[18O]-labeled singlet oxygen as a tool for mechanistic studies of 8-oxo-7,8-dihydroguanine oxidative damage: detection of spiroiminodihydantoin, imidazolone and oxazolone derivatives.

Abstract:

:A water-soluble [18O]-labeled endoperoxide derived from N,N'-di(2,3-dihydroxypropyl)-1,4-naphthalene-dipropanamide (DHPN18O2) has been shown to act as a clean chemical source of [18O]-labeled molecular singlet oxygen. This allows the assessment of the singlet oxygen (1O2) reactivity toward biological targets such as DNA. The present work focuses on the qualitative identification of the main 1O2-oxidation products of 8-oxo-7,8-dihydro-2'-deoxyguanosine, which was achieved using high performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS). Thus, the [18O]-labeled and unlabeled imidazolone and oxazolone, together with the diastereoisomeric spiroiminodihydantoin nucleosides, were detected as the main degradation products. In addition, a modified nucleoside that exhibits similar features as those of the oxidized guanidinohydantoin molecule was detected. Our data strongly suggest that the imidazolone and oxazolone nucleosides are generated via the rearrangement of an unstable 5-hydroperoxide intermediate. Interestingly, the combined use of appropriate tools, including isotopically labeled singlet oxygen and the high- resolution HPLC-ESI-MS/MS technique, has allowed to shed new light on the 1O2-mediated oxidation reactions of guanine DNA components.

journal_name

Biol Chem

journal_title

Biological chemistry

authors

Martinez GR,Medeiros MH,Ravanat JL,Cadet J,Di Mascio P

doi

10.1515/BC.2002.063

keywords:

subject

Has Abstract

pub_date

2002-03-01 00:00:00

pages

607-17

issue

3-4

eissn

1431-6730

issn

1437-4315

journal_volume

383

pub_type

杂志文章
  • Cytokine combinations differentially influence the SDF-1alpha-dependent migratory activity of cultivated murine hematopoietic stem and progenitor cells.

    abstract::Stromal cell-derived factor-1alpha (SDF-1alpha) is a strong migratory stimulant for hematopoietic stem and progenitor cells (HSPCs). The hematopoietic cytokines thrombopoietin (TPO), Flt3-ligand (FL), stem cell factor (SCF) and interleukin 11 (IL-11) are able to stimulate amplification of primitive murine hematopoieti...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2008.099

    authors: Kassmer SH,Niggemann B,Punzel M,Mieck C,Zänker KS,Dittmar T

    更新日期:2008-07-01 00:00:00

  • Central nervous system: cholesterol turnover, brain development and neurodegeneration.

    abstract::The average amount of cholesterol in the whole animal equals approximately 2100 mg/kg body weight, and 15% and 23% of this sterol in the mouse and human, respectively, is found in the central nervous system. There is no detectable uptake across the blood-brain barrier of cholesterol carried in lipoproteins in the plas...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2009.035

    authors: Dietschy JM

    更新日期:2009-04-01 00:00:00

  • Calpastatin exon 1B-derived peptide, a selective inhibitor of calpain: enhancing cell permeability by conjugation with penetratin.

    abstract::The ubiquitous calpains, mu- and m-calpain, have been implicated in essential physiological processes and various pathologies. Cell-permeable specific inhibitors are important tools to elucidate the roles of calpains in cultivated cells and animal models. The synthetic N-acetylated 27-mer peptide derived from exon B o...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2003.045

    authors: Gil-Parrado S,Assfalg-Machleidt I,Fiorino F,Deluca D,Pfeiler D,Schaschke N,Moroder L,Machleidt W

    更新日期:2003-03-01 00:00:00

  • Effect of silver nanoparticles on human primary keratinocytes.

    abstract::Silver nanoparticles (AgNPs) have many biological applications in biomedicine, biotechnology and other life sciences. Depending on the size, shape and the type of carrier, AgNPs demonstrate different physical and chemical properties. AgNPs have strong antimicrobial, antiviral and antifungal activity, thus they are use...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2012-0202

    authors: Szmyd R,Goralczyk AG,Skalniak L,Cierniak A,Lipert B,Filon FL,Crosera M,Borowczyk J,Laczna E,Drukala J,Klein A,Jura J

    更新日期:2013-01-01 00:00:00

  • Plasma prekallikrein/kallikrein processing by lysosomal cysteine proteases.

    abstract::Plasma kallikrein plays a role in coagulation, fibrinolysis and inflammation. Cathepsins B and L participate in (patho)physiological processes such as peptide antigen processing, tissue remodeling events, protein turnover in cells, hormone processing and tumor invasion. The present work analyzes the processing of prek...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2004.141

    authors: Barros NM,Puzer L,Tersariol IL,Oliva ML,Sampaio CA,Carmona AK,Motta G

    更新日期:2004-11-01 00:00:00

  • On the regulative role of the glutamate receptor in mitochondria.

