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Marine Drugs Sep 2021Nitrogen heterocycles are essential parts of the chemical machinery of life and often reveal intriguing structures. They are not only widespread in terrestrial habitats... (Review)
Review
Nitrogen heterocycles are essential parts of the chemical machinery of life and often reveal intriguing structures. They are not only widespread in terrestrial habitats but can also frequently be found as natural products in the marine environment. This review highlights the important class of marine pyrrole alkaloids, well-known for their diverse biological activities. A broad overview of the marine pyrrole alkaloids with a focus on their isolation, biological activities, chemical synthesis, and derivatization covering the decade from 2010 to 2020 is provided. With relevant structural subclasses categorized, this review shall provide a clear and timely synopsis of this area.
Topics: Alkaloids; Animals; Aquatic Organisms; Pyrroles; Structure-Activity Relationship
PubMed: 34564176
DOI: 10.3390/md19090514 -
The Journal of Organic Chemistry Jan 2023A novel method for the preparation of tetrahydropentaleno[1,2-]pyrroles () is described via the reaction of anilines with 1-en-4-yn-3-ols in the presence of Lewis acid....
A novel method for the preparation of tetrahydropentaleno[1,2-]pyrroles () is described via the reaction of anilines with 1-en-4-yn-3-ols in the presence of Lewis acid. Oxidation of with Br gave pentaleno[1,2-]pyrroles (), which is the first reported tricyclic 5/5/5 ring with a fully conjugated system. Structures of these obtained compounds were characterized by spectroscopic methods, and compounds , and were further confirmed by X-ray crystallographic determination.
Topics: Pyrroles; Crystallography, X-Ray; Oxidation-Reduction; Molecular Structure
PubMed: 36573709
DOI: 10.1021/acs.joc.2c02405 -
Surgical Endoscopy Oct 2023Vonoprazan is a new potassium-competitive acid blocker (P-CAB) that was recently approved by the FDA. It is associated with a fast onset of action and a longer acid...
BACKGROUND
Vonoprazan is a new potassium-competitive acid blocker (P-CAB) that was recently approved by the FDA. It is associated with a fast onset of action and a longer acid inhibition time. Vonoprazan-containing therapy for helicobacter pylori eradication is highly effective and several studies have demonstrated that a vonoprazan-antibiotic regimen affects gut microbiota. However, the impact of vonoprazan alone on gut microbiota is still unclear.Please check and confirm the authors (Maria Cristina Riascos, Hala Al Asadi) given name and family name are correct. Also, kindly confirm the details in the metadata are correct.Yes they are correct. METHODS: We conducted a prospective randomized 12-week experimental trial with 18 Wistar rats. Rats were randomly assigned to one of 3 groups: (1) drinking water as negative control group, (2) oral vonoprazan (4 mg/kg) for 12 weeks, and (3) oral vonoprazan (4 mg/kg) for 4 weeks, followed by 8 weeks off vonoprazan. To investigate gut microbiota, we carried out a metagenomic shotgun sequencing of fecal samples at week 0 and week 12.Please confirm the inserted city and country name is correct for affiliation 2.Yes it's correct.
RESULTS
For alpha diversity metrics at week 12, both long and short vonoprazan groups had lower Pielou's evenness index than the control group (p = 0.019); however, observed operational taxonomic units (p = 0.332) and Shannon's diversity index (p = 0.070) were not statistically different between groups. Beta diversity was significantly different in the three groups, using Bray-Curtis (p = 0.003) and Jaccard distances (p = 0.002). At week 12, differences in relative abundance were observed at all levels. At phylum level, short vonoprazan group had less of Actinobacteria (log fold change = - 1.88, adjusted p-value = 0.048) and Verrucomicrobia (lfc = - 1.76, p = 0.009).Please check and confirm that the author (Ileana Miranda) and their respective affiliation 3 details have been correctly identified and amend if necessary.Yes it's correct. At the genus level, long vonoprazan group had more Bacteroidales (lfc = 5.01, p = 0.021) and Prevotella (lfc = 7.79, p = 0.001). At family level, long vonoprazan group had more Lactobacillaceae (lfc = 0.97, p = 0.001), Prevotellaceae (lfc = 8.01, p < 0.001), and less Erysipelotrichaceae (lfc = - 2.9, p = 0.029).
CONCLUSION
This study provides evidence that vonoprazan impacts the gut microbiota and permits a precise delineation of the composition and relative abundance of the bacteria at all different taxonomic levels.
