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  • Wu, Chin-Chung  (89)
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  • 1
    Language: English
    In: Journal of medicinal chemistry, 09 August 2012, Vol.55(15), pp.6985
    Keywords: Pharmacy, Therapeutics, & Pharmacology ; Chemistry;
    E-ISSN: 1520-4804
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  • 2
    Language: English
    In: PLoS ONE, 2012, Vol.7(5), p.e37764
    Description: Withanolides are a large group of steroidal lactones found in Solanaceae plants that exhibit potential anticancer activities. We have previously demonstrated that a withanolide, tubocapsenolide A, induced cycle arrest and apoptosis in human breast cancer cells, which was associated with the inhibition of heat shock protein 90 (Hsp90). To investigate whether other withanolides are also capable of inhibiting Hsp90 and to analyze the structure-activity relationships, nine withanolides with different structural properties were tested in human breast cancer cells MDA-MB-231 and MCF-7 in the present study. Our data show that the 2,3-unsaturated double bond-containing withanolides inhibited Hsp90 function, as evidenced by selective depletion of Hsp90 client proteins and induction of Hsp70. The inhibitory effect of the withanolides on Hsp90 chaperone activity was further confirmed using in vivo heat shock luciferase activity recovery assays. Importantly, Hsp90 inhibition by the withanolides was correlated with their ability to induce cancer cell death. In addition, the withanolides reduced constitutive NF-κB activation by depleting IκB kinase complex (IKK) through inhibition of Hsp90. In estrogen receptor (ER)-positive MCF-7 cells, the withanolides also reduced the expression of ER, and this may be partly due to Hsp90 inhibition. Taken together, our results suggest that Hsp90 inhibition is a general feature of cytotoxic withanolides and plays an important role in their anticancer activity.
    Keywords: Research Article ; Biology ; Medicine ; Molecular Biology ; Cell Biology ; Oncology ; Biochemistry
    E-ISSN: 1932-6203
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  • 3
    Language: English
    In: Cancer Research, 10/01/2014, Vol.74(19 Supplement), pp.1637-1637
    ISSN: 0008-5472
    E-ISSN: 1538-7445
    Source: CrossRef
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  • 4
    Language: English
    In: Tetrahedron, 04 March 2014, Vol.70(9), pp.1800-1804
    Description: A four-component Ugi reaction (Ugi-4CR) utilizing formylphenyl boronic acids under mild condition was developed for the synthesis of arylboronic acid analogs. The reactions were performed in methanol and accelerated by microwave irradiation, which makes this strategy suitable for constructing boronic-containing chemical libraries. Two of the synthesized analogs were found to have cytotoxic activity against HepG2, MDA-MB231, and A549 cancer cell lines, demonstrating the potential application of this approach in developing novel boron-containing pharmaceuticals. In this study, an Ugi four-component reaction (Ugi-4CR) utilizing unprotected boronic acid building blocks under mild condition is developed. The described reactions were performed in methanol and accelerated by employing microwave irradiation. This strategy allows the direct generation of boronic acid analogs without protection and deprotection operations of boronic acid moiety, making it suitable for the preparation of boron-containing chemical libraries. The synthesized boronic acid analogs were subsequently evaluated for their cytotoxic activity by the MTT assay. Two potential lead compounds were found to be cytotoxic against HepG2, MDA-MB231, and A549 cancer cell lines, demonstrating the potential application of this approach in developing novel boron-containing pharmaceuticals.
    Keywords: Boronic Acids ; Ugi-4cr ; Multicomponent Reaction ; Microwave-Assisted Synthesis ; Acid/Base Extraction ; Chemistry
    ISSN: 0040-4020
    E-ISSN: 1464-5416
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  • 5
    Language: English
    In: PLoS ONE, 01 January 2011, Vol.6(8), p.e23922
    Description: Protoapigenone, a natural flavonoid possessing an unusual p-quinol moiety on its B-ring, is a novel prospective anticancer agent with low toxicity that is currently in development. The first economical, one-step synthesis of protoapigenone from...
