Harmful and beneficial effects of organic monosulfides, disulfides, and polysulfides in animals and humans.

Abstract:

:Many organic sulfides (mono-, di-, and polysulfides) are present in our environment. Simple derivatives are produced by some plants and animals, while complex sulfides are secondary metabolites of several genera of bacteria and fungi. Sulfides play an important role in the smell and taste of food, and many such compounds are used as food flavorings. Some sulfides are toxic, and there is evidence that such toxicity is caused by the ability of these substances to generate reactive oxygen species. Some sulfides, however, have been shown to protect against toxicants and carcinogens. These beneficial effects are believed to involve, at least in part, the ability of sulfides to inhibit the enzymatic activation of pro-toxicants and to increase tissue activities of enzymes that protect against electrophiles. Some sulfides also have potential as cancer chemotherapeutics. In this review, the toxic and beneficial effects of sulfides in animals are described, and the possible value of sulfides in cancer chemoprotection and cancer chemotherapy is discussed.

journal_name

Chem Res Toxicol

authors

Munday R

doi

10.1021/tx200373u

subject

Has Abstract

pub_date

2012-01-13 00:00:00

pages

47-60

issue

1

eissn

0893-228X

issn

1520-5010

journal_volume

25

pub_type

杂志文章,评审
  • Mechanism of formation of ethenoguanine adducts from 2-haloacetaldehydes: 13C-labeling patterns with 2-bromoacetaldehyde.

    abstract::The mechanism of formation of etheno (epsilon) adducts of nucleic acid bases from 2-haloacetaldehydes is generally assumed to occur via initial Schiff base formation resulting from reaction of the aldehyde with an exocyclic amine. We recently revised the 1H NMR assignments of the epsilon protons of 1,N2-epsilon-Guo (G...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00038a014

    authors: Guengerich FP,Persmark M

    更新日期:1994-03-01 00:00:00

  • Reactions of the Zn Proteome with Cd2+ and Other Xenobiotics: Trafficking and Toxicity.

    abstract::Understanding the molecular basis of inorganic chemical toxicity has lagged behind the proliferation of detailed mechanisms that explain the biochemical toxicology of many organic xenobiotics. In this perspective, general barriers to explicating the bioinorganic chemistry of toxic metals are considered, followed by a ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.6b00328

    authors: Petering DH

    更新日期:2017-01-17 00:00:00

  • Is diacetyl a respiratory sensitizer? A reconsideration using QSAR, QMM, and competition experiments.

    abstract::Concerns have been raised that diacetyl (DA) might be a respiratory sensitizer based on its LUMO energy similar to that of the respiratory allergen toluene-2,4-diisocyanate (TDI) and results of a local lymph node assay (LLNA) that reported an EC3 of 1.9%. To better understand the concerns, we performed a systematic li...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章,评审

    doi:10.1021/tx400097v

    authors: Dworak JJ,Roberts DW,Calter MA,Fields CA,Borak J

    更新日期:2013-05-20 00:00:00

  • Reactivity and Cross-Linking of 5'-Terminal Abasic Sites within DNA.

    abstract::Nicking of the DNA strand immediately upstream of an internal abasic (AP) site produces 5'-terminal abasic (dRp) DNA. Both the intact and the nicked abasic species are reactive intermediates along the DNA base excision repair (BER) pathway and can be derailed by side reactions. Aberrant accumulation of the 5'-terminal...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.7b00057

    authors: Admiraal SJ,O'Brien PJ

    更新日期:2017-06-19 00:00:00

  • Drug metabolite-specific lymphocyte responses in sulfamethoxazole allergic patients with cystic fibrosis.

