Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry.

PubWeight™: 0.88‹?›

🔗 View Article (PMC 46392)

Published in Proc Natl Acad Sci U S A on May 01, 1993

Authors

A Ding1, J C Ojingwa, A F McDonagh, A L Burlingame, L Z Benet

Author Affiliations

1: Department of Pharmacy, University of California, San Francisco 94143-0446.

Articles cited by this

Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomed Mass Spectrom (1984) 7.52

Atomic structure and chemistry of human serum albumin. Nature (1992) 6.68

Contributions of mass spectrometry to peptide and protein structure. Biomed Environ Mass Spectrom (1988) 3.33

Nonenzymatic glycosylation of albumin in vivo. Identification of multiple glycosylated sites. J Biol Chem (1986) 1.90

The Amadori rearrangement. Adv Carbohydr Chem (1955) 1.60

Structure and ligand binding properties of human serum albumin. Dan Med Bull (1990) 1.60

The principal site of nonenzymatic glycosylation of human serum albumin in vivo. J Biol Chem (1983) 1.58

Properties of acyl glucuronides: implications for studies of the pharmacokinetics and metabolism of acidic drugs. Drug Metab Rev (1984) 1.57

Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab Rev (1992) 1.32

Glucuronic acid conjugates of bilirubin-IXalpha in normal bile compared with post-obstructive bile. Transformation of the 1-O-acylglucuronide into 2-, 3-, and 4-O-acylglucuronides. Biochem J (1978) 1.25

Ion source for liquid matrix secondary ionization mass spectrometry. Anal Chem (1986) 1.19

Lysine residue 199 of human serum albumin is modified by acetylsalicyclic acid. FEBS Lett (1976) 1.19

Origin of mammalian biliprotein and rearrangement of bilirubin glucuronides in vivo in the rat. J Clin Invest (1984) 0.93

The active site of creatine kinase. Affinity labeling of cysteine 282 with N-(2,3-epoxypropyl)-N-amidinoglycine. J Biol Chem (1992) 0.92

Disposition and irreversible plasma protein binding of tolmetin in humans. Clin Pharmacol Ther (1988) 0.91

Site-specific chemical modification of interleukin-1 beta by acrylodan at cysteine 8 and lysine 103. J Biol Chem (1992) 0.88

Identification of lysine residue 199 of human serum albumin as a binding site for benzylpenicilloyl groups. FEBS Lett (1988) 0.88

Covalent binding of zomepirac glucuronide to proteins: evidence for a Schiff base mechanism. Drug Metab Dispos (1991) 0.84

Acylation of albumin by 1-O-acyl glucuronides. Drug Metab Dispos (1985) 0.83

Anaphylactoid reactions to tolmetin after interrupted dosage. West J Med (1985) 0.82

Irreversible binding of zomepirac to plasma protein in vitro and in vivo. J Clin Invest (1986) 0.82

Characterization of structural xenobiotic modifications in proteins by high sensitivity tandem mass spectrometry. Human hemoglobin treated in vitro with styrene 7,8-oxide. J Biol Chem (1989) 0.81

Interactions between oxaprozin glucuronide and human serum albumin. Xenobiotica (1987) 0.79

Reactions of oxaprozin-1-O-acyl glucuronide in solutions of human plasma and albumin. Adv Exp Med Biol (1986) 0.79

Irreversible binding of tolmetin glucuronic acid esters to albumin in vitro. Pharm Res (1990) 0.78

Reaction of bilirubin glucuronides with serum albumin. J Chromatogr (1986) 0.78

Articles by these authors

Structural identification of autoinducer of Photobacterium fischeri luciferase. Biochemistry (1981) 11.48

Bilirubin is an antioxidant of possible physiological importance. Science (1987) 11.26

Role of accurate mass measurement (+/- 10 ppm) in protein identification strategies employing MS or MS/MS and database searching. Anal Chem (1999) 5.03

Noncompartmental determination of the steady-state volume of distribution. J Pharm Sci (1979) 4.96

Identification of the site of phosphorylation of the chemotaxis response regulator protein, CheY. J Biol Chem (1989) 3.72

Structural studies of the scrapie prion protein using mass spectrometry and amino acid sequencing. Biochemistry (1993) 3.54

Histone chaperone Asf1 is required for histone H3 lysine 56 acetylation, a modification associated with S phase in mitosis and meiosis. Proc Natl Acad Sci U S A (2006) 2.98

