Induction of NADPH:quinone oxidoreductase in murine hepatoma cells by methylsulfinyl isothiocyanates: methyl chain length-activity study.

Hou, De‐Xing; Fukuda, Masahiro; Fujii, Makoto; Fuke, Yoko

doi:10.3892/ijmm.6.4.441

Cited by 12 publications

(15 citation statements)

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“…The bioactive compounds in wasabi have been identified as a series of isothiocynate analogs (Watanabe et al, 2003), of which 6-(methylsulfinyl)hexyl isothiocyanate (6-MSITC) is the major component. Several studies have shown the pharmacological properties of 6-MSITC, such as antiplatelet (Morimitsu et al, 2000), antimicrobial (Hasegawa et al, 1999), and anticancer effects (Hou et al, 2000). Moreover, Uto et al (2005) highlighted that 6-MSITC suppresses lipopolysaccharide-induced expression of pro-inflammatory genes and the expression of inducible nitric oxidase synthase during inflammation.…”

Section: Introductionmentioning

confidence: 98%

Neuroprotection by 6-(methylsulfinyl)hexyl isothiocyanate in a 6-hydroxydopamine mouse model of Parkinson׳s disease

Morroni¹,

Sita²,

Tarozzi³

et al. 2014

Brain Research

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Section: Introductionmentioning

confidence: 98%

Neuroprotection by 6-(methylsulfinyl)hexyl isothiocyanate in a 6-hydroxydopamine mouse model of Parkinson׳s disease

Morroni¹,

Sita²,

Tarozzi³

et al. 2014

Brain Research

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“…[7][8][9][10][11][12] In our previous study, we reported that 6-MITC induced QR activity in Hepa1c1c7 cells in a dose-dependent manner.…”

mentioning

confidence: 99%

Detection of 6-(Methylsulfinyl)hexyl Isothiocyanate (6-MITC) and Its Conjugate with N-Acetyl-L-cysteine (NAC) by High Performance Liquid Chromatograpy-Atmospheric Pressure Chemical Ionization Mass Spectrometry (HPLC-MS/APCI)

et al. 2008

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Previous reports have documented that some isothiocyanates (ITCs) prevent the formation of cancers in animal models.1-4) 6-(Methylsulfinyl)hexyl isothiocyanate (6-MITC) is found in wasabi (Wasabia japonica), a Japanese indigenous herb, and a variety of studies on the anticancer properties of 6-MITC have been described, 5,6) with 6-MITC attracting great attention as a new possible candidate for controlling cancer cell progression and metastasis. Anticancer activity of 6-MITC in vitro was studied with a human cancer cell (HCC) panel and 6-MITC directly affected the cells in the HCC panel.5) A suppression was found in the growth and survival of the cells in culture, and the affected cells were very specific, which included breast cancer and melanoma cell lines. A "COMPARE" analysis using a computerized algorithm, which was based on the HCC database, suggested the suppression mechanism of 6-MITC is unique, involving multiple pathways, and may be different from those of other known chemicals. Another 6-MITC-related anticancer study involves the oral administration of 6-MITC and its effects on the macroscopic pulmonary metastasis. Murine B16-BL6 melanoma cells were injected subcutaneously or intravenously in C57BL/6J mice and the effects of 6-MITC on the metastatic foci formation in the lungs were analyzed.6) The number of metastasized cells in the lungs was significantly reduced by the administration of 6-MITC, and 56% of foci formation was inhibited by the 2 week-prior administration, whereas only 27% inhibition was obtained by the concomitant administration with the cancer cell injection.Anti-cancer activities of ITCs largely involve modulation of metabolism for carcinogens through inhibition of the phase 1 enzymes and/or induction of the phase 2 enzymes, such as glutathione S-transferase and quinone reductase (QR). [7][8][9][10][11][12] In our previous study, we reported that 6-MITC induced QR activity in Hepa1c1c7 cells in a dose-dependent manner.13) However, when the dose level was high at 80 mM, the effect of 6-MITC was nullified and it significantly reduced QR activity. Augmentation of QR activity by 6-MITC seemed to be due to the increase in its mRNA expression, and the inhibition of its activity at 80 mM was ascribed to the reduced gene expression. This negative effect of 6-MITC at 80 mM was overcome by N-acetyl-L-cysteine (NAC) treatment but its mechanism is still unknown.High-performance liquid chromatography (HPLC) combined with mass spectrometry (MS) has been documented as a useful tool for detecting bioactive components, such as flavonoids, puerarin and saponins in herbal medicines, [14][15][16][17] and HPLC with an ultraviolet-ray (UV) detector and MS has been applied for determining some of these components. 18,19) Although HPLC-MS is a more expensive and complex option than other HPLC or TLC detectors, it can greatly simplify sample pre-treatment procedures and shorten separation times in HPLC due to the high selectivity and sensitivity of MS detection. 20) As mentioned earlier, the negative effect o...

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“…Hou et al [8] reported that an increase in the length of the carbon chain in alkyl isothiocyanates correlates with augmentation of their biological activities. Increasing the carbon-chain length appears to increase their log P values.…”

Section: Inhibitory Activities Against In-vitro Growth Of Tumor Cellsmentioning

confidence: 98%

“…The relationship between structure and the biological activity of alkyl isothiocyanates reveals that an increase in the length of the carbon chain correlates with augmented induction of the activity of NADPH:quinone oxidoreductase and its mRNA [8]. Morimitsu et al [5] and Prawan et al [9] reported that the phase-II detoxifying/ antioxidant enzyme inducer potency of sulforaphane and its analogs is influenced by the number of methylene (-CH 2 -) groups in the bridge linking the functional group and isothiocyanate moieties.…”

Section: Introductionmentioning

confidence: 99%

Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lipophilicity

Noshita

Kidachi

Funayama

et al. 2009

European Journal of Medicinal Chemistry

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Induction of NADPH:quinone oxidoreductase in murine hepatoma cells by methylsulfinyl isothiocyanates: methyl chain length-activity study.

Cited by 12 publications

References 0 publications

Neuroprotection by 6-(methylsulfinyl)hexyl isothiocyanate in a 6-hydroxydopamine mouse model of Parkinson׳s disease

Neuroprotection by 6-(methylsulfinyl)hexyl isothiocyanate in a 6-hydroxydopamine mouse model of Parkinson׳s disease

Detection of 6-(Methylsulfinyl)hexyl Isothiocyanate (6-MITC) and Its Conjugate with N-Acetyl-L-cysteine (NAC) by High Performance Liquid Chromatograpy-Atmospheric Pressure Chemical Ionization Mass Spectrometry (HPLC-MS/APCI)

Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lipophilicity

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