Synthesis, Electronic, and Antibacterial Properties of 3,7-Di(hetero)aryl-substituted Phenothiazinyl N-Propyl Trimethylammonium Salts.

In this study, a library of 3,7-di(hetero)aryl-substituted 10-(3-trimethylammoniumpropyl)10H-phenothiazine salts is prepared. These title compounds and their precursors are reversible redox systems with tunable potentials. The Hammett correlation gives a very good correlation of the first oxidation potentials with σp parameters. Furthermore, the title compounds and their precursors are blue to green-blue emissive. Screening of the salts reveals for some derivatives a distinct inhibition of several pathogenic bacterial strains (Mycobacterium tuberculosis, Staphylococcus aureus, Escherichia coli, Aconetobacter baumannii, and Klebsiella pneumoniae) in the lower micromolar range.

Collection and transportation of SARS-CoV-2 and influenza A virus diagnostic samples: Optimizing the usage of guanidine-based chaotropic salts for enhanced biosafety and viral genome preservation.

Many virus lysis/transport buffers used in molecular diagnostics, including the detection of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) RNA, contain guanidine-based chaotropic salts, primarily guanidine hydrochloride (GuHCl) or guanidine isothiocyanate (GITC). Although the virucidal effects of GuHCl and GITC alone against some enveloped viruses have been established, standardized data on their optimum virucidal concentrations against SARS-CoV-2 and effects on viral RNA stability are scarce. Thus, we aimed to determine the optimum virucidal concentrations of GuHCl and GITC against SARS-CoV-2 compared to influenza A virus (IAV), another enveloped respiratory virus. We also evaluated the effectiveness of viral RNA stabilization at the determined optimum virucidal concentrations under high-temperature conditions (35°C) using virus-specific real-time reverse transcription polymerase chain reaction. Both viruses were potently inactivated by 1.0 M GITC and 2.5 M GuHCl, but the GuHCl concentration for efficient SARS-CoV-2 inactivation was slightly higher than that for IAV inactivation. GITC showed better viral RNA stability than GuHCl at the optimum virucidal concentrations. An increased concentration of GuHCl or GITC increased viral RNA degradation at 35°C. Our findings highlight the need to standardize GuHCl and GITC concentrations in virus lysis/transport buffers and the potential application of these guanidine-based salts alone as virus inactivation solutions in SARS-CoV-2 and IAV molecular diagnostics.

Oxolane Ammonium Salts (Muscarine-Like)-Synthesis and Microbiological Activity.

Commercially available 2-deoxy-D-ribose was used to synthesize the appropriate oxolane derivative-(2R,3S)-2-(hydroxymethyl)oxolan-3-ol-by reduction and dehydration/cyclization in an acidic aqueous solution. Its monotosyl derivative, as a result of the quaternization reaction, allowed us to obtain eight new muscarine-type derivatives containing a quaternary nitrogen atom and a hydroxyl group linked to the oxolane ring. Their structure was fully confirmed by the results of NMR, MS and IR analyses. The crystal structure of the pyridinium derivative showed a high similarity of the conformation of the oxolane ring to previously published crystal structures of muscarine. Two reference strains of Gram-negative bacteria (Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853), two reference strains of Gram-positive staphylococci (Staphylococcus aureus ATCC 25923 and Staphylococcus aureus ATCC 29213) and four reference strains of pathogenic yeasts of the genus Candida spp. (Candida albicans SC5314, Candida glabrata DSM 11226, Candida krusei DSM 6128 and Candida parapsilosis DSM 5784) were selected for the evaluation of the antimicrobial potential of the synthesized compounds. The derivative containing the longest (decyl) chain attached to the quaternary nitrogen atom turned out to be the most active.

Quaternary ammonium salts for water treatment with balanced rate of sterilization and degradation.