    abstract::The purpose of this work was to study the regulative role of the glutamate receptor found earlier in the brain mitochondria. In the present work a glutamate-dependent signaling system with similar features was detected in mitochondria of the heart. The glutamate-dependent signaling system in the heart mitochondria was...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2015-0289

    authors: Selin AA,Lobysheva NV,Nesterov SV,Skorobogatova YA,Byvshev IM,Pavlik LL,Mikheeva IB,Moshkov DA,Yaguzhinsky LS,Nartsissov YR

    更新日期:2016-05-01 00:00:00

  • Family C1 cysteine proteases: biological diversity or redundancy?

    abstract::Recent progress in the identification and partial characterization of novel genes encoding cysteine proteases of the papain family has considerably increased our knowledge of this family of enzymes. Kinetic data available to date for this large family indicate relatively broad, overlapping specificities for most enzym...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2003.094

    authors: Nägler DK,Ménard R

    更新日期:2003-06-01 00:00:00

  • Annexins - insights from knockout mice.

    abstract::Annexins are a highly conserved protein family that bind to phospholipids in a calcium (Ca2+) - dependent manner. Studies with purified annexins, as well as overexpression and knockdown approaches identified multiple functions predominantly linked to their dynamic and reversible membrane binding behavior. However, mos...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/hsz-2016-0168

    authors: Grewal T,Wason SJ,Enrich C,Rentero C

    更新日期:2016-10-01 00:00:00

  • Activation profiles of human kallikrein-related peptidases by matrix metalloproteinases.

    abstract::The 15 human kallikrein-related peptidases (KLKs) are clinically important biomarkers and therapeutic targets of interest in inflammation, cancer, and neurodegenerative disease. KLKs are secreted as inactive pro-forms (pro-KLKs) that are activated extracellularly by specific proteolytic release of their amino-terminal...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2012-0249

    authors: Yoon H,Blaber SI,Li W,Scarisbrick IA,Blaber M

    更新日期:2013-01-01 00:00:00

  • Progress toward a malaria vaccine: efficient induction of protective anti-malaria immunity.

    abstract::Malaria can be a very severe disease, particularly in young children, pregnant women (mostly in primipara), and malaria naïve adults, and currently ranks among the most prevalent infections in tropical and subtropical areas throughout the world. The widespread occurrence and the increased incidence of malaria in many ...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2001.069

    authors: Tsuji M,Rodrigues EG,Nussenzweig S

    更新日期:2001-04-01 00:00:00

  • Structural models of the human copper P-type ATPases ATP7A and ATP7B.

    abstract::The human copper exporters ATP7A and ATP7B contain domains common to all P-type ATPases as well as class-specific features such as six sequential heavy-metal binding domains (HMBD1-HMBD6) and a type-specific constellation of transmembrane helices. Despite the medical significance of ATP7A and ATP7B related to Menkes a...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2011-0249

    authors: Gourdon P,Sitsel O,Lykkegaard Karlsen J,Birk Møller L,Nissen P

    更新日期:2012-04-01 00:00:00

  • A method to determine RNA and DNA oxidation simultaneously by HPLC-ECD: greater RNA than DNA oxidation in rat liver after doxorubicin administration.

    abstract::We developed a novel method for the simultaneous extraction and analysis of total tissue RNA and DNA to quantify the RNA and DNA oxidation products 8-oxo-7,8-dihydroguanosine and 8-oxo-7,8-dihydro-2'-deoxyguanosine using HPLC coupled to electrochemical detection (HPLC-ECD). The protein denaturing agents guanidine thio...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2006.014

    authors: Hofer T,Seo AY,Prudencio M,Leeuwenburgh C

    更新日期:2006-01-01 00:00:00

  • Redefining proteostasis transcription factors in organismal stress responses, development, metabolism, and health.

    abstract::Eukaryotic organisms have evolved complex and robust cellular stress response pathways to ensure maintenance of proteostasis and survival during fluctuating environmental conditions. Highly conserved stress response pathways can be triggered and coordinated at the cell-autonomous and cell-nonautonomous level by proteo...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/hsz-2019-0385

    authors: Jones LM,Chen Y,van Oosten-Hawle P

    更新日期:2020-08-27 00:00:00

  • Characterization of the nuclear import mechanisms of HSV-1 UL31.

