Synthesis and comparison of antileishmanial and cytotoxic activities of S-(−)-limonene benzaldehyde thiosemicarbazones with their R-(+)-analogues

Batista, Sabrina A. Almeida; Vandresen, Fábio; Falzirolli, Hugo; Britta, Elizandra Aparecida; Oliveira, Diogo Noin de; Catharino, Rodrigo Ramos; Gonçalves, Mateus A.; Ramalho, Teodorico C.; Porta, Felipe A. La; Nakamura, Celso V.; Silva, Cleuza C. da

doi:10.1016/j.molstruc.2018.11.017

Cited by 21 publications

(11 citation statements)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[44,45] Heteroatoms directly affect the reactivity of the target skeleton, activity (or toxicology) of the compounds, interactions between drugs target and different target inhibitors, as well as they are able to influence the metabolism and pharmacokinetics. [44] Another observation is the fact that the Sisomer compounds showed better results than the R-isomer compounds, [37,46] which means they presented low IC 50 and, consequently, greater antiproliferative activity.…”

Section: Limonene-derived Acylthiosemicarbazide Compounds Inhibited L...mentioning

confidence: 99%

“…In this regard, the antiprotozoal activity for both enantiomers were confirmed by in vitro and in vivo assays against promastigote and amastigote forms of L. amazonensis. [35][36][37][38] Thus, the objective of this work was the development and synthesis of a new series of limonene-acylthiosemicarbazide hybrids compounds that has antiproliferative activity against L. amazonensis and low cytotoxicity to mammalian cells.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Antiproliferative Activity and Ultrastructural Changes in Promastigote and Amastigote forms of Leishmania amazonensis Caused by Limonene‐Acylthiosemicarbazide Hybrids

Contato

Kaplum

Scariot

et al. 2023

Chemistry & Biodiversity

Self Cite

View full text Add to dashboard Cite

Leishmaniasis is a tropical zoonotic disease. It is found in 98 countries, with an estimated 1.3 million people being affected annually. During the life cycle, the Leishmania parasite alternates between promastigote and amastigote forms. The first line treatment for leishmaniasis are the pentavalent antimonials, such as N-methylglucamine antimoniate (Glucantime®) and sodium stibogluconate (Pentostam®). These drugs are commonly related to be associated with dangerous side effects such as cardiotoxicity, nephrotoxicity, hepatotoxicity, and pancreatitis. Considering these aspects, this work aimed to obtain a new series of limonene-acylthiosemicarbazides hybrids as an alternative for the treatment of leishmaniasis. For this, promastigotes, axenic amastigotes, and intracellular amasti-gotes of Leishmania amazonensis were used in the antiproliferative assay; J774-A1 macrophages for the cytotoxicity assay; and electron microscopy techniques were performed to analyze the morphology and ultrastructure of parasites. ATZÀ S-04 compound showed the best result in both tests. Its IC 50 , in promastigotes, axenic amastigotes and intracellular amastigotes was 0.35 � 0.08 μM, 0.49 � 0.06 μM, and 15.90 � 2.88 μM, respectively. Cytotoxicity assay determined a CC 50 of 16.10 � 1.76 μM for the same compound. By electron microscopy, it was observed that ATZÀ S-04 affected mainly the Golgi complex, in addition to morphological changes in promastigote forms of L. amazonensis.

show abstract

Section: Limonene-derived Acylthiosemicarbazide Compounds Inhibited L...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antiproliferative Activity and Ultrastructural Changes in Promastigote and Amastigote forms of Leishmania amazonensis Caused by Limonene‐Acylthiosemicarbazide Hybrids

Contato

Kaplum

Scariot

et al. 2023

Chemistry & Biodiversity

Self Cite

View full text Add to dashboard Cite

show abstract

“…In this regard, in the design of eugenol-ITC and cinnamaldehyde-ITC for malaria drug purposes, the substitution of tetrahydropyran, hydroxy, or acetate groups in the building block rings should be recommended to determine better anti-malaria potential. [52]. Synthesis of ITC in several natural compounds using amine groups has also been successfully formed with raw materials noscapine, bile acids, amino acids, and several aromatic compounds performed by transforming the-NH2 group into an ITC group [53].…”