The growing number of infections caused by drug-resistant bacteria which arise from the overuse of antibiotics has severely affected the normal operation of human society. The high antibacterial activity of QAS makes it promising as an alternative to antibiotics, but it suffers from secondary pollution due to its non-degradation. Here we have synthesized a class of gemini quaternary ammonium salts (GQAS) with different carbon chain lengths containing ester groups by using facile methylation reaction. Quaternary ammonium groups contribute to insert negatively charged bacterial membranes, resulting in membrane damage and bacteria death. Compared with conventional single-chain QAS, except for the more efficient antibacterial efficiency attribute to the presence of the second carbon chain, GQAS with alterable antibacterial properties can minimize the possibility of bacterial resistance and reduce the accumulation of GQAS in the environment through the introduction of degradable ester groups. GQAS is completely superior to the commercial bactericide benzalkonium chloride (BAC) in both antibacterial activity and degrade performance, which can be used as a more environmentally friendly bactericide.

Counterion influence on near-infrared-II heptamethine cyanine salts for photothermal therapy.

Photothermal therapy (PTT) has attracted extensive attention in cancer treatment. Heptamethine cyanine dyes with near-infrared (NIR) absorption performance have been investigated for PTT. However, they are often accompanied by poor photostability, suboptimal photothermal conversion and limited therapeutic efficacy. The photophysical properties of fluorescent organic salts can be tuned through counterion pairing. However, whether the counterion can influence the photostability and photothermal properties of heptamethine cyanine salts has not been clarified. In this work, we investigated the effects of eleven counter anions on the physical and photothermal properties of NIR-II heptamethine cyanine salts with the same heptamethine cyanine cation. The anions have great impacts on the physiochemical properties of dyes in solution including aggregation, photostability and photothermal conversion efficiency. The physical tuning enables the control over the cytotoxicity and phototoxicity of the dyes. The selected salts have been demonstrated to significantly suppress 4T1 breast tumor growth with low toxicity. The findings that the counterion has great effects on the photothermal properties of cationic NIR-II heptamethine cyanine dyes will provide a reference for the preparation of improved photothermal agents through counterion pairing with possible translation to humans.

Ovipositional responses of tortricid moths to sugars, salts and neem oil.

Oviposition is essential in the life history of insects and is mainly mediated by chemical and tactile cues present on the plant surface. Oviposition deterrents or stimulants can modify insect oviposition and be employed in pest control. Relatively few gustatory oviposition stimuli have been described for tortricid moths. In this study the effect of NaCl, KCl, sucrose, fructose and neem oil on the number of eggs laid by Cydia pomonella (L.), Grapholita molesta (Busck) and Lobesia botrana (Dennis & Schifermüller) was tested in laboratory arenas containing filter papers loaded with 3 doses of a given stimulus and solvent control. In general, salts increased oviposition at the mid dose (102 M) and sugars reduced it at the highest dose (103 mM), but these effects depended on the species. Neem oil dramatically reduced the number of eggs laid as the dose increased, but the lowest neem oil dose (0.1% v/v) increased L. botrana oviposition relative to solvent control. Our study shows that ubiquitous plant chemicals modify tortricid moth oviposition under laboratory conditions, and that neem oil is a strong oviposition deterrent. The oviposition arena developed in this study is a convenient tool to test the effect of tastants on the oviposition behavior of tortricid moths.

Influence of Organic and Inorganic Compounds of Various Metals on the Synthesis of Polysaccharides by the Medicinal Mushroom Trametes versicolor.

