Synthesis and Cytotoxic Activity of Azine Derivatives of 6-Hydroxyxanthanodiene

Neganova, Margarita E.; Клочков, С. Г.; Pukhov, S. A.; Afanasieva, Svetlana V.; Aleksandrova, Yulia; Yandulova, Ekaterina; Ávila-Rodriguez, Marco; Mikhaleva, L.M.; Николенко, В.Н.; Somasundaram, Siva G; Aliev, Gjumrakch

doi:10.2174/1568009620999200421200338

Cited by 4 publications

(3 citation statements)

References 26 publications

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“…Among natural compounds, sesquiterpene lactones also play an important role in the development of therapeutic agents due to their wide range of biological activities and promising pharmacological profiles [213][214][215][216][217][218]. One of the outstanding discoveries of traditional Chinese medicine is artemisinin, which exhibits excellent anti-malarial activity and is isolated from Artemisia annua L. [219,220].…”

Section: Potential Neuroprotective and Antitumor Therapeutic Candidat...mentioning

confidence: 99%

Deciphering the Mysterious Relationship between the Cross-Pathogenetic Mechanisms of Neurodegenerative and Oncological Diseases

Aleksandrova,

Neganova

2023

IJMS

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The relationship between oncological pathologies and neurodegenerative disorders is extremely complex and is a topic of concern among a growing number of researchers around the world. In recent years, convincing scientific evidence has accumulated that indicates the contribution of a number of etiological factors and pathophysiological processes to the pathogenesis of these two fundamentally different diseases, thus demonstrating an intriguing relationship between oncology and neurodegeneration. In this review, we establish the general links between three intersecting aspects of oncological pathologies and neurodegenerative disorders, i.e., oxidative stress, epigenetic dysregulation, and metabolic dysfunction, examining each process in detail to establish an unusual epidemiological relationship. We also focus on reviewing the current trends in the research and the clinical application of the most promising chemical structures and therapeutic platforms that have a modulating effect on the above processes. Thus, our comprehensive analysis of the set of molecular determinants that have obvious cross-functional pathways in the pathogenesis of oncological and neurodegenerative diseases can help in the creation of advanced diagnostic tools and in the development of innovative pharmacological strategies.

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Section: Potential Neuroprotective and Antitumor Therapeutic Candidat...mentioning

confidence: 99%

Deciphering the Mysterious Relationship between the Cross-Pathogenetic Mechanisms of Neurodegenerative and Oncological Diseases

Aleksandrova,

Neganova

2023

IJMS

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“…Since most sesquiterpene lactones contain an activated exo -methylene moiety, which readily reacts with nucleophiles by the Michael reaction, this makes it quite easy to obtain bipharmacophoric compounds on their basis [ 14 ]. For this purpose, various amines [ 15 , 16 ] such as fragments of drugs can be used, for example, the conjugates of lactones with anthracycline antibiotics which show both increased efficiency and reduced cardiotoxicity [ 17 ]. Interesting derivatives are described in [ 18 ], where the sesquiterpene lactone parthenolide was combined in one molecule with the drugs cytarabine and melphalan.…”

Section: Introductionmentioning

confidence: 99%

Design of Conjugates Based on Sesquiterpene Lactones with Polyalkoxybenzenes by “Click” Chemistry to Create Potential Anticancer Agents

et al. 2022

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Using the methodology of “click” chemistry, a singular method has been developed for the synthesis of unique conjugates based on sesquiterpene lactones: dehydrocostuslactone and alantolactone with polyalkoxybenzenes. To expand the structural range of the resulting conjugates, the length of the 1,2,3-triazole spacer was varied. For all synthesized compounds, the cytotoxic profile was determined on the cell lines of tumor origin (SH-SY5Y, HeLa, Hep-2, A549) and normal Hek 293 cells. It was found that the compounds based on alantolactone 7a–d with a long spacer and substances containing dehydrocostuslactone 10a–d with a short spacer have the greatest toxic effect. The decrease in cell survival under the action of these conjugates may be due to their ability to cause dissipation of the transmembrane potential of mitochondria and inhibit the process of glycolysis, leading to cell death. The obtained results confirm the assumption that the development of conjugates based on sesquiterpene lactones and polyalkoxybenzenes can be considered as a promising strategy for the search for potential antitumor agents.

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“…The presence of an exocyclic methylene group in the β‐position of the lactone ring allows such natural molecules to react with N‐nucleophiles. As a result of this transformation, other functional groups are usually retained; such compounds exhibit biological activity, including antitumor [9–12] . The biological activity of SL can be associated with the main chemical properties due to the structural features of this class of compounds: the ability to act as an alkylating agent, lipophilicity of the side chain, and dependence on the molecule geometry and its electronic characteristics.…”

Section: Introductionmentioning

confidence: 99%

New Conjugates of Daunorubicin with Sesquiterpene Lactones and Their Biological Activity

et al. 2021

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New conjugates of daunorubicin with sesquiterpene lactones at the 3′‐amino group of anthracycline were synthesized and their effect on the viability of cell lines (HL60, Jurkat, K562, and A549) was assessed using a resazurin test. The effect on the cell cycle and apoptosis by flow cytometry was studied. The following natural lactones were used for modification: telekin, isotelekin, reynosin, costunolide, dehydrocostuslactone, santamarine and epoxyisoalantolactone. The synthesized conjugates are characterized by a general high toxicity (8…0.14 μM) in relation to tumor cell lines (in some cases, higher than the toxicity of the initial antibiotic), as well as a comparable effect on the cell cycle (arrest in the G2/M‐phase) with a relatively low the effect on the initiation of apoptosis at concentrations close to the IC50.

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Synthesis and Cytotoxic Activity of Azine Derivatives of 6-Hydroxyxanthanodiene

Cited by 4 publications

References 26 publications

Deciphering the Mysterious Relationship between the Cross-Pathogenetic Mechanisms of Neurodegenerative and Oncological Diseases

Deciphering the Mysterious Relationship between the Cross-Pathogenetic Mechanisms of Neurodegenerative and Oncological Diseases

Design of Conjugates Based on Sesquiterpene Lactones with Polyalkoxybenzenes by “Click” Chemistry to Create Potential Anticancer Agents

New Conjugates of Daunorubicin with Sesquiterpene Lactones and Their Biological Activity

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