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1.
Anim Sci J ; 95(1): e13917, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38323750

RESUMO

Allicin is a sulfur-containing compound extracted from raw garlic (Allium sativum L.). We compared the effect of allicin addition on growth performance, serum biochemical parameters, and rumen microbiota of goats compared to monensin. Twenty-four Anhui white goats were assigned randomly to one of three dietary treatments: 1) a basal diet (CON); 2) the basal diet with allicin addition at 750 mg per head per day (AC); 3) the basal diet with monensin addition at 30 mg per kg of diet (MS). Animals were fed for 8 weeks. Results showed the average daily gain, and feed efficiency was increased with allicin and monensin addition. Serum levels of IgG, total superoxide dismutase, and glutathione peroxidase were higher in the AC group than those in the CON and MS groups. The microbiota analysis revealed that monensin addition mainly affected genera related to carbohydrate and protein metabolism, and allicin mainly affected genera related to energy metabolism and intestinal health. In conclusion, allicin could improve growth performance and have advantages over monensin in improving the antioxidant capacity and immune function of goats. Allicin may be a potential alternative to monensin.


Assuntos
Dissulfetos , Alho , Microbiota , Ácidos Sulfínicos , Animais , Ração Animal/análise , Antioxidantes/metabolismo , Dieta/veterinária , Suplementos Nutricionais/análise , Cabras/metabolismo , Monensin/farmacologia , Rúmen/metabolismo
2.
Mol Nutr Food Res ; 68(5): e2300622, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38339885

RESUMO

SCOPE: Allicin, a product of enzymatic reaction when garlic is injured, plays an important role in maintaining glucose homeostasis in mammals. However, the effect of allicin on glucose homeostasis in the state of insulin resistance remains to be elucidated. This study investigates the effect of allicin on glucose metabolism using different muscle fibers in a chicken model. METHODS AND RESULTS: Day-old male Arbor Acres broilers are randomly divided into three groups and fed a basal diet supplemented with 0, 150, or 300 mg kg-1 allicin for 42 days. Results show that allicin improves the zootechnical performance of broilers at the finishing stage. The glucose loading test (2 g kg-1 body mass) indicates the regulatory role of allicin on glucose homeostasis. In vitro results demonstrate allicin increases glutathione (GSH) level and the expression of cystathionine γ lyase (CSE), leading to endogenous hydrogen sulfide (H2S) production in M. pectoralis major (PM) muscle-derived myotubes. Allicin stimulates adenosine monophosphate-activated protein kinase (AMPK) S-sulfhydration and AMPK phosphorylation to promote glucose uptake, which is suppressed in the presence of d,l-propargylglycine (PAG, a CSE inhibitor). CONCLUSION: This study demonstrates that allicin induces AMPK S-sulfhydration and AMPK phosphorylation to promote glucose uptake via the CSE/H2S system in a muscle fiber-dependent manner.


Assuntos
Galinhas , Dissulfetos , Sulfeto de Hidrogênio , Ácidos Sulfínicos , Masculino , Animais , Galinhas/metabolismo , Proteínas Quinases Ativadas por AMP , Fibras Musculares Esqueléticas/metabolismo , Glucose/metabolismo , Sulfeto de Hidrogênio/metabolismo , Mamíferos/metabolismo
3.
J Econ Entomol ; 117(1): 1-7, 2024 Feb 12.
Artigo em Inglês | MEDLINE | ID: mdl-37972274

