Biological activity of Morita-Baylis-Hillman adduct homodimers in L. infantum and L. amazonensis: anti-Leishmania activity and cytotoxicity

Rocha, Juliana da Câmara; Rodrigues, Klinger Antônio da França; Néris, Patrícia Lima do Nascimento; Silva, Larisse Virgolino da; Almeida, Fernanda Silva; Lima, Viviane Silva; Peixoto, Rephany Fonseca; Rocha, Juliene da Câmara; Azevedo, Fátima de Lourdes Assunção Araújo de; Veras, Robson Cavalcante; Medeiros, Isac A.; Silva, Wagner André Vieira da; Lima-Júnior, Cláudio Gabriel; Vasconcellos, Mário Luiz Araújo de Almeida; Amaral, Ian P.G.; Oliveira, Márcia Rosa de; Keesen, Tatjana Souza Lima

doi:10.1007/s00436-019-06403-w

Cited by 10 publications

(6 citation statements)

References 31 publications

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“…The main spot was collected as product in pure form and it's purity was confirmed through spectral analysis. 7,9,17 The experimental 1 H NMR and mass spectrum is in good agreement with previous studies 18,19 and hence proves the purity of the final MBHA synthesized using this procedure. Preparation of the MBHA is shown below in scheme 1.…”

Section: Synthesis Of Mbha (Methyl 2-((4-chlorophenyl) (Hydroxy)methy...supporting

confidence: 89%

Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Nisar¹,

Ishfaq

Ali³

et al. 2022

ACSi

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Taking cognizance of the medicinal significance and diverse functions of synthetic Morita-Baylis-Hillman adducts (MBHA), the title ligand was synthesized and purified through column chromatography. Cr+3, Mn+2, Co+3, Ni+2, Cu+2 complexes of the ligand were synthesized under basic conditions, subjected to characterization through spectral analyses and verified with the IR spectrum that was generated computationally by the DFT B3LYP method, with 6-311++ G (d,p) basis set and Hartree Fock (HF) B3LYP method in conjunction with 3-21G(d,p) basis set. Powder XRD helped to testify crystals of the complexes. Moreover, the antibacterial, and antioxidant characteristics of MBHA and its complexes were also established. All of them were found to be active antioxidants. The antibacterial activities, examined against S. aureus, E. coli, B. pumilis and S. typhi have revealed that its Cobalt complex has an excellent potential to act against all of them. Hence, these compounds maybe having potentialities for the discovery of new, cheaper and efficient drugs against various infectious diseases. The study also uncovers the first example of utilization of MBHA towards metal complex formation.

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Section: Synthesis Of Mbha (Methyl 2-((4-chlorophenyl) (Hydroxy)methy...supporting

confidence: 89%

Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Nisar¹,

Ishfaq

Ali³

et al. 2022

ACSi

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“…Flow cytometry with annexin V-FITC and PI staining was used to identify cell death stages and pathways in parasites after treatment with LQOFG-2, LQOFG-6, and LQOFG-7. Annexin V and PI discriminate between early- (AV+, PI−) and late-apoptotic cells (AV+, PI+) as well as necrotic (AV−, PI+) and live cells (AV–, PI−) [ 31 , 32 ].…”

Section: Resultsmentioning

confidence: 99%

Leishmanicidal Activity of Guanidine Derivatives against Leishmania infantum

et al. 2023

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Leishmaniasis is a neglected tropical infectious disease with thousands of cases annually; it is of great concern to global health, particularly the most severe form, visceral leishmaniasis. Visceral leishmaniasis treatments are minimal and have severe adverse effects. As guanidine-bearing compounds have shown antimicrobial activity, we analyzed the cytotoxic effects of several guanidine-bearing compounds on Leishmania infantum in their promastigote and amastigote forms in vitro, their cytotoxicity in human cells, and their impact on reactive nitrogen species production. LQOFG-2, LQOFG-6, and LQOFG-7 had IC50 values of 12.7, 24.4, and 23.6 µM, respectively, in promastigotes. These compounds exhibited cytotoxicity in axenic amastigotes at 26.1, 21.1, and 18.6 µM, respectively. The compounds showed no apparent cytotoxicity in cells from healthy donors. To identify mechanisms of action, we evaluated cell death processes by annexin V and propidium iodide staining and nitrite production. Guanidine-containing compounds caused a significant percentage of death by apoptosis in amastigotes. Independent of L. infantum infection, LQOFG-7 increased nitrite production in peripheral blood mononuclear cells, which suggests a potential mechanism of action for this compound. Therefore, these data suggest that guanidine derivatives are potential anti-microbial molecules, and further research is needed to fully understand their mechanism of action, especially in anti-leishmanial studies.

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“…As expected, miltefosine, which is a well-known antileishmanial drug, was able to reduce the in vitro proliferation of both Leishmania species ( Table 4 ). Ceole et al (2017) and da Câmara Rocha et al (2019) [ 33 ] classified the antileishmanial activity of compounds based on the IC 50 values: 10 µg/mL—high activity; 10–50 µg/mL—considerate activity; 50–100 µg/mL—moderate activity, and 100 µg/mL—no activity. Thus, inclusion of ICaf in β-CD could increase its solubility at the same time maintaining high antileishmanial activity.…”

Section: Resultsmentioning

confidence: 99%

β-Cyclodextrin/Isopentyl Caffeate Inclusion Complex: Synthesis, Characterization and Antileishmanial Activity

et al. 2020

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Isopentyl caffeate (ICaf) is a bioactive ester widely distributed in nature. Our patented work has shown promising results of this molecule against Leishmania. However, ICaf shows poor solubility, which limits its usage in clinical settings. In this work, we have proposed the development of an inclusion complex of ICaf in β-cyclodextrin (β-CD), with the aim to improve the drug solubility, and thus, its bioavailability. The inclusion complex (ICaf:β-CD) was developed applying three distinct methods, i.e., physical mixture (PM), kneading (KN) or co-evaporation (CO) in different molar proportions (0.25:1, 1:1 and 2:1). Characterization of the complexes was carried out by thermal analysis, Fourier-transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM) and molecular docking. The ICaf:β-CD complex in a molar ratio of 1:1 obtained by CO showed the best complexation and, therefore, was selected for further analysis. Solubility assay showed a marked improvement in the ICaf:β-CD (CO, 1:1) solubility profile when compared to the pure ICaf compound. Cell proliferation assay using ICaf:β-CD complex showed an IC50 of 3.8 and 2.7 µg/mL against L. amazonesis and L. chagasi promastigotes, respectively. These results demonstrate the great potential of the inclusion complex to improve the treatment options for visceral and cutaneous leishmaniases.

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Biological activity of Morita-Baylis-Hillman adduct homodimers in L. infantum and L. amazonensis: anti-Leishmania activity and cytotoxicity

Cited by 10 publications

References 31 publications

Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Leishmanicidal Activity of Guanidine Derivatives against Leishmania infantum

β-Cyclodextrin/Isopentyl Caffeate Inclusion Complex: Synthesis, Characterization and Antileishmanial Activity

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