Bioisosteric modification on benzylidene‐carbonyl compounds improved the drug‐likeness and maintain the antifungal activity against Sporothrix brasiliensis

2021 ◽  
Author(s):  
Stefanie Bressan Waller ◽  
Marlete Brum Cleff ◽  
Márcia Kutscher Ripoll ◽  
Mário Carlos Araújo Meireles ◽  
Márcio Ferrarini ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Carbonyl Compounds ◽  
Sporothrix Brasiliensis

Synthesis and Antifungal Activity of Coumarins Derivatives Against Sporothrix spp.

2018 ◽  
Vol 18 (2) ◽  
pp. 164-171 ◽  
Author(s):  
Luana da S.M. Forezi ◽  
Luana Pereira Borba-Santos ◽  
Mariana F.C. Cardoso ◽  
Vitor F. Ferreira ◽  
Sonia Rozental ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Antifungal Agents ◽  
Sporothrix Schenckii ◽  
Public Health Problem ◽  
Domestic Animals ◽  
Coumarin Derivatives ◽  
Sporothrix Brasiliensis ◽  
Synthetic Routes ◽  
Effective Drugs

Sporotrichosis is a serious public health problem in Brazil that affects human patients and domestic animals, mainly cats. Thus, the search for new antifungal agents is required also due to the emergence and to the lack of effective drugs available in the therapeutic arsenal. The aim of this study was to evaluate the in vitro antifungal profile of two synthetic series of coumarin derivatives against Sporothrix schenckii and Sporothrix brasiliensis. The three-components synthetic routes used for the preparation of coumarin derivatives have proved to be quite efficient and compounds 16 and 17 have been prepared in good yields. The inhibitory activity of nineteen synthetic coumarins derivatives 16a-i and 17a-j were evaluated against Sporothrix spp. yeasts and the most potent compounds were 16b and 17i. However, according to concentrations able to inhibit (minimum inhibitory concentrations) and kill (minimum fungicidal concentrations) the cells, 17i was more effective than 16b against Sporothrix spp. Thus, 17i exhibited good antifungal activity against S. brasiliensis and S. schenckii, suggesting that it is an important scaffold for the development of novel antifungal agents.

Antifungal activity of different molecular weight chitosans against planktonic cells and biofilm of Sporothrix brasiliensis

2020 ◽  
Vol 143 ◽  
pp. 341-348 ◽  
Author(s):  
Lana Glerieide Silva Garcia ◽  
Glaucia Morgana de Melo Guedes ◽  
Xhaulla Maria Quariguasi Cunha Fonseca ◽  
Waldemiro Aquino Pereira-Neto ◽  
Débora Souza Collares Maia Castelo-Branco ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Antifungal Activity ◽  
Planktonic Cells ◽  
Sporothrix Brasiliensis ◽  
Different Molecular Weight

scholarly journals In vitro and in vivo antifungal activity of buparvaquone against Sporothrix brasiliensis

2021 ◽  
Author(s):  
Luana Pereira Borba-Santos ◽  
Thayná Lopes Barreto ◽  
Taissa Vila ◽  
Kung Darh Chi ◽  
Fabiana dos Santos Monti ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Mammalian Cells ◽  
Plasma Membranes ◽  
Galleria Mellonella ◽  
Fungal Growth ◽  
Sporothrix Brasiliensis ◽  
First Choice ◽  
Altered Cell

Sporotrichosis has become an important zoonosis in Brazil and Sporothrix brasiliensis is the primary species transmitted by cats. Improvement of animal treatment will help control and limit the spread and geographic expansion of sporotrichosis. Accordingly, buparvaquone, an antiprotozoal hydroxynaphthoquinone agent marketed as Butalex®, was evaluated in vitro and in vivo against feline-borne isolates of S. brasiliensis . Buparvaquone inhibited in vitro fungal growth at concentrations 4-fold lower than itraconazole (the first-choice antifungal used for sporotrichosis) and was 408 times more selective for S. brasiliensis than mammalian cells. Yeasts treated with a subinhibitory concentration of buparvaquone exhibited mitochondrial dysfunction, ROS and neutral lipid accumulation, and impaired plasma membranes. Also, scanning electron microscopy images revealed buparvaquone altered cell wall integrity and induced cell disruption. I n vivo experiments in a Galleria mellonella model revealed that buparvaquone (single dose of 5 mg/kg) is more effective than itraconazole against infections with S. brasiliensis yeasts. Combined, our results indicate that buparvaquone has a great in vitro and in vivo antifungal activity against S. brasiliensis , revealing the potential application of this drug as an alternative treatment for feline sporotrichosis.

scholarly journals Synthesis and Biological Activity of Novel Zinc-Itraconazole Complexes in Protozoan Parasites and Sporothrix spp.

