Effects of certain 5'-substituted adenosines on polyamine synthesis: selective inhibitors of spermine synthase.

Abstract:

:A number of nucleosides related to S-adenosylmethionine were tested for their inhibitory action on three enzymes involved in the biosynthesis of polyamines. The particular objective of the experiments was to determine whether any of the compounds could be used as selective inhibitors of the synthesis of spermine by spermine synthase. None of the nucleosides examined were potent inhibitors of S-adenosylmethionine decarboxylase. 5'-[(3-Aminopropyl)amino]-5'-deoxyadenosine dihydrochloride was quite a strong inhibitor of spermidine synthase (I50 of 7 microM) but was more than an order of magnitude less active than S-adenosyl-1,8-diamino-3-thiooctane, which is a mechanism-based inhibitor of this enzyme. 5'-[(3-Aminopropyl)amino]-5'-deoxyadenosine also inhibited spermine synthase with an I50 of 17 microM, but more selective inhibition of spermine synthase was produced by 9-[6(RS),8-diamino-5,6,7,8-tetradeoxy-beta-D-ribo-octofuranosyl]-9 H-purin-6- amine (I50 of 12 microM) and by dimethyl(5'-adenosyl)sulfonium perchlorate (I50 of 8 microM) since these compounds were much less active against spermidine synthase. Both 9-[6(RS),8-diamino-5,6,7,8-tetradeoxy-beta-D-ribo-octofuranosyl]-9 H-purin-6- amine and dimethyl(5'-adenosyl)sulfonium perchlorate were able to reduce the synthesis of spermine in SV-3T3 cells, but there was a compensatory increase in the concentration of spermidine, and there was no effect on cell growth. These results and those from experiments in which these spermine synthesis inhibitors were combined with inhibitors of spermidine synthase and ornithine decarboxylase indicated that the cells compensated for the inhibition of the aminopropyltransferases by increasing the production of decarboxylated S-adenosylmethionine and putrescine.(ABSTRACT TRUNCATED AT 250 WORDS)

journal_name

Biochemistry

journal_title

Biochemistry

authors

Pegg AE,Coward JK,Talekar RR,Secrist JA 3rd

doi

10.1021/bi00362a016

subject

Has Abstract

pub_date

1986-07-15 00:00:00

pages

4091-7

issue

14

eissn

0006-2960

issn

1520-4995

journal_volume

25

pub_type

杂志文章
  • Structure, topology, and tilt of cell-signaling peptides containing nuclear localization sequences in membrane bilayers determined by solid-state NMR and molecular dynamics simulation studies.

    abstract::Cell-signaling peptides have been extensively used to transport functional molecules across the plasma membrane into living cells. These peptides consist of a hydrophobic sequence and a cationic nuclear localization sequence (NLS). It has been assumed that the hydrophobic region penetrates the hydrophobic lipid bilaye...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi061895g

    authors: Ramamoorthy A,Kandasamy SK,Lee DK,Kidambi S,Larson RG

    更新日期:2007-01-30 00:00:00

  • Substrate binding to the peripheral site of acetylcholinesterase initiates enzymatic catalysis. Substrate inhibition arises as a secondary effect.

    abstract::Two sites of ligand interaction in acetylcholinesterase (AChE) were first demonstrated in ligand binding studies and later confirmed by crystallography, site-specific mutagenesis, and molecular modeling: an acylation site at the base of the active site gorge and a peripheral site at its mouth. We recently introduced a...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9813577

    authors: Szegletes T,Mallender WD,Thomas PJ,Rosenberry TL

    更新日期:1999-01-05 00:00:00

  • Post-translational modifications of aquaporin 0 (AQP0) in the normal human lens: spatial and temporal occurrence.

    abstract::Because of the lack of protein turnover in fiber cells of the ocular lens, Aquaporin 0 (AQP0), the most abundant membrane protein in the lens, undergoes extensive post-translational modification with fiber cell age. To map the distribution of modified forms of AQP0 within the lens, normal human lenses ranging in age f...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi0496034

    authors: Ball LE,Garland DL,Crouch RK,Schey KL

    更新日期:2004-08-03 00:00:00

  • Post-translational modification of Cu/Zn superoxide dismutase under anaerobic conditions.

