Curcumin inhibits influenza virus infection and haemagglutination activity

Chen, Da Yuan; Shien, Jui-Hung; Tiley, Laurence; Chiou, Shyan-Song; Wang, Sheng-Yang; Chang, Tien‐Jye; Lee, Ya-Jane; Chan, Kuei-Chuan; Hsu, Wei‐Li

doi:10.1016/j.foodchem.2009.09.011

Cited by 165 publications

(133 citation statements)

References 29 publications

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“…Our previous study indicated that inhibition of viral HA function, leading to interference with viral entry, participates in anti-IAV effect mediated by Cur [4]. It is important to investigate whether Cur analogues share this effect with Cur.…”

Section: Thc Inhibits Iav Infection and Plaque Formation But To A Lesmentioning

confidence: 99%

“…Proliferation of cells treated with Cur analogues was determined as described previously [4]. Cytotoxicity of the compounds was estimated by comparison of the cell survival rate of drug-treated cells with that of dimethylsulfoxidetreated cells.…”

Section: Cytotoxicity Testmentioning

confidence: 99%

“…Moreover, the anti-influenza activity of Cur and other two curcuminoids, DMC and BDMC, is indistinguishable, indicating that the methoxyl group on the phenyl rings was not the crucial portion contributing to the anti-IAV activity and the inhibition of viral HA function mediated by Cur [4]. At present, the effect of Cur derivatives on anti-IAV has not yet been studied.…”

Section: Introductionmentioning

confidence: 98%

“…Furthermore, a number of studies indicate curcumin (Cur) is a potent antiviral agent as a result of its ability to interfere with the cellular signalling pathways or with proteins required for viral replication [4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

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Structure–activity relationship analysis of curcumin analogues on anti‐influenza virus activity

Mizushina

Wang

et al. 2013

The FEBS Journal

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Curcumin (Cur) is a commonly used colouring agent and spice in food. Previously, we reported that Cur inhibits type A influenza virus (IAV) infection by interfering with viral haemagglutination (HA) activity. To search for a stable Cur analogue with potent anti-IAV activity and to investigate the structure contributing to its anti-IAV activity, a comparative analysis of structural and functional analogues of Cur, such as tetrahydrocurcumin (THC) and petasiphenol (Pet), was performed. The result of time-of-drug addition tests indicated that these curcuminoids were able to inhibit IAV production in cell cultures. Noticeably, Pet and THC inhibit IAV to a lesser extent than Cur, which is in line with their effect on reducing plaque formation when IAV was treated with Cur analogues before infection. Unexpectedly, both THC and Pet did not harbour any HA inhibitory effect. It should be noted that the structure of Pet and THC differs from Cur with respect to the number of double bonds present in the central seven-carbon chain, and structure modelling of Cur analogues indicates that the conformations of THC and Pet are distinct from that of Cur. Moreover, simulation docking of Cur with the HA structure revealed that Cur binds to the region constituting sialic acid anchoring residues, supporting the results obtained by the inhibition of HA activity assay. Collectively, structure-activity relationship analyses indicate that the presence of the double bonds in the central seven-carbon chain enhanced the Cur -dependent anti-IAV activity and also that Cur might interfere with IAV entry by its interaction with the receptor binding region of viral HA protein.

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Section: Thc Inhibits Iav Infection and Plaque Formation But To A Lesmentioning

confidence: 99%

Section: Cytotoxicity Testmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Structure–activity relationship analysis of curcumin analogues on anti‐influenza virus activity

Mizushina

Wang

et al. 2013

The FEBS Journal

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“…p300/CBP HATs are associated with tumorigenesis (14) and the development of many viral diseases (15)(16)(17)(18). Several small molecules have been shown to possess p300/CBP HAT inhibitory activity (19)(20)(21) and anti-influenza virus properties (22)(23)(24). Recently, the compound C646 was identified as the first selective inhibitor of p300/CBP HATs (25).…”

mentioning

confidence: 99%

C646, a Novel p300/CREB-Binding Protein-Specific Inhibitor of Histone Acetyltransferase, Attenuates Influenza A Virus Infection

