In vitro and computational studies of natural products related to perezone as anti-neoplastic agents

Hernández-Rodríguez, Maricarmen; Sánchez, Pablo I. Mendoza; Pérez, Martha Edith Macías; Cruz, Erika Rosales; Jimenez, Elvía Mera; Aceves-Hernández, Juan Manuel; Nicolás–Vázquez, María Inés; Ruvalcaba, René Miranda

doi:10.1016/j.biochi.2020.03.003

Cited by 11 publications

(14 citation statements)

References 43 publications

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“…As complement and according to obtained results it is possible to observe that according to the Pa values, the studied compounds share a potential activity as anti‐neoplasic agents and mucomembranous protector. These results acquire importance since it has been demonstrated the pro‐apoptotic activity of ( R )‐perezone and related compounds [39–41] . Consequently, it is important to note that the indicated potential activities are under study by our research group.…”

Section: Resultsmentioning

confidence: 76%

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Can (S)‐Stereoisomers of Perezone and Its Derivatives Show Similar Activity to Its (R)‐Stereoisomers? A Computational Characterization and Docking Study

et al. 2021

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Asymmetric synthesis, in particular enantioselectivity, has permitted the assembly of complex molecules; consequently, many clinical trials are going on to compare the efficacy and safety of each pair of enantiomers. In this sense, to envisage the suitability to synthesize the (S)-stereoisomers (hypothetical) of (R)-perezone, (R)-isoperezone and their corresponding sulfurderivatives, in this work, their molecular properties (geometrical, electronic, and spectroscopic) and chemical reactivity descriptors at the theoretical level were compared with the results of the previously studied (R)-stereoisomers, using DFT/ B3LYP/6-311 + + G(d,p), in agreement between both (S/R)enantiomers. Concerning the electronic properties, the 6isopropylsulfanyl-(8S)-perezone (1 a) and 6-benzylsulfanyl-(8R)-perezone (2 c) are hard molecules, in addition (8R)-isoperezone (4), 3-benzylsulfanyl-(8S)-isoperezone (3 c), and 6-benzylsulfanyl-(8S)-perezone (1 c) displayed comparable features to 6benzylsulfanyl-(8R)-perezone (2 c). The docking studies showed that (S)-derivatives exhibited a lower affinity to COX-2 due to steric hindrance. Thus, 2 c showed the highest affinity to COX-2 (ΔG = À 9.53 kcal/mol). The highest differences in ΔG values were shown between 1 c and 2 c, while the lowest differences in ΔG values were displayed by 3 a and 4 a. Finally, the biological activity prediction for the hypothetic (S)-compounds revealed anti-neoplasic activity, consequently their synthesis is recommended.

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Section: Resultsmentioning

confidence: 76%

“…These results acquire importance since it has been demonstrated the pro-apoptotic activity of (R)-perezone and related compounds. [39][40][41] Consequently, it is important to note that the indicated potential activities are under study by our research group.…”

Section: Pass Prediction Of Biological Activitymentioning

confidence: 99%

Can (S)‐Stereoisomers of Perezone and Its Derivatives Show Similar Activity to Its (R)‐Stereoisomers? A Computational Characterization and Docking Study

et al. 2021

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“…Migration of U373 in the presence and absence of perezone and perezone angelate was performed according to the methodology previously described [ 47 ]. For this purpose, microglia and U373 of GBM cells were cultured in 24-well microplates (10 5 per well) until confluence was reached, and a thin “wound” was introduced by scratching with a sterile pipette tip [ 48 ].…”

Section: Methodsmentioning

confidence: 99%

In Vitro and Computational Studies of Perezone and Perezone Angelate as Potential Anti-Glioblastoma Multiforme Agents

Hernández-Rodríguez¹,

Sánchez

Martínez

et al. 2022

Molecules

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Glioblastoma multiforme (GBM) represents the most malignant type of astrocytoma, with a life expectancy of two years. It has been shown that Poly (ADP-ribose) polymerase 1 (PARP-1) protein is over-expressed in GBM cells, while its expression in healthy tissue is low. In addition, perezone, a phyto-compound, is a PARP-1 inhibitor with anti-neoplastic activity. As a consequence, in the present study, both in vitro and computational evaluations of perezone and its chemically related compound, perezone angelate, as anti-GBM agents were performed. Hence, the anti-proliferative assay showed that perezone angelate induces higher cytotoxicity in the GBM cell line (U373 IC50 = 6.44 μM) than perezone (U373 IC50 = 51.20 μM) by induction of apoptosis. In addition, perezone angelate showed low cytotoxic activity in rat glial cells (IC50 = 173.66 μM). PARP-1 inhibitory activity (IC50 = 5.25 μM) and oxidative stress induction by perezone angelate were corroborated employing in vitro studies. In the other hand, the performed docking studies allowed explaining the PARP-1 inhibitory activity of perezone angelate, and ADMET studies showed its probability to permeate cell membranes and the blood–brain barrier, which is an essential characteristic of drugs to treat neurological diseases. Finally, it is essential to highlight that the results confirm perezone angelate as a potential anti-GBM agent.

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“…In the docking models, OHPer-MAng establishes great non-bonding interactions with the lateral chains of Tyr235, Hys201, Tyr246, Ser203, Asn207, and Gly233 located at the catalytic site of PARP-1. [56] Some polyacetylenes (26 -37) (Figure 9) were obtained from the bioassay-guided purification from the Desmanthodium guatemalense extract. The selectivity index of 26 for the non-MSL TNBC cell lines ranges from 5.3 to greater than 29, and the selectivity index of 27 ranges from 9.0 to 47.…”

Section: Terrestrial Natural Productsmentioning

confidence: 99%

“…The pro‐apoptotic activity of OHPer‐MAng mainly attributed to the induction of an oxidative stress state and PARP‐1 inhibition. In the docking models, OHPer‐MAng establishes great non‐bonding interactions with the lateral chains of Tyr235, Hys201, Tyr246, Ser203, Asn207, and Gly233 located at the catalytic site of PARP‐1 [56] …”

Section: Natural Products With Anti‐tnbc Activitiesmentioning

confidence: 99%

The Natural Products and Extracts: Anti‐Triple‐Negative Breast Cancer in Vitro

Chen¹,

Yang²,

Yang³

et al. 2021

Chemistry & Biodiversity

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Triple-negative breast cancer (TNBC) makes up 15 % to 20 % of all breast cancer (BC) cases, and represents one of the most challenging malignancies to treat. For many years, chemotherapy has been the main treatment option for TNBC. Natural products isolated from marine organisms and terrestrial organisms with great structural diversity and high biochemical specificity form a compound library for the assessment and discovery of new drugs. In this review, we mainly focused on natural compounds and extracts (from marine and terrestrial environments) with strong anti-TNBC activities (IC 50 < 100 μM) and their possible mechanisms reported in the past six years (2015)(2016)(2017)(2018)(2019)(2020)(2021).

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In vitro and computational studies of natural products related to perezone as anti-neoplastic agents

Cited by 11 publications

References 43 publications

Can (S)‐Stereoisomers of Perezone and Its Derivatives Show Similar Activity to Its (R)‐Stereoisomers? A Computational Characterization and Docking Study

Can (S)‐Stereoisomers of Perezone and Its Derivatives Show Similar Activity to Its (R)‐Stereoisomers? A Computational Characterization and Docking Study

In Vitro and Computational Studies of Perezone and Perezone Angelate as Potential Anti-Glioblastoma Multiforme Agents

The Natural Products and Extracts: Anti‐Triple‐Negative Breast Cancer in Vitro

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