Comparative reduction of 1-nitro-3-nitrosopyrene and 1-nitro-6-nitrosopyrene: implications for the tumorigenicity of dinitropyrenes.

Abstract:

:Dinitropyrenes are mutagenic environmental pollutants. Of these compounds, 1,6-dinitropyrene is a potent tumorigen while 1,3-dinitropyrene appears to be weakly or non-tumorigenic. Two-electron reduction of dinitropyrenes yields nitro-nitrosopyrenes, which have been shown previously to be the major aerobic metabolites of these compounds in vitro. Further reduction of nitrosopyrenes is required for their activation to a DNA-reactive N-hydroxylamines. In this work, 1-nitro-3-nitrosopyrene was synthesized and the electrochemical and enzyme-catalyzed reduction of 1-nitro-3-nitrosopyrene has been compared with that of 1-nitro-6-nitrosopyrene. As determined by cyclic voltammetry, the reduction potentials of 1-nitro-3-nitrosopyrene, 1-nitro-6-nitrosopyrene and their parent dinitropyrenes were similar, although 1-nitro-3-nitrosopyrene did have a slightly more negative cathodic peak potential than the other three compounds. The NADPH-mediated reduction of 1-nitro-6-nitrosopyrene to intermediates which reduce succinoylated cytochrome c was faster than that of 1-nitro-3-nitrosopyrene. In the presence of rat liver microsomes or cytosol, the reduction of 1-nitro-6-nitrosopyrene was faster than that of 1-nitro-3-nitrosopyrene. These differences in the rates of nitro-nitrosopyrene reduction may be one factor contributing to the lower tumorigenic potential of 1,3-dinitropyrene relative to 1,6-dinitropyrene.

journal_name

Cancer Lett

journal_title

Cancer letters

authors

Djuric Z

doi

10.1016/0304-3835(92)90215-h

keywords:

subject

Has Abstract

pub_date

1992-07-31 00:00:00

pages

73-8

issue

1

eissn

0304-3835

issn

1872-7980

pii

0304-3835(92)90215-H

journal_volume

65

pub_type

杂志文章
  • Reversal of weight loss induced by tumour necrosis factor-alpha.

    abstract::When injected into female NMRI mice tumour necrosis factor-alpha (TNF) produced a dose-related weight loss over the first 24 h, which was accompanied by and directly proportional to a decrease in both food and water intake. Body composition analysis after the first 8 h revealed that the weight loss was associated with...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(89)90072-4

    authors: Mahony SM,Tisdale MJ

    更新日期:1989-06-01 00:00:00

  • Expression of xenoantigen transformed human cancer cells to be susceptible to antibody-mediated cell killing.

    abstract::The carbohydrate epitope, alphaGal epitope, is known as a major xenoantigen. The epitope exists abundantly in non-primate mammals and has recently been found on C-type retroviruses. Humans and Old World monkeys have anti-alphaGal antibody, a natural antibody. The present study was performed to examine if the alphaGal ...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(01)00377-9

    authors: Yoshimura N,Sawada T,Furusawa M,Fuchinoue S

    更新日期:2001-03-26 00:00:00

  • Cullin7 enhances resistance to trastuzumab therapy in Her2 positive breast cancer via degrading IRS-1 and downregulating IGFBP-3 to activate the PI3K/AKT pathway.

    abstract::Patients with Her2-positive breast cancer exhibit de novo resistance or develop acquired resistance in less than one year after Her2 targeting treatment, but the mechanism is not fully elucidated. Compensatory pathways such as the IGF-1R/IRS-1 pathway, are activated, leading to aberrant enhanced PI3K/Akt/mTOR pathway ...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2019.08.008

    authors: Qiu N,He YF,Zhang SM,Zhan YT,Han GD,Jiang M,He WX,Zhou J,Liang HL,Ao X,Xia HM,Li J,Yang YY,He ZM,Zou ZZ,Li HS

    更新日期:2019-11-01 00:00:00

  • Cancer-related transcriptional targets of the circadian gene NPAS2 identified by genome-wide ChIP-on-chip analysis.