Identification of protein O-GlcNAcylation sites using electron transfer dissociation mass spectrometry on native peptides. Proc Natl Acad Sci U S A (2009) 2.54

The ready isomerization of bilirubin IX- in aqueous solution. Biochem J (1972) 2.50

HIV-infected liver and kidney transplant recipients: 1- and 3-year outcomes. Am J Transplant (2007) 2.50

Drug absorption interactions between oral targeted anticancer agents and PPIs: is pH-dependent solubility the Achilles heel of targeted therapy? Clin Pharmacol Ther (2012) 2.38

The enzymatic formation of bilirubin. Ann N Y Acad Sci (1975) 2.34

Overlapping substrate specificities and tissue distribution of cytochrome P450 3A and P-glycoprotein: implications for drug delivery and activity in cancer chemotherapy. Mol Carcinog (1995) 2.25

Role of intestinal P-glycoprotein (mdr1) in interpatient variation in the oral bioavailability of cyclosporine. Clin Pharmacol Ther (1997) 2.17

A new redox cofactor in eukaryotic enzymes: 6-hydroxydopa at the active site of bovine serum amine oxidase. Science (1990) 2.16

Clearance concepts in pharmacokinetics. J Pharmacokinet Biopharm (1973) 2.16

ERK phosphorylation drives cytoplasmic accumulation of hnRNP-K and inhibition of mRNA translation. Nat Cell Biol (2001) 2.14

Mammalian actin-related protein 2/3 complex localizes to regions of lamellipodial protrusion and is composed of evolutionarily conserved proteins. Biochem J (1997) 2.12

Relationship between the pharmacokinetics and pharmacodynamics of procainamide. Clin Pharmacol Ther (1976) 2.08

In-depth analysis of tandem mass spectrometry data from disparate instrument types. Mol Cell Proteomics (2008) 2.06

A crosslinked cofactor in lysyl oxidase: redox function for amino acid side chains. Science (1996) 2.06

Phytochrome chromophore biosynthesis. Treatment of tetrapyrrole-deficient Avena explants with natural and non-natural bilatrienes leads to formation of spectrally active holoproteins. J Biol Chem (1989) 2.01

Gender effects in pharmacokinetics and pharmacodynamics. Drugs (1995) 1.94

The meso-reactivity of porphyrins and related compounds. VI. Oxidative cleavage of the haem system. The four isomeric biliverdins of the IX series. J Chem Soc Perkin 1 (1973) 1.92

The characteristics of peptide collision-induced dissociation using a high-performance MALDI-TOF/TOF tandem mass spectrometer. Anal Chem (2000) 1.91

Patterns of protein synthesis and tolerance of anoxia in root tips of maize seedlings acclimated to a low-oxygen environment, and identification of proteins by mass spectrometry. Plant Physiol (2000) 1.82

Blue light and bilirubin excretion. Science (1980) 1.81

Subunits of the Saccharomyces cerevisiae signal recognition particle required for its functional expression. EMBO J (1994) 1.77

Configurational isomerization of bilirubin and the mechanism of jaundice phototherapy. Biochem Biophys Res Commun (1979) 1.76

Human stratum corneum lipids: characterization and regional variations. J Lipid Res (1983) 1.74

Determination of in vivo phosphorylation sites in protein kinase C. J Biol Chem (1995) 1.74

The gut as a barrier to drug absorption: combined role of cytochrome P450 3A and P-glycoprotein. Clin Pharmacokinet (2001) 1.72

Immunosuppressant pharmacokinetics and dosing modifications in HIV-1 infected liver and kidney transplant recipients. Am J Transplant (2007) 1.69

Glycosylinositol phospholipid anchors of the scrapie and cellular prion proteins contain sialic acid. Biochemistry (1992) 1.69

effect of OATP1B transporter inhibition on the pharmacokinetics of atorvastatin in healthy volunteers. Clin Pharmacol Ther (2006) 1.69

Phosphorylation site of NtrC, a protein phosphatase whose covalent intermediate activates transcription. J Bacteriol (1992) 1.60

Identification of the hepatic protein targets of reactive metabolites of acetaminophen in vivo in mice using two-dimensional gel electrophoresis and mass spectrometry. J Biol Chem (1998) 1.58

Copper binding to octarepeat peptides of the prion protein monitored by mass spectrometry. Protein Sci (2000) 1.57

