Chemical affinity matrix-based identification of prohibitin as a binding protein to anti-resorptive sulfonyl amidine compounds

Chang, Soo-Ho; Bae, Su Jung; Lee, Myung Yun; Baek, Seung‐Hwa; Chang, Sukbok; Kim, Seong Hwan

doi:10.1016/j.bmcl.2010.11.123

Cited by 41 publications

(25 citation statements)

References 24 publications

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“…Sulfonyl amidine A inhibits the osteoclastogenesis involved in bone remodeling with an IC 50 of 1.8 mM (Lee et al, 2010c; Figure 4E). Chang et al (2011) used affinity chromatography to identify the molecular target involved in this process and found Aurilide is a cytotoxic depsipeptide that binds to PHB1 and triggers remodeling of the mitochondrial cristae to lead to apoptosis. (B) Melanogenin binds to PHB1 to induce the expression of tyrosinase, the rate-limiting enzyme in melanogenesis.…”

Section: Sulfonyl Amidine Derivativesmentioning

confidence: 99%

Prohibitin Ligands in Cell Death and Survival: Mode of Action and Therapeutic Potential

Thuaud

Ribeiro

Nebigil

et al. 2013

Chemistry & Biology

183

234

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Prohibitins (PHBs) are scaffold proteins that modulate many signaling pathways controlling cell survival, metabolism, and inflammation. Several drugs that target PHBs have been identified and evaluated for various clinical applications. Preclinical and clinical studies indicate that these PHB ligands may be useful in oncology, cardiology, and neurology, as well as against obesity. This review covers the physiological role of PHBs in health and diseases and current developments concerning PHB ligands.

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Section: Sulfonyl Amidine Derivativesmentioning

confidence: 99%

Prohibitin Ligands in Cell Death and Survival: Mode of Action and Therapeutic Potential

Thuaud

Ribeiro

Nebigil

et al. 2013

Chemistry & Biology

183

234

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“…General Procedure for the Synthesis of Tert-butyl-(2-hydroxyethyl)carbamate 3a and Its Derivatives (3b-e) [25][26][27][28][29] To a solution of 2a (or 2b-e, 20 mmol) in a mixture of dioxane (15 mL) and H 2 O (7 mL), was added 5N NaOH (4.8 mL) and a solution of Boc 2 O (5.0 g, 23 mmol) in dioxane at 0 °C. After stirred at rt overnight, the reaction mixture was concentrated in vacuo.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Biological Evaluation of RGD-Conjugated MEK1/2 Kinase Inhibitors for Integrin-Targeted Cancer Therapy

Hou

Wang

et al. 2013

Molecules

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Two novel series of RGD-MEKI conjugates derived from a MEK1/2 kinase inhibitor-PD0325901-have been developed for integrin receptor mediated anticancer therapy. The first series, alkoxylamine analog RGD-MEKI conjugates 9a-g showed anti-proliferation activity in melanoma A375 cells by the same mechanism as that of PD0325901. PEGylation increased the IC 50 value of 9f three-fold in the A375 assay, and the multi-cRGD peptide cargo significantly improved the receptor specific anti-proliferation activity of 9g in integrin-overexpressing U87 cells. In the second series, RGD-PD0325901 13 exhibited significantly increased antitumor properties compared to the alkoxylamine analogs by both inhibition of the ERK pathway activity and DNA replication of the cancer cells. Furthermore, 13 displayed more potent anti-proliferation activity in the U87 assay than PD0325901 in a dose-dependent manner. All these data demonstrate that RGD-MEKI conjugates with an ester bond linkage enhanced anticancer efficacy with improved targeting capability toward integrin-overexpressing tumor cells.

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“…Flavaglines are a family of plant natural products that have potent anticancer and neuro‐ and cardio‐protective properties ; studies have shown that prohibitins are directly interacting targets of this class of molecules . The synthetic sulfonyl amidine 1 m, which inhibits bone remodeling, also reportedly binds PHB1 . This study therefore sought to determine whether the synthetic flavaglines FL3 and FL23 and sulfonyl amidine 1 m are able to interfere with the CHIKV–prohibitin interaction that occurs at the receptor binding stage of CHIKV infection of mammalian cells.…”

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confidence: 99%

Assessment of flavaglines as potential chikungunya virus entry inhibitors

Wintachai

Thuaud

Basmadjian

et al. 2015

Microbiology and Immunology

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Chikungunya virus (CHIKV) is a re-emerging mosquito-borne alphavirus that recently caused large epidemics in islands in, and countries around, the Indian Ocean. There is currently no specific drug for therapeutic treatment or for use as a prophylactic agent against infection and no commercially available vaccine. Prohibitin has been identified as a receptor protein used by chikungunya virus to enter mammalian cells. Recently, synthetic sulfonyl amidines and flavaglines (FLs), a class of naturally occurring plant compounds with potent anti-cancer and cytoprotective and neuroprotective activities, have been shown to interact directly with prohibitin. This study therefore sought to determine whether three prohibitin ligands (sulfonyl amidine 1 m and the flavaglines FL3 and FL23) were able to inhibit CHIKV infection of mammalian Hek293T/17 cells. All three compounds inhibited infection and reduced virus production when cells were treated before infection but not when added after infection. Pretreatment of cells for only 15 minutes prior to infection followed by washing out of the compound resulted in significant inhibition of entry and virus production. These results suggest that further investigation of prohibitin ligands as potential Chikungunya virus entry inhibitors is warranted.

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Chemical affinity matrix-based identification of prohibitin as a binding protein to anti-resorptive sulfonyl amidine compounds

Cited by 41 publications

References 24 publications

Prohibitin Ligands in Cell Death and Survival: Mode of Action and Therapeutic Potential

Prohibitin Ligands in Cell Death and Survival: Mode of Action and Therapeutic Potential

Synthesis and Biological Evaluation of RGD-Conjugated MEK1/2 Kinase Inhibitors for Integrin-Targeted Cancer Therapy

Assessment of flavaglines as potential chikungunya virus entry inhibitors

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