Synthesis and Biological Activities of Cyclodepsipeptides of Aurilide Family from Marine Origin

Aurilides are a class of depsipeptides occurring mainly in marine cyanobacteria. Members of the aurilide family have shown to exhibit strong cytotoxicity against various cancer cell lines. These compounds bear a pentapeptide, a polyketide, and an α-hydroxy ester subunit in their structure. A large number of remarkable studies on aurilides have emerged since 1996. This comprehensive account summarizes the biological activities and total syntheses of natural compounds of the aurilide family as well as their synthetic analogues.

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Naphthoquinone-based hydrazone hybrids: synthesis and potent activity against cancer cell lines

Medicinal Chemistry ◽

10.2174/1573406416666200817164308 ◽

2020 ◽

Vol 16 ◽

Author(s):

Délis Galvão Guimarães ◽

Arlan de Assis Gonsalves ◽

Larissa Araújo Rolim ◽

Edigênia Cavalcante Araújo ◽

Victória Laysna dos Anjos Santos ◽

...

Keyword(s):

Anticancer Activity ◽

Cell Lines ◽

Cancer Cell ◽

Biological Activities ◽

Supporting Electrolyte ◽

Cancer Cell Lines ◽

Molecular Structures ◽

Cytotoxic Activities ◽

Electrochemical Studies ◽

Ic50 Values

Background: Natural naphthoquinones have shown diversified biological activities including antibacterial, antifungal, antimalarial, and cytotoxic activities. However, they are also compounds with acute cytotoxicity, immunotoxicity, carcinogenesis, and cardio- and hepatotoxicity, then the modification at their redox center is an interesting strategy to overcome such harmful activity. Objective: In this study, four novel semisynthetic hydrazones, derived from the isomers α- and β-lapachones (α and β, respectively) and coupled with the drugs hydralazine (HDZ) and isoniazid (ACIL), were prepared, evaluated by electrochemical methods and assayed for anticancer activity. Method: The semisynthetic hydrazones were obtained and had their molecular structures established by NMR, IR, and MS. Anticancer activity was evaluated by cell viability determined by reduction of 3-(4,5-dimethyl-2-thiazol)-2,5-diphenyl-2H-tetrazolium bromide (MTT). The electrochemical studies, mainly cyclic voltammetry, were performed, in aprotic and protic media. Result: The study showed that the compounds 2, 3, and 4 were active against at least one of the cancer cell lines evaluated, being compounds 3 and 4 the most cytotoxic. Toward HL-60 cells, compound 3 was 20x more active than β-lapachone, and 3x more cytotoxic than doxorubicin. Furthermore, 3 showed an SI value of 39.62 for HL-60 cells. Compound 4 was active against all cancer cells tested, with IC50 values in the range 2.90–12.40 μM. Electrochemical studies revealed a profile typical of self-protonation and reductive cleavage, dependent on the supporting electrolyte. Conclusion: These results therefore indicate that compounds 3 and 4 are strong candidates as prototypes of new antineoplastic drugs.

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Synthesis of Lapachol-Based Glycosides and Glycosyl Triazoles with Antiproliferative Activity Against Several Cancer Cell Lines

10.21203/rs.3.rs-916974/v1 ◽

2021 ◽

Author(s):

Flaviano Melo Ottoni ◽

Lucas Bonfim Marques ◽

Juliana Martins Ribeiro ◽

Lucas Lopardi Franco ◽

José Dias Souza Filho ◽

...

Keyword(s):

Antitumor Activity ◽

Adverse Effects ◽

Dna Fragmentation ◽

Cell Lines ◽

Cancer Cell ◽

Antiproliferative Activity ◽

Biological Activities ◽

Cancer Cell Lines ◽

Tumor Cell Lines

Abstract Lapachol (1), a natural naphthoquinone, presents several biological activities including antitumor activity, used as anticancer coadjuvant whose use was abandoned because of adverse effects. Herein, we reported the synthesis and cytotoxicity evaluation against cancer cell lines of a series of Oglycosides and glycosyl triazoles derived from lapachol. In addition to the determination of IC50, the DNA fragmentation and clonogenicity were also evaluated. The glycoside derived from D-glucose (5) was far more active than lapachol (1) and more active in tumor cell lines HL60, Jurkat, THP-1 and MDA-MB-231 than to the non-tumoral PBMC cell line, indicating an improvement in activity and selectivity as compared with lapachol (1). Compound 5 and the glycosides derived from D-galactose (14), D-N-acetylglucosamine (15) and L-fucose (16) showed good results in the DNA fragmentation and clonogenicity assays in the studies of subdiploid DNA content, indicating a pro-apoptotic potential and a good antiproliferative activity of these glycosides.