BACKGROUND: To date, basidiomycetes are considered to be promising objects of biotechnology, due to a number of biologically active compounds, such as polysaccharides and triterpenes. These compounds have a high therapeutic potential and demonstrate immunomodulatory, antiviral, and antifungal activities. OBJECTIVE: The purpose of this study was to study the effect of various concentrations of metal citrates and sulphates on the content of exo- and endopolysaccharides of the fungus Trametes versicolor. METHOD: The mycelium was grown by deep cultivation on a semisyntheticglucose-peptone-yeast medium with different contents of zinc, copper, and manganese salts, after which the extraction and measurement of the concentration of polysaccharides were carried out. RESULTS: The results obtained showed that copper citrate at a concentration of 4 mg/L had the greatest positive effect on biomass yield. The intensity of biomass growth on a nutrient medium with copper citrate increased by 80%. Zinc citrate increased the content of exopolysaccharides by 29% compared to the medium without metal salts. When manganese citrate was added to the medium, the productivity of synthesis decreased, but an increase in the growth rate of mycelium biomass was observed. Sulphates of these metals led to a decrease in the productivity of exopolysaccharide synthesis by 12% for zinc and 35% for manganese. CONCLUSIONS: The addition of both copper citrate and copper sulphate to the medium led to a decrease in the synthesis productivity by 66 and 24%, respectively. The introduction of both citrates and sulphates of these metals into the culture medium led to an increase in the percentage of endopolysaccharides in the mycelium of the fungus. HIGHLIGHTS: Copper citrate enhances Trametes versicolor biomass by 80%. Zinc citrate increases exopolysaccharide content by 29%. Copper sulphate optimizes endopolysaccharide production.

Bioactivity of selenium-containing pyridinium salts: Prospecting future pharmaceutical constituents to treat liver diseases involving oxidative stress.

Redox imbalance leads to oxidative stress that causes irreversible cellular damage. The incorporation of the antioxidant element selenium (Se) in the structure of pyridinium salts has been used as a strategy in chemical synthesis and can be useful in drug development. We investigated the antioxidant activity of Se-containing pyridinium salts (named Compounds 3A, 3B, and 3C) through in vitro tests. We focused our study on liver protein carbonylation, liver lipoperoxidation, free radical scavenging activity (1,1-diphenyl-2-picryl-hydrazil [DPPH]; 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid [ABTS]), and enzyme-mimetic activity assays (glutathione S-transferase [GST]-like; superoxide dismutase [SOD]-like). In addition, 2-(4-chlorophenyl)-2-oxoethyl)-2-((phenylselanyl)methyl)pyridin-1-ium bromide (3C) was selected to evaluate the acute oral toxicity in mice due to the best antioxidant profile. The three compounds were effective in reducing the levels of protein carbonylation and lipoperoxidation in the liver in a µM concentration range. All compounds demonstrated scavenger activity of DPPH and ABTS radicals, and GST-like action. No significant effects were detected in the SOD-like assay. Experimental data also showed that the acute oral treatment of mice with Compound 3C (50 and 300 mg/kg) did not cause mortality or change markers of liver and kidney functions. In summary, our findings reveal the antioxidant potential of Se-containing pyridinium salts in liver tissue, which could be related to their radical scavenging ability and mimetic action on the GST enzyme. They also demonstrate a low toxicity potential for Compound 3C. Together, the promising results open space for future studies on the therapeutic application of these molecules.

Mechanical properties of simulated dentin caries treated with metal cations and L-ascorbic acid 2-phosphate.

This pH cycling study aimed to investigate the effects of L-Ascorbic acid 2-phosphate (AA2P) salts of Mg, Zn, Mn, Sr, and Ba on the surface microhardness, compressive strength, diametral tensile strength (DTS), and solubility of root canal dentin. 186 cylindrical dentin specimens from 93 teeth were fortified with optimal concentrations of AA2P salts of Mg (0.18 mM), Zn (5.3 µM), Mn (2.2 × 10-8 M), Sr (1.8 µM), and Ba (1.9 µM). Saline was used as the control group. These dentin specimens underwent a 3-day cycling process simulating dentin caries formation through repeated sequences of demineralization and remineralization. Surface microhardness at 100 and 500 µm depths (n = 10/subgroup), scanning electron microscopy (n = 3/group), compressive strength (n = 10/group), DTS (n = 6/group), and solubility (n = 5/group) tests were performed to analyze the dentin specimens. Data were analyzed using Kolmogorov-Smirnov, one-way ANOVA, and Post Hoc Tukey tests (p < 0.05). The control group had significantly lower microhardness at both depths (p < 0.001), reduced DTS (p = 0.001), decreased compressive strength (p < 0.001), and higher weight loss (p < 0.001) than all other groups. The Sr group had the highest compressive strength and microhardness among all the groups. The microhardness was significantly higher for the 500 µm depth than the 100 µm depth (p < 0.001), but the difference in microhardness between depths across groups was not significant (p = 0.211). All fortifying solutions provided some protection against artificial caries lesions. Therefore, these elements might have penetrated and reinforced the demineralized dentin against acid dissolution.