Topics: Animals; Rats; Anti-Bacterial Agents; Drug Therapy, Combination; Gastrointestinal Microbiome; Helicobacter Infections; Helicobacter pylori; Potassium; Prospective Studies; Proton Pump Inhibitors; Pyrroles; Rats, Wistar
PubMed: 37452210
DOI: 10.1007/s00464-023-10269-6 -
European Journal of Medicinal Chemistry Apr 2024In this review, we summarize pyrroloquinoline and pyrroloisoquinoline derivatives (PQs and PIQs) that act on a broad spectrum of biological targets and are used as... (Review)
Review
In this review, we summarize pyrroloquinoline and pyrroloisoquinoline derivatives (PQs and PIQs) that act on a broad spectrum of biological targets and are used as bacteriostatic, antiviral, plasmodial, anticancer, antidiabetic and anticoagulant agents. Many of these compounds play important roles in the study of DNA and its interactions, the regulation of the cell cycle and programmed cell death. This review involves twenty-five types of skeletally analogical compounds bearing pyrrole and (iso)quinoline scaffolds with different mutual annelations.
Topics: Quinolines; Pyrroles; Cell Cycle; Apoptosis; Antineoplastic Agents
PubMed: 38492334
DOI: 10.1016/j.ejmech.2024.116287 -
Bioorganic Chemistry Apr 2023Pyrrole-imidazole alkaloids (PIAs) constitute a highly diverse and densely functionalized subclass of marine natural products. Among them, the uncommon dimeric PIAs with... (Review)
Review
Pyrrole-imidazole alkaloids (PIAs) constitute a highly diverse and densely functionalized subclass of marine natural products. Among them, the uncommon dimeric PIAs with ornate molecular architectures, attractive biological properties and interesting biosynthetic origin have spurred a considerable interest of chemists and biologists. The present review comprehensively summarized 84 dimeric PIAs discovered during the period from 1981 to September 2022, covering their source organisms, chemical structures, biological activities as well as biosynthesis. For a better understanding, these structurally intricate PIA dimers are firstly classified and presented according to their carbon skeleton features as well as biosynthesis pathways. Furthermore, relevant summaries focusing on the source organisms and the associated bioactivities of these compounds belonging to different chemical classes are also provided, which will help elucidate the fascinating chemistry and biology of these unusual PIA dimers.
Topics: Alkaloids; Biological Products; Imidazoles; Pyrroles
PubMed: 36773454
DOI: 10.1016/j.bioorg.2022.106332 -
Molecular Diversity Oct 2022The chemistry of nitrogen-containing heterocyclic compound pyrrole and pyrrolidine has been a versatile field of study for a long time for its diverse biological and... (Review)
Review
The chemistry of nitrogen-containing heterocyclic compound pyrrole and pyrrolidine has been a versatile field of study for a long time for its diverse biological and medicinal importance. Biomolecules such as chlorophyll, hemoglobin, myoglobin, and cytochrome are naturally occurring metal complexes of pyrrole. These metal complexes play a vital role in a living system like photosynthesis, oxygen carrier, as well storage, and redox cycling reactions. Apart from this, many medicinal drugs are derived from either pyrrole, pyrrolidine, or by its fused analogs. This review mainly focuses on the therapeutic potential of pyrrole, pyrrolidine, and its fused analogs, more specifically anticancer, anti-inflammatory, antiviral, and antituberculosis. Further, this review summarizes more recent reports on the pyrrole, pyrrolidine analogs, and their biological potential.
Topics: Anti-Inflammatory Agents; Antiviral Agents; Chlorophyll; Coordination Complexes; Cytochromes; Heterocyclic Compounds; Myoglobin; Nitrogen; Oxygen; Pyrroles; Pyrrolidines
PubMed: 35079946
DOI: 10.1007/s11030-022-10387-8 -
International Journal of Molecular... Jan 2023As an energy storage technology, supercapacitors (SCs) have become an important part of many electronic systems because of their high-power density, long cycle life, and...
As an energy storage technology, supercapacitors (SCs) have become an important part of many electronic systems because of their high-power density, long cycle life, and maintenance-free characteristics. However, the widespread development and use of electronics, including SCs, have led to the generation of a large amount of e-waste. In addition, achieving compatibility between stability and biodegradability has been a prominent challenge for implantable electronics. Therefore, environmentally friendly SCs based on polypyrrole (PPy)-stabilized polypeptide (FF) are demonstrated in this study. The fully degradable SC has a layer-by-layer structure, including polylactic acid/chitosan (PLA-C) support layers, current collectors (Mg), FF/PPy composite layers, and a polyvinyl alcohol/phosphate buffer solution (PVA/PBS) hydrogel. It has the advantages of being light, thin, flexible, and biocompatible. After 5000 cycles in air, the capacitance retention remains at up to 94.7%. The device could stably operate for 7 days in a liquid environment and completely degrade in vitro within 90 days without any adverse effect on the environment. This work has important implications for eco-friendly electronics and will have a significant impact on the implantable biomedical electronics.
