Penicillixanthone A, a marine-derived dual-coreceptor antagonist as anti-HIV-1 agent

Tan, Suiyi; Yang, Bin; Liu, Juan; Xun, Tianrong; Liu, Yonghong; Zhou, Xuefeng

doi:10.1080/14786419.2017.1416376

Cited by 20 publications

(20 citation statements)

References 12 publications

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“…Over the past few decades, the application of natural products for chemoprevention and therapy has gained great importance [ 29 , 30 , 31 ]. More and more studies have demonstrated that pharmacological active marine-derived compounds have potent biological activity with little or no side effects [ 32 , 33 , 34 ]. Phycocyanin, a type of phycobiliprotein derived from Spirulina , is one of the compounds that have considerable anti-cancer effects on solid malignancies [ 35 , 36 ].…”

Section: Discussionmentioning

confidence: 99%

The In Vitro Anti-Tumor Activity of Phycocyanin against Non-Small Cell Lung Cancer Cells

Hao

Yan

et al. 2018

Marine Drugs

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Phycocyanin, a type of functional food colorant, is shown to have a potent anti-cancer property. Non-small cell lung cancer (NSCLC) is one of the most aggressive form of cancers with few effective therapeutic options. Previous studies have demonstrated that phycocyanin exerts a growth inhibitory effect on NSCLC A549 cells. However, its biological function and underlying regulatory mechanism on other cells still remain unknown. Here, we investigated the in vitro function of phycocyanin on three typical NSCLC cell lines, NCI-H1299, NCI-H460, and LTEP-A2, for the first time. The results showed that phycocyanin could significantly induce apoptosis, cell cycle arrest, as well as suppress cell migration, proliferation, and the colony formation ability of NSCLC cells through regulating multiple key genes. Strikingly, phycocyanin was discovered to affect the cell phenotype through regulating the NF-κB signaling of NSCLC cells. Our findings demonstrated the anti-neoplastic function of phycocyanin and provided valuable information for the regulation of phycocyanin in NSCLC cells.

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Section: Discussionmentioning

confidence: 99%

The In Vitro Anti-Tumor Activity of Phycocyanin against Non-Small Cell Lung Cancer Cells

Hao

Yan

et al. 2018

Marine Drugs

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“…Penicillixanthone A (3) was also already shown to possess moderate antibacterial activity against four tested bacterial strains (M. luteus, Pseudoalteromonas nigrifaciens, E. coli and B. subtilis [100], and its moderate cytotoxic effects on MDA-MB-435 human melanoma cells and SW620 human colorectal adenocarcinoma cell lines had been previously reported [101]. Furthermore, compound 3 was previously isolated from the marine-derived fungus Aspergillus fumigatus, and was reported to exhibit anti-HIV-1 activities by inhibiting CCR5-tropic HIV-1 and CXCR4-tropic HIV-1 infection [103]. These data also point toward non-selective effects of this metabolite in biological systems.…”

Section: Biological Activity Of Compounds 1-5mentioning

confidence: 97%

“…Compound 2 (4,4 -secalonic acid D; 4,4 -SAD) is a regioisomeric structure to SAD with 2,2 -biarylic connectivity, belonging to the secalonic acid family. This compound class has long been known to have non-selective antimicrobial and other biological activities [100][101][102][103][104][105][106]. The compound 4,4 -SAD (2) itself was recently reported to have low toxicity with "potent" antitumor activity against several cancer cell lines through cell proliferation inhibition and apoptosis induction [100].…”

Section: Biological Activity Of Compounds 1-5mentioning

confidence: 99%

“…Structure Elucidation of the New Compound HPLC chromatographic fractionation of the crude ethyl acetate extract from the yeast malt (YM 6.3) broth of Pseudopalawania siamensis resulted in the isolation of a new heterodimeric bistetrahydroxanthone, pseudopalawanone (1) together with three known tetrahydroxanthones, 4,4 -secalonic acid D (2) [100], penicillixanthone A (3) [101], paecilin B (4) [102] and the benzophenone, cephalanone F (5) [103](Figure 4). bistetrahydroxanthone, pseudopalawanone (1) together with three known tetrahydroxanthones, 4,4′secalonic acid D (2)[100], penicillixanthone A (3)[101], paecilin B (4)[102] and the benzophenone, cephalanone F (5)[103] (Figure 4).…”