RESUMO

Sulfuryl fluoride (SF) is a fumigant used to eliminate drywood termites (DWT: Kalotermitidae; Froggatt) and other structural pests. Because of its global warming potential, it has been suggested that SF be restricted as a greenhouse gas (GHG). We present an economic model to assess the net social cost of restricting SF. We consider 3 approaches to address DWT control- no treatment, allowing SF fumigation and localized treatments, and only local treatment. Each approach generates private and public benefits and costs. We estimate that the annual damage and home equity loss by DWT in California is US$4.5-16.8 billion without treatment. If fumigation is used on 20% of the houses and local treatments on the others, the combined social cost of treatment, damage, and GHG emissions are between US$1-US$2 billion annually. The annual cost of local treatments only would be between US$3.2 and US$4.9 billion. If the application of SF is severely restricted or banned, the social costs will increase between US$1.43 and US$4.31 billion annually. The implied cost per ton of CO2 eliminated is between US$624 and US$1,465, much above the price range of CO2 in other applications. The restriction/ban has significant equity and environmental effects, impacting low-income individuals living in rented properties and replacing damaged wood in housing will increase GHG emissions. We further recommend the continued use of SF until a comparable whole-structure alternative is developed that fits the parameters of our model.


Assuntos
Baratas , Isópteros , Praguicidas , Ácidos Sulfínicos , Animais , Dióxido de Carbono
4.
Naunyn Schmiedebergs Arch Pharmacol ; 397(2): 703-724, 2024 02.
Artigo em Inglês | MEDLINE | ID: mdl-37615709

RESUMO

The main objective of this review is to highlight the therapeutic potential of allicin, a defense molecule in garlic known for its diverse health benefits, and address the key challenges of its bioavailability and stability. The research further aims to evaluate various formulation strategies and nanotechnology-based delivery systems that can resolve these issues and improve allicin's clinical efficacy, especially in cancer therapy. We conducted a comprehensive review of the available literature and previous studies, focusing on the therapeutic properties of allicin, its bioavailability, stability issues, and novel formulation strategies. We assessed the mechanism of action of allicin in cancer, including its effects on signaling pathways, cell cycle, apoptosis, autophagy, and tumor development. We also evaluated the outcomes of both in vitro and in vivo studies on different types of cancers, such as breast, cervical, colon, lung, and gastric cancer. Despite allicin's significant therapeutic benefits, including cardiovascular, antihypertensive, cholesterol-lowering, antimicrobial, antifungal, anticancer, and immune-modulatory activity, its clinical utility is limited due to poor stability and unpredictable bioavailability. Allicin's bioavailability in the gastrointestinal tract is dependent on the activity of the enzyme alliinase, and its stability can be affected by various conditions like gastric acid and intestinal enzyme proteases. Recent advances in formulation strategies and nanotechnology-based drug delivery systems show promise in addressing these challenges, potentially improving allicin's solubility, stability, and bioavailability. Allicin offers substantial potential for cancer therapy, yet its application is hindered by its instability and poor bioavailability. Novel formulation strategies and nanotechnology-based delivery systems can significantly overcome these limitations, enhancing the therapeutic efficacy of allicin. Future research should focus on refining these formulation strategies and delivery systems, ensuring the safety and efficacy of these new allicin formulations. Clinical trials and long-term studies should be carried out to determine the optimal dosage, assess potential side effects, and evaluate their real-world applicability. The comparative analysis of different drug delivery approaches and the development of targeted delivery systems can also provide further insight into enhancing the therapeutic potential of allicin.


Assuntos
Dissulfetos , Neoplasias , Humanos , Disponibilidade Biológica , Ácidos Sulfínicos/uso terapêutico , Ácidos Sulfínicos/metabolismo , Ácidos Sulfínicos/farmacologia , Resultado do Tratamento , Neoplasias/tratamento farmacológico
5.
Int J Mol Sci ; 24(24)2023 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-38139348