Zhao

Fukuyama

Sakai‐Tagawa

et al. 2016

Antimicrob Agents Chemother

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e New strategies to develop novel broad-spectrum antiviral drugs against influenza virus infections are needed due to the emergence of antigenic variants and drug-resistant viruses. Here, we evaluated C646, a novel p300/CREB-binding protein-specific inhibitor of histone acetyltransferase (HAT), as an anti-influenza virus agent in vitro and in vivo and explored how C646 affects the viral life cycle and host response. Our studies highlight the value of targeting HAT activity for anti-influenza drug development. Vaccination and antiviral drugs are effective ways to prevent influenza virus infection (1, 2); however, there is an urgent need to screen novel broad-spectrum antiviral drugs with the emergence of antigenic variants and drug-resistant viruses (3, 4). Influenza viruses commandeer the host cellular machinery for their propagation (5). Targeting of host factors that are critical for viral replication by using small molecular analogues or chemical inhibitors has shown great promise in the development of novel antivirals with broad-spectrum coverage (6).Histone acetylation levels are regulated by histone acetyltransferases (HATs) and histone deacetylases (HDACs) (7). Several HDAC inhibitors that show therapeutic potential for human cancers (8) and nonmalignant diseases (9) have been developed. Roles for HATs in cancer, asthma, chronic obstructive pulmonary disease, and viral infection have been demonstrated (10-12), which indicates that specific HAT inhibitors are potential tools for pharmacological research and may have clinical applications (13). The transcriptional coactivators p300 and CREB-binding protein (CBP) are important members of HAT families possessing HAT activity to influence chromatin activity. p300/CBP HATs are associated with tumorigenesis (14) and the development of many viral diseases (15-18). Several small molecules have been shown to possess p300/CBP HAT inhibitory activity (19-21) and anti-influenza virus properties (22)(23)(24). Recently, the compound C646 was identified as the first selective inhibitor of p300/CBP HATs (25). Here, we evaluated the antiviral effects of C646 on influenza A viruses.C646 showed a 50% cytotoxic concentration (CC 50 ) of 107 M in A549 cells (ATCC). The antiviral potency of C646 in vitro was evaluated based on C646-induced suppression of viral replication. A549 cells were treated with C646 (dimethyl sulfoxide [DMSO] as vehicle) for 10 h and then infected with viruses at an multiplicity of infection (MOI) of 2 or 1. C646 was present throughout the infection. The concentration of DMSO was kept at 0.1%, and 0.4 g/ml tosyl phenylalanyl chloromethyl ketone (TPCK)-trypsin was used to cleave the hemagglutinin for multiple cycles of replication. The cell supernatants were collected for viral titration at the indicated times (26). , and 24 h postinfection (hpi) with a 50% effective concentration (EC 50 ) of 15.8 M (Fig. 1A to E). These findings demonstrate that C646 inhibition of influenza virus replication is not subtype specific.We tested whether C646 directly affects...

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A simple RP-HPLC method for the simultaneous determination of curcumin and its prodrug, curcumin didecanoate, in rat plasma and the application to pharmacokinetic study

Han

Zhu

Wang

et al. 2011

Biomed. Chromatogr.

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A high-performance liquid chromatographic (HPLC) method has been developed for the simultaneous determination of curcumin and its prodrug, curcumin didecanoate (CurDD), in rat plasma. The analytes were extracted by ethyl acetate following the addition of sodium dodecyl sulfate, and separated on a reverse-phase C(18) column using a gradient mobile phase system of acetonitrile-tetrahydrofuran-water containing 0.1% formic acid. Detection by UV absorption at 425 nm gave a lower limit of quantitation (LLOQ) of 5 and 10 ng/mL for curcumin and CurDD in 50 μL of plasma, respectively. Intra- and inter-day precisions of quality control samples except those at LLOQ were within 15% for curcumin and CurDD, respectively, and the accuracies for both compounds were between 93.9 and 108%. The method was successfully applied to determine plasma concentration-time curves of curcumin and CurDD in rats following intravenous (i.v.) administration of curcumin or CurDD at doses of 1 mg/kg (calculated as curcumin). The results suggested that i.v. dosed CurDD provided sustained plasma levels of curcumin.

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Curcumin inhibits influenza virus infection and haemagglutination activity

Cited by 165 publications

References 29 publications

Structure–activity relationship analysis of curcumin analogues on anti‐influenza virus activity

Structure–activity relationship analysis of curcumin analogues on anti‐influenza virus activity

C646, a Novel p300/CREB-Binding Protein-Specific Inhibitor of Histone Acetyltransferase, Attenuates Influenza A Virus Infection

A simple RP-HPLC method for the simultaneous determination of curcumin and its prodrug, curcumin didecanoate, in rat plasma and the application to pharmacokinetic study

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