2020 ◽  
Vol 64 (5) ◽  
Author(s):  
Jose Aleixo de Azevedo-França ◽  
Renato Granado ◽  
Sara Teixeira de Macedo Silva ◽  
Gabrielle dos Santos-Silva ◽  
Sandra Scapin ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Sporothrix Schenckii ◽  
Parasitic Diseases ◽  
Protozoan Parasites ◽  
Content Type ◽  
Sporothrix Brasiliensis ◽  
Low Concentrations ◽  
Elemental Analyses ◽  
Zinc Salts ◽  
Medical Importance

ABSTRACT The new complexes Zn(ITZ)2Cl2 (1) and Zn(ITZ)2(OH)2 (2) were synthetized by a reaction of itraconazole with their respective zinc salts under reflux. These Zn-ITZ complexes were characterized by elemental analyses, molar conductivity, mass spectrometry, 1H and 13C{1H} nuclear magnetic resonance, and UV-vis and infrared spectroscopies. The antiparasitic and antifungal activity of Zn-ITZ complexes was evaluated against three protozoans of medical importance, namely, Leishmania amazonensis, Trypanosoma cruzi, and Toxoplasma gondii, and two fungi, namely, Sporothrix brasiliensis and Sporothrix schenckii. The Zn-ITZ complexes exhibited a broad spectrum of action, with antiparasitic and antifungal activity in low concentrations. The strategy of combining zinc with ITZ was efficient to enhance ITZ activity since Zn-ITZ-complexes were more active than the azole alone. This study opens perspectives for future applications of these Zn-ITZ complexes in the treatment of parasitic diseases and sporotrichosis.

Benzylidene-carbonyl compounds are active against itraconazole-susceptible and itraconazole-resistant Sporothrix brasiliensis

2020 ◽  
Vol 65 (6) ◽  
pp. 1033-1038
Author(s):  
Stefanie Bressan Waller ◽  
Marlete Brum Cleff ◽  
Márcia Kutscher Ripoll ◽  
Mário Carlos Araújo Meireles ◽  
Marina Themoteo Varela ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Sporothrix Brasiliensis

scholarly journals Chemical and cytotoxic analyses of three varieties of Brazilian propolis (green propolis, jataí propolis and brown propolis) and its anti-Sporothrix brasiliensis in vitro activity

2019 ◽  
Vol 71 (3) ◽  
pp. 819-827
Author(s):  
C.M. Peter ◽  
S.B. Waller ◽  
T. Picoli ◽  
L.G. Osório ◽  
J.L. Zani ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
High Performance ◽  
Inhibitory Concentration ◽  
Chemical Compounds ◽  
Coumaric Acid ◽  
Minimum Fungicidal Concentration ◽  
Sporothrix Brasiliensis ◽  
Ethanolic Extraction ◽  
Brazilian Propolis

ABSTRACT In this study, we described the antifungal activity of three Brazilian propolis extracts: brown, green and from jataí bees against Sporothrix brasiliensis. The extracts were obtained from ethanolic extraction and their chemical composition was determined by high-performance liquid chromatography coupled to mass spectrometry. The cellular toxicity was measured in MDBK (Madin-Darby Bovine Kidney) cells and quantified by the MTT assay (3- (4,5 dimethylthiazol-2yl -2,5-diphenyl-2H bromine tetrazolato). For antifungal activity, the minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) were determined by broth microdilution. The results showed that cell toxicity was not observed at lower concentrations (0.097 to 0.39μg/ml) for all extracts in comparison to cell control. Among the chemical compounds identified, caffeic acid, p-coumaric acid, chlorogenic acid, ferulic acid and rutin were quantified. In antifungal activity, green and jataí did not exhibit activity against the isolates (MIC and MFC greater than 0.78mg/ml). However, all isolates of S. brasiliensis were sensitive to brown propolis (MIC of 0.09 to 0.78mg/ml), including the standard strain (P<0.001). Among the Brazilian propolis studied, the brown propolis showed activity against the S. brasiliensis isolates and more studies should be undertaken in order to evaluate its promising use in the treatment of sporotrichosis.

