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Chemical Reviews Aug 2017The formation of oximes and hydrazones is employed in numerous scientific fields as a simple and versatile conjugation strategy. This imine-forming reaction is applied... (Review)
Review
The formation of oximes and hydrazones is employed in numerous scientific fields as a simple and versatile conjugation strategy. This imine-forming reaction is applied in fields as diverse as polymer chemistry, biomaterials and hydrogels, dynamic combinatorial chemistry, organic synthesis, and chemical biology. Here we outline chemical developments in this field, with special focus on the past ∼10 years of developments. Recent strategies for installing reactive carbonyl groups and α-nucleophiles into biomolecules are described. The basic chemical properties of reactants and products in this reaction are then reviewed, with an eye to understanding the reaction's mechanism and how reactant structure controls rates and equilibria in the process. Recent work that has uncovered structural features and new mechanisms for speeding the reaction, sometimes by orders of magnitude, is discussed. We describe recent studies that have identified especially fast reacting aldehyde/ketone substrates and structural effects that lead to rapid-reacting α-nucleophiles as well. Among the most effective new strategies has been the development of substituents near the reactive aldehyde group that either transfer protons at the transition state or trap the initially formed tetrahedral intermediates. In addition, the recent development of efficient nucleophilic catalysts for the reaction is outlined, improving greatly upon aniline, the classical catalyst for imine formation. A number of uses of such second- and third-generation catalysts in bioconjugation and in cellular applications are highlighted. While formation of hydrazone and oxime has been traditionally regarded as being limited by slow rates, developments in the past 5 years have resulted in completely overturning this limitation; indeed, the reaction is now one of the fastest and most versatile reactions available for conjugations of biomolecules and biomaterials.
Topics: Biocompatible Materials; Catalysis; Hydrazones; Imines; Molecular Structure; Oximes
PubMed: 28640998
DOI: 10.1021/acs.chemrev.7b00090 -
Molecules (Basel, Switzerland) Feb 2021The search for new biomedical applications of dendrimers has promoted the synthesis of new radical-based molecules. Specifically, obtaining radical dendrimers has opened... (Review)
Review
The search for new biomedical applications of dendrimers has promoted the synthesis of new radical-based molecules. Specifically, obtaining radical dendrimers has opened the door to their use in various fields such as magnetic resonance imaging, as anti-tumor or antioxidant agents, or the possibility of developing new types of devices based on the paramagnetic properties of organic radicals. Herein, we present a mini review of radical dendrimers based on polyphosphorhydrazone, a new type of macromolecule with which, thanks to their versatility, new metal-free contrast agents are being obtained, among other possible applications.
Topics: Dendrimers; Free Radicals; Humans; Hydrazones; Molecular Structure; Organophosphonates; Polymers
PubMed: 33669016
DOI: 10.3390/molecules26051230 -
Molecules (Basel, Switzerland) Apr 2023Photoresponsive biomaterials have garnered increasing attention recently due to their ability to dynamically regulate biological interactions and cellular behaviors in... (Review)
Review
Photoresponsive biomaterials have garnered increasing attention recently due to their ability to dynamically regulate biological interactions and cellular behaviors in response to light. This review provides an overview of recent advances in the design, synthesis, and applications of photoresponsive biomaterials, including photochromic molecules, photocleavable linkers, and photoreactive polymers. We highlight the various approaches used to control the photoresponsive behavior of these materials, including modulation of light intensity, wavelength, and duration. Additionally, we discuss the applications of photoresponsive biomaterials in various fields, including drug delivery, tissue engineering, biosensing, and optical storage. A selection of significant cutting-edge articles collected in recent years has been discussed based on the structural pattern and light-responsive performance, focusing mainly on the photoactivity of azobenzene, hydrazone, diarylethenes, and spiropyrans, and the design of smart materials as the most targeted and desirable application. Overall, this review highlights the potential of photoresponsive biomaterials to enable spatiotemporal control of biological processes and opens up exciting opportunities for developing advanced biomaterials with enhanced functionality.