    abstract::Sulfamethoxazole (SMX) is an important antibiotic in the management of patients with cystic fibrosis, but allergic reactions may develop thus restricting therapy. The aim of this study was to utilize drug (metabolite) antigens to diagnose SMX-mediated allergic reactions in patients with cystic fibrosis. Lymphocytes fr...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx100151v

    authors: Lavergne SN,Whitaker P,Peckham D,Conway S,Park BK,Naisbitt DJ

    更新日期:2010-06-21 00:00:00

  • Copper-2 Hypothesis for Causation of the Current Alzheimer's Disease Epidemic Together with Dietary Changes That Enhance the Epidemic.

    abstract::Alzheimer's disease, the most common cause of dementia, is at epidemic proportions (15 to 44% depending on age, of those age 65 to 84) in the U.S. and other developed countries but remains relatively rare in undeveloped countries. Surprisingly, solid historical data reveal the epidemic is a creature of the last centur...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章,评审

    doi:10.1021/acs.chemrestox.6b00373

    authors: Brewer GJ

    更新日期:2017-03-20 00:00:00

  • Reaction of CO2 with ONOO-: One Molecule of CO2 Is Not Enough.

    abstract::With CO2 present in excess, ONOO- reacts to form an adduct in solution and in the solid state, most likely ONOOCO2-. In solution, the adduct appears within 2 ms and absorbs at 300 with an extinction coefficient, which is either 50% or 100% (preferred) of that of ONOO-, 1.70 × 103 M-1 cm-1, and at 685 nm with an extinc...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.8b00068

    authors: Serrano-Luginbuehl S,Kissner R,Koppenol WH

    更新日期:2018-08-20 00:00:00

  • In Vitro Cytotoxicity and Adaptive Stress Responses to Selected Haloacetic Acid and Halobenzoquinone Water Disinfection Byproducts.

    abstract::The process of disinfecting drinking water inadvertently leads to the formation of numerous disinfection byproducts (DBPs). Some of these are mutagenic, genotoxic, teratogenic, and cytotoxic, as well as potentially carcinogenic both in vivo and in vitro. We investigated the in vitro biological activity of five DBPs: t...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.5b00283

    authors: Procházka E,Escher BI,Plewa MJ,Leusch FD

    更新日期:2015-10-19 00:00:00

  • Identification of colchicine in placental blood from patients using herbal medicines.

    abstract::While characterizing natural antiinflammatory substances in human placental blood, we discovered a factor that affected human neutrophils and their adherence. Rigorous chemical and stereochemical analyses revealed this factor to be the well-known alkaloid, colchicine. When samples from individual patients were analyze...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0155101

    authors: Petty HR,Fernando M,Kindzelskii AL,Zarewych BN,Ksebati MB,Hryhorczuk LM,Mobashery S

    更新日期:2001-09-01 00:00:00

  • Inhibition of gap junctional intercellular communication by toxic metals.

    abstract::As metals are ubiquitous in the environment, humans are continuously exposed to them. Although some metallic ions play key roles in human physiology, most metals are redundant and are actually hazardous to humans. A frequent event in the toxicological cascade triggered by nonessential metals concerns the abrogation of...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章,评审

    doi:10.1021/tx100276f

    authors: Vinken M,Ceelen L,Vanhaecke T,Rogiers V

    更新日期:2010-12-20 00:00:00

  • Oxidative Release of Thiol-Conjugated Forms of the Mycotoxin 4-Deoxynivalenol.

    abstract::Deoxynivalenol (DON) is a trichothecene mycotoxin that is produced by several species of Fusarium, which may infect grain crops. DON, as well as other type-B trichothecenes, contain an α,β-unsaturated carbonyl group that may react with sulfhydryl groups in, for example, amino acids and peptides. Such conjugates have b...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00385

    authors: Uhlig S,Ivanova L,Miles CO

    更新日期:2020-02-17 00:00:00

  • Identification of antrocin from Antrodia camphorata as a selective and novel class of small molecule inhibitor of Akt/mTOR signaling in metastatic breast cancer MDA-MB-231 cells.