    abstract::The transcription factor NPAS2 is one of nine human core circadian genes that influence a variety of biological processes by regulating the 24-h circadian rhythm. Recently, it has been shown that NPAS2 is a risk biomarker in human cancers and plays a role in tumorigenesis by affecting cancer-related gene expression, a...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2009.04.017

    authors: Yi CH,Zheng T,Leaderer D,Hoffman A,Zhu Y

    更新日期:2009-11-01 00:00:00

  • Effects of noradrenaline on interstitial fluid pressure in induced rat mammary tumours.

    abstract::Interstitial fluid pressure was measured by the wick-in-needle technique in DMBA-induced rat mammary tumours during resting conditions and during noradrenaline infusion. The rate of infusion was chosen to increase the systemic blood pressure by 30-40 mmHg, known to result in a markedly increased vascular resistance of...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(85)90181-8

    authors: Tveit E,Hultborn R,Weiss L

    更新日期:1985-07-01 00:00:00

  • FoxO3 reverses 5-fluorouracil resistance in human colorectal cancer cells by inhibiting the Nrf2/TR1 signaling pathway.

    abstract::5-fluorouracil (5-FU) is widely used in chemotherapy for colorectal cancer (CRC), but a high rate of chemoresistance reduces its effectiveness in clinical treatment. We found remarkably decreased expression of forkhead box 3 (FoxO3) protein, a tumor inhibitor, in 5-FU-resistant SW620 and HCT-8 (SW620/5-FU and HCT-8/5-...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2019.11.042

    authors: Liu C,Zhao Y,Wang J,Yang Y,Zhang Y,Qu X,Peng S,Yao Z,Zhao S,He B,Mi Q,Zhu Y,Liu X,Zou J,Zhang X,Du Q

    更新日期:2020-02-01 00:00:00

  • Analysis of E6 variants of human papillomavirus type 33, 52 and 58 in Japanese women with cervical intraepithelial neoplasia/cervical cancer in relation to their oncogenic potential.

    abstract::The variation of the E6 region of human papillomavirus type 16 (HPV16) is associated with a high risk for cervical carcinogenesis. To see whether the same is the case with HPV33, 52 and 58, known to have high homology with HPV16, we analyzed the E6 sequence variation of these HPVs in 107 Japanese women with cervical i...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(01)00570-5

    authors: Xin CY,Matsumoto K,Yoshikawa H,Yasugi T,Onda T,Nakagawa S,Yamada M,Nozawa S,Sekiya S,Hirai Y,Shiromizu K,Fujii T,Taketani Y

    更新日期:2001-09-10 00:00:00

  • Anti-tumor promoting effects of naphthoquinone derivatives on short term Epstein-Barr early antigen activation assay and in mouse skin carcinogenesis.

    abstract::In continuation of our studies of natural and synthetic products as cancer chemopreventive agents, we have examined a number of naphthoquinone derivatives including monomeric, dimeric and tetrameric naphthaquinones occurring in the Diospyros and other selected plant genera. Several synthetic naphthoquinones were also ...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(96)04582-x

    authors: Kapadia GJ,Balasubramanian V,Tokuda H,Konoshima T,Takasaki M,Koyama J,Tagahaya K,Nishino H

    更新日期:1997-02-26 00:00:00

  • Folate and breast cancer: the role of polymorphisms in methylenetetrahydrofolate reductase (MTHFR).

    abstract::Evidence is growing that low folate status may be a factor in the aetiology of several cancers, including breast cancer. The methylenetetrahydrofolate reductase gene (MTHFR), which has a key role in folate metabolism, is polymorphic. We report a case-control study of two functional polymorphisms in MTHFR, dietary fola...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(02)00030-7

    authors: Sharp L,Little J,Schofield AC,Pavlidou E,Cotton SC,Miedzybrodzka Z,Baird JO,Haites NE,Heys SD,Grubb DA

    更新日期:2002-07-08 00:00:00

  • Phenotypically selective promotion of diethylnitrosamine-initiated altered hepatocyte foci by dietary phenobarbital or a topically applied coal-derived organic mixture in male and female rats.

