Halogenated pyrrolopyrimidine analogues of adenosine from marine organisms: pharmacological activities and potent inhibition of adenosine kinase.

Abstract:

:Two novel halogenated pyrrolopyrimidine analogues of adenosine, isolated from marine sources, have been examined for pharmacological and biochemical activities. 4-Amino-5-bromo-pyrrolo[2,3-d]pyrimidine, from a sponge of the genus Echinodictyum, had bronchodilator activity at least as potent as theophylline but with a different biochemical profile; unlike theophylline it had no antagonist activity at CNS adenosine receptors and it was quite a potent inhibitor of adenosine uptake and adenosine kinase in brain tissue. 5'-Deoxy-5-iodotubercidin, isolated from the red alga Hypnea valentiae, caused potent muscle relaxation and hypothermia when injected into mice. This compound was a very potent inhibitor of adenosine uptake into rat and guinea-pig brain slices and an extremely potent inhibitor of adenosine kinase from guinea-pig brain and rat brain and liver. Neither of these two pyrrolopyrimidine analogues was a substrate for, or an inhibitor of, adenosine deaminase. Neither compound appeared to have any direct agonist activity on guinea-pig brain adenosine-stimulated adenylate cyclase (A2 adenosine receptors). 5'-Deoxy-5-iodotubercidin is unique in two respects: it appears to be the first naturally-occurring example of a 5'-deoxyribosyl nucleoside and is the first example of a specifically iodinated nucleoside from natural sources. It may be the most potent adenosine kinase inhibitor yet described and, by virtue of its structure, may prove to be the most specific.

journal_name

Biochem Pharmacol

journal_title

Biochemical pharmacology

authors

Davies LP,Jamieson DD,Baird-Lambert JA,Kazlauskas R

doi

10.1016/0006-2952(84)90225-9

subject

Has Abstract

pub_date

1984-02-01 00:00:00

pages

347-55

issue

3

eissn

0006-2952

issn

1873-2968

pii

0006-2952(84)90225-9

journal_volume

33

pub_type

杂志文章
  • Differential effects of sedative and anticonvulsant barbiturates on specific [3H]GABA binding to membrane preparations from rat brain cortex.

    abstract::The sensitivity to barbiturates of [3H]GABA binding to synaptosomal membrane fractions from rat cortex has been examined. We show that a range of anaesthetic/sedative barbiturates enhance GABA binding in the presence of chloride or other ions that interact with the associated ionophore. Furthermore, picrotoxinin and t...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(82)90260-x

    authors: Whittle SR,Turner AJ

    更新日期:1982-09-15 00:00:00

  • Antiviral activity of 2',3'-dideoxy-beta-L-5-fluorocytidine (beta-L-FddC) and 2',3'-dideoxy-beta-L-cytidine (beta-L-ddC) against hepatitis B virus and human immunodeficiency virus type 1 in vitro.

    abstract::2',3'-Dideoxy-beta-L-5-fluorocytidine (beta-L-FddC) and 2',3'-dideoxy-beta-L-cytidine (beta-L-ddC), two nucleosides with "unnatural L-configuration," have been synthesized and found to have potent antiviral activity against hepatitis B virus (HBV) and human immunodeficiency virus type 1 (HIV-1) in vitro with very litt...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(94)90002-7

    authors: Lin TS,Luo MZ,Liu MC,Pai SB,Dutschman GE,Cheng YC

    更新日期:1994-01-20 00:00:00

  • Distamycin inhibits the binding of a nuclear factor to the -278/-256 upstream sequence of the human HLA-DR alpha gene.

    abstract::In this study we analyse the effects of the anti-tumor compound distamycin on the binding of nuclear factor(s) to a synthetic oligonucleotide (GTATA/IFN-gamma) mimicking a putative regulatory region of the human HLA-DR alpha gene. This region contains the sequence (GTATA), that is required for nuclear protein binding ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(91)90620-k

    authors: Gambari R,Barbieri R,Nastruzzi C,Chiorboli V,Feriotto G,Natali PG,Giacomini P,Arcamone F

    更新日期:1991-02-15 00:00:00

  • Interaction of the DNA topoisomerase II catalytic inhibitor meso-2,3-bis(3,5-dioxopiperazine-1-yl)butane (ICRF-193), a bisdioxopiperazine derivative, with the conserved region(s) of eukaryotic but not prokaryotic enzyme.

    abstract::ICRF-193 [meso-2,3-bis(3,5-dioxopiperazine-1-yl)butane], a bisdioxopiperazine compound, has been shown to be a catalytic inhibitor of DNA topoisomerase II by stabilizing the enzyme in the form of a closed "protein clamp," an intermediate form in the catalytic cycle (Roca et al., Proc Natl Acad Sci USA 91: 1781-1785, 1...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(97)00201-3

    authors: Sato M,Ishida R,Narita T,Kato J,Ikeda H,Fukazawa H,Andoh T

    更新日期:1997-09-01 00:00:00

  • Potentiated hepatotoxicity from concurrent administration of acetaminophen and allyl alcohol to rats.