Topics: Polymers; Pyrroles; Polyvinyl Alcohol; Peptides
PubMed: 36768819
DOI: 10.3390/ijms24032497 -
Topics in Current Chemistry (Cham) Jan 2023The incorporation of aryl substituents at the meso-positions of calix[4]pyrrole (C4P) scaffolds produces aryl-extended (AE) and super-aryl-extended (SAE)... (Review)
Review
The incorporation of aryl substituents at the meso-positions of calix[4]pyrrole (C4P) scaffolds produces aryl-extended (AE) and super-aryl-extended (SAE) calix[4]pyrroles. The cone conformation of the all-α isomers of "multi-wall" AE-C4Ps and SAE-C4Ps displays deep aromatic clefts or cavities. In particular, "four-wall" receptors feature an aromatic polar cavity closed at one end with four convergent pyrrole rings and fully open at the opposite end. This makes AE- and SAE-C4P scaffolds effective receptors for the molecular recognition of negatively charged ions and neutral guest molecules with donor-acceptor and hydrogen bonding motifs. In addition, adequately functionalized all-α isomers of multi wall AE- and SAE-C4P scaffolds self-assemble into uni-molecular and supra-molecular aggregates displaying capsular and cage-like structures. The self-assembly process requires the presence of template ions or molecules that lock the C4P cone conformation and complementing the inner polar functions and volumes of their cavities. We envisioned performing an in-depth revision of AE- and SAE-C4P scaffolds owing to their importance in different domains such as supramolecular chemistry, biology, material sciences and pharmaceutical chemistry. Herewith, besides the synthetic details on the elaboration of their structures, we also draw attention to their diverse applications. The organization of this review is mainly based on the number of "walls" present in the AE-C4P derivatives and their structural modifications. The sections are further divided based on the C4P functions and applications. The authors are convinced that this review will be of interest to researchers working in the general area of supramolecular chemistry as well as those involved in the study of the binding properties and applications of C4P derivatives.
Topics: Pyrroles; Porphyrins; Models, Molecular; Ions; Molecular Conformation
PubMed: 36607442
DOI: 10.1007/s41061-022-00419-0 -
Biomaterials Science Dec 2023Bacterial infections with emerging resistance to antibiotics require urgent development of antibacterial agents with new core skeletons. Recently, a series of...
Bacterial infections with emerging resistance to antibiotics require urgent development of antibacterial agents with new core skeletons. Recently, a series of antibacterial agents have been reported based on positively charged organic groups, such as ammonium, guanidine, and phosphonium groups, which can selectively bind and destroy negatively charged bacterial membranes. To achieve imaging-guided precise antibacterial therapy, these positively charged organic groups usually require further decoration with imaging modalities, such as fluorescence. However, most fluorophores with electron-closed shell structures usually suffer from tedious synthetic procedures for preparation. We herein prepare a series of positively charged and deep-red fluorescent supramolecular pyrrole radical cations (P˙-CB[7]) based on the simple mixing of pyrroles and CB[7] in water under air. The readily available deep-red fluorescent P˙-CB[7] can not only be used for selective imaging and killing of live Gram-positive bacteria with excellent biocompatibility, but also for imaging of dead Gram-negative bacteria killed by drugs and monitoring of phagocytosis of bacteria by innate immune cells in zebrafish. It is believed that the deep-red fluorescent pyrrole radical cations as a new core skeleton are promising in bacterial theranostics.
Topics: Animals; Pyrroles; Precision Medicine; Zebrafish; Anti-Bacterial Agents; Bacteria; Cations
PubMed: 37982447
DOI: 10.1039/d3bm01472j -
Angewandte Chemie (International Ed. in... Jun 2023We report a two-step approach to obtain synthetically versatile bicyclo[1.1.1]pentane (BCP) derivatives using Grignard reagents. This method allows the incorporation of...
We report a two-step approach to obtain synthetically versatile bicyclo[1.1.1]pentane (BCP) derivatives using Grignard reagents. This method allows the incorporation of BCP units in tetrapyrrolic macrocycles and the synthesis of a new class of calix[4]pyrrole analogues by replacing two bridging methylene groups with two BCP units. In addition, a doubly N-confused system was also formed in the presence of electron-withdrawing substituents at the BCP bridgeheads. The pyrrole rings in BCP containing macrocycles exist in 1,3-alternate or αβαβ conformations, as observed from single-crystal X-ray diffraction analyses and 2D NMR spectroscopy.
Topics: Pentanes; Pyrroles; Molecular Conformation; Crystallography, X-Ray
PubMed: 36988343
DOI: 10.1002/anie.202302771