Topics: Biocompatible Materials; Polymers; Drug Delivery Systems; Hydrazones; Light
PubMed: 37175122
DOI: 10.3390/molecules28093712 -
JACC. Heart Failure Apr 2013
Topics: Cardiotonic Agents; Female; Heart Failure; Humans; Hydrazones; Male; Pyridazines; Simendan
PubMed: 24621842
DOI: 10.1016/j.jchf.2013.02.002 -
Biomedicine & Pharmacotherapy =... Jul 2023The hydrazones and hydrazide-hydrazones beside possessing crucial bioactivity can serve as useful intermediates in the synthesis of heterocyclic systems like... (Review)
Review
The hydrazones and hydrazide-hydrazones beside possessing crucial bioactivity can serve as useful intermediates in the synthesis of heterocyclic systems like 1,3-benzothiazin-4-one, 1,3-thiazolidin-4-one, azetidin-2-one and 1,3,4-oxadiazole derivatives. The azetidin-2-one derivatives show mainly antibacterial, antitubercular and antifungal activity as well as anti-inflammatory, antioxidant, anticonvulsant and antidepressant activity and activity against Parkinson's disease. This review is focused on the literature reports which consider the synthesis and biological properties of azetidin-2-one derivatives.
Topics: Hydrazones; Hydrazines; Anti-Bacterial Agents; Antifungal Agents; Anticonvulsants; Structure-Activity Relationship
PubMed: 37178574
DOI: 10.1016/j.biopha.2023.114853 -
Indian Pediatrics Jul 2009
Review
Topics: Cardiotonic Agents; Heart Failure; Humans; Hydrazones; Pyridazines; Simendan
PubMed: 19638658
DOI: No ID Found -
Journal of Inorganic Biochemistry Oct 2022We report the synthesis and characterization of a family of benzohydrazones (L, n = 1-6) derived from 2-carbaldehyde-8-hydroxyquinoline and benzylhydrazides containing...
We report the synthesis and characterization of a family of benzohydrazones (L, n = 1-6) derived from 2-carbaldehyde-8-hydroxyquinoline and benzylhydrazides containing different substituents in the para position. Their oxidovanadium(IV) complexes were prepared and compounds with 1:1 and 1:2 metal-to-ligand stoichiometry were obtained. All compounds were characterized by elemental analyses and mass spectrometry as well as FTIR, UV-visible absorption, NMR (ligand precursors) and EPR (complexes) spectroscopies, and by DFT computational methods. Proton dissociation constants, lipophilicity and solubility in aqueous media were determined for all ligand precursors. Complex formation with V(IV)O was evaluated by spectrophotometry for L (Me-substituted) and L (OH-substituted) and formation constants for mono [VO(HL)], [VO(L)] and bis [VO(HL)], [VO(HL)(L)], [VO(L)] complexes were determined. EPR spectroscopy indicates the formation of [VO(HL)] and [VO(HL)], with this latter being the major species at the physiological pH. Noteworthy, the EPR data suggest a different behaviour for L and L, which confirm the results obtained in the solid state. The antiproliferative activity of all compounds was evaluated in malignant melanoma (A-375) and lung (A-549) cancer cells. All complexes show much higher activity on A-375 (IC < 6.3 μM) than in A-549 cells (IC > 20 μM). Complex 3 (F-substituted) shows the lowest IC on both cell lines and lower than cisplatin (in A-375). Studies identified this compound as the one showing the highest increase in Annexin-V staining, caspase activity and induction of double stranded breaks, corroborating the cytotoxicity results. The mechanism of action of the complexes involves reactive oxygen species (ROS) induced DNA damage, and cell death by apoptosis.
