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nitrofuran cancer

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https://www.readbyqxmd.com/read/27505854/n-pentyl-nitrofurantoin-induces-apoptosis-in-hl-60-leukemia-cell-line-by-upregulating-bax-and-downregulating-bcl-xl-gene-expression
#1
Jeyce K F Andrade, Márcia I F Souza, Manoel A Gomes Filho, Diogo M F Silva, André L S Barros, Maria D Rodrigues, Paulo B N Silva, Silene C Nascimento, Jaciana S Aguiar, Dalci J Brondani, Gardênia C G Militão, Teresinha G Silva
BACKGROUND: Nitrofurantoin is a nitroderivative antibiotic that has bactericidal activity against pathogens causing urinary tract infection. A few studies have reported that nitrofurantoin has cytotoxic activity against cancer cells; however, nitrofurans remain a poorly explored class of compounds with respect to their anticancer potential. The aim of this study was to investigate the anticancer effects of a nitrofurantoin derivative, n-pentyl-nitrofurantoin (NFP), on HL-60 leukemia cells...
October 2016: Pharmacological Reports: PR
https://www.readbyqxmd.com/read/27487252/azoreductases-in-drug-metabolism
#2
Ali Ryan
Azoreductases are flavoenzymes that have been characterized in a range of prokaryotes and eukaryotes. Bacterial azoreductases are associated with the activation of two classes of drug, azo drugs for the treatment of inflammatory bowel disease and nitrofuran antibiotics. The mechanism of reduction of azo compounds is presented; it requires tautomerisation of the azo compound to a quinoneimine and provides a unifying mechanism for the reduction of azo and quinone substrates by azoreductases. The importance of further work in the characterization of azoreductases from enteric bacteria is highlighted to aid in the development of novel drugs for the treatment of colon related disorders...
August 3, 2016: British Journal of Pharmacology
https://www.readbyqxmd.com/read/26116180/identification-of-5-nitrofuran-2-amide-derivatives-that-induce-apoptosis-in-triple-negative-breast-cancer-cells-by-activating-c-ebp-homologous-protein-expression
#3
Hongliang Duan, Yu Li, Hui-Ying Lim, Weidong Wang
The transcription factor C/EBP-homologous protein (CHOP) is a key component of the terminal unfolded protein response (UPR) that mediates unresolvable endoplasmic reticulum stress-induced apoptosis. CHOP induction is known to cause cancer cell death. Chemicals that induce CHOP expression would thus be valuable as potential cancer therapeutics and as research tools. Here, we identified 5-nitrofuran-2-amide derivatives as small molecule activators of CHOP expression that induced apoptosis in triple negative breast cancer (TNBC) cells...
August 1, 2015: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/25467291/discovery-of-2-2-5-nitrofuran-2-yl-vinyl-quinoline-derivatives-as-a-novel-type-of-antimetastatic-agents
#4
Chih-Hua Tseng, Cherng-Chyi Tzeng, Chien-Chih Chiu, Chih-Yao Hsu, Chon-Kit Chou, Yeh-Long Chen
A number of 2-furanylvinylquinoline derivatives were synthesized and evaluated for antiproliferative activities against the growth of four cancer cell lines including non-small cell lung cancer (A549 and H1299), breast cancer (MCF-7 and MDA-MB-231) and normal diploid embryonic lung cell line (MRC-5). Among them, (E)-6-methoxy-3-(4-methoxyphenyl)-2-[2-(5-nitrofuran-2-yl)vinyl]quinoline (10c) was found low cytotoxic in all cancer cells and normal cell. The aim of this study was to investigate the anti-invasive and anti-metastatic activity of compound 10c in H1299 human lung cancer cells...