Fluoroquinolone-Based Organic Salts (GUMBOS) with Antibacterial Potential.

Antimicrobial resistance is a silent pandemic considered a public health concern worldwide. Strategic therapies are needed to replace antibacterials that are now ineffective. One approach entails the use of well-known antibacterials along with adjuvants that possess non-antibiotic properties but can extend the lifespan and enhance the effectiveness of the treatment, while also improving the suppression of resistance. In this regard, a group of uniform materials based on organic salts (GUMBOS) presents an alternative to this problem allowing the combination of antibacterials with adjuvants. Fluoroquinolones are a family of antibacterials used to treat respiratory and urinary tract infections with broad-spectrum activity. Ciprofloxacin and moxifloxacin-based GUMBOS were synthesized via anion exchange reactions with lithium and sodium salts. Structural characterization, thermal stability and octanol/water partition ratios were evaluated. The antibacterial profiles of most GUMBOS were comparable to their cationic counterparts when tested against Gram-positive S. aureus and Gram-negative E. coli, except for deoxycholate anion, which demonstrated the least effective antibacterial activity. Additionally, some GUMBOS were less cytotoxic to L929 fibroblast cells and non-hemolytic to red blood cells. Therefore, these agents exhibit promise as an alternative approach to combining drugs for treating infections caused by resistant bacteria.

Exploring Alkyl Ester Salts of L-Amino Acid Derivatives of Ibuprofen: Physicochemical Characterization and Transdermal Potential.

This research presents novel ibuprofen derivatives in the form of alkyl ester salts of L-amino acids with potential analgesic, anti-inflammatory, and antipyretic properties for potential use in transdermal therapeutic systems. New derivatives of (RS)-2-[4-(2-methylpropyl)phenyl]propionic acid were synthesized using hydrochlorides of alkyl esters (ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, and pentyl) of L-glutamine. These were further transformed into alkyl esters of L-amino acid ibuprofenates through neutralization and protonation reactions. Characterization involved spectroscopic methods, including nuclear magnetic resonance and Fourier-transform infrared spectroscopy. Various physicochemical properties were investigated, such as UV-Vis spectroscopy, polarimetric analysis, thermogravimetric analysis, differential scanning calorimetry, X-ray diffraction, water solubility, octanol/water partition coefficient, and permeability through pig skin using Franz diffusion cells. The research confirmed the ionic structure of the obtained hydrochlorides of alkyl esters of L-amino acids and ibuprofenates of alkyl esters of L-glutamic acid. It revealed significant correlations between ester chain length and thermal stability, crystallinity, phase transition temperatures, lipophilicity, water solubility, skin permeability, and skin accumulation of these compounds. Compared to the parent ibuprofen, the synthesized derivatives exhibited higher water solubility, lower lipophilicity, and enhanced skin permeability. This study introduces promising ibuprofen derivatives with improved physicochemical properties, highlighting their potential for transdermal therapeutic applications. The findings shed light on the structure-activity relationships of these derivatives, offering insights into their enhanced solubility and skin permeation, which could lead to more effective topical treatments for pain and inflammation.

Benzimidazolium Salts Bearing Nitrile Moieties: Synthesis, Enzyme Inhibition Profiling, and Molecular Docking Analysis for Carbonic Anhydrase and Acetylcholinesterase.

