Design, synthesis and biological evaluation of novel β-pinene-based thiazole derivatives as potential anticancer agents via mitochondrial-mediated apoptosis pathway

Wang, Yunyun; Wu, Chenliang; Zhang, Qiangjian; Yu, Shan; Gu, Wen; Wang, Shifa

doi:10.1016/j.bioorg.2018.12.010

Cited by 73 publications

(40 citation statements)

References 41 publications

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“…Three human cancer cell lines, namely, cervical carcinoma HeLa cells, colon cancer CT-26, and hepatocarcinoma SMMC-7721 cells were used in the study [39]. Out of all derivatives, the compound 5g was found to inhibit cell proliferation by stimulating cell cycle arrest in HeLa cells by ROS-mediated mitochondrial dysfunction signaling pathways [40].…”

Section: Preclinical Pharmacological Activities Of α- and β-Pinenementioning

confidence: 99%

Therapeutic Potential of α- and β-Pinene: A Miracle Gift of Nature

et al. 2019

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α- and β-pinene are well-known representatives of the monoterpenes group, and are found in many plants’ essential oils. A wide range of pharmacological activities have been reported, including antibiotic resistance modulation, anticoagulant, antitumor, antimicrobial, antimalarial, antioxidant, anti-inflammatory, anti-Leishmania, and analgesic effects. This article aims to summarize the most prominent effects of α- and β-pinene, namely their cytogenetic, gastroprotective, anxiolytic, cytoprotective, anticonvulsant, and neuroprotective effects, as well as their effects against H2O2-stimulated oxidative stress, pancreatitis, stress-stimulated hyperthermia, and pulpal pain. Finally, we will also discuss the bioavailability, administration, as well as their biological activity and clinical applications.

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Section: Preclinical Pharmacological Activities Of α- and β-Pinenementioning

confidence: 99%

Therapeutic Potential of α- and β-Pinene: A Miracle Gift of Nature

et al. 2019

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“…Another example presents a library of β -pinene-based thiazole derivatives 88 ( Figure 20 ) [ 82 ]. The obtained compounds were evaluated for their antitumor in vitro activities, and the results demonstrated that most target compounds showed potent antiproliferative activities against three human cancer cell lines.…”

Section: Monoterpene Bicyclic Derivativesmentioning

confidence: 99%

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

Zielińska-Błajet

Feder‐Kubis

2020

IJMS

220

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Monoterpenes, comprising hydrocarbons, are the largest class of plant secondary metabolites and are commonly found in essential oils. Monoterpenes and their derivatives are key ingredients in the design and production of new biologically active compounds. This review focuses on selected aliphatic, monocyclic, and bicyclic monoterpenes like geraniol, thymol, myrtenal, pinene, camphor, borneol, and their modified structures. The compounds in question play a pivotal role in biological and medical applications. The review also discusses anti-inflammatory, antimicrobial, anticonvulsant, analgesic, antiviral, anticancer, antituberculosis, and antioxidant biological activities exhibited by monoterpenes and their derivatives. Particular attention is paid to the link between biological activity and the effect of structural modification of monoterpenes and monoterpenoids, as well as the introduction of various functionalized moieties into the molecules in question.

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“…Twenty-four β-pinene-based thiazole derivatives were synthesized and 5 g compound showed cytotoxic against three different cancer cell lines (Hela, CT-26, and SMMC-7721). Cytotoxic effect have been described to be mediated by action in the following signaling pathways: i) increased ROS activity, ii) loss of mitochondrial membrane potential, and iii) altered expression of Bax/Bcl-2, ultimately provoking cell injury and even cell death [171]. Concerning its antiviral and antifungal activity, it was shown its beneficial effects against Rhizopus stolonifer (the common bread mold) and Absidia coerulea fungi, as well as against herpes simplex virus type 1 (HSV-1), in vitro [172,173].…”

Section: Alpha (α)-And β-Pinenementioning

confidence: 99%

Terpenoids, Cannabimimetic Ligands, beyond the Cannabis Plant

et al. 2020

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Medicinal use of Cannabis sativa L. has an extensive history and it was essential in the discovery of phytocannabinoids, including the Cannabis major psychoactive compound—Δ9-tetrahydrocannabinol (Δ9-THC)—as well as the G-protein-coupled cannabinoid receptors (CBR), named cannabinoid receptor type-1 (CB1R) and cannabinoid receptor type-2 (CB2R), both part of the now known endocannabinoid system (ECS). Cannabinoids is a vast term that defines several compounds that have been characterized in three categories: (i) endogenous, (ii) synthetic, and (iii) phytocannabinoids, and are able to modulate the CBR and ECS. Particularly, phytocannabinoids are natural terpenoids or phenolic compounds derived from Cannabis sativa. However, these terpenoids and phenolic compounds can also be derived from other plants (non-cannabinoids) and still induce cannabinoid-like properties. Cannabimimetic ligands, beyond the Cannabis plant, can act as CBR agonists or antagonists, or ECS enzyme inhibitors, besides being able of playing a role in immune-mediated inflammatory and infectious diseases, neuroinflammatory, neurological, and neurodegenerative diseases, as well as in cancer, and autoimmunity by itself. In this review, we summarize and critically highlight past, present, and future progress on the understanding of the role of cannabinoid-like molecules, mainly terpenes, as prospective therapeutics for different pathological conditions.

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Design, synthesis and biological evaluation of novel β-pinene-based thiazole derivatives as potential anticancer agents via mitochondrial-mediated apoptosis pathway

Cited by 73 publications

References 41 publications

Therapeutic Potential of α- and β-Pinene: A Miracle Gift of Nature

Therapeutic Potential of α- and β-Pinene: A Miracle Gift of Nature

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

Terpenoids, Cannabimimetic Ligands, beyond the Cannabis Plant

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