    abstract::Relative frequencies of diethylnitrosamine (DEN)-initiated foci of altered hepatocytes appearing in response to promotion by either dietary phenobarbital or a topically applied coal-derived organic mixture (CDM) were investigated in male and female rats. The focus population was examined for two histochemical markers,...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(87)90155-8

    authors: Peraino C,Haugen DA,Carnes BA,Reilly CA Jr,Springer DL,Mahlum DD

    更新日期:1987-10-30 00:00:00

  • Helicobacter pylori upregulates Nanog and Oct4 via Wnt/β-catenin signaling pathway to promote cancer stem cell-like properties in human gastric cancer.

    abstract::Helicobacter pylori (H. pylori) infection is considered a major risk factor for gastric cancer. CagA behaves as a major bacterial oncoprotein playing a key role in H. pylori-induced tumorigenesis. Cancer stem cells (CSCs) are believed to possess the ability to initiate tumorigenesis and promote progression. Although s...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2016.02.032

    authors: Yong X,Tang B,Xiao YF,Xie R,Qin Y,Luo G,Hu CJ,Dong H,Yang SM

    更新日期:2016-05-01 00:00:00

  • Identification of human acinar cell carcinoma by monoclonal antibody and in vitro differentiation.

    abstract::Methylnitrosourea (MNU)-induced carcinomas in organ-cultured human pancreas when injected into nude mice produced subcutaneous carcinomas none of which recognizable as being of acinar cell origin. Both monoclonal antibody to acinar cell surface marker produced by hybridoma, and in vitro tumor cell differentiation were...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(82)90040-4

    authors: Parsa I

    更新日期:1982-02-01 00:00:00

  • Involvement of reactive oxygen species in 2-methoxyestradiol-induced apoptosis in human neuroblastoma cells.

    abstract::Neuroblastoma is the most common extra-cranial solid tumor in children. Despite advances in the treatment of childhood cancer, outcomes for children with advanced-stage neuroblastoma remain poor. Here we reported that 2-methoxyestradiol (2-ME) inhibited the proliferation and induced apoptosis in human neuroblastoma SK...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2011.09.005

    authors: Zhang Q,Ma Y,Cheng YF,Li WJ,Zhang Z,Chen SY

    更新日期:2011-12-27 00:00:00

  • Melanoma circulating tumor cells: Benefits and challenges required for clinical application.

    abstract::The implementation of novel therapeutic interventions has improved the survival rates of melanoma patients with metastatic disease. Nonetheless, only 33% of treated cases exhibit long term responses. Circulating tumor cell (CTC) measurements are currently of clinical value in breast, prostate and colorectal cancers. H...

    journal_title:Cancer letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.canlet.2018.03.013

    authors: Marsavela G,Aya-Bonilla CA,Warkiani ME,Gray ES,Ziman M

    更新日期:2018-06-28 00:00:00

  • Inhibition of tumour promotion in mouse skin by extracts of rooibos (Aspalathus linearis) and honeybush (Cyclopia intermedia), unique South African herbal teas.

    abstract::The modulating effect of ethanol/acetone (E/A) soluble fractions, prepared from methanolic extracts of processed and unprocessed rooibos (Aspalathus linearis) and honeybush (Cyclopia intermedia) as well as green (Camellia sinensis) teas was established in a two-stage mouse skin carcinogenesis assay. Topical applicatio...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2004.11.014

    authors: Marnewick J,Joubert E,Joseph S,Swanevelder S,Swart P,Gelderblom W

    更新日期:2005-06-28 00:00:00

  • Viral therapy for pancreatic cancer: tackle the bad guys with poison.

    abstract::Pancreatic cancer is one of the most devastating diseases with very poor prognosis. Only a small proportion is curable by surgical resection, whilst standard chemotherapy for patients with advanced disease has only modest effect with substantial toxicity. Therefore, there is an urgent need for the development of novel...

    journal_title:Cancer letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.canlet.2013.01.035

    authors: Xu C,Li H,Su C,Li Z

    更新日期:2013-06-01 00:00:00

  • TGFbeta regulation of mitogen-activated protein kinases in human breast cancer cells.

