Benzophenone derivatives as cysteine protease inhibitors and biological activity against Leishmania(L.) amazonensis amastigotes

Almeida, Letícia de; Alves, Karina Ferreira; Maciel-Rezende, Claudia Mara; Jesus, Larissa de Oliveira Passos; Pires, Francieli Ribeiro; Viegas, Cláudio; Izidoro, Mario Augusto; Júdice, Wagner Alves de Souza; Santos, Marcelo H. dos; Marques, Marcos José

doi:10.1016/j.biopha.2015.08.030

Cited by 24 publications

(18 citation statements)

References 28 publications

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“…In addition, we observed a potent leishmanicidal activity towards promastigotes in vitro, with IC 50 values of 23.66 µM (1) 27.73 µM (2) and 88.02 µM (3) [5] and the best selectivity index in relation to amastigote form, which the values were 6.7 (1); 11.9 (2) and 7.3 (3) [6]. It seems that there is a close relationship between the increase of lipophilicity of the compounds with the absorption rates and action in different routes [18,19].…”

Section: Resultsmentioning

confidence: 83%

“…Thus, testing of new compounds with leishmanicidal activity is of paramount importance to improve disease treatment and control. Recently, we described the synthesis of benzophenones derivatives with potent activity against Leishmania (L.) amazonensis in vitro [5,6]. In this work, we evaluated the anti-parasitic effect of the benzophenone derivatives 1-3 in vivo in hamsters with established infection (50 days post-inoculation) with L. (L.) infantum chagasi.…”

Section: Resultsmentioning

confidence: 99%

“…These compounds were prepared from the commercial 2,4-dihydroxybenzophenone, 4-hydroxybenzophenone and 4,4´-dihydroxybenzophenone, respectively, as previously reported [5,6]. Briefly, the target compounds were performed using the method described by Yang et al with the chemical precursors being subjected to alkylation in DMF/acetone, in the presence of K 2 CO 3 and an alkylating reagent.…”

Section: Compoundsmentioning

confidence: 99%

“…Despite their promising activity and low toxicity in vitro, these compounds have not been tested in vivo to evaluate their effectiveness in controlling or treating the disease in animal models of experimental leishmaniasis. Then, here in, we report the evaluation of the most active and promising hydroxy-alkylbenzophenone derivatives 1-3 described previously [5,6], in an in vivo model of leishmaniasis by L. (L.) infantum chagasi in hamsters. To improve treatment monitoring, the detection and quantification of amastigote forms was performed by quantitative real-time PCR (qPCR).…”

Section: Introductionmentioning

confidence: 99%

“…More recently, these benzophenone derivatives were further evaluated in vitro against amastigote form of L. amazonensis and compounds LFQM-117 (1), LFQM-120 (2) and LFQM-121 (3) showed the best relationship between their potency (IC50) and safety (SI), considering their effects towards amastigote forms and murine macrophages, respectively [6]. Despite their promising activity and low toxicity in vitro, these compounds have not been tested in vivo to evaluate their effectiveness in controlling or treating the disease in animal models of experimental leishmaniasis.…”

Section: Introductionmentioning

confidence: 99%

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In Vivo Evaluation of Leishmanicidal Activity of Benzophenone Derivatives by qPCR

Colombo¹,

Reis²,

Nunes³

et al. 2017

Med chem

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In many tropical areas, infections by Leishmania species are endemic and include visceral leishmaniasis (VL), which is often fatal if untreated. Outside India, VL treatment and control are based on long-term administration of highly toxic pentavalent antimonials. Previously, we described the synthesis and in vitro leishmanicidal activity of a series of nine benzophenone derivatives with low toxicity towards murine macrophages. Here in, we report the in vivo evaluation of the most promising active compounds of that series in an experimental model of established VL by L. (L). infantum chagasi in hamsters. Importantly, parasite DNA (amastigote form) quantification in infected tissues was performed by real time PCR, for improved detection accuracy and speed. Compounds 2-Hydroxy-4-O-(3,3-dimethyl)-allylbenzophenone (LFQM-117 (1)), 4-O-(3,3-Dimethyl)-allylbenzophenone (LFQM-120 (2)) and 4,4′-Di-methoxybenzophenone (LFQM-121 (3)) were administered as oral suspensions (50 mg/kg/day)