This report presents the synthesis and characterization of a range of benzimidazolium salts featuring 3-cyanopropyl groups on the 1st nitrogen atom and varied alkyl groups on the 3rd nitrogen atom within the benzimidazole structure. Benzimidazolium salts were synthesized by N-alkylation of 1-alkyl benzimidazole with 3-cyanopropyl-bromide. The new salts were characterized by 1 H and 13 C-NMR, FT-IR spectroscopic and elemental analysis techniques. In this study, the enzyme inhibition abilities of seven nitrile substituted benzimidazolium salts were investigated against acetylcholinesterase (AChE) and carbonic anhydrase isoenzymes I and II (hCA I and hCA II). They showed a highly potent inhibition effect on AChE, hCA I and hCA II (Ki values are in the range of 26.71-119.09 nM for AChE, 19.77 to 133.68 nM for hCA I and 13.09 to 266.38 nM for hCA II). Reflecting the binding mode of the synthesized cyanopropyl series, the importance of the 2,3,5,6-tetramethylbenzyl, 3-methylbenzyl and 3-benzyl groups for optimal interactions with target proteins, evaluated by molecular docking studies. At the same time, the docking findings support the inhibition constants (Ki ) values of the related compounds in this study. Potential compounds were also evaluated by their pharmacokinetic properties were predicted.

Synthesis and characterization of novel chitosan derivatives (containing dipyridinium quaternary salts) with antimicrobial potential.

Chitosan derivatives are versatile materials, biocompatible and biodegradable, that can be tailor-made to suit specific biomedical applications. In this study, two N-heterocyclic salts (N,N'-diphenacyl-[4,4'-dipyridinium] dibromide (DP) and N,N'-diphenacyl-1,2-bis-(4-pyridinium)ethane dibromide (DPE)) were used for chitosan functionalization to enhance its antimicrobial potential. Physico-chemical characterization of the newly synthesized derivatives (Ch-DP and Ch-DPE) was performed by elemental analysis, spectrometry (UV-Vis, FTIR), electrochemistry (OCP, CV), and electron microscopy (SEM) proving that the highest degree of functionalization was obtained for Ch-DP. The antimicrobial effect of chitosan functionalization was further tested in terms of its interaction with Listeria monocytogenes Scott A, and Staphylococcus aureus ATCC 25923, as Gram-positive bacteria and Escherichia coli ATCC 25922, as Gram-negative bacterium, respectively, showing that the Ch-DP had a good inhibitory activity compared with Ch-DPE.

Synthesis of phenylethanoid glycosides from acrylic esters of glucose and aryldiazonium salts via palladium-catalyzed cross-coupling reactions and evaluation of their anti-Alzheimer activity.

Cinnamic acid-containing sugar compounds such as phenylethanoid glycosides are widely present in nature and display various biological activities. In this work, the synthesis of trans-cinnamic acid containing phenylethanoid glycosides was achieved via palladium-catalyzed cross-coupling reactions between glycosyl acrylic esters and aryldiazonium salts. A wide range of functionalized aryldiazonium salts were successfully coupled with 6-O- and 4-O-acrylic esters of glucose under optimized conditions. The reactions proceeded at room temperature in the absence of additives and base. The desired products were obtained in good to excellent yields. Selected compounds from the library were screened for anti-Alzheimer activity, while compound 16 displayed significant inhibitory activities against butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) enzymes.

Self-Aggregation, Antimicrobial Activity and Cytotoxicity of Ester-Bonded Gemini Quaternary Ammonium Salts: The Role of the Spacer.