RESUMO

Invasive fungal (IF) diseases are a leading global cause of mortality, particularly among immunocompromised individuals. The SARS-CoV-2 pandemic further exacerbated this scenario, intensifying comorbid IF infections such as mucormycoses of the nasopharynx. In the work reported here, it is shown that zygomycetes, significant contributors to mycoses, are sensitive to the natural product allicin. Inhibition of Mucorales fungi by allicin in solution and by allicin vapor was demonstrated. Mathematical modeling showed that the efficacy of allicin vapor is comparable to direct contact with the commercially available antifungal agent amphotericin B (ampB). Furthermore, the study revealed a synergistic interaction between allicin and the non-volatile ampB. The toxicity of allicin solution to human cell lines was evaluated and it was found that the half maximal effective concentration (EC50) of allicin was 25-72 times higher in the cell lines as compared to the fungal spores. Fungal allicin sensitivity depends on the spore concentration, as demonstrated in a drop test. This study shows the potential of allicin, a sulfur-containing defense compound from garlic, to combat zygomycete fungi. The findings underscore allicin's promise for applications in infections of the nasopharynx via inhalation, suggesting a novel therapeutic avenue against challenging fungal infections.


Assuntos
Infecções Fúngicas Invasivas , Mucorales , Micoses , Humanos , Antifúngicos/farmacologia , Antifúngicos/uso terapêutico , Mucorales/metabolismo , Anfotericina B/farmacologia , Ácidos Sulfínicos/farmacologia , Ácidos Sulfínicos/uso terapêutico , Dissulfetos/farmacologia , Micoses/tratamento farmacológico , Infecções Fúngicas Invasivas/tratamento farmacológico
6.
J Agric Food Chem ; 71(49): 19207-19220, 2023 Dec 13.
Artigo em Inglês | MEDLINE | ID: mdl-37943254

RESUMO

Garlic has been used worldwide as a spice due to its pungent taste and flavor-enhancing properties. As a main biologically active component of the freshly crushed garlic extracts, allicin (diallyl thiosulfinate) is converted from alliin by alliinase upon damaging the garlic clove, which has been reported to have many potent beneficial biological functions. In this work, allicin formation, stability, bioavailability, and metabolism process are examined and summarized. The biological functions of allicin and potential underlying mechanisms are reviewed and discussed, including antioxidation, anti-inflammation, antidiabetic, cardioprotective, antineurodegenerative, antitumor, and antiobesity effects. Novel delivery systems of allicin with enhanced stability, encapsulation efficiency, and bioavailability are also evaluated, such as nanoparticles, gels, liposomes, and micelles. This study could provide a comprehensive understanding of the physiochemical properties and health benefits of allicin, with great potential for further applications in the food and nutraceutical industries.


Assuntos
Dissulfetos , Alho , Disponibilidade Biológica , Suplementos Nutricionais , Alho/química , Ácidos Sulfínicos/química , Antioxidantes/metabolismo
7.
J Agric Food Chem ; 71(42): 15785-15795, 2023 Oct 25.
Artigo em Inglês | MEDLINE | ID: mdl-37830900

RESUMO

Acrylamide (AA), commonly formed in carbohydrate-rich thermally processed foods, exerts harmful effects on the kidney. Allicin, from crushed garlic cloves, exhibits strong biological activities. In the current study, the protection mechanisms of allicin against AA-caused nephrotoxicity were comprehensively examined using an in vivo rat model based on previous research that allicin plays a key role in improving renal function. The results showed that allicin attenuated histological changes of the kidney and ameliorated renal function. Damaged mitochondrial structures, upregulated voltage-dependent anion channel 1 expression, and decreased membrane potential and adenosine 5'-triphosphate levels were observed after AA treatment. Surprisingly, allicin notably reversed the adverse effects. Further, allicin effectively restored mitochondrial function via modulating mitochondrial biogenesis and dynamics, which might be associated with the upregulated expression of sirtuin 1 (SIRT1). Meanwhile, allicin dramatically activated the SIRT1 activity and subsequently inhibited p53 acetylation, prevented the translocation of cytochrome c to the cytoplasm, and reduced the caspase expression, thus further inhibiting mitochondrial apoptosis caused by AA. In summary, the relieving effect of allicin on AA-caused nephrotoxicity lies in its inhibition of mitochondrial dysfunction and mitochondrial apoptosis.


