Dregamine and tabernaemontanine derivatives as ABCB1 modulators on resistant cancer cells

Paterna, Angela; Kincses, Annamária; Mulhovo, Silva; Molnár, Joséph; Ferreira, Maria‐José U.

doi:10.1016/j.ejmech.2017.01.044

Cited by 32 publications

(26 citation statements)

References 26 publications

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“…Being key moieties of a range of alkaloids medium‐ and macro‐sized N‐containing heterocycles are widespread in nature. Thus, dibenzazecine fragment is a structural part of alkaloids A – cryptopine, muramine and protopine (Figure ), which exhibit a broad spectrum of biological activities including anticholinergic, antihistaminic, antithrombotic, antiinflammatory and antihemeostatic . 15‐Membered macrocyclic lactone Laingolide B ( B ) with exocyclic vinyl chloride fragment at C‐7 was recently isolated from a strain of the marine cyanobacterium Lyngbya bouillonii collected from shallow patch reefs in Apra Harbor, Guam, later its total synthesis was successfully conducted by Cui and et al In 2019 Lopes and et al performed synthesis of potentially bioactive ylidene substituted benzimidazobenzothiazecines C .…”

Section: Introductionmentioning

confidence: 99%

Facile Methods for the Synthesis of 8‐Ylidene‐1,2,3,8‐tetrahydrobenzazecines

et al. 2020

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We have elaborated a general and simple microwave-assisted method for the synthesis of original 8-ylidene decorated benzazecines. We have shown that under the action of electron-deficient alkynes in acetic acid the starting benzoannulated azacyclic allenes or 1-alkyl(benzyl)-1-phenylethynylsubstituted isoquinolines underwent transformations leading to benzazecines in high yields. In acetic acid all reactions pro-[a] Dr. A. A. Titov, M. S. Results and DiscussionWe initiated our study with estimating the influence of protonic solvents on the transformations of phenylethynyl decorated isoquinolines 1a-g under the action electron-deficient alkynes. The starting 1-alkyl(benzyl)-1-phenylethynyl-6,7-dimethoxyisoquinolines 1a-g were synthesized according to the previously described procedure [23] from 1-alkyl(benzyl)-3,4-dihydroisoquinolinium methiodide derived via the Bischler-Napieralski reaction followed by alkylation [20] (Scheme 1). Scheme 1. Synthesis of starting 1-alkyl(benzyl)-1-phenylethynyl-6,7-dimethoxyisoquinolines 1a-g.Scheme 3. Reactions of isoquinolines 1b-g with methyl propiolate in HFIP.

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Section: Introductionmentioning

confidence: 99%

Facile Methods for the Synthesis of 8‐Ylidene‐1,2,3,8‐tetrahydrobenzazecines

et al. 2020

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“…As mentioned before, these compounds (1-28) were previously assessed for their ability to modulate the transport activity of P-gp in a functional assay [12,13]. Interestingly, some compounds Compounds 16,18,20,22,24, and 26 were ineffective in the sensitive and resistant variants of carcinoma cells (IC 50 > 100 µM). 1 The IC 50 values with 95 % confidence intervals (CI 95 %) given in parentheses indicate the mean of n = 3 to 4 independent experiments (each concentration was performed in triplicate per experiment).…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 1-10, namely, balsaminol A (1), balsaminol D (2), balsaminol F (3), balsaminagenin A (4), balsaminagenin B (5), balsaminosides A-C (6-8), cucurbalsaminol A (9), and karavilagenin C (10), were previously isolated from the methanol extract of M. balsamina as reported [12,[21][22][23]. Compound 10, isolated in a large amount, gave rise to 18 compounds, namely, karavoates A-R (11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28), by using several alkanoyl and aroyl acylating reagents, as described [12,24]. The purity of the compounds was more than 95 % by HPLC.…”

Section: Tested Compoundsmentioning

confidence: 99%

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Triterpenoids from Momordica balsamina with a Collateral Sensitivity Effect for Tackling Multidrug Resistance in Cancer Cells

et al. 2018

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The collateral sensitivity effect is among the most promising strategies for overcoming multidrug resistance in cancer. In this work, 28 cucurbitane-type triterpenoids (1: -28: ), previously isolated from the African medicinal plant and its derivatives, were evaluated for their collateral sensitivity effect on three different human cancer entities, gastric (EPG85-257), pancreatic (EPP85-181), and colon (HT-29), each with two different multidrug-resistant variants. One was selected for its resistance to daunorubicin (EPG85-257RDB, EPP85-181RDB, HT-29RDB) and the other was selected for its resistance to mitoxantrone (EPG85-257RNOV, EPP85-181RNOV, HT-29RNOV). On gastric cell lines, the best results were obtained for compounds 3: and 10: , which exhibited a collateral sensitivity effect together with high antiproliferative activity. In turn, on colon cancer cell lines, the best multidrug resistance-selective antiproliferative effects were observed for derivatives 11, 13: , and 15: , which showed collateral sensitivity effects against both resistant variants. Compounds 11: and 3: were also the most selective against the multidrug resistance pancreatic cells lines. Some compounds, such 6, 10, 11: and 15: , were previously found to be strong P-glycoprotein modulators, thus highlighting their potential as promising leads for overcoming multidrug resistance in cancer cells.

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“…These natural products decrease P-gp expression [ 21 , 28 , 29 ]. Recent studies have shown that natural terpenoids reverse MDR in cancer cells [ 30 , 31 ]. However, their mechanism of action is unknown.…”

Section: Introductionmentioning

confidence: 99%

Tomentodione M sensitizes multidrug resistant cancer cells by decreasing P-glycoprotein via inhibition of p38 MAPK signaling

et al. 2017

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In this study, we investigated the mechanism by which tomentodione M (TTM), a novel natural syncarpic acid-conjugated monoterpene, reversed multi-drug resistance (MDR) in cancer cells. TTM increased the cytotoxicity of chemotherapeutic drugs such as docetaxel and doxorubicin in MCF-7/MDR and K562/MDR cells in a dose- and time-dependent manner. TTM reduced colony formation and enhanced apoptosis in docetaxel-treated MCF-7/MDR and K562/MDR cells, and it enhanced intracellular accumulation of doxorubicin and rhodamine 123 in MDR cancer cells by reducing drug efflux mediated by P-gp. TTM decreased expression of both P-gp mRNA and protein by inhibiting p38 MAPK signaling. Similarly, the p38 MAPK inhibitor SB203580 reversed MDR in cancer cells by decreasing P-gp expression. Conversely, p38 MAPK-overexpressing MCF-7 and K562 cells showed higher P-gp expression than controls. These observations indicate that TTM reverses MDR in cancer cells by decreasing P-gp expression via p38 MAPK inhibition.

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Dregamine and tabernaemontanine derivatives as ABCB1 modulators on resistant cancer cells

Cited by 32 publications

References 26 publications

Facile Methods for the Synthesis of 8‐Ylidene‐1,2,3,8‐tetrahydrobenzazecines

Facile Methods for the Synthesis of 8‐Ylidene‐1,2,3,8‐tetrahydrobenzazecines

Triterpenoids from Momordica balsamina with a Collateral Sensitivity Effect for Tackling Multidrug Resistance in Cancer Cells

Tomentodione M sensitizes multidrug resistant cancer cells by decreasing P-glycoprotein via inhibition of p38 MAPK signaling

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