    abstract::As an important protein, UL31 has been demonstrated to play multiple roles in herpes simplex virus 1 (HSV-1) replication. Previous studies showed that UL31 predominantly locates in the nucleus in chemical fixed cells and live cells, however, the determining mechanisms for its nuclear translocation is not clear. In the...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2015-0299

    authors: Cai M,Si J,Li X,Zeng Z,Li M

    更新日期:2016-06-01 00:00:00

  • Small-angle X-ray and neutron scattering as a tool for structural systems biology.

    abstract::Small-angle scattering (SAS) of X-rays and neutrons reveals low-resolution structures of biological macromolecules in solution. With the recent experimental and methodological advances, SAS became a unique tool for characterising biological systems. The method covers an extremely broad range of molecule sizes (from a ...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2010.093

    authors: Svergun DI

    更新日期:2010-07-01 00:00:00

  • Activation of GPR119 by fatty acid agonists augments insulin release from clonal β-cells and isolated pancreatic islets and improves glucose tolerance in mice.

    abstract::G-protein coupled receptor 119 (GPR119) is emerging as a potential target for the treatment of type 2 diabetes with beneficial effects on glucose homeostasis. This study assessed the insulin-secreting properties of various GPR119 agonists and the distribution of GPR119 in pancreatic islets. Endogenous ligands [oleoyle...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2013-0255

    authors: Moran BM,Abdel-Wahab YH,Flatt PR,McKillop AM

    更新日期:2014-04-01 00:00:00

  • The DEAH helicase DHX36 and its role in G-quadruplex-dependent processes.

    abstract::DHX36 is a member of the DExD/H box helicase family, which comprises a large number of proteins involved in various cellular functions. Recently, the function of DHX36 in the regulation of G-quadruplexes (G4s) was demonstrated. G4s are alternative nucleic acid structures, which influence many cellular pathways on a tr...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2020-0292

    authors: Schult P,Paeschke K

    更新日期:2020-10-01 00:00:00

  • Characterization of a new toxin from the entomopathogenic fungus Metarhizium anisopliae: the ribotoxin anisoplin.

    abstract::Metarhizium anisopliae is an entomopathogenic fungus relevant in biotechnology with applications like malaria vector control. Studies of its virulence factors are therefore of great interest. Fungal ribotoxins are toxic ribonucleases with extraordinary efficiency against ribosomes and suggested as potential insecticid...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2016-0119

    authors: Olombrada M,Medina P,Budia F,Gavilanes JG,Martínez-Del-Pozo Á,García-Ortega L

    更新日期:2017-01-01 00:00:00

  • Molecular interactions within the plant TOC complex.

    abstract::Protein transport, especially into different cellular compartments, is a highly coordinated and regulated process. The molecular machineries which carry out these transport processes are highly complex in structure, function, and regulation. In the case of chloroplasts, thousands of protein molecules have been estimat...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2009.051

    authors: Sommer MS,Schleiff E

    更新日期:2009-08-01 00:00:00

  • Differences in the activation mechanism between the alpha and beta subunits of human meprin.

    abstract::Meprins are zinc-endopeptidases of the astacin family, which are expressed as membrane-bound or secreted forms in renal and intestinal brush-border membranes of mouse, rat and man. There are two types of meprin subunits, alpha and beta, which form disulfide-bonded homo- and heterodimers; further oligomerization is med...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2003.092

    authors: Becker C,Kruse MN,Slotty KA,Köhler D,Harris JR,Rösmann S,Sterchi EE,Stöcker W

    更新日期:2003-05-01 00:00:00

  • Characterization of the subcellular localization and nuclear import molecular mechanisms of herpes simplex virus 1 UL2.

    abstract::As a crucial protein, the herpes simplex virus 1 (HSV-1) UL2 protein has been shown to take part in various stages of viral infection, nonetheless, its exact subcellular localization and transport molecular determinants are not well known thus far. In the present study, by using live cells fluorescent microscopy assay...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2016-0268

    authors: Cai M,Huang Z,Liao Z,Chen T,Wang P,Jiang S,Chen D,Peng T,Bian Y,Hong G,Yang H,Zeng Z,Li X,Li M

    更新日期:2017-04-01 00:00:00

  • miR-221/222 suppression protects against endoplasmic reticulum stress-induced apoptosis via p27(Kip1)- and MEK/ERK-mediated cell cycle regulation.

    abstract::Cancer cells are relatively resistant to endoplasmic reticulum (ER) stress-induced apoptosis. However, the underlying mechanisms remain largely unclear. We observed that the microRNAs miR-221/222 are associated with apoptosis regulation under ER stress in human hepatocellular carcinoma (HCC) cells. Induction of ER str...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2010.072

    authors: Dai R,Li J,Liu Y,Yan D,Chen S,Duan C,Liu X,He T,Li H

    更新日期:2010-07-01 00:00:00

  • The YidC/Oxa1/Alb3 protein family: common principles and distinct features.