    abstract::In eukaryotic organisms, the largely cytosolic copper- and zinc-containing superoxide dismutase (Cu/Zn SOD) enzyme represents a key defense against reactive oxygen toxicity. Although much is known about the biology of this enzyme under aerobic conditions, less is understood regarding the effects of low oxygen levels o...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi201353y

    authors: Leitch JM,Li CX,Baron JA,Matthews LM,Cao X,Hart PJ,Culotta VC

    更新日期:2012-01-17 00:00:00

  • Consequences of cAMP-binding site mutations on the structural stability of the type I regulatory subunit of cAMP-dependent protein kinase.

    abstract::The regulatory (R) subunit of cAMP-dependent protein kinase (cAPK) is a multidomain protein with two tandem cAMP-binding domains, A and B. The importance of cAMP binding on the stability of the R subunit was probed by intrinsic fluorescence and circular dichroism (CD) in the presence and absence of urea. Several mutan...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi001563q

    authors: Cànaves JM,Leon DA,Taylor SS

    更新日期:2000-12-12 00:00:00

  • Solution structure of prokaryotic ribosomal protein S17 by high-resolution NMR spectroscopy.

    abstract::The solution of a primary 16S rRNA-binding ribosomal protein, S17, was investigated by two- and three-dimensional homonuclear and heteronuclear magnetic resonance spectroscopy. Almost complete chemical shift assignments for the 1H, 15N, and 13C resonances have been obtained. The NMR data have been rigorously analyzed ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi951062i

    authors: Jaishree TN,Ramakrishnan V,White SW

    更新日期:1996-03-05 00:00:00

  • Synthesis and biological activity of a lambda pseudo operator.

    abstract::The chemical and enzymatic syntheses of bacteriophage lambda pseudo operator DNA are described. The 17 base-paired duplex contains the DNA which has been proposed as the binding site for cI repressor protein. The synthetic duplex is twofold symmetric and represents the best possible nucleotide summation of the six pro...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00638a013

    authors: Kawashima E,Gadek T,Caruthers MH

    更新日期:1977-09-20 00:00:00

  • Photochemical cleavage of DNA by nitrobenzamides linked to 9-aminoacridine.

    abstract::Nitrobenzamido ligands linked to the DNA intercalator 9-aminoacridine via poly(methylene) chains induce single-strand nicks in DNA upon irradiation with long-wavelength ultraviolet light (lambda greater than or equal to 300 nm). Optimal photocleavage activity was found for the reagent 9-[[6-(4-nitrobenzamido)hexyl]ami...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00417a021

    authors: Nielsen PE,Jeppesen C,Egholm M,Buchardt O

    更新日期:1988-08-23 00:00:00

  • Energetics of coiled coil folding: the nature of the transition states.

    abstract::Coiled coils are simple models for studying the association of two polypeptide chains to form a folded protein. Previous work has shown that the folding of a coiled coil can be described by a two-state transition between two unfolded monomeric peptide chains and a folded coiled coil dimer. Here we report the thermodyn...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi002161l

    authors: Bosshard HR,Dürr E,Hitz T,Jelesarov I

    更新日期:2001-03-27 00:00:00

  • Three-dimensional structure of acyl carrier protein determined by NMR pseudoenergy and distance geometry calculations.

    abstract::Distance constraints from two-dimensional NMR cross-relaxation data are used to derive a three-dimensional structure for acyl carrier protein from Escherichia coli. Several approaches to structure determination are explored. The most successful proves to be an approach that combines the early stages of a distance geom...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00416a046

    authors: Holak TA,Kearsley SK,Kim Y,Prestegard JH

    更新日期:1988-08-09 00:00:00

  • Sequence-selective targeting of long stretches of the DNA minor groove by a novel dimeric bis-benzimidazole.