scholarly journals Antifungal Activity of Acylhydrazone Derivatives against Sporothrix spp.

2021 ◽  
Vol 65 (5) ◽  
Author(s):  
Jhon Jhamilton Artunduaga Bonilla ◽  
Leandro Honorato ◽  
Krupanandan Haranahalli ◽  
Isabella Dib Ferreira Gremião ◽  
Sandro Antonio Pereira ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Cell Cycle Progression ◽  
Treatment Options ◽  
Sporothrix Schenckii ◽  
Fungal Species ◽  
Sporothrix Brasiliensis ◽  
Drug Of Choice ◽  
Transmission Electron ◽  
Itraconazole Treatment

ABSTRACT Sporotrichosis is an emerging mycosis caused by members of the genus Sporothrix. The disease affects humans and animals, particularly cats, which play an important role in zoonotic transmission. Feline sporotrichosis treatment options include itraconazole (ITC), potassium iodide, and amphotericin B, drugs usually associated with deleterious adverse reactions and refractoriness in cats, especially when using ITC. Thus, affordable, nontoxic, and clinically effective anti-Sporothrix agents are needed. Recently, acylhydrazones (AH), molecules targeting vesicular transport and cell cycle progression, exhibited a potent antifungal activity against several fungal species and displayed low toxicity compared to the current drugs. In this work, the AH derivatives D13 and SB-AF-1002 were tested against Sporothrix schenckii and Sporothrix brasiliensis. MICs of 0.12 to 1 μg/ml were observed for both species in vitro. D13 and SB-AF-1002 showed an additive effect with itraconazole. Treatment with D13 promoted yeast disruption with the release of intracellular components, as confirmed by transmission electron microscopy of S. brasiliensis exposed to the AH derivatives. AH-treated cells displayed thickening of the cell wall, discontinuity of the cell membrane, and an intense cytoplasmic degeneration. In a murine model of sporotrichosis, treatment with AH derivatives was more efficient than ITC, the drug of choice for sporotrichosis. Our results expand the antifungal broadness of AH derivatives and suggest that these drugs can be exploited to combat sporotrichosis.

scholarly journals Review on Synthesis of Thiazole Derivatives from α-Halo- ketones and Thiourea or N-Substituted Thiourea

2020 ◽  
pp. 221-225
Author(s):  
Sagar Ramdas Shrimandilkar
Keyword(s):  
Antifungal Activity ◽  
Carbonyl Compounds ◽  
Heterocyclic Compounds ◽  
Scientific Literature ◽  
Research Work ◽  
Synthetic Approach ◽  
Important Class ◽  
Thiazole Derivatives ◽  
Thiourea Derivatives ◽  
Methods Of Synthesis

Thiazole represents important class of heterocyclic compounds. Thiazole and its derivatives have been reported to possess antitubercular, antibacterial, anti-inflammatory, anticancer, antifungal activity. Several methods of synthesis of thiazole derivatives have been reported, but most widely used synthetic approach to obtained thiazole derivatives is Hantzsch process. It involved synthesis of thiazole derivative from ?-halo-carbonyl compounds and thiourea or thiourea derivatives. This review mainly focuses on the research work reported in the scientific literature on the different procedures of synthesis of 2-amino thiazole and their derivatives.

Antifungal activity of a flavonoid-rich fraction from Costus spicatus leaves against dermatophytes

Planta Medica ◽  
2008 ◽  
Vol 74 (09) ◽  
Author(s):  
DN Silva ◽  
MJ Gonçalves ◽  
MT Amaral ◽  
MT Batista
Keyword(s):  
Antifungal Activity
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