    abstract::The PI3K/Akt/mTOR pathway is considered to be an attractive target for the development of novel anticancer molecules. This paper reports for the first time that a small molecule, antrocin (MW = 234), from Antrodia camphorata was a potent antagonist in various cancer types, being highest in metastatic breast cancer MDA...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx100318m

    authors: Rao YK,Wu AT,Geethangili M,Huang MT,Chao WJ,Wu CH,Deng WP,Yeh CT,Tzeng YM

    更新日期:2011-02-18 00:00:00

  • Effect of intestinal glucuronidation in limiting hepatic exposure and bioactivation of raloxifene in humans and rats.

    abstract::Raloxifene (Evista) is a second generation selective estrogen receptor modulator used in the treatment of osteoporosis and for chemoprevention of breast cancer. It is bioactivated to reactive intermediates, which covalently bind to proteins and form GSH conjugates upon incubation with NADPH and GSH-supplemented human ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx800323w

    authors: Dalvie D,Kang P,Zientek M,Xiang C,Zhou S,Obach RS

    更新日期:2008-12-01 00:00:00

  • Assessment of DNA Epigenetic Modifications.

    abstract::DNA molecules utilize adenine, thymine, cytosine, and guanine for coding genetic information. In addition to these four canonical nucleobases, DNA molecules also contain a variety of modified nucleobases that can control and regulate gene expression and chromosome structure. Elucidating the functions of DNA modificati...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.9b00372

    authors: Yuan BF

    更新日期:2020-03-16 00:00:00

  • The pattern of p53 mutations caused by PAH o-quinones is driven by 8-oxo-dGuo formation while the spectrum of mutations is determined by biological selection for dominance.

    abstract::PAHs (polycyclic aromatic hydrocarbons) are suspect lung cancer carcinogens that must be metabolically converted into DNA-reactive metabolites. P4501A1/P4501B1 plus epoxide hydrolase activate PAH to (+/-)- anti-benzo[ a]pyrene diol epoxide ((+/-)- anti-BPDE), which causes bulky DNA adducts. Alternatively, aldo-keto re...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx700404a

    authors: Park JH,Gelhaus S,Vedantam S,Oliva AL,Batra A,Blair IA,Troxel AB,Field J,Penning TM

    更新日期:2008-05-01 00:00:00

  • Studies on the chemical reactivity of 2-phenylpropionic acid 1-O-acyl glucuronide and S-acyl-CoA thioester metabolites.

    abstract::Chemically reactive species formed from the metabolism of carboxylic acid-containing compounds have been proposed as mediators of their toxic side-effects. Two alternative metabolic pathways known to be involved in the generation of reactive acylating metabolites of carboxylic acids are acyl glucuronidation and acyl-C...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx020013l

    authors: Li C,Benet LZ,Grillo MP

    更新日期:2002-10-01 00:00:00

  • Induction of cytotoxicity, aldehydic DNA lesions, and poly(ADP-ribose) polymerase-1 activation by catechol derivatives of pentachlorophenol in calf thymus DNA and in human breast cancer cells.

    abstract::The purpose of this study was to investigate the degree of chlorination of catechol (CAT) derivatives of pentachlorophenol (PCP) on the induction of cytotoxicity and DNA damaging effects in calf thymus DNA (ct-DNA) and in two human breast carcinoma cell lines. Results indicated that with the addition of the transition...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0498511

    authors: Lin CH,Leow HT,Huang SC,Nakamura J,Swenberg JA,Lin PH

    更新日期:2005-02-01 00:00:00

  • Neuroprotection in the MPTP Parkinsonian C57BL/6 mouse model by a compound isolated from tobacco.

    abstract::Epidemiological evidence suggests a lower incidence of Parkinson's disease in smokers than in nonsmokers. This evidence, together with the lower levels of brain monoamine oxidase (MAO) activity in smokers and the potential neuroprotective properties of MAO inhibitors, prompted studies which led to the isolation and ch...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx000224v

    authors: Castagnoli KP,Steyn SJ,Petzer JP,Van der Schyf CJ,Castagnoli N Jr

    更新日期:2001-05-01 00:00:00

  • Oxidative bioactivation of abacavir in subcellular fractions of human antigen presenting cells.

