Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines

Said, Bastián; Montenegro, Iván; Valenzuela, Manuel; Olguín, Yusser; Caro, Nelson; Werner, Enrique; Godoy, Patrício; Villena, Joan; Madrid, Alejandro

doi:10.3390/molecules23092323

Cited by 7 publications

(5 citation statements)

References 47 publications

(50 reference statements)

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“…The antiproliferative effect was related to induction of apoptosis and G2/M cell cycle arrest. CVN could inhibit cell invasion and the expression of the p-P38 protein at this IC 50 .…”

Section: Carvone and Its Derivativesmentioning

confidence: 87%

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Selected Monocyclic Monoterpenes and Their Derivatives as Effective Anticancer Therapeutic Agents

Zielińska-Błajet

Pietrusiak

Feder‐Kubis

2021

IJMS

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Terpenes—a diverse group of secondary metabolites—constitute the largest class of natural products abundant in almost every plant species. The properties of concrete terpenes and essential oils have been intensively studied due to their widespread use in the pharmaceutical, food and cosmetics industries. Despite the popularity of these aromatic compounds, their derivatives, terpenoids, are still not comprehensively characterized despite exhibiting potent bioactive properties. This review aims to assess the anticancer properties of selected monoterpenes including carvone, carvacrol, perillyl alcohol, perillaldehyde, limonene, menthol and their derivatives while also evaluating potential applications as novel anticancer treatments. Special attention is paid to functional groups that improve the bioactivity of monoterpene molecules. This review also covers the therapeutic potential of deep eutectic solvents that contain monoterpene substances. Taken together, the literature supports the use of monoterpene derivatives in the development of new alternatives for disease treatment and prevention.

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“…The antiproliferative effect was related to induction of apoptosis and G2/M cell cycle arrest. CVN could inhibit cell invasion and the expression of the p-P38 protein at this IC 50 .…”

Section: Carvone and Its Derivativesmentioning

confidence: 87%

“…In comparison, compounds 26b and 26c showed moderate activity. This research highlights the need for additional studies to support the therapeutical potential of these new derivatives [ 50 ].…”

Section: Perillyl Alcohol and Its Derivativesmentioning

confidence: 99%

Selected Monocyclic Monoterpenes and Their Derivatives as Effective Anticancer Therapeutic Agents

Zielińska-Błajet

Pietrusiak

Feder‐Kubis

2021

IJMS

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“…Several studies have demonstrated that natural extracts have the capacity to induce cytotoxicity in cancer cells while sparing normal cells. Tis property renders them attractive candidates for the development of therapeutic agents [33][34][35][36]. A possible explanation for this diference may be the higher metabolic rates of cancer cells and the consequent increase in the demand for nutrient acquisition, which sensitize them to treatment compared with normal cells [37,38].…”

Section: Discussionmentioning

confidence: 99%

Proapoptotic and Antiproliferative Effects of the Desert Truffle Terfezia boudieri on Colon Cancer Cell Lines

Sawaya

Najem

Khawaja

et al. 2023

Evidence-Based Complementary and Alternative Medicine

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Background. Colon cancer is the second leading cause of cancer-related mortality, and ranks third among cancers in terms of prevalence. Despite advances in early detection and treatment with chemotherapy and surgery, colon cancer continues to be associated with high recurrence rates, thereby resulting in a heavy disease burden. Moreover, the effectiveness of currently available treatment modalities is limited by the occurrence of toxic side effects. Hence, there is an urgent need to develop alternative treatments. Extracts from the black desert truffle Terfezia boudieri (T. boudieri) have shown promising anticancer properties. However, the cellular mechanisms underlying this activity remain poorly understood. Methods. In this study, the colon cancer cell lines HCT-116 and Caco-2 were treated with either water or ethanolic extract of T. boudieri. Cell viability and the half-maximal inhibitory concentration were determined using MTT assays. Then, the activity of the more potent water extract was further verified using crystal violet assays, and its role in inhibiting colony formation and wound healing was investigated. Protein levels of p53, B-cell lymphoma 2 (Bcl-2), Bcl-2-associated X (Bax), cyclin D1 (CCND1), and c-Myc were measured in cells treated with different doses of the water extract. Results. Treatment with the water extract of T. boudieri reduced the capacity of cells for wound healing and colony formation in a dose-dependent manner. The Bax/Bcl-2 ratio and p53 expression were elevated in both cell lines. In contrast, the levels of cyclin D1 and c-Myc were suppressed. Conclusion. T. boudieri water extract exerted a cytotoxic effect on colon cancer cells, and blocked colony formation and wound healing potentially through inhibition of proliferation. Mechanistically, these effects are attributed to influence the mitochondrial pathway of apoptosis, proteins involved in cellular proliferation, and the cell cycle.

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“…This group identified several new compounds that exerted greater in vitro cytotoxicity than POH, with POH 4 -azido-D-glucoside as the most potent POH adduct. Similarly, a series of cyclodiprenyl phenols were synthesized from perillyl alcohol and synthetic phenols, and some of these meroterpenes showed strong antiproliferative and apoptosis-inducing activity against three different cancer cell lines in vitro [157]. POH was also complexed with β-cyclodextrin, which resulted in improved anticancer potency in vitro and in a sarcoma S180-induced mouse model in vivo [158].…”

Section: Perillyl Alcohol Derivatives Analogs and Conjugatesmentioning

confidence: 99%

The Monoterpenoid Perillyl Alcohol: Anticancer Agent and Medium to Overcome Biological Barriers

et al. 2021

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Perillyl alcohol (POH) is a naturally occurring monoterpenoid related to limonene that is present in the essential oils of various plants. It has diverse applications and can be found in household items, including foods, cosmetics, and cleaning supplies. Over the past three decades, it has also been investigated for its potential anticancer activity. Clinical trials with an oral POH formulation administered to cancer patients failed to realize therapeutic expectations, although an intra-nasal POH formulation yielded encouraging results in malignant glioma patients. Based on its amphipathic nature, POH revealed the ability to overcome biological barriers, primarily the blood–brain barrier (BBB), but also the cytoplasmic membrane and the skin, which appear to be characteristics that critically contribute to POH’s value for drug development and delivery. In this review, we present the physicochemical properties of POH that underlie its ability to overcome the obstacles placed by different types of biological barriers and consequently shape its multifaceted promise for cancer therapy and applications in drug development. We summarized and appraised the great variety of preclinical and clinical studies that investigated the use of POH for intranasal delivery and nose-to-brain drug transport, its intra-arterial delivery for BBB opening, and its permeation-enhancing function in hybrid molecules, where POH is combined with or conjugated to other therapeutic pharmacologic agents, yielding new chemical entities with novel mechanisms of action and applications.

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Synthesis and Antiproliferative Activity of New Cyclodiprenyl Phenols against Select Cancer Cell Lines

Cited by 7 publications

References 47 publications

Selected Monocyclic Monoterpenes and Their Derivatives as Effective Anticancer Therapeutic Agents

Selected Monocyclic Monoterpenes and Their Derivatives as Effective Anticancer Therapeutic Agents

Proapoptotic and Antiproliferative Effects of the Desert Truffle Terfezia boudieri on Colon Cancer Cell Lines

The Monoterpenoid Perillyl Alcohol: Anticancer Agent and Medium to Overcome Biological Barriers

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