January 1, 2015: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/25460368/cfs-1686-causes-cell-cycle-arrest-at-intra-s-phase-by-interference-of-interaction-of-topoisomerase-1-with-dna
#5
Ru-Wei Lin, Chia-Ning Yang, ShengYu Ku, Cheng-Jung Ho, Shih-Bo Huang, Min-Chi Yang, Hsin-Wen Chang, Chun-Mao Lin, Jaulang Hwang, Yeh-Long Chen, Cherg-Chyi Tzeng, Chihuei Wang
CFS-1686 (chemical name (E)-N-(2-(diethylamino)ethyl)-4-(2-(2-(5-nitrofuran-2-yl)vinyl)quinolin-4-ylamino)benzamide) inhibits cell proliferation and triggers late apoptosis in prostate cancer cell lines. Comparing the effect of CFS-1686 on cell cycle progression with the topoisomerase 1 inhibitor camptothecin revealed that CFS-1686 and camptothecin reduced DNA synthesis in S-phase, resulting in cell cycle arrest at the intra-S phase and G1-S boundary, respectively. The DNA damage in CFS-1686 and camptothecin treated cells was evaluated by the level of ATM phosphorylation, γH2AX, and γH2AX foci, showing that camptothecin was more effective than CFS-1686...
2014: PloS One
https://www.readbyqxmd.com/read/25132107/frxa-is-an-s-nitrosoglutathione-reductase-enzyme-that-contributes-to-helicobacter%C3%A2-pylori-pathogenicity
#6
Marta C Justino, Margarida R Parente, Ivo G Boneca, Lígia M Saraiva
Helicobacter pylori is a pathogen that infects the gastric mucosa of a large percentage of the human population worldwide, and predisposes to peptic ulceration and gastric cancer. Persistent colonization of humans by H. pylori triggers an inflammatory response that leads to the production of reactive nitrogen species. However, the mechanisms of H. pylori defence against nitrosative stress remain largely unknown. In this study, we show that the NADH-flavin oxidoreductase FrxA of H. pylori, besides metabolizing nitrofurans and metronidazole, has S-nitrosoglutathione reductase activity...
October 2014: FEBS Journal
https://www.readbyqxmd.com/read/24070777/the-toxicity-of-nitrofuran-compounds-on-melanoma-and-neuroblastoma-cells-is-enhanced-by-olaparib-and-ameliorated-by-melanin-pigment
#7
Ewan M McNeil, Ann-Marie Ritchie, David W Melton
Nitrofurans are commonly used for the treatment of trypanosomal diseases including Chagas disease. More recently, following the fortuitous discovery that nifurtimox was clinically active against neuroblastoma, nitrofuran compounds are being investigated for activity against cancer. Herein, we show that nitrofuran compounds are similarly potent to human malignant melanoma and neuroblastoma cells. Furthermore, a recently discovered nitrofuran compound, NFN1, was 50- to 175-fold more potent than nifurtimox against human melanoma and neuroblastoma cell lines...
November 2013: DNA Repair
https://www.readbyqxmd.com/read/23011016/combretastatin-a-4-derivatives-synthesis-and-evaluation-of-2-4-5-triaryl-1h-imidazoles-as-potential-agents-against-h1299-non-small-cell-lung-cancer-cell
#8
Chih-Hua Tseng, Chi-Yi Li, Chien-Chih Chiu, Huei-Ting Hu, Chein-Hwa Han, Yeh-Long Chen, Cherng-Chyi Tzeng
A number of 2,4,5-triaryl-1H-imidazole derivatives were synthesized and evaluated for their antiproliferative activities against the growth of five cell lines including three non-small cell lung cancers (H460, H1299, and A549), one breast cancer (MCF-7), and one normal diploid embryonic lung cell line (MRC-5). Preliminary results indicated that both 2-(5-bromofuran-2-yl)-4,5-bis{4-[3-(dimethylamino) propoxy] phenyl}-1H-imidazole (10f) and 4,5-bis{4-[3-(dimethylamino)propoxy]phenyl}-2-(5-nitrofuran-2-yl)-1H -imidazole (10g) were selectively active against the growth of H1229 with an IC(50) of less than 0...