Topics: Cisplatin; Coordination Complexes; Hydrazones; Ligands; Oxyquinoline; Vanadium
PubMed: 35940023
DOI: 10.1016/j.jinorgbio.2022.111932 -
International Journal of Molecular... Mar 2024Fluorinated imines (Schiff bases) and fluorinated hydrazones are of particular interest in medicinal chemistry due to their potential usefulness in treating... (Review)
Review
Fluorinated imines (Schiff bases) and fluorinated hydrazones are of particular interest in medicinal chemistry due to their potential usefulness in treating opportunistic strains of bacteria that are resistant to commonly used antibacterial agents. The present review paper is focused on these fluorinated molecules revealing strong, moderate or weak in vitro antibacterial activities, which have been reported in the scientific papers during the last fifteen years. Fluorinated building blocks and reaction conditions used for the synthesis of imines and hydrazones are mentioned. The structural modifications, which have an influence on the antibacterial activity in all the reported classes of fluorinated small molecules, are highlighted, focusing mainly on the importance of specific substitutions. Advanced research techniques and innovations for the synthesis, design and development of fluorinated imines and hydrazones are also summarized.
Topics: Hydrazones; Anti-Bacterial Agents; Imines; Schiff Bases; Bacteria
PubMed: 38542315
DOI: 10.3390/ijms25063341 -
Molecules (Basel, Switzerland) Feb 2021Based on the broad spectrum of biological activity of hydrazide-hydrazones, trifluoromethyl compounds, and clinical usage of cholinesterase inhibitors, we investigated...
Based on the broad spectrum of biological activity of hydrazide-hydrazones, trifluoromethyl compounds, and clinical usage of cholinesterase inhibitors, we investigated hydrazones obtained from 4-(trifluoromethyl)benzohydrazide and various benzaldehydes or aliphatic ketones as potential inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). They were evaluated using Ellman's spectrophotometric method. The hydrazide-hydrazones produced a dual inhibition of both cholinesterase enzymes with IC values of 46.8-137.7 µM and 19.1-881.1 µM for AChE and BuChE, respectively. The majority of the compounds were stronger inhibitors of AChE; four of them (2-bromobenzaldehyde, 3-(trifluoromethyl)benzaldehyde, cyclohexanone, and camphor-based , , , and , respectively) produced a balanced inhibition of the enzymes and only 2-chloro/trifluoromethyl benzylidene derivatives and were found to be more potent inhibitors of BuChE. 4-(Trifluoromethyl)-'-[4-(trifluoromethyl)benzylidene]benzohydrazide produced the strongest inhibition of AChE via mixed-type inhibition determined experimentally. Structure-activity relationships were identified. The compounds fit physicochemical space for targeting central nervous systems with no apparent cytotoxicity for eukaryotic cell line together. The study provides new insights into this CF-hydrazide-hydrazone scaffold.
Topics: Acetylcholinesterase; Blood-Brain Barrier; Butyrylcholinesterase; Central Nervous System; Cholinesterase Inhibitors; Humans; Hydrazines; Hydrazones; Kinetics
PubMed: 33668452
DOI: 10.3390/molecules26040989 -
International Journal of Molecular... Aug 2021Hydrazide-hydrazones possess a wide spectrum of bioactivity, including antibacterial, antitubercular, antifungal, anticancer, anti-inflammatory, anticonvulsant,... (Review)
Review
Hydrazide-hydrazones possess a wide spectrum of bioactivity, including antibacterial, antitubercular, antifungal, anticancer, anti-inflammatory, anticonvulsant, antidepressant, antiviral, and antiprotozoal properties. This review is focused on the latest scientific reports regarding antibacterial, antimycobacterial, and antifungal activities of hydrazide-hydrazones published between 2017 and 2021. The molecules and their chemical structures presented in this article are the most active derivatives, with discussed activities having a hydrazide-hydrazone moiety as the main scaffold or as a side chain. Presented information constitute a concise summary, which may be used as a practical guide for further design of new molecules with antimicrobial activity.
Topics: Animals; Anti-Bacterial Agents; Bacteria; Humans; Hydrazones
PubMed: 34502297
DOI: 10.3390/ijms22179389