Five ester-bonded gemini quaternary ammonium surfactants C12-En-C12 (n = 2, 4, 6), with a flexible spacer group, and C12-Bm-C12 (m = 1, 2), with rigid benzene spacers, were synthesized via a two-step reaction and analyzed. Furthermore, the effects of the spacer structure, spacer length and polymerization degree on the self-aggregation, antimicrobial activity and cytotoxicity of C12-En-C12 and C12-Bm-C12 and their corresponding monomer N-dodecyl-N,N,N-trimethyl ammonium chloride DTAC were investigated. The results showed that C12-En-C12 and C12-Bm-C12 had markedly lower critical micellar concentration (CMC) values and lower surface tension than DTAC. Moreover, the CMC values of C12-En-C12 and C12-Bm-C12 decreased with increasing spacer length. In the case of equivalent chain length, the rigidity and steric hindrance of phenylene and 1,4-benzenediyl resulted in larger CMC values for C12-Bm-C12 than for C12-En-C12. The antibacterial ability of C12-En-C12 and C12-Bm-C12 was assessed using Escherichia coli (E. coli) and Staphylococcus albus (S. aureus) based on minimum inhibitory concentrations (MICs). Furthermore, C12-En-C12 and C12-Bm-C12 exhibited higher antimicrobial activity than DTAC and had stronger function toward S. aureus than E. coli. The antimicrobial activity was enhanced by increasing the spacer chain length and decreased with the increased rigidity of the spacers. The cytotoxic effects of C12-En-C12 and C12-Bm-C12 in cultured Hela cells were evaluated by the standard CCK8 method based on half-maximal inhibitory concentration (IC50). The cytotoxicity of C12-En-C12 and C12-Bm-C12 was significantly lower than alkanediyl-α,ω-bis(dimethyldodecylammonium) bromide surfactants and DTAC. The spacer structure and the spacer length could induce significant cytotoxic effects on Hela cells. These findings indicate that the five ester-bonded GQASs have stronger antibacterial activity and lower toxicity profile, and thus can be used in the pharmaceutical industry.

Research Advances on the Bioactivity of 1,2,3-Triazolium Salts.

1,2,3-Triazolium salts have demonstrated significant potential in the fields of medicine and agriculture, exhibiting exceptional antibacterial, antifungal, anticancer, and antileishmanial properties. Moreover, these salts can be utilized as additives or components to produce nano- and fiber-based materials with antibacterial properties. In this review, we summarize several synthetic strategies to obtain 1,2,3-triazolium salts and the structures of 1,2,3-triazolium derivatives with biological activities in the domains of pharmaceuticals, pesticides, and functional materials. Additionally, the structure-activity relationship (SAR) of 1,2,3-triazolium salts with different biological activities has been analyzed. Finally, this review presents the potential applications and prospects of 1,2,3-triazolium salts in the fields of agriculture, medicine, and industrial synthesis.

Antimicrobial dichloroisocyanurate-salts for controlled release of chlorine.

Sodium dichloroisocyanurate (Na-DCC), a disinfectant known for rapid decomposition in water, loses its effectiveness with complete release of free available chlorine (FAC) in under an hour. To overcome this, a series of chlorine rich transition metal complexes/tetrabutylammonium (TBA) salts of DCC, including 2Na[Cu(DCC)4], 2Na[Fe(DCC)4], 2Na[Co(DCC)4]·6H2O, 2Na[Ni(DCC)4]·6H2O, and TBA[DCC]·4H2O have been developed for extended chlorine release studies. The DCC-salts are synthesized based on the metathesis reaction process and are characterized using IR, NMR, CHN analyses, TGA,DSC, and Lovi bond colorimeter. The DCC-salts displayed poor water solubility and low decomposition chlorine release profile compared to Na-DCC. The water solubility of DCC-salts was reduced by a factor of 5.37 to 2500 compared to Na-DCC. The decomposition release of FAC from DCC-salts has been studied over time in comparison to Na-DCC in distilled water using a Lovi-bond colorimeter. DCC-salts displayed controlled FAC release profiles that varied from 1-13 days depending on the type of metal/TBA unit in them, whereas the parent Na-DCC displayed complete FAC release in about 0.91 h. For a proof of concept, the controlled release of metal from one of the DCC-metal complex salts, i.e., copper from the Cu-DCC is also investigated with a function of time in distilled water at RT. The 100% release of copper from Cu-DCC was identified over a period of 10 days. In addition, the applicability of DCC-salts as excellent antiviral agents against the bacteriophage T4 and antibacterial agents against Erwinia, Pseudomonas aeruginosa PA014 (Gram-negative), and Staphylococcus epidermidis (Gram-positive) compared to Na-DCC has been demonstrated.

Surface charge regulation of imidazolium salts/starch/carboxymethyl cellulose ternary polymer blend films for controlling antimicrobial performance and hydrophobicity.