November 2012: Molecular Diversity
https://www.readbyqxmd.com/read/21846841/epoxyeicosatrienoic-acids-attenuate-reactive-oxygen-species-level-mitochondrial-dysfunction-caspase-activation-and-apoptosis-in-carcinoma-cells-treated-with-arsenic-trioxide
#9
Liu Liu, Chen Chen, Wei Gong, Yuanjing Li, Matthew L Edin, Darryl C Zeldin, Dao Wen Wang
Epoxyeicosatrienoic acids (EETs) and the cytochrome P450 epoxygenase CYP2J2 promote tumorogenesis in vivo and in vitro via direct stimulation of tumor cell growth and inhibition of tumor cell apoptosis. Herein, we describe a novel mechanism of inhibition of tumor cell apoptosis by EETs. In Tca-8113 cancer cells, the antileukemia drug arsenic trioxide (ATO) led to the generation of reactive oxygen species (ROS), impaired mitochondrial function, and induced apoptosis. 11,12-EET pretreatment increased expression of the antioxidant enzymes superoxide dismutase and catalase and inhibited ATO-induced apoptosis...
November 2011: Journal of Pharmacology and Experimental Therapeutics
https://www.readbyqxmd.com/read/21723735/synthesis-of-some-new-1-2-4-triazolo-3-4-b-1-3-4-thiadiazines-and-1-2-4-triazolo-3-4-b-1-3-4-thiadiazoles-starting-from-5-nitro-2-furoic-acid-and-evaluation-of-their-antimicrobial-activity
#10
Sahar M I Badr, Rasha M Barwa
New series of fused 1,2,4-triazoles such as, 6-(aryl)-3-(5-nitrofuran-2-yl)-5,6-dihydro-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 4-8, 6-(alkyl/aryl amino)-3-(5-nitrofuran-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 9-13 and 6-(4-substituted phenyl)-3-(5-nitrofuran-2-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines 14-18 have been synthesized via the reaction of 4-amino-5-(5-nitrofuran-2-yl)-4H-1,2,4-triazole-3-thiol 3 with various reagents such as hetero aromatic aldehydes, alkyl/aryl isothiocyanates and 4-substituted phenacyl bromides, respectively...
August 1, 2011: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/21124757/the-erad-inhibitor-eeyarestatin-i-is-a-bifunctional-compound-with-a-membrane-binding-domain-and-a-p97-vcp-inhibitory-group
#11
Qiuyan Wang, Bidhan A Shinkre, Jin-gu Lee, Marc A Weniger, Yanfen Liu, Weiping Chen, Adrian Wiestner, William C Trenkle, Yihong Ye
BACKGROUND: Protein homeostasis in the endoplasmic reticulum (ER) has recently emerged as a therapeutic target for cancer treatment. Disruption of ER homeostasis results in ER stress, which is a major cause of cell death in cells exposed to the proteasome inhibitor Bortezomib, an anti-cancer drug approved for treatment of multiple myeloma and Mantle cell lymphoma. We recently reported that the ERAD inhibitor Eeyarestatin I (EerI) also disturbs ER homeostasis and has anti-cancer activities resembling that of Bortezomib...
2010: PloS One
https://www.readbyqxmd.com/read/20106631/polyamine-reduced-diet-prd-nutrition-therapy-in-hormone-refractory-prostate-cancer-patients
#12
Bernard G Cipolla, René Havouis, Jacques-Philippe Moulinoux
BACKGROUND: Reducing polyamine uptake by selecting low polyamine-containing foodstuffs and reducing bacterial gut production can improve performance status and pain control in hormone refractory prostate cancer (HRPC) patients. Long term PRD observance and tolerance were assessed. Cancer specific survival was studied in function of PRD and time of PRD initiation. METHODS: Twenty-six volunteers, age: 68+/-10 years with metastatic HRPC accepted a polyamine reduced diet and partial gut decontamination with oral neomycin or nifuroxazide (750 mg daily, one week out of two)...