    abstract::A dimeric bis-benzimidazole molecule has been designed by computer modeling to bind to a DNA sequence via the DNA minor groove that covers a complete turn of B-DNA. A series of bis-benzimidazole dimers incorporating a -O-(CH(2))(n)()-X-CH(2))(n)()-O- linker, with n = 2 or 3 and X = O or N(+)H(Me), were screened for th...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi026926w

    authors: Joubert A,Sun XW,Johansson E,Bailly C,Mann J,Neidle S

    更新日期:2003-05-27 00:00:00

  • Reduction of cytochrome b in mitochondria from yeast lacking coenzyme Q.

    abstract::Mitochondria isolated from coenzyme Q deficient yeast cells had no detectable NADH:cytochrome c reductase or succinate:cytochrome c reductase but had comparable amounts of cytochromes b and c1 as wild-type mitochondria. Addition of succinate to the mutant mitochondria resulted in a slight reduction of cytochrome b; ho...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00372a029

    authors: Clejan L,Beattie DS

    更新日期:1986-12-02 00:00:00

  • Substrate specificity of the heparan sulfate hexuronic acid 2-O-sulfotransferase.

    abstract::The interaction of heparan sulfate with different ligand proteins depends on the precise location of O-sulfate groups in the polysaccharide chain. We have previously shown that overexpression in human kidney 293 cells of a mouse mastocytoma 2-O-sulfotransferase (2-OST), previously thought to catalyze the transfer of s...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi002926p

    authors: Rong J,Habuchi H,Kimata K,Lindahl U,Kusche-Gullberg M

    更新日期:2001-05-08 00:00:00

  • The complete amino acid sequence of the major component myoglobin of dwarf sperm whale (Kogia simus).

    abstract::The complete amino acid sequence of the major component myoglobin from the dwarf sperm whale, Kogia simus, was determined by specific cleavage of the protein to obtain large peptides which are readily degraded by the automatic sequenator. Three easily separable peptides were obtained by cleaving the protein at its two...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00624a010

    authors: Dwulet FE,Jones BN,Lehman LD,Gurd FR

    更新日期:1977-03-08 00:00:00

  • Analysis of the kinetics of ovine follitropin agonist-antagonist interactions with pig ovarian membranes.

    abstract::The binding of 125I-labeled ovine follitropin (oFSH) and 125I-labeled deglycosylated ovine follitropin (DG-oFSH) to porcine granulosa cell membranes was studied at equilibrium and nonequilibrium binding conditions and statistically analyzed. Saturation and competition binding experiments revealed homogeneity in the po...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00386a059

    authors: Sebok K,De Lean A,Sairam MR

    更新日期:1987-06-16 00:00:00

  • Excitation energy transfer studies on the proximity between SH1 and the adenosinetriphosphatase site in myosin subfragment 1.

    abstract::Excitation energy transfer studies were carried out to determine the distance between the adenosinetriphosphatase (ATPase) site and a unique "fast-reacting" sulfhydryl (referred to as SH1) in myosin subfragment 1. The fluorescent moiety of the probe N-(iodoacetyl)-N'-(5-sulfo-1-naphthyl)ethylene-diamine was used as th...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00520a035

    authors: Tao T,Lamkin M

    更新日期:1981-08-18 00:00:00

  • Steady-state FTIR spectra of the photoreduction of QA and QB in Rhodobacter sphaeroides reaction centers provide evidence against the presence of a proposed transient electron acceptor X between the two quinones.

    abstract::In the reaction center (RC) of the photosynthetic bacterium Rhodobacter sphaeroides, two ubiquinone molecules, QA and QB, play a pivotal role in the conversion of light energy into chemical free energy by coupling electron transfer to proton uptake. In native RCs, the transfer of an electron from QA to QB takes place ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi700297b

    authors: Breton J

    更新日期:2007-04-17 00:00:00

  • Recognition of heteropolysaccharide alginate by periplasmic solute-binding proteins of a bacterial ABC transporter.