    abstract::Human exposure to abacavir, a primary alcohol antiretroviral, is associated with the development of immunological drug reactions in individuals carrying the HLA risk allele B*57:01. Interaction of abacavir with antigen presenting cells results in cell activation through an Hsp70-mediated Toll-like receptor pathway and...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx400041v

    authors: Bell CC,Santoyo Castelazo A,Yang EL,Maggs JL,Jenkins RE,Tugwood J,O'Neill PM,Naisbitt DJ,Park BK

    更新日期:2013-07-15 00:00:00

  • Genotoxicity-related chemistry of human metabolites of benzo[ghi]perylene (B[ghi]P) investigated using electro-optical arrays and DNA/microsome biocolloid reactors with LC-MS/MS.

    abstract::There is limited and sometimes contradictory information about the genotoxicity of the polycyclic aromatic hydrocarbon benzo[ghi]perylene (B[ghi]P). Using recently developed metabolic toxicity screening arrays and a biocolloid reactor-LC-MS/MS approach, both featuring films of DNA and human metabolic enzymes, we demon...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx400147c

    authors: Pan S,Li D,Zhao L,Schenkman JB,Rusling JF

    更新日期:2013-08-19 00:00:00

  • Reactive metabolite trapping screens and potential pitfalls: bioactivation of a homomorpholine and formation of an unstable thiazolidine adduct.

    abstract::Successful early attrition of potential problematic compounds is of great importance in the pharmaceutical industry. The lead compound in a recent project targeting neuropathic pain was susceptible to metabolic bioactivation, which produced reactive metabolites and showed covalent binding to protein. Therefore, as a p...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx5000409

    authors: Lenz EM,Martin S,Schmidt R,Morin PE,Smith R,Weston DJ,Bayrakdarian M

    更新日期:2014-06-16 00:00:00

  • Hypochlorous acid-mediated oxidation of lipid components and antioxidants present in low-density lipoproteins: absolute rate constants, product analysis, and computational modeling.

    abstract::Oxidation of low-density lipoproteins (LDL) is believed to contribute to the increased uptake of LDL by macrophages, which is an early event in atherosclerosis. Hypochlorous acid (HOCl) has been implicated as one of the major oxidants involved in these processes. In a previous study, the rates of reaction of HOCl with...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx025670s

    authors: Pattison DI,Hawkins CL,Davies MJ

    更新日期:2003-04-01 00:00:00

  • Kinetics of paraquat and copper reactions with nitroxides: the effects of nitroxides on the aerobic and anoxic toxicity of paraquat.

    abstract::The toxicity of paraquat (PQ2+) is attributed to intracellularly formed PQ*+, O(2)*-, H(2)O(2), and secondary.OH radicals generated through Fenton-like reactions. Yet, no antidote for PQ2+ toxicity in human has been found also due to poor cell permeability of many common antioxidants that remove toxic species predomin...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx0155956

    authors: Goldstein S,Samuni A,Aronovitch Y,Godinger D,Russo A,Mitchell JB

    更新日期:2002-05-01 00:00:00

  • A novel pectenotoxin, PTX-12, in Dinophysis spp. and shellfish from Norway.

    abstract::Two novel pectenotoxins (PTXs) were detected by LC-MS in solid phase extracts of net hauls taken at Flødevigen, Norway, in June 2002 that were dominated by Dinophysis acuminata and Dinophysis norvegica. The new compounds were isolated as minor components from a large collection of a Dinophysis acuta-dominated bloom ob...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx049870a

    authors: Miles CO,Wilkins AL,Samdal IA,Sandvik M,Petersen D,Quilliam MA,Naustvoll LJ,Rundberget T,Torgersen T,Hovgaard P,Jensen DJ,Cooney JM