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Synthesis of Novel Aza-aromatic Curcuminoids with Improved Biological Activities towards Various Cancer Cell Lines

ChemistryOpen ◽

10.1002/open.201800029 ◽

2018 ◽

Vol 7 (5) ◽

pp. 381-392 ◽

Cited By ~ 10

Author(s):

Atiruj Theppawong ◽

Tim Van de Walle ◽

Charlotte Grootaert ◽

Margot Bultinck ◽

Tom Desmet ◽

...

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Biological Activities ◽

Cancer Cell Lines

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In VitroAntibacterial, Antioxidant, and Cytotoxic Activities ofParthenium hysterophorusand Characterization of Extracts by LC-MS Analysis

BioMed Research International ◽

10.1155/2014/495154 ◽

2014 ◽

Vol 2014 ◽

pp. 1-10 ◽

Cited By ~ 14

Author(s):

Shashank Kumar ◽

Sanjay Pandey ◽

Abhay K. Pandey

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Biological Activities ◽

Beta Carotene ◽

Cancer Cell Lines ◽

Salmonella Typhi ◽

Cytotoxic Activities ◽

Plant Parts ◽

Colon Cancer Cell Lines

Present work reports the biological activities ofP. hysterophorusleaf, stem, flower, and root. Dried samples were sequentially extracted with many solvents. Hexane (HX), benzene (BZ), and chloroform (CH) extracts of leaf showed considerable antibacterial activity againstStreptococcus mutans(MTCC 497),Proteus vulgaris(MTCC 7299), andSalmonella typhi(MTCC 3917). Flower extracts exhibited presence of higher amount of flavonoids (13.9–59.6 μgQE/mg) followed by leaf, stem, and root. Stem (HX, BZ, and CH), leaf ethanol (ET), and root (HX, BZ, and CH) fractions showed noticeable antioxidant capacity in phosphomolybdate assay. Most of the extracts demonstrated beta carotene bleaching inhibition capability. BZ, ethyl acetate (EA), and ET fractions of leaves, stem aqueous (AQ), and flower EA extracts showed membrane protective activities (40–55%). Middle fractions of the plant parts displayed moderate antihemolytic potential. Most of the flower extracts exhibited cytotoxic activity (80–100%) against lung and colon cancer cell lines. Root (HX and ET) and leaf ET extracts showed considerable inhibition (90–99%) of colon and ovary cancer cell lines. The LC-MS scan demonstrated presence of different compounds showing 3–20 min retention time. The study revealed considerable antibacterial, antioxidant, lipo-protective, antihemolytic, and anticancer potential in all parts ofP. hysterophorus.

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Biological Effects of Glucosinolate Degradation Products from Horseradish: A Horse that Wins the Race

Biomolecules ◽

10.3390/biom10020343 ◽

2020 ◽

Vol 10 (2) ◽

pp. 343 ◽

Cited By ~ 3

Author(s):

Marijana Popović ◽

Ana Maravić ◽

Vedrana Čikeš Čulić ◽

Azra Đulović ◽

Franko Burčul ◽

...

Keyword(s):

Cytotoxic Activity ◽

Cell Lines ◽

Cancer Cell ◽

Degradation Products ◽

Human Cancer ◽

Biological Activities ◽

Biological Effects ◽

Cancer Cell Lines ◽

Cytotoxic Activities ◽

Minimal Inhibitory Concentrations

Horseradish degradation products, mainly isothiocyanates (ITC) and nitriles, along with their precursors glucosinolates, were characterized by GC-MS and UHPLC-MS/MS, respectively. Volatiles from horseradish leaves and roots were isolated using microwave assisted-distillation (MAD), microwave hydrodiffusion and gravity (MHG) and hydrodistillation (HD). Allyl ITC was predominant in the leaves regardless of the isolation method while MAD, MHG, and HD of the roots resulted in different yields of allyl ITC, 2-phenylethyl ITC, and their nitriles. The antimicrobial potential of roots volatiles and their main compounds was assessed against sixteen emerging food spoilage and opportunistic pathogens. The MHG isolate was the most active, inhibiting bacteria at minimal inhibitory concentrations (MICs) from only 3.75 to 30 µg/mL, and fungi at MIC50 between <0.12 and 0.47 µg/mL. Cytotoxic activity of volatile isolates and their main compounds were tested against two human cancer cell lines using MTT assay after 72 h. The roots volatiles showed best cytotoxic activity (HD; IC50 = 2.62 μg/mL) against human lung A549 and human bladder T24 cancer cell lines (HD; IC50 = 0.57 μg/mL). Generally, 2-phenylethyl ITC, which was tested for its antimicrobial and cytotoxic activities along with two other major components allyl ITC and 3-phenylpropanenitrile, showed the best biological activities.

