5-(3-Hydroxymethyl-3-methyl-1-triazeno imidazole-4-carboxamide is a metabolite of 5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide (DIC, DTIC NSC-45388).

Abstract:

:The cancer chemotherapeutic drug, 5-(3,3-dimethyl-1-triazeno) imidazole-4-carboxamide (DIC, DTIC, NSC-45388), is metabolised in rats to a structurally related product which was detected by thin-layer chromatography. The novel metabolite has a lower mobility and a colour reaction that is indistinguishable from the parent compound. The metabolite is not retained on an anionic exchanger which is inconsistent with the expected covalent binding of the drug to endogenic anionic substrates (e.g. glucuronic acid). Since both DIC and the metabolite yielded 5-[(4-ethylamino-1-napthyl)-azo]imidazole-4-carboxamide through release of 5-diazoimidazole-4-carboxamide, followed by coupling with N-ethyl-1-napthylamine, no biotransformation (hydroxylation) of the imidazole moiety of the injected DIC had occurred. By corollary, the lowered chromatographic mobility of the metabolite was explicable by the introduction of a polar but non-acidic function into the terminal dimethylamino group of the triazene side-chain. The metabolite was identified as 5-(3-hydroxymethyl-3-methyl-1-triazeno)imidazole-4-carboxamide by co-chromatography with an authentic sample of HMIC and by its methylating capacity for nucleophilic substrates.

journal_name

Cancer Lett

journal_title

Cancer letters

authors

Kolar GF,Maurer M,Wildschütte M

doi

10.1016/0304-3835(80)90076-2

subject

Has Abstract

pub_date

1980-09-01 00:00:00

pages

235-41

issue

3

eissn

0304-3835

issn

1872-7980

pii

0304-3835(80)90076-2

journal_volume

10

pub_type

杂志文章
  • 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

  • Feedback loop between p66(Shc) and Nrf2 promotes lung cancer progression.

    abstract::p66(Shc), one of the SHC1 gene encoding proteins, promotes cell death and reports cell anchorage status, mediating anoikis in vitro and functioning as a metastasis suppressor in vivo. However, very little is known about p66(Shc) gene regulation in cancer cells. Here, we show that methylation of a specific CpG site in ...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2013.05.016

    authors: Du W,Jiang Y,Zheng Z,Zhang Z,Chen N,Ma Z,Yao Z,Terada L,Liu Z

    更新日期:2013-08-28 00:00:00

  • Histone deacetylase inhibitors prevent activation of tumour-reactive NK cells and T cells but do not interfere with their cytolytic effector functions.

    abstract::Histone deacetylase inhibitors (HDIs) exert direct tumour-toxic activity and sensitise tumour cells for other therapeutic regimens as well as the cytotoxic effects of activated immune cells. However, the HDI suberoylanilide hydroxamic acid (SAHA; vorinostat) interfered with the IL-2 activation of human NK cells and th...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2010.02.024

    authors: Schmudde M,Friebe E,Sonnemann J,Beck JF,Bröker BM

    更新日期:2010-09-28 00:00:00

  • Influence of supplemental glutathione on selenite-mediated growth inhibition of canine mammary cells.

    abstract::Present studies show the in vitro addition of glutathione (GSH) can significantly alter selenite induced growth inhibition of mammary tumor cell line 13 (CMT-13). Preincubation with 100 microM GSH for 24 h partially prevented the growth inhibition caused by 12.6 microM selenite. Pre-incubation with 100 microM GSH for ...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(91)90213-2

    authors: Kuchan MJ,Milner JA

    更新日期:1991-05-01 00:00:00

  • Carcinogenic effect of di-isopropanolnitrosamine on the rat thyroid gland.

    abstract::Up to a 50% rate of thyroid gland tumours was induced in Sprague-Dawley rats after s.c. administration of di-isopropanolnitrosamine (DIPN). The neoplasms occurred both unilaterally and bilaterally, and were identified histologically as adenomas and adenocarcinomas of follicular epithelium origin. In a few instances, a...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(77)80022-0

    authors: Reznik G,Mohr U

    更新日期:1977-03-01 00:00:00

  • Inhibition by 9alpha-fluoromedoroxyprogesterone acetate (FMPA) against mammary carcinoma induced by dimethylbenz[a]anthracene in rats and angiogenesis in the rabbit cornea - comparison with medroxyprogesterone acetate (MPA).

    abstract::Medroxyprogesterone acetate (MPA) is currently used therapeutically in the treatment of mammary and endometrial carcinomas. In order to develop a more potent and useful drug, we synthesized the novel compound, 9alpha-fluoromedoroxyprogesterone acetate (FMPA), by fluorinating MPA, and we also previously reported that F...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(00)00375-x

    authors: Uchida M,Tsuboi H,Yamaji T,Murata N,Kohno T,Sugino E,Hibino S,Shimamura M,Oikawa T