    Keywords: Sciences (General)
    E-ISSN: 1932-6203
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  • 6
    Language: English
    In: Food Chemistry, 01 September 2013, Vol.140(1-2), pp.305-314
    Description: roots showed oestrogenic and anti-platelet activities. ► Twenty-six compounds were isolated and divided into 10 different skeletons. ► The biosynthetic pathway of the isolated dihydrobenzofuroisocoumarins was proposed. can be used to develop nutritional dietary supplements. The ethanolic extract of (Liliaceae) roots showed potential oestrogenic and anti-platelet activities. Twenty-six compounds were isolated and classified as 10 skeletons, including two unusual new dihydrobenzofuroisocoumarins, (+)-platyphyllarin A ( ) and B ( ), one new butanoate, ethyltributanoate ( ), and two new homoisoflavanones, (−)-liriopein A ( ) and B ( ), along with 21 known compounds, including six homoisoflavonoids, one chalcone, six amides, one lignan, one fatty acid derivative, one alkaloid, three benzenoids, and two steroids. The biosynthetic pathway of compounds and was proposed in the current investigation. The oestrogenic activity of the isolates was evaluated utilising the pER8:GUS reporter assay system in transgenic plant as well as the SEAP reporter assay system in MCF-7 breast cancer cell-line; the anti-platelet activity was evaluated using the anti-platelet aggregation assay. Several components exhibited significant oestrogenic and anti-platelet activities; demonstrating for the first time the potential use of as a nutritional supplement for cardiovascular and endocrine diseases.
    Keywords: Liriope Platyphylla ; Dihydrobenzofuroisocoumarin ; Homoisoflavonoid ; Oestrogenic Activity ; Anti-Platelet Effect ; Arabidopsis Per8:Gus Reporter Assay ; Chemistry ; Diet & Clinical Nutrition ; Economics
    ISSN: 0308-8146
    E-ISSN: 1873-7072
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  • 7
    Language: English
    In: Bioorganic & Medicinal Chemistry, 2010, Vol.18(2), pp.518-525
    Description: Three new flavonlignans ( – ) and five new 8- -4′ neolignan derivatives ( – ) were isolated from the EtOAc extract of . Eight new lignin derivatives, termed quiquelignan A–H ( – ), comprising three tricin-type flavonolignans ( – ) and five 8- -4′ neolignans ( – ), were isolated from the ethanol extract of stems. Structural elucidation of the new isolates was accomplished on the basis of spectroscopic data. Compounds – showed strong-to-moderate antioxidant activity against the hydroxy radical ( OH). Among them, compound showed significantly higher hydroxy radical scavenging activity (IC 4.4 μg/mL). Compounds – and – dose-dependently suppressed the LPS-stimulated production of nitric oxide (NO) in RAW 264.7 cells. The anti-inflammatory potency of and was 2.7–4.5-fold higher compared with quercetin. Compounds – , and also exhibited mild collagen-antagonistic activity, but were inactive with respect to thrombin-induced platelet aggregation.
    Keywords: Calamus Quiquesetinervius ; Flavonolignans ; Neolignans ; Antioxidant ; Anti-Inflammatory ; Platelet Aggregation ; Medicine ; Chemistry ; Anatomy & Physiology
    ISSN: 0968-0896
    E-ISSN: 1464-3391
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  • 8
    Language: English
    In: Toxicology and Applied Pharmacology, 01 December 2015, Vol.289(2), pp.330-340
    Description: Anoikis is defined as apoptosis, which is induced by inappropriate cell–matrix interactions. Cancer cells with anoikis resistance tend to undergo metastasis, and this phenomenon has been reported to be associated with integrin and FAK activity. HPW-RX40 is a derivative of 3,4-methylenedioxy-β-nitrostyrene, which is known to prevent platelet aggregation by inhibition of integrin. In the present study, we investigated the effect of HPW-RX40 on an anoikis-resistant human breast cancer cell line MDA-MB-231. HPW-RX40 inhibited cell aggregation and induced cell death in suspending MDA-MB-231 cells, but had only little effect on the monolayer growth of adherent cells. Analysis of caspase activation and poly (ADP-ribose) polymerase (PARP) cleavage confirmed anoikis in HPW-RX40-treated suspending cancer cells. HPW-RX40 also affected the Bcl-2 family proteins in detached cancer cells. Furthermore, HPW-RX40 inhibited detachment-induced activation of FAK and the downstream phosphorylation of Src and paxillin, but did not affect this pathway in adherent cancer cells. We also found that the expression and activation of β1 integrin in MDA-MB-231 cells were reduced by HPW-RX40. The combination of HPW-RX40 with an EGFR inhibitor led to enhanced anoikis and inhibition of the FAK pathway in breast cancer cells. Taken together, our results suggest that HPW-RX40 restores the anoikis sensitivity in the metastatic breast cancer cells by inhibiting integrin and subsequent FAK activation, and reveal a potential strategy for prevention of tumor metastasis.
