-catalyzed Suzuki-Miyaura cross-coupling of 2-aryl-4-azido-3-iodo-quinolines with arylboronic acids afforded the corresponding primary 4-amino-2,3-diarylquinolines in a single-pot operation along with symmetrical biaryls and traces of the 2,3-diaryl-4-azidoquinolines. A plausible mechanism, which implicates palladium hydride species in the reduction of the incipient 2,3-diaryl-4-azidoquinolines to afford the 4-amino-2,3-diarylquinolines is proposed. Full article