    更新日期:2000-06-01 00:00:00

  • Effect of protease inhibitors on DNA amplification in SV40-transformed Chinese hamster embryo cells.

    abstract::We have examined the effect of protease inhibitors on radiation-induced DNA amplification in vitro using an SV40-transformed Chinese hamster embryo cell line. DNA from cells irradiated with X-rays (10 Gy) or ultraviolet radiation (8 J/m2) resulted in an 8-fold or greater amplification of SV40 sequences compared with u...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(91)90083-t

    authors: Flick MB,Kennedy AR

    更新日期:1991-02-01 00:00:00

  • RNA aptamers targeting cancer stem cell marker CD133.

    abstract::The monoclonal antibody against the AC133 epitope of CD133 has been widely used as a cell surface marker of cancer stem cells in several different cancer types. Here, we describe the isolation and characterisation of two RNA aptamers, including the smallest described 15 nucleotide RNA aptamer, which specifically recog...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2012.11.032

    authors: Shigdar S,Qiao L,Zhou SF,Xiang D,Wang T,Li Y,Lim LY,Kong L,Li L,Duan W

    更新日期:2013-03-01 00:00:00

  • Retinoid-X-receptor alpha (RXRalpha) expression during laryngeal carcinogenesis: detrimental or beneficial event?

    abstract::RXRalpha is an obligatory heterodimerization partner in many signal transducing pathways. To evaluate RXRalpha expression during laryngeal carcinogenesis, immunohistochemistry was performed on laryngeal epithelial specimens of 154 patients with normal-appearing, hyperplastic, dysplastic laryngeal epithelium and squamo...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(03)00346-x

    authors: Karamouzis MV,Sotiropoulou-Bonikou G,Vandoros G,Varakis I,Papavassiliou AG

    更新日期:2003-09-25 00:00:00

  • Inhibition of MDR1 gene expression by H-87, a selective inhibitor of cAMP-dependent protein kinase.

    abstract::N-[2-(p-bromocinnamylmethylamino) ethyl]-5-isoquinolinesulfonamide (H-87), a newly synthesized inhibitor of protein kinase A, significantly decreased the drug resistance of multidrug resistant human U937/M cells, mouse FM3A/M and P388/M cells. Northern blot analysis showed MDR1 gene expression was decreased in H-87-tr...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(93)90041-7

    authors: Kim SH,Park JI,Chung BS,Kang CD,Hidaka H

    更新日期:1993-10-15 00:00:00

  • p53 mutations in betel-associated oral cancer from Thailand.

    abstract::The p53 mutations in betel-related oral cancer have been studied but the results may be confounded by tobacco and alcohol due to tobacco components in the quid or concomitant habits of smoking and drinking. In this study, p53 mutations in tumors from Thai betel chewers who neither smoke nor drink were studied in compa...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(03)00417-8

    authors: Thongsuksai P,Boonyaphiphat P,Sriplung H,Sudhikaran W

    更新日期:2003-11-10 00:00:00

  • Immune repertoire: A potential biomarker and therapeutic for hepatocellular carcinoma.

    abstract::The immune repertoire (IR) refers to the sum of B cells and T cells with functional diversity in the circulatory system of one individual at any given time. Immune cells, which reside within microenvironments and are responsible for protecting the human body, include T cells, B cells, macrophages, and dendritic cells....

    journal_title:Cancer letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.canlet.2015.06.022

    authors: Han Y,Li H,Guan Y,Huang J

    更新日期:2016-09-01 00:00:00

  • Suppression of Akt1-β-catenin pathway in advanced prostate cancer promotes TGFβ1-mediated epithelial to mesenchymal transition and metastasis.

    abstract::Akt1 is essential for the oncogenic transformation and tumor growth in various cancers. However, the precise role of Akt1 in advanced cancers is conflicting. Using a neuroendocrine TRansgenic Adenocarcinoma of the Mouse Prostate (TRAMP) model, we first show that the genetic ablation or pharmacological inhibition of Ak...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2017.05.028

    authors: Gao F,Alwhaibi A,Sabbineni H,Verma A,Eldahshan W,Somanath PR

    更新日期:2017-08-28 00:00:00

  • Metabolism of xenobiotics in the human adrenal gland.

    abstract::The capacity of the human adrenal gland to metabolize various xenobiotics was investigated. Adrenal microsomal and mitochondrial preparations showed a maximal absorption at 450 nm for dithionite-reduced cytochromes in the presence of carbon monoxide. Occasionally, absorption maxima at 448 nm were observed with both mi...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(84)90039-9

    authors: Papadopoulos D,Seidegard J,Rydström J

    更新日期:1984-02-01 00:00:00

  • The ineffectiveness of reduced glutathione in preventing the development of liver tumours from aflatoxin-induced pre-neoplastic liver lesions.