Assuntos
Acrilamida , Sirtuína 1 , Ratos , Animais , Sirtuína 1/genética , Sirtuína 1/metabolismo , Acrilamida/toxicidade , Acrilamida/metabolismo , Apoptose , Ácidos Sulfínicos/farmacologia , Dissulfetos/metabolismo , Rim/metabolismo , Mitocôndrias/metabolismo
8.
Zhongguo Zhong Yao Za Zhi ; 48(13): 3409-3420, 2023 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-37474979

RESUMO

Cardiovascular diseases(CVD) with high morbidity and mortality pose severe threats to human life. Allicin, a main active ingredient of garlic, possesses multiple pharmaceutical activities. It not only exerts cardioprotective effects but also prevents the risk factors for CVD. Allicin exerts cardioprotective effects via a variety of mechanisms, including inhibiting oxidative stress, apoptosis, autophagy, and inflammatory responses, regulating lipid metabolism and gut microbiota, inducing hydrogen sulfide production, and dilating vessels. Despite the valuable cardioprotective effects, the instability of allicin has hindered the basic research and clinical application. This paper reviews the progress in the cardioprotective effects and mechanisms of allicin in the last decade and summarizes the methods to improve the stability of allicin. In addition, this review provides a reference for further research and development of allicin in cardiovascular protection.


Assuntos
Doenças Cardiovasculares , Dissulfetos , Humanos , Coração , Ácidos Sulfínicos/farmacologia , Doenças Cardiovasculares/tratamento farmacológico , Doenças Cardiovasculares/prevenção & controle , Preparações Farmacêuticas
9.
Org Lett ; 25(24): 4478-4482, 2023 Jun 23.
Artigo em Inglês | MEDLINE | ID: mdl-37306334

RESUMO

Multicomponent reactions represent a powerful method for building complex molecules from structurally simple starting materials. Herein, we report a novel three-component radical-polar crossover reaction involving a tandem addition reaction of two different olefins, which is initiated by the selective addition of fluorosulfonyl radicals to alkyl alkenes. This tandem process provides facile and effective access to multiple functionalized aliphatic sulfonyl fluoride molecules. Further transformation of the products is also demonstrated.


Assuntos
Alcenos , Ácidos Sulfínicos
10.
Artigo em Inglês | MEDLINE | ID: mdl-37031569

RESUMO

Allicin is a major thiosulfinate found in garlic and other Allium sp. and it is responsible for their pungent aroma. It is formed during the tissue lysis of garlic, by the initial action of alliinase upon alliin, the major cysteine sulfoxide. Simultaneous detection of these two analytes is usually performed using HPLC. Contrary to the most important phytoconstituents in other samples, allicin is scarcely detected using the simple HPTLC technique, due to challenges caused by its unique structure, despite its simplicity and high needs in the analytical monitoring of the Allium sp. In this work, a cost-effective, simple, sensitive and accurate method was developed for the determination of allicin together with alliin, using HPTLC. Allicin is quickly pre-derivatised with cysteine in excess to the stable S-allylmercaptocysteine that is then simultaneously detected with alliin, using ninhydrin reagent. The method was validated in terms of accuracy (recoveries of 90-120 %), precision (RSD% of 4-12 %), selectivity, robustness, peak purity and limit of detection (LOD = 0.05 µg/band for allicin and LOD = 0.10 µg/band for alliin). The method was successfully applied using real Allium sp. samples and the results were in good agreement with HPLC data.


Assuntos
Cisteína , Alho , Alho/química , Ácidos Sulfínicos , Dissulfetos , Antioxidantes
11.
Methods Enzymol ; 683: 291-308, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-37087193

