Griseofulvin, an oral antifungal agent, suppresses hepatitis C virus replication <i>in vitro</i>

Jin, Hai; Yamashita, Atsuya; Maekawa, Shinya; Yang, Pinting; He, Ling; Takayanagi, Satoru; Wakita, Takaji; Sakamoto, Naoya; Enomoto, Nobuyuki; Ito, Masahiko

doi:10.1111/j.1872-034x.2008.00352.x

Cited by 27 publications

(34 citation statements)

References 33 publications

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“…Nine of the compounds were active against both fungi within the same order of magnitude compared to griseofulvin (17,20,21,23,26,32,36,49, and 54).…”

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confidence: 96%

“…17−19 Several investigators have proposed tubulin as the main target for griseofulvin, although for mammalian cells this suggestion is not undisputed. 9,17,18,20,21,23,24 Recently, Panda et al 25 proposed two griseofulvin binding sites on tubulin using molecular docking studies and similar to Oda 21 reported that microtubule dynamics were disrupted by 1. Using the hepatitis C virus-1b cell culture system Huh7/Rep-Feo, Jin et al reported that G 2 /M phase arrest in infected cells was induced by griseofulvin (1).…”

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confidence: 99%

“…Using the hepatitis C virus-1b cell culture system Huh7/Rep-Feo, Jin et al reported that G 2 /M phase arrest in infected cells was induced by griseofulvin (1). 20 It was speculated that the effect was due to interaction with microtubule polymerization. 20 Griseofulvin exhibits activity against fungi and mammalian cancer cells as well as suppressing RNA replication by the hepatitis C virus, with tubulin having been proposed to be involved in all three cases.…”

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confidence: 99%

“…20 It was speculated that the effect was due to interaction with microtubule polymerization. 20 Griseofulvin exhibits activity against fungi and mammalian cancer cells as well as suppressing RNA replication by the hepatitis C virus, with tubulin having been proposed to be involved in all three cases. Tubulins are very conserved within different eukaryotic cell types, 24 and most of the variation among different tubulin isoforms is found in the amino acids near the C-terminus, which form a ridge on the surface of microtubules.…”

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confidence: 99%

“…Although the initial isolation of 1 was completed in 1939, 1 both anticancer 16−19 and antiviral 20 properties of griseofulvin have been discovered recently. Three analogues tested for the former by Oda et al 21 against chinese hamster V79 cells showed increased cytotoxicity, with 2′-propoxy-2′demethoxy-griseofulvin being the most potent (46, IC 50 0.7 μM; 1, 8 μM), and it was proposed that additional structural modifications at the 2′ position could enhance activity further.…”

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confidence: 99%

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Disparate SAR Data of Griseofulvin Analogues for the Dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 Cancer Cells

et al. 2012

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Griseofulvin and 53 analogues of this compound have been tested against the pathogenic dermatophytes Trichophyton rubrum and Trichophyton mentagrophytes as well as against the breast cancer cell line MDA-MB-231. The modifications to griseofulvin include the 4, 5, 6, 2′, 3′, and 4′ positions. The SAR of the griseofulvin analogues toward the two fungi followed the same trend with the majority being less active than griseofulvin and none had more than twice the potency of the parent compound. A comparison of the antifungal and the anticancer SAR revealed distinct differences, as the majority of analogues showed increased activity against the cancer cell line MDA-MB-231, highlighted by 2′-benzyloxy-2′-demethoxy-griseofulvin, which showed low activity against both fungi but was among the most potent compounds against MDA-MB-231 cancer cells. Tubulin has been proposed as the target of griseofulvin in both fungal and mammalian cells, but the differences revealed by this SAR study strongly suggest that the mode-of-action of the compound class toward fungi and mammalian cancer cells is different.

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“…Nine of the compounds were active against both fungi within the same order of magnitude compared to griseofulvin (17,20,21,23,26,32,36,49, and 54).…”

mentioning

confidence: 96%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Disparate SAR Data of Griseofulvin Analogues for the Dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 Cancer Cells

et al. 2012

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Catalytic Asymmetric Synthesis of Chiral Benzofuranones

Cheng

2014

Adv Synth Catal

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The chiral benzofuranone structural motif is a prominent feature in many natural products, which exhibit a broad range of biological and pharmaceutical activities. In the past few years, a survey of chiral benzofuranone derivatives based on asymmetric catalysis reveals an increasing number of papers, which reflects the latest achievements to facilitate the synthesis of sufficient quantities of related compounds as potential medicinal agents and biological probes. Recent advances in this area are summarized and classified according to the structure of the starting substrate.

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Functional Ionic Liquids Promoted Double Michael Reaction of Benzofuran‐3‐one or 1‐Indone and Symmetric Dienones: Construction of Spiro[benzofuran‐2,1’‐cyclohexane]‐3‐one or Spiro[cyclohexane‐1,2’‐indene]‐1’,4(3’H)‐dione Derivatives

Liu

Niu

et al. 2017

Chin. J. Chem.

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The double Michael reactions between benzofuran-3-one or 1-indone and symmetric dienones in the presence of catalytic ionic liquids were successfully developed and spiro[benzofuran-2,1'-cyclohexane]-3-one or spiro[cyclohexane-1,2'-indene]-1',4(3'H)-dione derivatives containing a spiro quaternary stereogenic center, which widely exist in biologically active products and building blocks in organic synthesis, were obtained in excellent yields (up to 99%). This catalytic system was also extended to the double Michael reaction of less reactive 1-indone and the desired products were also obtained in 31%-62% yields. The catalytic system was highly active and efficient for a broad of substrates under mild conditions.

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Griseofulvin, an oral antifungal agent, suppresses hepatitis C virus replication in vitro

Abstract: Our results suggest that griseofulvin may represent a new approach to the development of a novel therapy for HCV infection.

Cited by 27 publications

References 33 publications

Disparate SAR Data of Griseofulvin Analogues for the Dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 Cancer Cells

Disparate SAR Data of Griseofulvin Analogues for the Dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 Cancer Cells

Catalytic Asymmetric Synthesis of Chiral Benzofuranones

Functional Ionic Liquids Promoted Double Michael Reaction of Benzofuran‐3‐one or 1‐Indone and Symmetric Dienones: Construction of Spiro[benzofuran‐2,1’‐cyclohexane]‐3‐one or Spiro[cyclohexane‐1,2’‐indene]‐1’,4(3’H)‐dione Derivatives

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