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Section: Resultsmentioning

confidence: 83%

Section: Resultsmentioning

confidence: 99%

Section: Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

In Vivo Evaluation of Leishmanicidal Activity of Benzophenone Derivatives by qPCR

Colombo¹,

Reis²,

Nunes³

et al. 2017

Med chem

Self Cite

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New mixed‐ligand iron(III) complexes containing thiocarbohydrazones: Preparation, characterization, and chemical reactivity analysis through theoretical calculations

Kaya

Erçağ

Katin

et al. 2022

Applied Organom Chemis

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Five new mixed ligand Fe(III) complexes, namely, [FeL1(acac)] (L1Fe), [FeL2(acac)] (L2Fe), [FeL3(acac)] (L3Fe), [FeL4(acac)] (L4Fe), and [FeL5(acac)] (L5Fe), were synthesized from the reaction of iron(III) acetylacetonate with [ONS] donor dibasic tridentate symmetrical bisthiocarbohydrazone ligands. Synthesized mixed ligand Fe(III) complexes were characterized with infrared spectra, UV‐Vis spectra, mass spectra, elemental analysis, magnetic susceptibility measurements, and thermogravimetric analysis. The molar conductance measurement in DMF solution confirmed that the complexes are nonelectrolytic. TGA analysis results showed that the thermal stability of the ligands and complexes was high. Antioxidant capacity and free radical scavenging activity of the mixed ligand Fe(III) complexes were investigated using CUPRAC and the DPPH radical scavenging method. Mixed ligand Fe(III) complexes showed higher antioxidant activity than ligands and reference compound. Popular conceptual density functional parameters like hardness, electrophilicity, dipole moment, and chemical potential for new ligands and their Fe(III) complexes were calculated and discussed. Chemical reactivity and stabilities of the studied chemical systems were analyzed with the help of well‐known electronic structure principles like maximum hardness principle (MHP), hard and soft acid–base (HSAB) principle, minimum polarizability principle, and minimum electrophilicity principle. L1Fe, which has the highest chemical hardness value, is the most stable complex according to MHP.

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Synthesis of Benzophenones and in vitro Evaluation of Their Anticancer Potential in Breast and Prostate Cancer Cells

et al. 2019

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Breast and prostate cancers are frequently treated with chemotherapy. Several novel chemicals are being reported for this purpose, particularly synthetic and natural benzophenones. This work reports the synthesis of substituted 2‐hydroxybenzophenones through 1,4‐conjugate addition/intramolecular cycloaddition/dehydration of nitromethane on key intermediate chromones. Structures were extensively studied by means of 2D NMR spectroscopy and single‐crystal XRD. Their cytotoxicity was evaluated in vitro in two breast cancer cell lines (MDA‐MB‐231 and T47‐D) and one prostate cancer cell line (PC3). The most potent compound exhibited good cytotoxic effects against the three cancer cell lines (IC50 values ranging from 12.09 to 26.49 μm) and induced cell‐cycle retardation only on prostate cancer cells, which suggested that it might exert cell‐type‐specific effects.

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Benzophenone derivatives as cysteine protease inhibitors and biological activity against Leishmania(L.) amazonensis amastigotes

Cited by 24 publications

References 28 publications

In Vivo Evaluation of Leishmanicidal Activity of Benzophenone Derivatives by qPCR

In Vivo Evaluation of Leishmanicidal Activity of Benzophenone Derivatives by qPCR

New mixed‐ligand iron(III) complexes containing thiocarbohydrazones: Preparation, characterization, and chemical reactivity analysis through theoretical calculations

Synthesis of Benzophenones and in vitro Evaluation of Their Anticancer Potential in Breast and Prostate Cancer Cells

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