May 2010: Biomedicine & Pharmacotherapy, Biomédecine & Pharmacothérapie
https://www.readbyqxmd.com/read/20086055/a-novel-geranylgeranyl-transferase-inhibitor-in-combination-with-lovastatin-inhibits-proliferation-and-induces-autophagy-in-sts-26t-mpnst-cells
#13
Komal M Sane, Michelle Mynderse, Daniel T Lalonde, Ivory S Dean, Jonathan W Wojtkowiak, Farid Fouad, Richard F Borch, John J Reiners, Richard A Gibbs, Raymond R Mattingly
Prenylation inhibitors have gained increasing attention as potential therapeutics for cancer. Initial work focused on inhibitors of farnesylation, but more recently geranylgeranyl transferase inhibitors (GGTIs) have begun to be evaluated for their potential antitumor activity in vitro and in vivo. In this study, we have developed a nonpeptidomimetic GGTI, termed GGTI-2Z [(5-nitrofuran-2-yl)methyl-(2Z,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl 4-chlorobutyl(methyl)phosphoramidate], which in combination with lovastatin inhibits geranylgeranyl transferase I (GGTase I) and GGTase II/RabGGTase, without affecting farnesylation...
April 2010: Journal of Pharmacology and Experimental Therapeutics
https://www.readbyqxmd.com/read/19944612/synthesis-and-antiproliferative-evaluations-of-certain-2-phenylvinylquinoline-2-styrylquinoline-and-2-furanylvinylquinoline-derivatives
#14
Feng-Shuo Chang, Weichung Chen, Chihuei Wang, Cherng-Chyi Tzeng, Yeh-Long Chen
The present study describes the synthesis of 2-phenylvinylquinoline (styrylquinoline) and 2-furanylvinylquinoline derivatives and evaluation for their antiproliferative activities. (E)-2-Styrylquinolin-8-ol (14a) was inactive against a 3-cell line panel consisting of MCF-7 (Breast), NCI-H460 (Lung), and SF-268 (CNS). Replacement of the phenyl ring with 5-nitrofuran-2-yl group significantly enhanced antiproliferative activity in which (E)-2-(2-(5-nitrofuran-2-yl)vinyl)quinolin-8-ol (14i) and its 4-substituted derivatives 15-19 exhibited strong inhibitory effects against the growth of all three cancer cells...
January 1, 2010: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/19673692/2-substituted-5-nitroheterocycles-in-vitro-anti-helicobacter-pylori-activity-and-structure-activity-relationship-study
#15
Alireza Foroumadi, Maedeh Sorkhi, Mohammad Hassan Moshafi, Maliheh Safavi, Ardeshir Rineh, Farideh Siavoshi, Abbas Shafiee, Saeed Emami
Helicobacter pylori infection is the main cause of gastritis and gastroduodenal ulcer disease, and is associated with gastric cancer. In order to develop new potential anti-Helicobacter pylori candidates, we have investigated the antimicrobial activity of some 2-substituted-5-nitroheterocycles against H. pylori. The anti-Helicobacter pylori activity of selected compounds along with commercially available antibacterial metronidazole was evaluated by comparing the inhibition zone diameters determined using the paper disc diffusion bioassay...
November 2009: Medicinal Chemistry
https://www.readbyqxmd.com/read/19455141/e-coli-nfsa-an-alternative-nitroreductase-for-prodrug-activation-gene-therapy-in-combination-with-cb1954
#16
S O Vass, D Jarrom, W R Wilson, E I Hyde, P F Searle
Prodrug activation gene therapy is a developing approach to cancer treatment, whereby prodrug-activating enzymes are expressed in tumour cells. After administration of a non-toxic prodrug, its conversion to cytotoxic metabolites directly kills tumour cells expressing the activating enzyme, whereas the local spread of activated metabolites can kill nearby cells lacking the enzyme (bystander cell killing). One promising combination that has entered clinical trials uses the nitroreductase NfsB from Escherichia coli to activate the prodrug, CB1954, to a potent bifunctional alkylating agent...