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confidence: 99%

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Polyketide-Derived Secondary Metabolites from a Dothideomycetes Fungus, Pseudopalawania siamensis gen. et sp. nov., (Muyocopronales) with Antimicrobial and Cytotoxic Activities

et al. 2020

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Pseudopalawania siamensis gen. et sp. nov., from northern Thailand, is introduced based on multi-gene analyses and morphological comparison. An isolate was fermented in yeast malt culture broth and explored for its secondary metabolite production. Chromatographic purification of the crude ethyl acetate (broth) extract yielded four tetrahydroxanthones comprised of a new heterodimeric bistetrahydroxanthone, pseudopalawanone (1), two known dimeric derivatives, 4,4′-secalonic acid D (2) and penicillixanthone A (3), the corresponding monomeric tetrahydroxanthone paecilin B (4), and the known benzophenone, cephalanone F (5). Compounds 1–3 showed potent inhibitory activity against Gram-positive bacteria. Compounds 2 and 3 were inhibitory against Bacillus subtilis with minimum inhibitory concentrations (MIC) of 1.0 and 4.2 μg/mL, respectively. Only compound 2 showed activity against Mycobacterium smegmatis. In addition, the dimeric compounds 1–3 also showed moderate cytotoxic effects on HeLa and mouse fibroblast cell lines, which makes them less attractive as candidates for development of selectively acting antibiotics.

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“…Other dual CXCR4/CCR5 antagonists include, peptide-based triazoles analogues ( Tuzer et al., 2013 ), diterpene derivatives ( EC 50 0.02 and 0.09 µM against R5 and X4 HIV strains, respectively ( Abreu et al., 2014 )), and pyrazole derivatives ( IC 50 3.8 and 0.8 µM against CCR5- and CXCR4-utilizing HIV-1 strains) ( Cox et al., 2015 ). An analogue of the antiparasitic drug suramin NF279 ( Giroud et al., 2015 ), the natural penicillixanthone A ( Tan et al., 2019 ) and a coumarin-based analogue GUT-70 ( Kudo et al., 2013 ) are also known as dual CCR5/CXCR4 antagonists ( Fig. 1 ).…”

Section: Introductionmentioning

confidence: 99%

Discovery of HIV entry inhibitors via a hybrid CXCR4 and CCR5 receptor pharmacophore‐based virtual screening approach

Mirza

Saadabadi

Vanmeert

et al. 2020

European Journal of Pharmaceutical Sciences

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Chemokine receptors are key regulators of cell migration in terms of immunity and inflammation. Among these, CCR5 and CXCR4 play pivotal roles in cancer metastasis and HIV-1 transmission and infection. They act as essential co-receptors for HIV and furnish a route to the cell entry. In particular, inhibition of either CCR5 or CXCR4 leads very often the virus to shift to a more virulent dual-tropic strain. Therefore, dual receptor inhibition might improve the therapeutic strategies against HIV. In this study, we aimed to discover selective CCR5, CXCR4, and dual CCR5/CXCR4 antagonists using both receptor- and ligand-based computational methods. We employed this approach to fully incorporate the interaction attributes of the binding pocket together with molecular dynamics (MD) simulations and binding free energy calculations. The best hits were evaluated for their anti-HIV-1 activity against CXCR4- and CCR5-specific NL4.3 and BaL strains. Moreover, the Ca 2+ mobilization assay was used to evaluate their antagonistic activity. From the 27 tested compounds, three were identified as inhibitors: compounds 27 (CCR5), 6 (CXCR4) and 3 (dual) with IC 50 values ranging from 10.64 to 64.56 μM. The binding mode analysis suggests that the active compounds form a salt bridge with the glutamates and π-stacking interactions with the aromatic side chains binding site residues of the respective co-receptor. The presented hierarchical virtual screening approach provides essential aspects in identifying potential antagonists in terms of selectivity against a specific co-receptor. The compounds having multiple heterocyclic nitrogen atoms proved to be relatively more specific towards CXCR4 inhibition as compared to CCR5. The identified compounds serve as a starting point for further development of HIV entry inhibitors through synthesis and quantitative structure-activity relationship studies.

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Penicillixanthone A, a marine-derived dual-coreceptor antagonist as anti-HIV-1 agent

Cited by 20 publications

References 12 publications

The In Vitro Anti-Tumor Activity of Phycocyanin against Non-Small Cell Lung Cancer Cells

The In Vitro Anti-Tumor Activity of Phycocyanin against Non-Small Cell Lung Cancer Cells

Polyketide-Derived Secondary Metabolites from a Dothideomycetes Fungus, Pseudopalawania siamensis gen. et sp. nov., (Muyocopronales) with Antimicrobial and Cytotoxic Activities

Discovery of HIV entry inhibitors via a hybrid CXCR4 and CCR5 receptor pharmacophore‐based virtual screening approach

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