    abstract::Oral treatment with reduced glutathione for 10 weeks has no effect on the development of tumours from aflatoxin B1-induced gamma-glutamyl transpeptidase-positive pre-neoplastic focal lesions. ...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(83)90086-1

    authors: Neal GE,Legg RF

    更新日期:1983-11-01 00:00:00

  • An enzyme immunoassay for the detection of human tumor nucleolar antigens.

    abstract::An enzyme immunoassay (EIA) was developed in which nuclear extracts were bound to the wells of polystyrene microtiter plates. The presence of various antigens in the extracts could be detected using antiserum raised against HeLa cell nucleoli. Normal human cell extracts, coupled to Sepharose as a solid phase absorbent...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(81)90171-3

    authors: Kelsey DE,Busch RK,Busch H

    更新日期:1981-05-01 00:00:00

  • Clastogenic and cytotoxic effects of spermine oxidation products in mouse lymphoma L5178Y cells.

    abstract::Treatment of mouse lymphoma L5178Y cells with spermine in Fischer's medium containing bovine serum lead to formation of chromatid aberrations. The cause of this effect seems to be that bovine serum contains spermine oxidase which catalyzes oxidation of spermine to unstable aldehyde derivatives (oxidized spermine) and ...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(88)90044-4

    authors: Bouzyk E,Rosiek O

    更新日期:1988-02-01 00:00:00

  • Loss of heterozygosity and the smoking index increase with decrease in differentiation of lung adenocarcinomas: etiologic implications.

    abstract::To better understand causative relations of smoking to lung adenocarcinomas, the frequency of loss of heterozygosity (LOH) of all autosomal chromosomes was compared among the three grades of histological differentiation with 119 pulmonary adenocarcinomas (AC) and 41 squamous cell carcinomas (SCC), using Southern blott...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(02)00383-x

    authors: Ishikawa Y,Furuta R,Miyoshi T,Satoh Y,Okumura S,Nakagawa K,Tsuchiya E

    更新日期:2002-12-10 00:00:00

  • Alantolactone selectively suppresses STAT3 activation and exhibits potent anticancer activity in MDA-MB-231 cells.

    abstract::The important goal of cancer drug discovery is to develop therapeutic agents that are effective, safe, and affordable. In the present study, we demonstrated that alantolactone, which is a sesquiterpene lactone, has potential activity against triple-negative breast cancer MDA-MB-231 cells by suppressing the signal tran...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2014.11.049

    authors: Chun J,Li RJ,Cheng MS,Kim YS

    更新日期:2015-02-01 00:00:00

  • Isolinderalactone regulates the BCL-2/caspase-3/PARP pathway and suppresses tumor growth in a human glioblastoma multiforme xenograft mouse model.

    abstract::Glioblastoma multiforme (GBM) is the most common malignant brain tumor, which remains incurable. Plant extracts are a potential source of potent anticancer medicines. In this study, we investigated the effect of isolinderalactone from Lindera aggregata on tumor growth using U-87 human glioblastoma cells. Treatment wit...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2018.11.027

    authors: Hwang JY,Park JH,Kim MJ,Kim WJ,Ha KT,Choi BT,Lee SY,Shin HK

    更新日期:2019-02-28 00:00:00

  • Non-specific cyclic nucleotide binding in leukemic leukocytes.

    abstract::Extracts of leukemic lymphocytes and leukemic myelomonocytic cells bind significantly more cAMP/mg protein than do normal cells. The binding of cAMP in leukemic cells is non-specific since the binders are unable to effectively discriminate between cAMP and cGMP in contrast to normal cells. When normal lymphocytes are ...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(80)90004-x

    authors: Weber TH,Linkola J

    更新日期:1980-01-01 00:00:00

  • Nitrotyrosine in esophageal squamous cell carcinoma and relevance to p53 expression.

    abstract::We have examined the expression of nitrotyrosine, a marker of peroxynitrite formation, in 55 esophageal cancers by immunohistochemistry. Nitrotyrosine was detected in 21 of 55 (38.2%) esophageal cancers. Comparison of nitrotyrosine expression and the pathological findings showed that there was a significant associatio...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(00)00358-x

    authors: Kato H,Miyazaki T,Yoshikawa M,Nakajima M,Fukai Y,Tajima K,Masuda N,Tsutsumi S,Tsukada K,Nakajima T,Kuwano H

    更新日期:2000-05-29 00:00:00

  • Adipocytokines visfatin and resistin in breast cancer: Clinical relevance, biological mechanisms, and therapeutic potential.