RESUMO

Among the biologically relevant reactive oxygen species (ROS), hydrogen peroxide (H2O2) has special properties. H2O2 can diffuse across membranes, has a low reactivity, and is very stable. Deprotonated cysteine residues in proteins can be oxidized by H2O2 into a highly reactive sulfenic acid derivative (-SOH), which can react with another cysteine to form a disulfide. Under higher oxidative stress the sulfenic acid undergo further oxidation to sulfinic acid (Cys-SO2H), which can subsequently be reduced. The sulfinic acid can be hyperoxidized to sulfonic acid (Cys-SO3H), whose reduction is irreversible. Formation of sulfenic acids can have a role in sensing oxidative stress, signal transduction, modulating localization and activity to regulate protein functions. Therefore, there is an emerging interest in trying to understand the pool of proteins that result in these sorts of modification in response to oxidative stress. This is known as the sulfenome and several approaches have been developed in animal and plant cells to analyze the sulfenome under different stress responses. These approaches can be proteomic, molecular, immunological (i.e., antibodies), or expressing genetically encoded probes that specifically react to sulfenic modifications. In this chapter, we describe an additional approach that allows visualization of sulfenic modification in vivo. This is newly developed fluorescent probe DCP-Rho1 can be implemented in any plant cell to analyze the sulfenic modification.


Assuntos
Cisteína , Ácidos Sulfênicos , Animais , Ácidos Sulfênicos/química , Cisteína/química , Corantes Fluorescentes , Células Vegetais/metabolismo , Peróxido de Hidrogênio/química , Proteômica , Ácidos Sulfínicos , Proteínas/química , Oxirredução
12.
Molecules ; 28(7)2023 Mar 29.
Artigo em Inglês | MEDLINE | ID: mdl-37049805

RESUMO

SuFEx chemistry is based on the unique reactivity of the sulfonyl fluoride group with a range of nucleophiles. Accordingly, sulfonyl fluorides label multiple nucleophilic amino acid residues, making these reagents popular in both chemical biology and medicinal chemistry applications. The reactivity of sulfonyl fluorides nominates this warhead chemotype as a candidate for an external, activation-free general labelling tag. Here, we report the synthesis and characterization of a small sulfonyl fluoride library that yielded the 3-carboxybenzenesulfonyl fluoride warhead for tagging tractable targets at nucleophilic residues. Based on these results, we propose that coupling diverse fragments to this warhead would result in a library of sulfonyl fluoride bits (SuFBits), available for screening against protein targets. SuFBits will label the target if it binds to the core fragment, which facilitates the identification of weak fragments by mass spectrometry.


Assuntos
Aminoácidos , Fluoretos , Fluoretos/química , Aminoácidos/química , Ácidos Sulfínicos/química , Espectrometria de Massas
13.
Int J Mol Sci ; 24(4)2023 Feb 14.
Artigo em Inglês | MEDLINE | ID: mdl-36835218

RESUMO

Dairy farming is the most important economic activity in animal husbandry. Mastitis is the most common disease in dairy cattle and has a significant impact on milk quality and yield. The natural extract allicin, which is the main active ingredient of the sulfur-containing organic compounds in garlic, has anti-inflammatory, anticancer, antioxidant, and antibacterial properties; however, the specific mechanism underlying its effect on mastitis in dairy cows needs to be determined. Therefore, in this study, whether allicin can reduce lipopolysaccharide (LPS)-induced inflammation in the mammary epithelium of dairy cows was investigated. A cellular model of mammary inflammation was established by pretreating bovine mammary epithelial cells (MAC-T) with 10 µg/mL LPS, and the cultures were then treated with varying concentrations of allicin (0, 1, 2.5, 5, and 7.5 µM) added to the culture medium. MAC-T cells were examined using RT-qPCR and Western blotting to determine the effect of allicin. Subsequently, the level of phosphorylated nuclear factor kappa-B (NF-κB) was measured to further explore the mechanism underlying the effect of allicin on bovine mammary epithelial cell inflammation. Treatment with 2.5 µM allicin considerably decreased the LPS-induced increase in the levels of the inflammatory cytokines interleukin-1ß (IL-1ß), interleukin-6 (IL-6), interleukin-8 (IL-8), and tumor necrosis factor-α (TNF-α) and inhibited activation of the NOD-like receptor protein 3 (NLRP3) inflammasome in cow mammary epithelial cells. Further research revealed that allicin also inhibited the phosphorylation of inhibitors of nuclear factor kappa-B-α (IκB-α) and NF-κB p65. In mice, LPS-induced mastitis was also ameliorated by allicin. Therefore, we hypothesize that allicin alleviated LPS-induced inflammation in the mammary epithelial cells of cows probably by affecting the TLR4/NF-κB signaling pathway. Allicin will likely become an alternative to antibiotics for the treatment of mastitis in cows.


