Synthesis and <i>in vitro</i> cytotoxicity evaluation of β-carboline-linked 2,4-thiazolidinedione hybrids: potential DNA intercalation and apoptosis-inducing studies

Tokala, Ramya; Thatikonda, Sowjanya; Sana, Sravani; Phanindranath, Regur; Godugu, Chandraiah; Shankaraiah, Nagula

doi:10.1039/c8nj03248c

Cited by 53 publications

(19 citation statements)

References 65 publications

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“…Initially, the assay was optimized by seeding HaCaT cells at cell density 4 × 10 4 and allowed to adhere, and further treated with SeNPs (0.5, 1 and 2.5 µg/ml) for 1 h followed by stimulation with EGF and incubated for 24 h. Then the assay was performed with aforementioned kit and followed the manufacturer protocol. Later the samples from all groups were analyzed by flow cytometry [ 41 ].…”

Section: Methodsmentioning

confidence: 99%

Selenium nanoparticles produce a beneficial effect in psoriasis by reducing epidermal hyperproliferation and inflammation

et al. 2021

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Background Psoriasis is a chronic autoimmune skin disease characterized by hyperproliferation of keratinocytes. Wide treatment options used to treat psoriasis is associated with various adverse effects. To overcome this nanoformulation is prepared. Selenium is an essential trace element and plays major role in oxidation reduction system. Toxicity and stability limits the applications of selenium. Toxicity can be reduced and stabilized upon preparation into nanoparticles. Results Selenium nanoparticles (SeNPs) exhibit potent apoptosis through the generation of reactive oxygen species (ROS) with cell cycle arrest. SeNPs topical gel application produced significant attenuation of psoriatic severity with the abrogation of acanthosis and splenomegaly. SeNPs reduced the phosphorylation and expressions of MAPKs, STAT3, GSK-3β, Akt along with PCNA, Ki67, and cyclin-D1. Conclusion SeNPs inhibit various inflammation and proliferation mediated pathways and could be an ideal candidate for psoriasis therapy. Materials and methods SeNPs were characterized and various techniques were used to determine apoptosis and other molecular mechanisms. In vivo studies were performed by inducing psoriasis with imiquimod (IMQ). SeNPs were administered via topical route. Graphic Abstract

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Section: Methodsmentioning

confidence: 99%

Selenium nanoparticles produce a beneficial effect in psoriasis by reducing epidermal hyperproliferation and inflammation

et al. 2021

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“…General procedure for the synthesis of thiazolidiene-2,4 dione-1,3,4-oxadiazole hybrids (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21) A mixture of compound 6 (0.01 mol) and different substituted aromatic hydrazides (0.01 mmol) in POCl 3 (20 ml) was stirred and refluxed for 10-12 h. After reaction completion, the reaction mixture was poured onto crushed ice and neutralised with NaHCO 3 solution. The resulting precipitate 7-21 was filtered, washed with excess cold water and dried.…”

Section: Chemistrymentioning

confidence: 99%

“…[10][11] Beside hypoglycaemic agents, thiazolidinedione derivatives are reported as anti-inflammatory, 12 antimicrobial 13 and anticancer agents. [14][15][16] It has been mentioned that compounds which activate PPAR-c might lead to differentiation induction of cancer cells. 17 For example, a TZD analogue, efatutazone (CS-7017) is a potent PPAR-c full agonist as well as a cancer differentiation-inducing agent.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis andin vitroantiproliferative activity of new thiazolidinedione-1,3,4-oxadiazole hybrids as thymidylate synthase inhibitors

Alzhrani

Alam

Neamatallah

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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Thymidylate synthase (TS) has been an attention-grabbing area of research for the treatment of cancers due to their role in DNA biosynthesis. In the present study, we have synthesised a library of thiazolidinedione-1,3,4-oxadiazole hybrids as TS inhibitors. All the synthesised hybrids followed Lipinski and Veber rules which indicated good drug likeness properties upon oral administration. Among the synthesised hybrids, compound 9 and 10 displayed 4.5 and 4.4 folds activity of 5-Fluorouracil, respectively against MCF-7 cell line whereas 3.1 and 2.5 folds cytotoxicity against HCT-116 cell line. Furthermore, compound 9 and 10 also inhibited TS enzyme with IC 50 ¼ 1.67 and 2.21 mM, respectively. Finally, the docking studies of 9 and 10 were found to be consistent with in vitro TS results. From these studies, compound 9 and 10 has the potential to be developed as TS inhibitors.

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“…[1] Based on pyridine ring saturation, these molecules are categorized as: i) β-carbolines (Cs, unsaturated), ii) dihydro-βcarbolines (DHCs, partially saturated), iii) tetrahydro-β-carbolines (THCs, completely saturated). [4] β-Carboline alkaloids and their derivatives possess a significant array of pharmacological properties, including anti-inflammatory [5][6][7] (Eleagnine), anticonvulsant [8][9] (ZK91296), antiviral [10][11] (Harmine), antimicrobial [12] (Eudistomin W), antidepressant [13] (Harmane), anticancer [14][15][16][17][18][19][20] (Arborescidine C) as depicted in Figure 1. Numerous mechanisms has been displayed by this class of molecules like interaction with DNA, [21] topoisomerase I & II inhibition , [16,22] Mitogen-activated protein kinase inhibition (MAPK), [23] action on CDK's, [24] IĸB kinase (IKK) inhibition, [25] MAO-A and MAO-B inhibition etc.…”

Section: Introductionmentioning

confidence: 99%

Application of Transition Metal‐Catalyzed C−H Activation Strategies in the Synthesis and Functionalization of β‐Carbolines

2021

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β-Carboline and its derivatives are well-known for their biological and pharmacological properties and are considered as an important source of drug or drug leads. The traditional methods employed for the construction of βcarbolines present certain limitations surfacing requirements for a better approach. The catalytic CÀ H activation strategy offers an attractive route owing to step-and atom-economy. The transition metal-catalyzed CÀ H activation has not just been employed for the synthesis of β-carboline scaffold but also has paved the way for functionalization, scrutinizing the intrinsic directing property of β-carbolines. This review focuses on exploring the efficiency of CÀ H activation in fabricating and functionalizing β-carbolines, including the overview of substrate scope, regioselectivity and synthesis of some of the related natural products.

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Synthesis and in vitro cytotoxicity evaluation of β-carboline-linked 2,4-thiazolidinedione hybrids: potential DNA intercalation and apoptosis-inducing studies

Abstract: A series of β-carboline-linked 2,4-thiazolidinedione hybrids was synthesized and studied for their DNA affinities and cytotoxicities. The most potent compound was 19e with IC50 of 0.97 ± 0.13 μM.

Cited by 53 publications

References 65 publications

Selenium nanoparticles produce a beneficial effect in psoriasis by reducing epidermal hyperproliferation and inflammation

Selenium nanoparticles produce a beneficial effect in psoriasis by reducing epidermal hyperproliferation and inflammation

Design, synthesis andin vitroantiproliferative activity of new thiazolidinedione-1,3,4-oxadiazole hybrids as thymidylate synthase inhibitors

Application of Transition Metal‐Catalyzed C−H Activation Strategies in the Synthesis and Functionalization of β‐Carbolines

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