Starch (SR)/carboxymethyl cellulose (CMC) based antimicrobial films have been widely applied in packaging field. As a high-effect antimicrobial agent, the surface charge of imidazolium salt plays an important effect on antimicrobial performances of starch/carboxymethyl cellulose. Here in, the surface charge of dodecyl imidazolium bromide salt was regulated via thiol-ene reaction. Furthermore, antibacterial films were prepared by mixing imidazolium salts with SR/CMC via solution casting method. Under the optimized ratio of CMC to SR, the antibacterial activity for as-prepared ternary polymer blend films was enhanced with the increasing of surface charge of imidazolium salt. The sample of ADSC-01 film with highest surface charge showed best antibacterial properties for E. coli and S. aureus with the inhibition zone of 3.20 cm and 3.00 cm, respectively. In addition, hydrophobic property exhibited similar positive correlation with the surface charge. Therefore, this work provides a new route to regulate the antibacterial activity of bio-based ternary polymer blend films in the packaging.

The Effect of Terbinafine and Its Ionic Salts on Certain Fungal Plant Pathogens.

Terbinafine, an inhibitor of squalene epoxidase in ergosterol biosynthesis, is chiefly utilized as an antifungal medication with potential uses in pesticide applications. This study explores the fungicidal efficacy of terbinafine against prevalent plant pathogens and confirms its effectiveness. To augment its water solubility, five ionic salts of terbinafine were synthesized by pairing them with organic acids. Among these salts, TIS 5 delivered the most impressive results, amplifying the water solubility of terbinafine by three orders of magnitude and lessening its surface tension to facilitate better dispersion during spraying. The in vivo experiments on cherry tomatoes showed that TIS 5 had a superior therapeutic activity compared to its parent compound and two commonly used broad-spectrum fungicides, pyraclostrobin and carbendazim. The results highlight the potential of terbinafine and its ionic salts, particularly TIS 5, for use as fungicides in agriculture due to their synergistic effects with furan-2-carboxylate.

New Insights into the Phototoxicity of Anthracene-Based Chromophores: The Chloride Salt Effect†.

Unraveling the causes underlying polycyclic aromatic hydrocarbon phototoxicity is an essential step in understanding the harmful effects of these compounds in nature. Toward this end, we have studied the DNA interactions and photochemistry of N1-(anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride in the presence and absence of NaF, KF, NaCl, KCl, NaBr, KBr, NaI, and KI (350 nm hν, pH 7.0). Exposing pUC19 plasmid to UV light in solutions containing 400 mM KCl formed significantly more direct strand breaks in DNA compared to no-salt control reactions. In contrast, NaCl increased DNA damage moderately, while the sodium(I) and potassium(I) fluoride, bromide, and iodide salts generally inhibited cleavage (I- > Br- > F-). A halide anion-induced heavy-atom effect was indicated by monitoring anthracene photodegradation and by employing the hydroxyl radical (•OH) probe hydroxyphenyl fluorescein (HPF). These studies revealed that among no-salt controls and the eight halide salts, only NaCl and KCl enabled the anthracene to photosensitize the production of high levels of DNA-damaging reactive oxygen species (ROS). Pre-irradiation of N1-(anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride at 350 nm increased the amounts of chloride salt-induced •OH detected by HPF in subsequent anthracene photoactivation experiments. Taking into consideration that •OH and other highly reactive ROS are extremely short-lived, this result suggests that the pre-irradiation step might lead to the formation of oxidized anthracene photoproducts that are exceedingly redox-active. The fluorometric probes HPF and Singlet Oxygen Sensor Green revealed that KCl concentrations ranging from 150 to 400 mM and from 100 to 400 mM, respectively, enhanced N1-(anthracen-9-ylmethyl)ethane-1,2-diaminium dichloride photosensitized •OH and singlet oxygen (1O2) production over no-salt controls. Considering the relatively high levels of Na+, K+, and Cl- ions that exist in the environment and in living organisms, our findings may be relevant to the phototoxic effects exhibited by anthracenes and other polycyclic hydrocarbons in vivo.