Assuntos
Dissulfetos , Mastite Bovina , NF-kappa B , Ácidos Sulfínicos , Animais , Bovinos , Feminino , Camundongos , Dissulfetos/uso terapêutico , Células Epiteliais/metabolismo , Inflamação/metabolismo , Interleucina-6/metabolismo , Lipopolissacarídeos , Mastite Bovina/tratamento farmacológico , NF-kappa B/metabolismo , Transdução de Sinais , Ácidos Sulfínicos/uso terapêutico , Receptor 4 Toll-Like/metabolismo
14.
BMC Genomics ; 24(1): 87, 2023 Feb 24.
Artigo em Inglês | MEDLINE | ID: mdl-36829121

RESUMO

BACKGROUND: Facility cultivation is widely applied to meet the increasing demand for high yield and quality, with light intensity and light quality being major limiting factors. However, how changes in the light environment affect development and quality are unclear in garlic. When garlic seedlings are grown, they can also be exposed to blanching culture conditions of darkness or low-light intensity to ameliorate their appearance and modify their bioactive compounds and flavor. RESULTS: In this study, we determined the quality and transcriptomes of 14-day-old garlic and blanched garlic seedlings (green seedlings and blanched seedlings) to explore the mechanisms by which seedlings integrate light signals. The findings revealed that blanched garlic seedlings were taller and heavier in fresh weight compared to green garlic seedlings. In addition, the contents of allicin, cellulose, and soluble sugars were higher in the green seedlings. We also identified 3,872 differentially expressed genes between green and blanched garlic seedlings. The Kyoto Encyclopedia of Genes and Genomes analysis suggested enrichment for plant-pathogen interactions, phytohormone signaling, mitogen-activated protein kinase signaling, and other metabolic processes. In functional annotations, pathways related to the growth and formation of the main compounds included phytohormone signaling, cell wall metabolism, allicin biosynthesis, secondary metabolism and MAPK signaling. Accordingly, we identified multiple types of transcription factor genes involved in plant-pathogen interactions, plant phytohormone signaling, and biosynthesis of secondary metabolites among the differentially expressed genes between green and blanched garlic seedlings. CONCLUSIONS: Blanching culture is one facility cultivation mode that promotes chlorophyll degradation, thus changing the outward appearance of crops, and improves their flavor. The large number of DEGs identified confirmed the difference of the regulatory machinery under two culture system. This study increases our understanding of the regulatory network integrating light and darkness signals in garlic seedlings and provides a useful resource for the genetic manipulation and cultivation of blanched garlic seedlings.


Assuntos
Alho , Alho/genética , Reguladores de Crescimento de Plantas/metabolismo , Dissulfetos/metabolismo , Ácidos Sulfínicos , Transcriptoma , Plântula/genética , Regulação da Expressão Gênica de Plantas
15.
Environ Sci Technol ; 57(10): 4180-4186, 2023 03 14.
Artigo em Inglês | MEDLINE | ID: mdl-36848521