    abstract::Alginate is a heteropolysaccharide that consists of β-D-mannuronate (M) and α-L-guluronate (G). The Gram-negative bacterium Sphingomonas sp. A1 directly incorporates alginate into the cytoplasm through the periplasmic solute-binding protein (AlgQ1 and AlgQ2)-dependent ABC transporter (AlgM1-AlgM2/AlgS-AlgS). Two bindi...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi300194f

    authors: Nishitani Y,Maruyama Y,Itoh T,Mikami B,Hashimoto W,Murata K

    更新日期:2012-05-01 00:00:00

  • Binding analysis of 1alpha- and 17alpha-dihydrotestosterone derivatives to homodimeric sex hormone-binding globulin.

    abstract::Binding studies of the interaction of immobilized 1alpha- and 17alpha-aminoalkyl derivatives of 5alpha-dihydrotestosterone (DHT) with purified N-deglycosylated homodimeric human sex hormone-binding globulin (SHBG) were performed using a surface plasmon resonance biosensor. These 1alpha- and 17alpha-derivatives with sp...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi035269k

    authors: Metzger J,Schnitzbauer A,Meyer M,Söder M,Cuilleron CY,Hauptmann H,Huber E,Luppa PB

    更新日期:2003-11-25 00:00:00

  • Importance of the β5-β6 Loop for the Structure, Catalytic Efficiency, and Stability of Carbapenem-Hydrolyzing Class D β-Lactamase Subfamily OXA-143.

    abstract::The class D β-lactamase OXA-143 has been described as an efficient penicillinase, oxacillinase, and carbapenemase. The D224A variant, known as OXA-231, was described in 2012 as exhibiting less activity toward imipenem and increased oxacillinase activity. Additionally, the P227S mutation was reported as a case of conve...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.9b00365

    authors: Antunes VU,Llontop EE,Vasconcelos FNDC,López de Los Santos Y,Oliveira RJ,Lincopan N,Farah CS,Doucet N,Mittermaier A,Favaro DC

    更新日期:2019-08-27 00:00:00

  • Comparison of Alicyclobacillus acidocaldarius o-Succinylbenzoate Synthase to Its Promiscuous N-Succinylamino Acid Racemase/ o-Succinylbenzoate Synthase Relatives.

    abstract::Studying the evolution of catalytically promiscuous enzymes like those from the N-succinylamino acid racemase/ o-succinylbenzoate synthase (NSAR/OSBS) subfamily can reveal mechanisms by which new functions evolve. Some enzymes in this subfamily have only OSBS activity, while others catalyze OSBS and NSAR reactions. We...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.8b00088

    authors: Odokonyero D,McMillan AW,Ramagopal UA,Toro R,Truong DP,Zhu M,Lopez MS,Somiari B,Herman M,Aziz A,Bonanno JB,Hull KG,Burley SK,Romo D,Almo SC,Glasner ME

    更新日期:2018-07-03 00:00:00

  • Kinetic mechanism of DNA polymerase I (Klenow fragment): identification of a second conformational change and evaluation of the internal equilibrium constant.

    abstract::In a previously determined minimal kinetic scheme for DNA polymerization catalyzed by the Klenow fragment (KF) of Escherichia coli DNA polymerase I, a nonchemical step that interconverted the KF'.DNAn+1.PPi and KF.DNAn+1PPi complexes was not observed in correct incorporation [Kuchta, R. D., Mizrahi, V., Benkovic, P.A....

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00234a002

    authors: Dahlberg ME,Benkovic SJ

    更新日期:1991-05-21 00:00:00

  • Active site of bee venom phospholipase A2: the role of histidine-34, aspartate-64 and tyrosine-87.

    abstract::In bee venom phospholipase A2, histidine-34 probably functions as a Brønsted base to deprotonate the attacking water. Aspartate-64 and tyrosine-87 form a hydrogen bonding network with histidine-34. We have prepared mutants at these positions and studied their kinetic properties. The mutant in which histidine-34 is cha...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi9528412

    authors: Annand RR,Kontoyianni M,Penzotti JE,Dudler T,Lybrand TP,Gelb MH

    更新日期:1996-04-09 00:00:00

  • Expression and structural and functional properties of human ferritin L-chain from Escherichia coli.