Section: Physicochemical Pharmacokinetics and Bioactivities Of Compoundmentioning

confidence: 99%

Natural Isothiocyanate Anti-Malaria: Molecular Docking, Physicochemical, Adme, Toxicity and Synthetic Accessibility Study of Eugenol and Cinnamaldehyde

et al. 2021

View full text Add to dashboard Cite

Objective: This study aims to evaluate novel compounds of isothiocyanate (ITC) based on eugenol and cinnamaldehyde derivatives as the drug candidate of Plasmodium falciparum anti-malaria using in silico method, physicochemical, pharmacokinetics, toxicity, and synthetic accessibility prediction. This present study also describes molecular docking and pharmacoinformatics of natural ITC in Moringa oleifera leaves. Methods: A series of novel ITC compounds (3, 5, and 6) were designed and analyzed with a series of natural ITC compounds (7, 8, 9, 10) for P. falciparum anti-malaria. This research is descriptive qualitative and uses the reverse molecular docking method, proving the biological activity of compounds theoretically using software and database information. Results: Molecular docking study showed that compound 6 exhibits binding affinity (-5.3 Kcal/mol) on Van der Waals interaction with the residual active site (His159, Cys25) of cysteine protease. All designed ITC compounds are obeyed the Lipinski and Veber Rule, have a well-brain penetrant character and have a medium risk for mutagenic, tumorigenic, and reproductive prediction. They are also in the simple rate of synthetic accessibility (SA) estimation. In regards to natural ITCs, they all have better assay characteristics except the SA. Conclusion: Molecular docking, physicochemical, pharmacokinetic, and toxicity studies show that methyl eugenol isothiocyanate and cinnamaldehyde isothiocyanate are promising anti-malaria compounds. Substituents of hydroxy, acetate and tetrahydropyran groups in the building block ring are suggested for better in silico profiles enhancement.

show abstract

“…Epidemics worldwide caused by common antibiotic-resistant microorganisms susceptible to mutations, together with the lack of vaccines and efficient treatments, as well as their associated hospital infections, are a serious risk to global health, particularly in underdeveloped countries [1] , [2] , [3] , [4] . The pandemic caused by the outbreak of the new coronavirus (severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2)), responsible for the coronavirus disease (COVID)-19, led to the use of personal protective masks as a mandatory non-pharmacological measure in every country [5] , [6] , [7] , [8] .…”

Section: Introductionmentioning

confidence: 99%

Prospects of ZnS and ZnO as smart semiconductor materials in light-activated antimicrobial coatings for mitigation of severe acute respiratory syndrome coronavirus-2 infection

Benatto

Jesus

Castro

et al. 2023

Materials Today Communications

View full text Add to dashboard Cite

Synthesis and comparison of antileishmanial and cytotoxic activities of S-(−)-limonene benzaldehyde thiosemicarbazones with their R-(+)-analogues

Cited by 21 publications

References 48 publications

Antiproliferative Activity and Ultrastructural Changes in Promastigote and Amastigote forms of Leishmania amazonensis Caused by Limonene‐Acylthiosemicarbazide Hybrids

Antiproliferative Activity and Ultrastructural Changes in Promastigote and Amastigote forms of Leishmania amazonensis Caused by Limonene‐Acylthiosemicarbazide Hybrids

Natural Isothiocyanate Anti-Malaria: Molecular Docking, Physicochemical, Adme, Toxicity and Synthetic Accessibility Study of Eugenol and Cinnamaldehyde

Prospects of ZnS and ZnO as smart semiconductor materials in light-activated antimicrobial coatings for mitigation of severe acute respiratory syndrome coronavirus-2 infection

Contact Info

Product

Resources

About