    abstract::The members of the YidC/Oxa1/Alb3 protein family are evolutionary conserved in all three domains of life. They facilitate the insertion of membrane proteins into bacterial, mitochondrial, and thylakoid membranes and have been implicated in membrane protein folding and complex formation. The major classes of substrates...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/hsz-2012-0199

    authors: Saller MJ,Wu ZC,de Keyzer J,Driessen AJ

    更新日期:2012-11-01 00:00:00

  • Homo- and heterodimerization is a common feature of the solute carrier family SLC10 members.

    abstract::The solute carrier family SLC10 consists of seven members, including the bile acid transporters Na+/taurocholate co-transporting polypeptide (NTCP) and apical sodium-dependent bile acid transporter (ASBT), the steroid sulfate transporter SOAT as well as four orphan carriers (SLC10A3, SLC10A4, SLC10A5 and SLC10A7). Pre...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/hsz-2019-0148

    authors: Noppes S,Müller SF,Bennien J,Holtemeyer M,Palatini M,Leidolf R,Alber J,Geyer J

    更新日期:2019-09-25 00:00:00

  • Oxygen(es) and the hypoxia-inducible factor-1.

    abstract::The hypoxia-inducible factor-1 (HIF-1) is a basic-helix-loop-helix (bHLH) heterodimeric transcription factor activated by reductions in oxygen concentration (hypoxia). Activated HIF-1 upregulates expression of genes involved in the adaptation of higher organisms to hypoxic conditions, caused by e.g. high altitude, ane...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:

    authors: Wenger RH,Gassmann M

    更新日期:1997-07-01 00:00:00

  • Developing an effective RNA interference strategy against a plus-strand RNA virus: silencing of coxsackievirus B3 and its cognate coxsackievirus-adenovirus receptor.

    abstract::Coxsackievirus B3 (CVB-3) is a plus-strand RNA virus that is believed to be the most common causal agent of viral myocarditis. Since no specific treatment for CVB-3 infections is available to date, we and others have recently started to develop RNA interference (RNAi) approaches to prevent virus propagation. Here we d...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2005.100

    authors: Werk D,Schubert S,Lindig V,Grunert HP,Zeichhardt H,Erdmann VA,Kurreck J

    更新日期:2005-09-01 00:00:00

  • Isoaspartate-containing amyloid precursor protein-derived peptides alter efficacy and specificity of potential beta-secretases.

    abstract::Neuritic plaques of Alzheimer patients are composed of multiple protein components. Among them, the amyloid beta-peptides (Abeta) 1-40/42 and further N- and C-terminally modified fragments of Abeta are highly abundant. Most prominent are the isoaspartate (isoAsp)-Abeta peptides and pyroglutamyl (pGlu)-Abeta. While pGl...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:10.1515/BC.2008.125

    authors: Böhme L,Hoffmann T,Manhart S,Wolf R,Demuth HU

    更新日期:2008-08-01 00:00:00

  • DNA-binding specificity of PAR and C/EBP leucine zipper proteins: a single amino acid substitution in the C/EBP DNA-binding domain confers PAR-like specificity to C/EBP.

    abstract::PAR and C/EBP family proteins are liver-enriched basic leucine zipper (bZip) transcription factors that bind similar sites on the promoters of albumin and cholesterol 7 alpha hydroxylase genes. However, C/EBP proteins have a more relaxed binding specificity than PAR proteins, in that they recognize many sites within p...

    journal_title:Biological chemistry

    pub_type: 杂志文章

    doi:

    authors: Falvey E,Marcacci L,Schibler U

    更新日期:1996-12-01 00:00:00

  • Assembly and function of small RNA - argonaute protein complexes.

    abstract::Small RNAs such as microRNAs (miRNAs), short interfering RNAs (siRNAs) or Piwi-interacting RNAs (piRNAs) are important regulators of gene expression in various organisms. Small RNAs bind to a member of the Argonaute protein family and are incorporated into larger structures that mediate diverse gene silencing events. ...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/hsz-2014-0116

    authors: Dueck A,Meister G

    更新日期:2014-06-01 00:00:00

  • Tapasin and other chaperones: models of the MHC class I loading complex.

    abstract::MHC (major histocompatibility complex) class I molecules bind intracellular virus-derived peptides in the endoplasmic reticulum (ER) and present them at the cell surface to cytotoxic T lymphocytes. Peptide-free class I molecules at the cell surface, however, could lead to aberrant T cell killing. Therefore, cells ensu...

    journal_title:Biological chemistry

    pub_type: 杂志文章,评审

    doi:10.1515/BC.2004.100

    authors: Wright CA,Kozik P,Zacharias M,Springer S

    更新日期:2004-09-01 00:00:00