RESUMO

Perfluorooctane sulfonyl fluoride (PFOSF) and perfluorohexane sulfonyl fluoride (PFHxSF) were listed as persistent organic pollutants by the Stockholm Convention in 2009 and 2022, respectively. To date, their concentrations in environmental samples have not been reported due to the lack of sensitive methods. Herein, a novel chemical derivatization was developed for quantitative analysis of trace PFOSF and PFHxSF in soil by derivatizing them to the corresponding perfluoroalkane sulfinic acids. The method showed good linearity in the range from 25 to 500 ng L-1 with correlation coefficients (R2) better than 0.99. The detection limit of PFOSF in soil was 0.066 ng g-1 with recoveries in the range of 96-111%. Meanwhile, the detection limit of PFHxSF was 0.072 ng g-1 with recoveries in the range of 72-89%. Simultaneously, perfluorooctane sulfonic acid (PFOS) and perfluorohexane sulfonic acid (PFHxS) were also detected accurately without being affected by the derivative reaction. By applying this method in an abandoned fluorochemical manufacturing facility, PFOSF and PFHxSF were successfully detected at concentrations ranging from 2.7 to 357 ng g-1 and 0.23 to 26 ng g-1 dry weight, respectively. It is very interesting that 2 years after factory relocation, there still exists high concentrations of PFOSF and PFHxSF, which is of concern.


Assuntos
Fluorocarbonos , Ácidos Sulfínicos , Espectrometria de Massas em Tandem/métodos , Solo , Cromatografia Líquida , Fluorocarbonos/análise
16.
Mol Pharm ; 20(2): 1061-1071, 2023 02 06.
Artigo em Inglês | MEDLINE | ID: mdl-36638322

RESUMO

Molecules that feature a sulfonyl fluoride (SO2F) moiety have been gaining increasing interest due to their unique reactivity and potential applications in synthetic chemistry, medicinal chemistry, and other biological uses. A particular interest is towards 18F-radiochemistry where sulfonyl fluorides can be used as a method to radiolabel biomolecules or can be used as radiofluoride relay reagents that facilitate radiolabeling of other molecules. The low metabolic stability of sulfonyl fluoride S-F bonds, however, presents an issue and limits the applicability of sulfonyl fluorides. The aim of this work was to increase understanding of what features contribute to the metabolic instability of the S-F bond in model aryl sulfonyl fluorides and identify approaches to increasing sulfonyl fluoride stability for 18F-radiochemistry and other medicinal, synthetic chemistry and biological applications. To undertake this, 14 model aryl sulfonyl fluorides compounds with varying functional groups and substitution patterns were investigated, and their stabilities were examined in various media, including phosphate-buffered saline and rat serum as a model for biological conditions. The results indicate that both electronic and steric factors affect the stability of the S-F bond, with the 2,4,6-trisubstituted model aryl sulfonyl fluorides examined displaying the highest in vitro metabolic stability.


Assuntos
Química Farmacêutica , Fluoretos , Animais , Ratos , Radioquímica/métodos , Fluoretos/química , Ácidos Sulfínicos
17.
Crit Rev Food Sci Nutr ; 63(25): 7722-7748, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-35293826

RESUMO

Allicin, a thiosulfonate extract from freshly minced garlic, has been reported to have various biological effects on different organs and systems of animals and human. It can reduce oxidative stress, inhibit inflammatory response, resist pathogen infection and regulate intestinal flora. In addition, dozens of studies also demonstrated allicin could reduce blood glucose level, protect cardiovascular system and nervous system, and fight against cancers. Allicin was widely used in disease prevention and health care. However, more investigations on human cohort study are needed to verify the biological or clinical effects of allicin in the future. In this review, we summarized the biological effects of allicin from previous outstanding and valuable studies and provided useful information for future studies on the health effects of allicin.


Assuntos
Dissulfetos , Alho , Animais , Humanos , Dissulfetos/farmacologia , Ácidos Sulfínicos/farmacologia , Ácidos Sulfínicos/uso terapêutico , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico
18.
J Agric Food Chem ; 71(1): 535-545, 2023 Jan 11.
Artigo em Inglês | MEDLINE | ID: mdl-36574498

