Isopropyl Caffeate: A Caffeic Acid Derivative—Antioxidant Potential and Toxicity

Lira, Andressa Brito; Montenegro, Camila de Albuquerque; Oliveira, Kardilandia Mendes de; Filho, Abrahão Alves de Oliveira; Paz, Alexandre Rolim da; Araújo, Marianna Oliveira de; Sousa, Damião Pergentino de; Almeida, Cynthia Layse Ferreira de; Silva, Teresinha Gonçalves da; Lima, Caliandra Maria Bezerra Luna; Diniz, Margareth de Fátima Formiga Melo; Pessôa, Hilzeth de Luna Freire

doi:10.1155/2018/6179427

Cited by 10 publications

(19 citation statements)

References 55 publications

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“…Compound 6 presented an IC 50 of 154.99 ± 33.14 μM; an increase in trypanocidal potency as compared to compound 1 , this is possibly related to the lipophilicity of the derivative, increasing its penetration across the parasite cell membrane, and consequently influencing the parasite cell membrane and increasing trypanocidal activity [45,46].…”

Section: Resultsmentioning

confidence: 99%

Trypanocidal Mechanism of Action and in silico Studies of p-Coumaric Acid Derivatives

Lopes

Castillo

Monteiro

et al. 2019

IJMS

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Trypanosoma species are responsible for chronic and systemic infections in millions of people around the world, compromising life quality, and family and government budgets. This group of diseases is classified as neglected and causes thousands of deaths each year. In the present study, the trypanocidal effect of a set of 12 ester derivatives of the p-coumaric acid was tested. Of the test derivatives, pentyl p-coumarate (7) (5.16 ± 1.28 μM; 61.63 ± 28.59 μM) presented the best respective trypanocidal activities against both epimastigote and trypomastigote forms. Flow cytometry analysis revealed an increase in the percentage of 7-AAD labeled cells, an increase in reactive oxygen species, and a loss of mitochondrial membrane potential; indicating cell death by necrosis. This mechanism was confirmed by scanning electron microscopy, noting the loss of cellular integrity. Molecular docking data indicated that of the chemical compounds tested, compound 7 potentially acts through two mechanisms of action, whether by links with aldo-keto reductases (AKR) or by comprising cruzain (CZ) which is one of the key Trypanosoma cruzi development enzymes. The results indicate that for both enzymes, van der Waals interactions between ligand and receptors favor binding and hydrophobic interactions with the phenolic and aliphatic parts of the ligand. The study demonstrates that p-coumarate derivatives are promising molecules for developing new prototypes with antiprotozoal activity.

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Section: Resultsmentioning

confidence: 99%

Trypanocidal Mechanism of Action and in silico Studies of p-Coumaric Acid Derivatives

Lopes

Castillo

Monteiro

et al. 2019

IJMS

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“…Compounds presenting three side chain carbons ( 3 , 4 , and 5 ) exhibited differing EC 50 values (respectively 6.3 ± 1.14 μg/mL, 28.33 ± 0.27 μg/mL, and 86.98 ± 18.13 μg/mL). This may be due to an alteration in the n-propyl radical ( 3 ) to isopropyl ( 4 ), contributing to the decrease in leishmanicidal activity seen in further branching in compound 4 [ 47 , 48 ]. Compound 3 was fourteen times more active than compound 5 .…”

Section: Resultsmentioning

confidence: 99%

Alkyl and Aryl Derivatives Based on p-Coumaric Acid Modification and Inhibitory Action against Leishmania braziliensis and Plasmodium falciparum

et al. 2020

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In low-income populations, neglected diseases are the principal cause of mortality. Of these, leishmaniasis and malaria, being parasitic, protozoan infections, affect millions of people worldwide and are creating a public health problem. The present work evaluates the leishmanicidal and antiplasmodial action of a series of twelve p-coumaric acid derivatives. Of the tested derivatives, eight presented antiparasitic activities 1–3, 8–12. The hexyl p-coumarate derivative (9) (4.14 ± 0.55 μg/mL; selectivity index (SI) = 2.72) showed the highest leishmanicidal potency against the Leishmania braziliensis amastigote form. The results of the molecular docking study suggest that this compound inhibits aldehyde dehydrogenase (ALDH), mitogen-activated kinase protein (MPK4), and DNA topoisomerase 2 (TOP2), all of which are key enzymes in the development of Leishmania braziliensis. The data indicate that these enzymes interact via Van der Waals bonds, hydrophobic interactions, and hydrogen bonds with phenolic and aliphatic parts of this same compound. Of the other compounds analyzed, methyl p-coumarate (64.59 ± 2.89 μg/mL; IS = 0.1) demonstrated bioactivity against Plasmodium falciparum. The study reveals that esters presenting a p-coumarate substructure are promising for use in synthesis of derivatives with good antiparasitic profiles.

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“…Human erythrocytes types A, B, AB, O were used, which were obtained from the Transfusion Unit of the Lauro Wanderley University Hospital at the Federal University of Paraíba. Samples were obtained from blood unusable for blood transfusions (blood to be discarded) (De Araújo et al, 2018;Lira et al, 2018).…”

Section: Cytotoxicity Analysis In Human Erythrocytesmentioning

confidence: 99%

“…The samples were incubated (1 h at 22 ± 2°C) under agitation (0,25 g). After that were centrifuged (1540 g for 5 min) and hemolysis was quantified by spectrophotometry at a wavelength of 540 nm (De Araújo et al, 2018;Lira et al, 2018).…”

Section: Hemolytic Potential Of Sc Extract On Human Erythrocytesmentioning

confidence: 99%

Phytochemical composition, antifungal activity, in vitro and in vivo toxicity of Syzygium cumini (L.) Skeels leaves extract

Júnior¹,

Cavalcanti²,

Lira³

et al. 2021

BLACPMA

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This study determined phytochemical composition, antifungal activity and toxicity in vitro and in vivo of Syzygium cumini leaves extract (Sc). Thus, was characterized by gas chromatography coupled to mass spectrometry and submitted to determination of Minimum Inhibitory (MIC) and Fungicidal concentrations (MFC) on reference and clinical strains of Candida spp. and by growth kinetics assays. Toxicity was verified using in vitro assays of hemolysis, osmotic fragility, oxidant and antioxidant activity in human erythrocytes and by in vivo acute systemic toxicity in Galleria mellonella larvae. Fourteen different compounds were identified in Sc, which showed antifungal activity (MIC between 31.25-125 μg/mL) with fungistatic effect on Candida. At antifungal concentrations, it demonstrated low cytotoxicity, antioxidant activity and neglible in vivo toxicity. Thus, Sc demonstrated a promising antifungal potential, with low toxicity, indicating that this extract can be a safe and effective alternative antifungal agent.

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Isopropyl Caffeate: A Caffeic Acid Derivative—Antioxidant Potential and Toxicity

Cited by 10 publications

References 55 publications

Trypanocidal Mechanism of Action and in silico Studies of p-Coumaric Acid Derivatives

Trypanocidal Mechanism of Action and in silico Studies of p-Coumaric Acid Derivatives

Alkyl and Aryl Derivatives Based on p-Coumaric Acid Modification and Inhibitory Action against Leishmania braziliensis and Plasmodium falciparum

Phytochemical composition, antifungal activity, in vitro and in vivo toxicity of Syzygium cumini (L.) Skeels leaves extract

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