    更新日期:2004-11-01 00:00:00

  • Urinary sulfur-containing metabolite produced by intestinal bacteria following oral administration of dimethylarsinic acid to rats.

    abstract::Our long-term oral administration of dimethylarsinic acid (DMAV) in rats revealed that three unidentified metabolites, M-1, M-2, and M-3, were detected in urine and feces. DMAV and trimethylarsine oxide (TMAO) were converted to M-2 and M-3 and M-1 by Escherichia coli strain A3-6 isolated from the ceca of DMAV-administ...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx030008x

    authors: Yoshida K,Kuroda K,Zhou X,Inoue Y,Date Y,Wanibuchi H,Fukushima S,Endo G

    更新日期:2003-09-01 00:00:00

  • Hydroxyl Radicals in E-Cigarette Vapor and E-Vapor Oxidative Potentials under Different Vaping Patterns.

    abstract::Available studies, while limited in number, suggest that e-cigarette vaping induces oxidative stress, with one potential mechanism being the direct formation of reactive oxygen species (ROS) in e-vapor. In the present studies, we measured the formation of hydroxyl radical (•OH), the most destructive ROS, in e-vapor un...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.8b00400

    authors: Son Y,Mishin V,Laskin JD,Mainelis G,Wackowski OA,Delnevo C,Schwander S,Khlystov A,Samburova V,Meng Q

    更新日期:2019-06-17 00:00:00

  • Notopterygium forbesii boiss extract and its active constituents increase reactive species and heme oxygenase-1 in human fetal hepatocytes: mechanisms of action.

    abstract::Notopterygium forbesii Boiss (NF) has been used as a traditional Chinese medicine for the treatment of common cold and rheumatism. However, there has been limited research on the biological properties of NF, and the mechanisms of action remain unknown. Here, we aimed to study the mechanism of NF-induced heme oxygenase...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx800301f

    authors: Tang SY,Wang H,Zhang W,Halliwell B

    更新日期:2008-12-01 00:00:00

  • Thioproline Serves as an Efficient Antioxidant Protecting Human Cells from Oxidative Stress and Improves Cell Viability.

    abstract::Oxidative stress is associated with the pathophysiology of many degenerative human diseases, including Alzheimer's disease, atherosclerosis, Parkinson's disease, and cancers. We discovered in our previous study that thioproline (SPro), a proline analogue, is generated in oxidant-exposed cells. With the prior observati...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/acs.chemrestox.0c00055

    authors: Ham YH,Jason Chan KK,Chan W

    更新日期:2020-07-20 00:00:00

  • Metabolism of the food-borne mutagen 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline in humans.

    abstract::The metabolism of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) was investigated in five human volunteers given a dietary equivalent of 14C-labeled MeIQx. The amount of the dose excreted in urine ranged from 20.2% to 58.6%, with unmetabolized MeIQx accounting for 0.7-2.8% of the dose. Five principal metabolite...

    journal_title:Chemical research in toxicology

    pub_type: 临床试验,杂志文章

    doi:10.1021/tx9701891

    authors: Turesky RJ,Garner RC,Welti DH,Richoz J,Leveson SH,Dingley KH,Turteltaub KW,Fay LB

    更新日期:1998-03-01 00:00:00

  • Molecular recognition between oligopeptides and nucleic acids: DNA binding selectivity of a series of 1,2,4-triazole-containing lexitropsins.

    abstract::The synthesis of a series of 1,2,4-triazole-containing oligopeptide lexitropsins related to the natural antitumor antibiotic distamycin is described. The binding properties of these new agents to both native DNAs and synthetic polydeoxyribonucleotides were determined by UV absorption and circular dichroism studies. Th...

    journal_title:Chemical research in toxicology

    pub_type: 杂志文章

    doi:10.1021/tx00020a019

    authors: Rao KE,Krowicki K,Burckhardt G,Zimmer C,Lown JW

    更新日期:1991-03-01 00:00:00