The role of singlet oxygen in bilirubin photo-oxidation. Biochem Biophys Res Commun (1971) 1.55

Tacrolimus oral bioavailability doubles with coadministration of ketoconazole. Clin Pharmacol Ther (1997) 1.55

Mass spectrometric analysis of protein mixtures at low levels using cleavable 13C-isotope-coded affinity tag and multidimensional chromatography. Mol Cell Proteomics (2003) 1.53

Elderly, conscious patients have an accentuated hypotensive response to nitroglycerin. Anesthesiology (1992) 1.53

Photobilirubin: an early bilirubin photoproduct detected by absorbance difference spectroscopy. Proc Natl Acad Sci U S A (1979) 1.53

Kaposi's sarcoma-associated herpesvirus K-bZIP protein is phosphorylated by cyclin-dependent kinases. J Virol (2001) 1.51

Characterization of Tetrahymena histone H2B variants and posttranslational populations by electron capture dissociation (ECD) Fourier transform ion cyclotron mass spectrometry (FT-ICR MS). Mol Cell Proteomics (2004) 1.50

Disposition kinetics of ethambutol in man. J Pharmacokinet Biopharm (1980) 1.50

Photodynamic therapy of malignant tumours. Lancet (1972) 1.48

Pharmacokinetics/pharmacodynamics of furosemide in man: a review. J Pharmacokinet Biopharm (1979) 1.47

Identification of GlcNAcylation sites of peptides and alpha-crystallin using Q-TOF mass spectrometry. J Am Soc Mass Spectrom (2001) 1.45

Rapid mass spectrometric peptide sequencing and mass matching for characterization of human melanoma proteins isolated by two-dimensional PAGE. Proc Natl Acad Sci U S A (1995) 1.45

Effect of route of administration and distribution on drug action. J Pharmacokinet Biopharm (1978) 1.44

Identification of glycoinositol phospholipid linked and truncated forms of the scrapie prion protein. Biochemistry (1990) 1.44

Employing target modifications for the investigation of liquid infrared matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun Mass Spectrom (2000) 1.43

Application of clearance concepts to the assessment of exposure to lead in drinking water. Am J Public Health (1989) 1.43

Structure and heterogeneity of the oligosaccharides from the lipopolysaccharides of a pyocin-resistant Neisseria gonorrhoeae. Proc Natl Acad Sci U S A (1989) 1.41

Site-specific characterization of the N-linked glycans of murine prion protein by high-performance liquid chromatography/electrospray mass spectrometry and exoglycosidase digestions. Biochemistry (1999) 1.40

Lactonization is the critical first step in the disposition of the 3-hydroxy-3-methylglutaryl-CoA reductase inhibitor atorvastatin. Drug Metab Dispos (2000) 1.40

Identification of new JNK substrate using ATP pocket mutant JNK and a corresponding ATP analogue. J Biol Chem (2001) 1.39

Role of P-glycoprotein and cytochrome P450 3A in limiting oral absorption of peptides and peptidomimetics. J Pharm Sci (1998) 1.37

Soluble lactose-binding lectin from rat intestine with two different carbohydrate-binding domains in the same peptide chain. J Biol Chem (1993) 1.36

Acyl glucuronides revisited: is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab Rev (1992) 1.32

Preparation and properties of crystalline biliverdin IX alpha. Simple methods for preparing isomerically homogeneous biliverdin and [14C[biliverdin by using 2,3-dichloro-5,6-dicyanobenzoquinone. Biochem J (1980) 1.29

Role of hyperbilirubinemia in the impairment of osteoblast proliferation associated with cholestatic jaundice. J Clin Invest (1995) 1.29

Cytosolic phox proteins interact with and regulate the assembly of coronin in neutrophils. J Cell Sci (1997) 1.29

Differentiation of absorption and first-pass gut and hepatic metabolism in humans: studies with cyclosporine. Clin Pharmacol Ther (1995) 1.28

Turning green to gold. Nat Struct Biol (2001) 1.27

Identification of the major adducts formed by reaction of benzo(a)pyrene diol epoxide with DNA in vitro. Proc Natl Acad Sci U S A (1977) 1.25

The effects of ketoconazole on the intestinal metabolism and bioavailability of cyclosporine. Clin Pharmacol Ther (1995) 1.25