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Synthesis and Biological Evaluation of matrine derivatives as a Novel Family of Potential Anticancer Agents

Medicinal Chemistry ◽

10.2174/1573406415666191022145534 ◽

2019 ◽

Vol 15 ◽

Author(s):

Jing Wang ◽

Hang Liu ◽

Xiao-Bin Zhuo ◽

Guang-Ming Ye ◽

Qing-Jie Zhao

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Anticancer Agents ◽

Human Cancer ◽

Biological Activities ◽

Parent Compound ◽

Human Tumor ◽

Cancer Cell Lines ◽

Biological Evaluation ◽

Novel Scaffold

Background: ‘FufangKushen injection’ was a Chinese Traditional anticancer drug, which has been widely used to treat cancer in combination with other anticancer drugs. Objective: Our goal is to synthesize a series of novel 13-dithiocarbamates matrine derivatives using matrine (1) as the lead compounnd, and evaluate biological activities of obtained compounds. Method: The in vitro cytotoxicity of the target compounds against three human cancer cell lines (Hep3B, LM3 and BeL-7404) was evaluated. To investigate the mechanism of biological activity, Cell cycle analysis were performed. Result: The results revealed that compound 6o and 6v displayed the most significant anticancer activity against three cancer cell lines with IC50 values in range of 3.42–8.05 μM, which showed better activity than the parent compound (Matrine). SAR analysis indicated that introduction of a substituted amino dithiocarbamate might significantly enhance the antiproliferative activity. Conclusion: During the newly synthesized compounds, matrine analogue 6v exhibited a potent effect against three human tumor cell lines. The mode of action of 6v was to inhibit the G0/G1 phase arrest. Therefore, compound 6v has been selected as a novel-scaffold lead for further structural optimizations or as a chemical probe for exploring anticancer pathways of this kinds of compounds.

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Comparison of Chemical Composition and Biological Activities of Eight Selaginella Species

Pharmaceuticals ◽

10.3390/ph14010016 ◽

2020 ◽

Vol 14 (1) ◽

pp. 16

Author(s):

Bára Křížkovská ◽

Rohitesh Kumar ◽

Kateřina Řehořová ◽

David Sýkora ◽

Simona Dobiasová ◽

...

Keyword(s):

Antioxidant Capacity ◽

Cell Lines ◽

Cancer Cell ◽

High Performance ◽

High Resolution Mass Spectrometry ◽

Biological Activities ◽

Cancer Cell Lines ◽

Absorption Capacity ◽

Dependent Manner ◽

Half Maximal Effective Concentration

Selaginella P. Beauv. is a group of vascular plants in the family Selaginellaceae Willk., found worldwide and numbering more than 700 species, with some used as foods and medicines. The aim of this paper was to compare methanolic (MeOH) and dichloromethane (DCM) extracts of eight Selaginella species on the basis of their composition and biological activities. Six of these Selaginella species are underinvestigated. Using ultra-high performance liquid chromatography–high-resolution mass spectrometry (UHPLC–HRMS) analysis, we identified a total of 193 compounds among the tested Selaginella species, with flavonoids predominating. MeOH extracts recovered more constituents that were detected, including selaginellins, the occurrence of which is only typical for this plant genus. Of all the tested species, Selaginellaapoda contained the highest number of identified selaginellins. The majority of the compounds were identified in S. apoda, the fewest compounds in Selaginellacupressina. All the tested species demonstrated antioxidant activity using oxygen radical absorption capacity (ORAC) assay, which showed that MeOH extracts had higher antioxidant capacity, with the half maximal effective concentration (EC50) ranging from 12 ± 1 (Selaginellamyosuroides) to 124 ± 2 (Selaginellacupressina) mg/L. The antioxidant capacity was presumed to be correlated with the content of flavonoids, (neo)lignans, and selaginellins. Inhibition of acetylcholinesterase (AChE) was mostly discerned in DCM extracts and was only exhibited in S. myosuroides, S. cupressina, Selaginellabiformis, and S. apoda extracts with the half maximal inhibitory concentration (IC50) in the range of 19 ± 3 to 62 ± 1 mg/L. Substantial cytotoxicity against cancer cell lines was demonstrated by the MeOH extract of S. apoda, where the ratio of the IC50 HEK (human embryonic kidney) to IC50 HepG2 (hepatocellular carcinoma) was 7.9 ± 0.2. MeOH extracts inhibited the production of nitrate oxide and cytokines in a dose-dependent manner. Notably, S. biformis halved the production of NO, tumor necrosis factor (TNF)-α, and interleukin (IL)-6 at the following concentrations: 105 ± 9, 11 ± 1, and 10 ± 1 mg/L, respectively. Our data confirmed that extracts from Selaginella species exhibited cytotoxicity against cancer cell lines and AChE inhibition. The activity observed in S. apoda was the most promising and is worth further exploration.

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