    abstract::We demonstrate herein the ability of transforming growth factor-beta-2 (TGFbeta2) to potently activate extracellular signal-regulated kinase 2 (ERK2) in the highly TGFbeta-sensitive breast cancer cell (BCC) line Hs578T. The ERK2 isoform was activated by 3-fold within 5 min of TGFbeta2 addition to Hs578T cells. However...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(97)00211-5

    authors: Frey RS,Mulder KM

    更新日期:1997-07-15 00:00:00

  • Inhibitory effect of munetone, an isoflavonoid, on 12-O-tetradecanoylphorbol 13-acetate-induced ornithine decarboxylase activity.

    abstract::Starting with an extract derived from the bark of Mundulea sericea Willd. (Leguminosae) that was active in the process of inhibiting 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ornithine decarboxylase activity (ODC) in cultured mouse epidermal ME 308 cells, the isoflavonoid munetone was isolated and identified ...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(98)00309-7

    authors: Lee SK,Luyengi L,Gerhäuser C,Mar W,Lee K,Mehta RG,Kinghorn AD,Pezzuto JM

    更新日期:1999-02-08 00:00:00

  • Multi-microarray identifies lower AQP9 expression in adjuvant chemotherapy nonresponders with stage III colorectal cancer.

    abstract::Approximately 25% of stage III colorectal cancer patients do not benefit from standard adjuvant chemotherapies. To identify biomarkers for nonresponders, fresh-frozen tissues of 19 nonresponders and 16 responders were analyzed with gene expression and microRNA arrays. Fifty-nine genes and 17 miRNAs were differentially...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2013.04.017

    authors: Dou R,Deng Y,Huang L,Fu S,Tan S,Wang L,Lian L,Fang L,Fan X,Jin G,Liu H,Wang J

    更新日期:2013-08-09 00:00:00

  • A synthetic chalcone, 2'-hydroxy-2,3,5'-trimethoxychalcone triggers unfolded protein response-mediated apoptosis in breast cancer cells.

    abstract::The primary aim of this study was to find novel chemopreventive agents effective against breast cancer. Endoplasmic reticulum (ER) stress can induce apoptosis through the unfolded protein response (UPR). 2'-Hydroxy-2,3,5'-trimethoxychalcone (DK143) is a synthetic flavonoid derivative. The present study provides eviden...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2015.12.017

    authors: Lee DH,Jung Jung Y,Koh D,Lim Y,Lee YH,Shin SY

    更新日期:2016-03-01 00:00:00

  • Effect of alcohol consumption, cigarette smoking and flushing response on esophageal cancer risk: a population-based cohort study (JPHC study).

    abstract::We examined the effect of alcohol consumption, cigarette smoking and flushing response on esophageal squamous cell carcinoma (ESCC) in a large-scale population-based cohort study. 44,970 middle-aged and older Japanese men were followed. A total of 215 cases of ESCC were newly diagnosed. Alcohol consumption and cigaret...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2008.10.020

    authors: Ishiguro S,Sasazuki S,Inoue M,Kurahashi N,Iwasaki M,Tsugane S,JPHC Study Group.

    更新日期:2009-03-18 00:00:00

  • Cancer metabolism and mass spectrometry-based proteomics.

    abstract::Cancer metabolism has been extensively investigated by various tools, and the fact of diverse metabolic reprogramming in cancer cells has been gradually unveiled. In this review, we discuss some contributions in cancer metabolism by general proteomic analysis and post-translational modification analysis using mass spe...

    journal_title:Cancer letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.canlet.2013.11.003

    authors: Zhou W,Liotta LA,Petricoin EF

    更新日期:2015-01-28 00:00:00

  • Simultaneous mitochondrial Ca(2+) overload and proteasomal inhibition are responsible for the induction of paraptosis in malignant breast cancer cells.

    abstract::In this study, we investigated the role of Ca(2+) in curcumin-induced paraptosis, a cell death mode that is accompanied by dilation of mitochondria and the endoplasmic reticulum (ER). Curcumin induced mitochondrial Ca(2+) overload selectively in the malignant breast cancer cells, but not in the normal breast cell, con...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2012.05.018

    authors: Yoon MJ,Kim EH,Kwon TK,Park SA,Choi KS

    更新日期:2012-11-28 00:00:00

  • P5 HER2/neu-derived peptide conjugated to liposomes containing MPL adjuvant as an effective prophylactic vaccine formulation for breast cancer.