    abstract::The human ferritin L-chain cDNA was cloned into a vector for overproduction in Escherichia coli, under the regulation of a lambda promoter. The plasmid obtained contains the full L-chain coding region modified at the first two codons. It is able to direct the synthesis of the L-chain which can constitute up to 15% of ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00438a040

    authors: Levi S,Salfeld J,Franceschinelli F,Cozzi A,Dorner MH,Arosio P

    更新日期:1989-06-13 00:00:00

  • Rate and extent of poly(ethylene glycol)-induced large vesicle fusion monitored by bilayer and internal contents mixing.

    abstract::Poly(ethylene glycol) (PEG) of average molecular weight 8000 was used to mediate the fusion of large unilamellar vesicles composed of dipalmitoylphosphatidylcholine. Fusion was monitored by fluorescence assays of lipid mixing and aqueous contents mixing. The extent of lipid mixing, as monitored by DPHpPC fluorescence ...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00369a053

    authors: Parente RA,Lentz BR

    更新日期:1986-10-21 00:00:00

  • A kissing complex together with a stable dimer is involved in the HIV-1Lai RNA dimerization process in vitro.

    abstract::Retroviruses contain a dimeric RNA consisting of two identical molecules of genomic RNA. The interaction between the two monomers is thought to occur near their 5'ends. We previously identified a region upstream from the splice donor site, comprising an autocomplementary sequence, responsible for the formation of dime...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi952822s

    authors: Muriaux D,Fossé P,Paoletti J

    更新日期:1996-04-16 00:00:00

  • Arginine vasopressin inhibition of cyclin D1 gene expression blocks the cell cycle and cell proliferation in the mouse Y1 adrenocortical tumor cell line.

    abstract::Arginine vasopressin (AVP) is a nonapeptide long known as an endocrine and paracrine regulator of important systemic functions, namely, vasoconstriction, gluconeogenesis, corticosteroidogenesis, and excretion of water and urea. Here we report, for the first time, that AVP specifically inhibits expression of the cyclin...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi026807g

    authors: Schwindt TT,Forti FL,Juliano MA,Juliano L,Armelin HA

    更新日期:2003-02-25 00:00:00

  • Rapid laser flash photoaffinity labeling of binding sites for a noncompetitive inhibitor of the acetylcholine receptor.

    abstract::Photoaffinity labeling of the nicotinic acetylcholine receptor from Torpedo marmorata electric tissue was performed in the presence of cholinergic effectors in the millisecond to second time range by a combination of a stopped-flow apparatus and a high-energy pulse laser. The label applied was [3H]triphenylmethylphosp...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi00307a029

    authors: Muhn P,Fahr A,Hucho F

    更新日期:1984-06-05 00:00:00

  • Conformational Dynamics of Asparagine at Coiled-Coil Interfaces.

    abstract::Coiled coils (CCs) are among the best-understood protein folds. Nonetheless, there are gaps in our knowledge of CCs. Notably, CCs are likely to be structurally more dynamic than often considered. Here, we explore this in an abundant class of CCs, parallel dimers, focusing on polar asparagine (Asn) residues in the hydr...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/acs.biochem.7b00848

    authors: Thomas F,Niitsu A,Oregioni A,Bartlett GJ,Woolfson DN

    更新日期:2017-12-19 00:00:00

  • Packing is a key selection factor in the evolution of protein hydrophobic cores.

    abstract::The energy derived from optimized van der Waals interactions in closely packed, folded proteins has been proposed to be of similar energetic magnitude to hydrophobicity in stabilizing the native state. If packing is this energetically important, it should influence the evolution of protein core sequences. To test this...

    journal_title:Biochemistry

    pub_type: 杂志文章

    doi:10.1021/bi011776v

    authors: Chen J,Stites WE

    更新日期:2001-12-18 00:00:00