RESUMO

Cancer is one of the most serious malignant diseases, and chemotherapy is cancer's main clinical treatment method. However, chemotherapy inevitably produces drug resistance, and side effects accompany them. Adjuvant therapy is an effective way to enhance chemotherapeutic drug sensitivity and reduce side effects. This study found allicin, garlic's active ingredient, is an inhibitor of transmembrane protein 16A (TMEM16A), a novel drug target of lung adenocarcinoma. Allicin concentration-dependently inhibited TMEM16A currents with an IC50 of 24.35 ± 4.14 µM. Allicin thiosulfinate moieties bound with R535A/E624A/E633A residues of TMEM16A blocked the ion transport function and downregulated TMEM16A protein expression affecting the mitogen-activated protein kinase signal transduction. Then, allicin reduced the viability and migration of LA795 cells, and induced cell apoptosis. Moreover, multitarget combination administration results indicated that the therapeutic effect of 3.56 mg/kg allicin and 3 mg/kg cisplatin combined administration was superior to the superposition of the two drugs alone, demonstrating that the anticancer effects of allicin and cisplatin were synergistic. In addition, low-concentration combined administration also avoided the side effects of cisplatin in mice. Based on the good tumor suppressor effect and high biosafety of allicin and cisplatin combination in vivo, allicin can be used for food adjuvant therapy of cisplatin chemotherapy.


Assuntos
Cisplatino , Neoplasias Pulmonares , Animais , Camundongos , Anoctamina-1 , Neoplasias Pulmonares/dietoterapia , Neoplasias Pulmonares/tratamento farmacológico , Ácidos Sulfínicos/farmacologia
19.
Pak J Pharm Sci ; 35(4(Special)): 1181-1190, 2022 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-36218096

RESUMO

Garlic (known as; Allium sativum) is one of the most widely used medicinal plants in the world. Allicin is the major agent of garlic that gives its known pharmacological activities as anti-inflammatory, antibacterial, antifungal, antiviral and antioxidant agent. It could be extracted from bulbs of Allium sativum by water extraction to give allicin in low yield therefore other better methods were followed for extraction such as ultrasonic-assisted method that gives good yield. Attempts to optimize allicin extraction were found with sliced garlic at 25 °C for 90 minute of extraction for maximum yield (112µg/mL). Allicin was subjected to its evaluation as anti-herpetic against herpes simplex virus 1 (HSV-1) and exhibited a promising activity compared to acyclovir which was used as a reference standard. On the other hand, a novel synthetic amantadine derivative was evaluated as antiherpetic agent and prepared from the reaction of 2-thiouracil-5-sulphonyl chloride with amantadine hydrochloride in pyridine. The synergestic effect of allicin and the amantadine derivative was evaluated against HSV-1, using both in silico molecular docking as for dynamics simulations. Thymidine kinase target enzyme was chosen to analyze any possible interactions, as well as any protein-ligand stability. Furthermore, some of properties of the potential HSV-1 thymidine kinase target inhibitor of the amantadine derivative were analyzed.


Assuntos
Alho , Herpesvirus Humano 1 , Aciclovir/farmacologia , Amantadina , Antibacterianos , Antifúngicos , Antioxidantes , Antivirais/farmacologia , Cloretos , Dissulfetos , Ligantes , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Extratos Vegetais/farmacologia , Piridinas , Ácidos Sulfínicos , Tiouracila , Timidina Quinase , Água
20.
Org Biomol Chem ; 20(38): 7640-7644, 2022 10 05.
Artigo em Inglês | MEDLINE | ID: mdl-36124914

RESUMO

The late-stage functionalization of drugs and natural products has been identified as a promising approach to accelerate the discovery of new bioactive compounds. Due to the presence of the "Magic Methyl Effect", the direct deoxymethylation of phenolic hydroxyl groups, which are widespread in natural molecules, is a challenging task. A mild and rapid strategy for direct phenol deoxymethylation under metal catalysis using SO2F2 is described in this paper, while good functional group tolerance and high chemoselectivity allow this strategy to be one of the powerful tools for LSF. The power of this new platform is showcased through gram-scale and orthogonal experiments.


Assuntos
Produtos Biológicos , Fenóis , Catálise , Fenol , Ácidos Sulfínicos
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