    abstract::Obesity is one of the major modifiable risk factors in breast cancer, with obese adipose tissue showing a pathological role in breast cancer development and malignancy via the release of secretory factors, such as proinflammatory cytokines and adipocytokines. The current article focuses on visfatin and resistin, two s...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2020.10.045

    authors: Wang YY,Hung AC,Lo S,Yuan SF

    更新日期:2021-02-01 00:00:00

  • The aflatoxin-induced TP53 mutation at codon 249 (R249S): biomarker of exposure, early detection and target for therapy.

    abstract::Hepatocellular Carcinoma (HCC) in high-incidence areas (sub-Saharan Africa, South-Eastern Asia) often contains a somatic mutation at codon 249 in TP53 (R249S). This mutation is rare in low-incidence areas of Europe and the United States. There is evidence that R249S occurs as the result of mutagenesis by aflatoxin in ...

    journal_title:Cancer letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.canlet.2009.02.057

    authors: Gouas D,Shi H,Hainaut P

    更新日期:2009-12-01 00:00:00

  • Antimutagenic activity of anthocyanins isolated from Aronia melanocarpa fruits.

    abstract::Anthocyanins belong to the flavonoid family and are ubiquitous in plants, especially in flower petals and fruit peels. We established that anthocyanins isolated from fruits of Aronia melanocarpa markedly inhibited the mutagenic activity of benzo(a)pyrene and 2-amino fluorene in the Ames test. In the Sister Chromatid E...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/s0304-3835(97)00248-6

    authors: Gasiorowski K,Szyba K,Brokos B,Kołaczyńska B,Jankowiak-Włodarczyk M,Oszmiański J

    更新日期:1997-10-28 00:00:00

  • Mechanisms of immune evasion of human neuroblastoma.

    abstract::Neuroblastoma (NB) is a common neuroectodermal tumor of childhood with low response to conventional therapy in patients with advanced stage disease. Among novel strategies, immumotherapy has attracted much interest. However, scanty information is available about the immunogenicity of human NB. Here, we review our data...

    journal_title:Cancer letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.canlet.2004.11.064

    authors: Raffaghello L,Prigione I,Airoldi I,Camoriano M,Morandi F,Bocca P,Gambini C,Ferrone S,Pistoia V

    更新日期:2005-10-18 00:00:00

  • Stress resistant human embryonic stem cells as a potential source for the identification of novel cancer stem cell markers.

    abstract::Cancer stem cells are known for their inherent resistance to therapy. Here we investigated whether normal stem cells with acquired resistance to stress can be used to identify novel markers of cancer stem cells. For this, we generated a human embryonic stem cell line resistant to Trichostatin A and analyzed changes in...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2009.08.018

    authors: Mousa SA,Sudha T,Dyskin E,Dier U,Gallati C,Hanko C,Chittur SV,Rebbaa A

    更新日期:2010-03-28 00:00:00

  • Bacteria-derived minicells for cancer therapy.

    abstract::Bacteria are always a considerable tool for the cancer therapy. The bacteria-derived minicells are re-emerged as a promising drug delivery system for cancer therapy. The minicells are nano-sized, anucleated, non-dividing, and metabolically active cells produced by abnormal bacterial cell division that are able to tran...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2020.07.024

    authors: Ali MK,Liu Q,Liang K,Li P,Kong Q

    更新日期:2020-10-28 00:00:00

  • NVP-BEZ235, a dual PI3K/mTOR inhibitor, inhibits osteosarcoma cell proliferation and tumor development in vivo with an improved survival rate.

    abstract::Despite recent improvements in chemotherapy and surgery, the problem of non-response osteosarcoma to chemotherapy remains, and is a parameter that is critical for prognosis. The present work investigated the therapeutic value of NVP-BEZ235, a dual class I PI3K/mTOR inhibitor. NVP-BEZ235 inhibited osteosarcoma cell pro...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/j.canlet.2013.11.017

    authors: Gobin B,Battaglia S,Lanel R,Chesneau J,Amiaud J,Rédini F,Ory B,Heymann D

    更新日期:2014-03-28 00:00:00

  • Increased sensitivity to indomethacin of mice bearing the BCL1-leukemia.

    abstract::Indomethacin is a non-steroidal anti-inflammatory agent that inhibits prostaglandin synthesis. Administration of indomethacin, in doses which were non-toxic to normal BALB/c mice, to mice bearing the BCL1 leukemia resulted in increased mortality of these animals. This effect was only observed if the indomethacin was a...

    journal_title:Cancer letters

    pub_type: 杂志文章

    doi:10.1016/0304-3835(84)90147-2

    authors: Hart DA

    更新日期:1984-06-01 00:00:00