Identification of chlorinated dibenzofurans in American polychlorinated biphenyls. Nature (1975) 1.24

O-sulfonation of serine and threonine: mass spectrometric detection and characterization of a new posttranslational modification in diverse proteins throughout the eukaryotes. Mol Cell Proteomics (2004) 1.23

Matching cross-linked peptide spectra: only as good as the worse identification. Mol Cell Proteomics (2013) 1.23

Regulated expression of apolipoprotein E by human retinal pigment epithelial cells. J Lipid Res (2003) 1.23

Hydrocarbons of Biological Origin from a One-Billion-Year-Old Sediment. Science (1964) 1.22

Pharmacokinetics and pharmacodynamics of metformin in healthy subjects and patients with noninsulin-dependent diabetes mellitus. J Clin Pharmacol (1996) 1.20

Atmospheric pressure matrix-assisted laser desorption/ionization mass spectrometry. Anal Chem (2000) 1.20

Active secretion and enterocytic drug metabolism barriers to drug absorption. Adv Drug Deliv Rev (2001) 1.20

Bioavailability of cyclosporine with concomitant rifampin administration is markedly less than predicted by hepatic enzyme induction. Clin Pharmacol Ther (1992) 1.19

Automated, fast and sensitive quantification of drugs in blood by liquid chromatography-mass spectrometry with on-line extraction: immunosuppressants. J Chromatogr B Biomed Sci Appl (2000) 1.18

Attenuation of furosemide's diuretic effect by indomethacin: pharmacokinetic evaluation. J Pharmacokinet Biopharm (1979) 1.17

Evaluation of orally administered highly variable drugs and drug formulations. Pharm Res (1996) 1.17

Statistical analysis of Peptide electron transfer dissociation fragmentation mass spectrometry. Anal Chem (2010) 1.17

Phototherapy for neonatal hyperbilirubinemia: efficacy, mechanism and toxicity. Adv Pediatr (1980) 1.17

Search of sequence databases with uninterpreted high-energy collision-induced dissociation spectra of peptides. J Am Soc Mass Spectrom (1996) 1.16

Pharmacokinetics of cefamandole using a HPLC assay. J Pharmacokinet Biopharm (1978) 1.15

Structure and bacterial receptor activity of a human salivary proline-rich glycoprotein. J Biol Chem (1991) 1.15

Furosemide pharmacokinetics and pharmacodynamics in health and disease--an update. J Pharmacokinet Biopharm (1989) 1.15

Elucidating rifampin's inducing and inhibiting effects on glyburide pharmacokinetics and blood glucose in healthy volunteers: unmasking the differential effects of enzyme induction and transporter inhibition for a drug and its primary metabolite. Clin Pharmacol Ther (2008) 1.14

Hyperbilirubinemia results in reduced oxidative injury in neonatal Gunn rats exposed to hyperoxia. Free Radic Biol Med (1995) 1.14

Degradation of hepatic haem to porphyrins and oxophlorins in rats treated with 2-allyl-2-isopropylacetamide. Biochem Soc Trans (1976) 1.14

Liquid-chromatographic measurement of endogenous and exogenous glucocorticoids in plasma. Clin Chem (1979) 1.13

Identification of hepatic protein targets of the reactive metabolites of the non-hepatotoxic regioisomer of acetaminophen, 3'-hydroxyacetanilide, in the mouse in vivo using two-dimensional gel electrophoresis and mass spectrometry. Adv Exp Med Biol (2001) 1.12

Functional assignment of the 20 S proteasome from Trypanosoma brucei using mass spectrometry and new bioinformatics approaches. J Biol Chem (2001) 1.11

Antioxidant activities of bile pigments: biliverdin and bilirubin. Methods Enzymol (1990) 1.11

Critical compilation of terminal half-lives, percent excreted unchanged, and changes of half-life in renal and hepatic dysfunction for studies in humans with references. J Pharmacokinet Biopharm (1975) 1.10

Kidney function and age are both predictors of pharmacokinetics of metformin. J Clin Pharmacol (1995) 1.10

'Like a shrivelled blood orange'--bilirubin, jaundice, and phototherapy. Pediatrics (1985) 1.10

Molecular and physical mechanisms of first-pass extraction. Drug Metab Dispos (1999) 1.09

The pharmacokinetics and metabolic disposition of tacrolimus: a comparison across ethnic groups. Clin Pharmacol Ther (2001) 1.09