    Keywords: Anoikis ; Β-Nitrostyrene ; Integrin ; Fak ; Metastasis ; Breast Cancer ; Pharmacy, Therapeutics, & Pharmacology ; Public Health
    ISSN: 0041-008X
    E-ISSN: 1096-0333
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  • 9
    Language: English
    In: Natural product communications, January 2014, Vol.9(1), pp.83-4
    Description: Three phenanthrenes (1-3), four indole alkaloids (4-7) and one steroid (8) were isolated from the leaves of Calanthe arisanensis for the first time. In the antiplatelet aggregation assay, phenanthrenes 1 and 2 showed potential antiplatelet activity. We have reported and discussed here the antiplatelet aggregation properties of the eleven naturally-occurring phenanthrenes (1-2 and 9-17) isolated from the underground part of the plant and eighteen chemically synthesized phenanthrenes (18-35). Overall, our data demonstrated that 1,4-phenanthrenequinones 20, 21 and 22 (collagen, IC50 0.2, 0.2, 0.1 microg/mL; thrombin, IC50 0.8, 1.0, 1.1 microg/mL, respectively) could be promising lead candidates for further cardiovascular disease studies.
    Keywords: Orchidaceae -- Chemistry ; Phenanthrenes -- Isolation & Purification ; Platelet Aggregation Inhibitors -- Isolation & Purification
    ISSN: 1934-578X
    E-ISSN: 15559475
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  • 10
    Language: English
    In: Biochimie, March 2015, Vol.110, pp.81-92
    Description: Triple negative breast cancer (TNBC) exhibits an aggressive clinical course by high metastatic potential. It is known that integrin-mediated cell adhesion and migration are important for cancer metastasis. In the present study, a synthetic compound, 3, 4-methyenedioxy-β-nitrostyrene (MNS), significantly inhibited adhesion of TNBC cell lines to different extracellular matrix (ECM) components. The antimetastatic capacity of MNS was also observed through reducing TNBC cells migration and invasion without affecting cell viability. Confocal microscopy revealed that MNS disrupted the formation of focal adhesion complex and actin stress fiber networks. Consistent with this finding, MNS inhibited phosphorylation of focal adhesion kinase (FAK) and paxillin as detected by Western blot analysis. In exploring the underlying mechanism, we found that MNS inhibited phosphorylation of FAK as a result of reducing β1 integrin activation and clustering. A cell-impermeable dithiol reagent, 2, 3-dimercaptopropane-1-sulfonic acid abrogated all of MNS's actions, indicating that MNS may react with thiol groups of cell surface proteins that are involved in regulation of β1 integrin function as well as cell adhesion and migration. Cell surface protein disulfide isomerase (PDI) has been reported to be essential for the affinity modulation of β integrins. We also demonstrated that MNS inhibited PDI activity both in a pure enzyme system and in intact cancer cells. Taken together, our results suggest that MNS inhibits metastatic properties of TNBC cells through suppression of β1 integrin activation and focal adhesion signaling. Moreover, inhibition of surface PDI may contribute, at least in part, to the actions of MNS. These results suggest that MNS has a potential to be developed as an anticancer agent for treatment of TNBC.
    Keywords: 3,4-Methylenedioxy-Β-Nitrostyrene (Mns) ; Triple-Negative Breast Cancer ; Metastasis ; Β1 Integrin ; Protein Disulfide Isomerase ; Engineering ; Chemistry ; Anatomy & Physiology
    ISSN: 0300-9084
    E-ISSN: 1638-6183
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