Antimalarial activity of abietane ferruginol analogues possessing a phthalimide group

González, Miguel A.; Clark, Julie; Connelly, Michele; Rivas, Fátima

doi:10.1016/j.bmcl.2014.09.061

Cited by 41 publications

(37 citation statements)

References 29 publications

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“…Arrest of the cell cycle is regarded as an effective strategy to inhibit tumor cell proliferation [13]. Our results show that all three compounds (7,43 and 61) caused cell cycle arrest at G0/G1 (50.76%, 63.41%, and 61.26%, respectively; positive control 43%, negative control 48.36%). The compounds (7,43 and 61) also showed inhibition of cell cycle progression at G2/M phase (19%,16.9% and 18.3%,respectively (see SI).…”

Section: Resultsmentioning

confidence: 75%

“…Our results show that all three compounds (7,43 and 61) caused cell cycle arrest at G0/G1 (50.76%, 63.41%, and 61.26%, respectively; positive control 43%, negative control 48.36%). The compounds (7,43 and 61) also showed inhibition of cell cycle progression at G2/M phase (19%,16.9% and 18.3%,respectively (see SI). Furthermore, compounds 43 and 61 were observed to cause DNA fragmentation in a time dependent manner (12 h point treatment shown in SI).…”

Section: Resultsmentioning

confidence: 83%

“…All three compounds (7,43 and 61) showed a time dependent PARP increase. Significant amount of cleaved-PARP for compound 43 and 61 at the 12 h time point was observed.…”

Section: Resultsmentioning

confidence: 96%

“…1) [6]. They are found in the resin of various terrestrial plants of the Podocarpaceae and Cupressaceae families and in other angiosperms [7]. The abietanes have demonstrated a broad range of biological properties, particularly anticancer activities.…”

Section: Resultsmentioning

confidence: 99%

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(+)-Dehydroabietylamine derivatives target triple-negative breast cancer

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González

et al. 2015

European Journal of Medicinal Chemistry

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Section: Resultsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 83%

“…All three compounds (7,43 and 61) showed a time dependent PARP increase. Significant amount of cleaved-PARP for compound 43 and 61 at the 12 h time point was observed.…”

Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

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(+)-Dehydroabietylamine derivatives target triple-negative breast cancer

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González

et al. 2015

European Journal of Medicinal Chemistry

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“…In some studies, diterpenes in nanoformulations (Roy et al ., ; Mondal et al ., ) as well as their laboratory derivatives have been reported to exhibit promising anti‐NTDs activities (Watson and Preedy, ; Mander and Liu, ). Additionally, a number of diterpenes have been reported to act against multiple strains responsible for a particular NTD (Sanchez et al ., ; Dea‐Ayuela et al ., ; Johnson et al ., ; Riel et al ., ; Clarkson et al ., ; Kalauni et al ., ; Ojo‐Amaize et al ., ; Wangchuk et al ., ; González et al ., ; Namukobe et al ., ; Liu et al ., ; Prabu et al ., ; Encarnación‐Dimayuga et al ., ; Rijo et al ., ; Arai et al ., ; Xu et al ., ; Xu et al ., ) and NTDs (Schmidt et al ., ; Al Musayeib et al ., ; Ramírez‐Macías et al ., ; Mothana et al ., ; Falodun et al ., ; Mizuno et al ., ; Mongkolvisut and Sutthivaiyakit, ; Rangkaew et al ., ; Ospina and Rodríguez, ; Lekphrom et al ., ; Almutairi et al ., ).…”

Section: Discussionmentioning

confidence: 99%

Diterpenes as lead molecules against neglected tropical diseases

et al. 2016

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Nowadays, neglected tropical diseases (NTDs) are reported to be present everywhere. Poor and developing areas in the world have received great attention to NTDs. Drug resistance, safety profile, and various challenges stimulate the search for alternative medications. Plant-based drugs are viewed with great interest, as they are believed to be devoid of side effects. Diterpenes, a family of essential oils, have showed attractive biological effects. A systematic review of the literature was carried out to summarize available evidences of diterpenes against NTDs. For this, databases were searched using specific search terms. Among the 2338 collected reports, a total of 181 articles were included in this review. Of them, 148 dealt with investigations using single organisms, and 33 used multiple organisms. No mechanisms of action were reported in the case of 164 reports. A total of 93.92% were related to nonclinical studies, and 4.42% and 1.66% dealt with preclinical and clinical studies, respectively. The review displays that many diterpenes are effective upon Chagas disease, chikungunya, echinococcosis, dengue, leishmaniasis, leprosy, lymphatic filariasis, malaria, schistosomiasis, and tuberculosis. Indeed, diterpenes are amazing drug candidates against NTDs. Copyright © 2016 John Wiley & Sons, Ltd.

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Dual Parasiticidal Activities of Phthalimides: Synthesis and Biological Profile against Trypanosoma cruzi and Plasmodium falciparum

et al. 2020

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Chagas disease and malaria are two neglected tropical diseases (NTDs) that prevail in tropical and subtropical regions in 149 countries. Chagas is also present in Europe, the US and Australia due to immigration of asymptomatic infected individuals. In the absence of an effective vaccine, the control of both diseases relies on chemotherapy. However, the emergence of parasite drug resistance is rendering currently available drugs obsolete. Hence, it is crucial to develop new molecules. Phthalimides, thiosemicarbazones, and 1,3-thiazoles have been used as scaffolds to obtain antiplasmodial and anti-Trypanosoma cruzi agents. Herein we present the synthesis of 24 phthalimido-thiosemicarbazones (3 ax) and 14 phthalimidothiazoles (4 an) and the corresponding biological activity against T. cruzi, Plasmodium falciparum, and cytotoxicity against mammalian cell lines. Some of these compounds showed potent inhibition of T. cruzi at low cytotoxic concentrations in RAW 264.7 cells. The most active compounds, 3 t (IC 50 = 3.60 μM), 3 h (IC 50 = 3.75 μM), and 4 j (IC 50 = 4.48 μM), were more active than the control drug benznidazole (IC 50 = 14.6 μM). Overall, the phthalimido-thiosemicarbazone derivatives were more potent than phthalimido-thiazole derivatives against T. cruzi. Flow cytometry assay data showed that compound 4 j was able to induce necrosis and apoptosis in trypomastigotes. Analysis by scanning electron microscopy showed that T. cruzi trypomastigote cells treated with compounds 3 h, 3 t, and 4 j at IC 50 concentrations promoted changes in the shape, flagella, and surface of the parasite body similar to those observed in benznidazole-treated cells. The compounds with the highest antimalarial activity were the phthalimido-thiazoles 4 l (IC 50 = 1.2 μM), 4 m (IC 50 = 1.7 μM), and 4 n (IC 50 = 2.4 μM). Together, these data revealed that phthalimido derivatives possess a dual antiparasitic profile with potential effects against T. cruzi and lead-like characteristics.

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Antimalarial activity of abietane ferruginol analogues possessing a phthalimide group

Cited by 41 publications

References 29 publications

(+)-Dehydroabietylamine derivatives target triple-negative breast cancer

(+)-Dehydroabietylamine derivatives target triple-negative breast cancer

Diterpenes as lead molecules against neglected tropical diseases

Dual Parasiticidal Activities of Phthalimides: Synthesis and Biological Profile against Trypanosoma cruzi and Plasmodium falciparum

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