June 16, 2009: British Journal of Cancer
https://www.readbyqxmd.com/read/18824601/nifuroxazide-inhibits-survival-of-multiple-myeloma-cells-by-directly-inhibiting-stat3
#17
Erik A Nelson, Sarah R Walker, Alicia Kepich, Laurie B Gashin, Teru Hideshima, Hiroshi Ikeda, Dharminder Chauhan, Kenneth C Anderson, David A Frank
Constitutive activation of the transcription factor STAT3 contributes to the pathogenesis of many cancers, including multiple myeloma (MM). Since STAT3 is dispensable in most normal tissue, targeted inhibition of STAT3 is an attractive therapy for patients with these cancers. To identify STAT3 inhibitors, we developed a transcriptionally based assay and screened a library of compounds known to be safe in humans. We found the drug nifuroxazide to be an effective inhibitor of STAT3 function. Nifuroxazide inhibits the constitutive phosphorylation of STAT3 in MM cells by reducing Jak kinase autophosphorylation, and leads to down-regulation of the STAT3 target gene Mcl-1...
December 15, 2008: Blood
https://www.readbyqxmd.com/read/18355323/the-npra-nitroreductase-required-for-2-4-dinitrophenol-reduction-in-rhodobacter-capsulatus-is-a-dihydropteridine-reductase
#18
Eva Pérez-Reinado, María Dolores Roldán, Francisco Castillo, Conrado Moreno-Vivián
The Rhodobacter capsulatus nprA gene codes for a putative nitroreductase. A recombinant His(6)-NprA protein was overproduced in Escherichia coli and purified by affinity chromatography. This protein contained FMN and showed nitroreductase activity with a wide range of nitroaromatic compounds, such as 2-nitrophenol, 2,4-dinitrophenol, 2,6-dinitrophenol, 2,4,6-trinitrophenol (picric acid), 2,4-dinitrobenzoate and 2,4-dinitrotoluene, and with the nitrofuran derivatives nitrofurazone and furazolidone. NADPH was the main electron donor and the ortho nitro group was preferably reduced to the corresponding amino derivative...
November 2008: Environmental Microbiology
https://www.readbyqxmd.com/read/17578651/polyamine-contents-in-current-foods-a-basis-for-polyamine-reduced-diet-and-a-study-of-its-long-term-observance-and-tolerance-in-prostate-carcinoma-patients
#19
B G Cipolla, R Havouis, J P Moulinoux
Polyamine contents were assessed by mass spectrometry in 233 current foods and beverages. In order to reduce gut polyamine uptake, a polyamine reduced diet (PRD) and partial intermittent intestinal tract decontamination (PIITD) with neomycin or nifuroxazide was proposed as nutritional therapy to 33 prostate carcinoma patients, 30 of whom with hormone refractory prostate cancer (HRPC). Mean PRD observance was 22 +/- 19 (median: 16; range: 3-72) months. 10, 8 and 3 patients were respectively on PRD for more than 30, 36 and 64 months...
August 2007: Amino Acids
https://www.readbyqxmd.com/read/16616835/assessment-of-chronic-toxicity-and-carcinogenicity-in-an-accelerated-cancer-bioassay-in-rats-of-nifurtimox-an-antitrypanosomiasis-drug
#20
M J Iatropoulos, C X Wang, E von Keutz, G M Williams
The chronic toxicity and carcinogenicity of Nifurtimox (NFX), a 5-nitrofuran derivative used in the treatment of American trypanosomiasis, were studied in male and female Wistar rats in an accelerated cancer bioassay (ACB). The ACB is a mechanistic initiation/promotion chronic toxicity and carcinogenicity bioassay designed to assess potential carcinogenic activity of a test substance in critical organs and tissues of rodents in which human carcinogens are active. The organs studied were liver, lungs, urinary bladder (UB), mammary gland (MG), bone marrow, spleen, kidneys, colon, stomach and any grossly observed lesions...
July 2006: Experimental and Toxicologic Pathology: Official Journal of the Gesellschaft Für Toxikologische Pathologie
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