    abstract::Vaccines containing synthetic peptides derived from tumor-associated antigens (TAA) can elicit potent cytotoxic T lymphocyte (CTL) response if they are formulated in an optimal vaccine delivery system. The aim of this study was to develop a simple and effective lipid-based vaccine delivery system using P5 HER2/neu-der...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2014.09.016

    authors: Shariat S,Badiee A,Jalali SA,Mansourian M,Yazdani M,Mortazavi SA,Jaafari MR

    更新日期:2014-12-01 00:00:00

  • Microvessel density and p53 mutations in advanced-stage epithelial ovarian cancer.

    abstract::We planned to determine the relationship between angiogenesis and p53 mutational status in advanced-stage epithelial ovarian cancer. Using 190 tumor samples from patients with stage III and IV ovarian cancer we performed p53 sequencing, immunohistochemistry, and CD31 microvessel density (MVD) determination. MVD was el...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2012.12.016

    authors: Nadkarni NJ,Geest KD,Neff T,Young BD,Bender DP,Ahmed A,Smith BJ,Button A,Goodheart MJ

    更新日期:2013-04-30 00:00:00

  • Carcinogenicity of heterocyclic amines for the pancreatic duct epithelium in hamsters.

    abstract::Effects of eight heterocyclic amines (HCAs) on pancreatic duct carcinogenesis were investigated in a rapid production model in hamsters. N-Nitrosobis(2-oxopropyl)amine (BOP) was given to effect initiation, followed by augmentation pressure consisting of four daily i.p. injections of 500 mg/kg DL-ethionine, a choline-d...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(99)00131-7

    authors: Yoshimoto M,Tsutsumi M,Iki K,Sasaki Y,Tsujiuchi T,Sugimura T,Wakabayashi K,Konishi Y

    更新日期:1999-09-01 00:00:00

  • Interaction of tamoxifen with cytosolic and nuclear type II estrogen binding sites (type II EBS).

    abstract::The aim of this study was to investigate the interaction of tamoxifen (TAM) with the so-called Type II estrogen binding sites (Type II EBS) in both the cytosolic and the nuclear fraction of the ER-negative A 2780 human ovarian cancer cell line and in an ER-negative ovarian cancer tissue. Although cytosolic and nuclear...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(95)03922-j

    authors: Ferrandina G,Ranelletti FO,Scambia G,Benedetti Panici P,D'Agostino G,Piantelli M,Isola G,Mancuso S

    更新日期:1995-09-04 00:00:00

  • Rectal epithelial proliferation characteristics of first degree relatives of sporadic colon cancer patients.

    abstract::Hyperproliferation of rectal epithelium is characteristic of families at high genetic risk for large bowel neoplasia, but has not been well-documented in families of sporadic colorectal cancer patients. This was studied in 119 such first degree relatives and 44 comparison subjects without this family history. All scre...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(90)90047-2

    authors: Rozen P,Fireman Z,Fine N,Chetrit A,Lubin F

    更新日期:1990-05-30 00:00:00

  • Metronomic chemotherapy in metastatic colorectal cancer.

    abstract::Overall survival and quality of life of patients with metastatic colorectal cancer (mCRC) have improved due to the development of standard systemic treatment. However, many patients are still suffering from the eventual progression of cancer, treatment-related toxicities, and the economic burden of new drugs. Salvage ...

    journal_title:Cancer letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.canlet.2017.02.034

    authors: Woo IS,Jung YH

    更新日期:2017-08-01 00:00:00

  • Glutathione S-transferase-placental form expression and proliferation of hepatocytes in fumonisin B1-treated male and female Sprague-Dawley rats.

    abstract::Fumonisin B1 (FB1), a mycotoxin produced by a common corn contaminant Fusarium moniliforme and a hepatocarcinogen in rats, has been previously suggested to act as a poor initiator, but a better promoter of gamma-glutamyltranspeptidase (GGT)-positive rat liver preneoplastic lesions. Using glutathione S-transferase-plac...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(98)00046-9

    authors: Mehta R,Lok E,Rowsell PR,Miller JD,Suzuki CA,Bondy GS

    更新日期:1998-06-05 00:00:00