The effect of griseofulvin on the gene regulation of β-tubulin in the dermatophyte pathogen Trichophyton rubrum

Zomorodian, Kamiar; Uthman, Umed; Tarazooie, Bita; Rezaie, Sassan

doi:10.1007/s10156-007-0552-5

Cited by 9 publications

(9 citation statements)

References 43 publications

(42 reference statements)

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“…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: 93%

“…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. Therefore, variations among different isoforms are expected to affect primarily the association of accessory proteins with the surface of microtubules rather than microtubule polymerization per se.…”

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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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confidence: 93%

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confidence: 99%

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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“…The clinical resistance to griseofulvin, or relapses after treatment, is common in dermatophytosis. In a study conducted by Zomorodian, et al (2007), a decreased expression of the gene encoding beta-tubulin was observed for the fungus T. rubrum during drug administration, with the decrease being concentration dependent. This information contributed to a better understanding of the mechanism of action and therefore can assist in more rational use of pharmacological therapy.…”

Section: Resistance To Drugsmentioning

confidence: 99%

Anti dermatophytic therapy: prospects for the discovery of new drugs from natural products

Soares¹,

Sardi²,

Gullo³

et al. 2013

Braz. J. Microbiol.

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Millions of people and animals suffer from superficial infections caused by a group of highly specialized filamentous fungi, the dermatophytes, which only infect keratinized structures. With the appearance of AIDS, the incidence of dermatophytosis has increased. Current drug therapy used for these infections is often toxic, long-term, and expensive and has limited effectiveness; therefore, the discovery of new anti dermatophytic compounds is a necessity. Natural products have been the most productive source for new drug development. This paper provides a brief review of the current literature regarding the presence of dermatophytes in immunocompromised patients, drug resistance to conventional treatments and new anti dermatophytic treatments.

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“…13, 22, 23 Thus, aside from being an antifungal drug, it may also be a clinically-viable candidate for cancer chemotherapy. 21–26 Due to these reasons, it was decided that the isolation and semi-synthesis of griseofulvin analogues was worth further investigation.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective fluorination and chemoinformatic analysis of griseofulvin: Natural vs fluorinated fungal metabolites

Paguigan

Al‐Huniti

Raja

et al. 2017

Bioorganic & Medicinal Chemistry

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Griseofulvin is a fungal metabolite and antifungal drug used for the treatment of dermatophytosis in both humans and animals. Recently, griseofulvin and its analogues have attracted renewed attention due to reports of their potential anticancer effects. In this study griseofulvin (1) and related analogues (2–6, with 4 being new to literature) were isolated from Xylaria cubensis. Six fluorinated analogues (7–12) were synthesized, each in a single step using the isolated natural products and Selectflour, so as to examine the effects of fluorine incorporation on the bioactivities of this structural class. The isolated and synthesized compounds were screened for activity against a panel of cancer cell lines (MDA-MB-435, MDA-MB-231, OVCAR3, and Huh7.5.1) and for antifungal activity against Microsporum gypseum. A comparison of the chemical space occupied by the natural and fluorinated analogues was carried out by using principal component analysis, documenting that the isolated and fluorinated analogues occupy complementary regions of chemical space. However, the most active compounds, including two fluorinated derivatives, were centered around the chemical space that was occupied by the parent compound, griseofulvin, suggesting that modifications must preserve certain attributes of griseofulvin to conserve its activity.

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The effect of griseofulvin on the gene regulation of β-tubulin in the dermatophyte pathogen Trichophyton rubrum

Cited by 9 publications

References 43 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

Anti dermatophytic therapy: prospects for the discovery of new drugs from natural products

Chemoselective fluorination and chemoinformatic analysis of griseofulvin: Natural vs fluorinated fungal metabolites

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