    abstract::Female Wistar rats were treated with acetaminophen 3.0 g/kg BW and allyl alcohol 75 microliter/kg BW by gastric tube. Hepatic function, measured as galactose elimination capacity and prothrombin index, was reduced to about 0.40 times control value. Plasma alanine transferase activity was elevated more and earlier afte...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(85)90750-6

    authors: Poulsen HE,Lerche A,Pedersen NT

    更新日期:1985-03-15 00:00:00

  • Iron complexes of deferiprone and dietary plant catechols as cytoprotective superoxide radical scavengers(1).

    abstract::Superoxide radicals have been implicated in the pathogenesis of aging, cataract, ischemia-reperfusion, cancer and inflammatory diseases. In the present work, we found that deferiprone (L1), an iron-chelating drug, and dietary dihydroxycinnamic acids (catechols) were much more effective at protecting isolated rat hepat...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(01)00821-8

    authors: Moridani MY,O'Brien PJ

    更新日期:2001-12-15 00:00:00

  • Inhibition of ATP-induced surfactant exocytosis by dihydropyridine (DHP) derivatives: a non-stereospecific, photoactivated effect and independent of L-type Ca2+ channels.

    abstract::Purinergic stimulation of surfactant secretion via exocytosis of lamellar bodies is mediated by an elevation of the intracellular Ca2+ concentration ([Ca2+](i)). We tested the dihydropyridine (DHP) analogues isradipine (+/-enantiomers), nifedipine and Bay K 8644 (racemic forms) on ATP-induced surfactant secretion and ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(01)00582-2

    authors: Frick M,Siber G,Haller T,Mair N,Dietl P

    更新日期:2001-05-01 00:00:00

  • Peripheral nitric oxide signaling directly blocks inflammatory pain.

    abstract::Pain is a classical sign of inflammation, and sensitization of primary sensory neurons (PSN) is the most important mediating mechanism. This mechanism involves direct action of inflammatory mediators such as prostaglandins and sympathetic amines. Pharmacologic control of inflammatory pain is based on two principal str...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/j.bcp.2020.113862

    authors: Gomes FIF,Cunha FQ,Cunha TM

    更新日期:2020-06-01 00:00:00

  • Alteration of spinal protein kinase C expression and kinetics in morphine, but not clonidine, tolerance.

    abstract::Antinociceptive synergism between spinally administered morphine and clonidine decreases to an additive interaction in morphine- and clonidine-tolerant mice. Spinally administered protein kinase C (PKC) inhibitors also decrease the synergism to addition. To determine whether chronic morphine or clonidine treatment alt...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(99)00107-0

    authors: Li Y,Roerig SC

    更新日期:1999-08-01 00:00:00

  • Flavonoid dimers are highly potent killers of multidrug resistant cancer cells overexpressing MRP1.

    abstract::MRP1 overexpression in multidrug-resistant cancer cells has been shown to be responsible for collateral sensitivity to some flavonoids that stimulate a huge MRP1-mediated GSH efflux. This massive GSH depletion triggers the death of these cancer cells. We describe here that bivalent flavonoid dimers strikingly stimulat...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2016.10.013

    authors: Dury L,Nasr R,Lorendeau D,Comsa E,Wong I,Zhu X,Chan KF,Chan TH,Chow L,Falson P,Di Pietro A,Baubichon-Cortay H

    更新日期:2017-01-15 00:00:00

  • Subcellular localization of the camptothecin analogues, topotecan and gimatecan.

    abstract::Lipophilicity of camptothecins derivatives has been reported to improve the stability of the lactone ring and to favor rapid uptake and intracellular accumulation. Recently, a novel series of lipophilic camptothecins substituted at position 7 was developed, and gimatecan (ST1481) was selected for clinical development ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2003.10.034

    authors: Croce AC,Bottiroli G,Supino R,Favini E,Zuco V,Zunino F

    更新日期:2004-03-15 00:00:00

  • Inhibition of glutathione reductase by flavonoids. A structure-activity study.

    abstract::A structure-activity study of fourteen chemically related flavonoids was conducted to evaluate their abilities to inhibit glutathione reductase (GR). By comparing the I50 values of flavonoids from different classes possessing an identical hydroxyl configuration, we determined the following order of potency for inhibit...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(92)90478-2

    authors: Elliott AJ,Scheiber SA,Thomas C,Pardini RS

    更新日期:1992-10-20 00:00:00

  • Structure-guided creation of AcAP5-derived and platelet targeted factor Xa inhibitors.

    abstract::Anticoagulants and anti-platelet agents are simultaneously administrated in clinical practice (i.e. percutaneous coronary intervention), which cause significant risk of systemic bleeding. Targeted delivery of anticoagulants to the activated platelets at sites of vascular injuries may condense the site-specific anticoa...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2015.04.004

    authors: Zhu Y,Lin Y,Liu A,Shui M,Li R,Liu X,Hu W,Wang Y

    更新日期:2015-06-15 00:00:00

  • Evidence for the involvement of Ca2+-calmodulin and cyclic AMP in the regulation of the tyrosine hydroxylase system in rat striatal tissue slices.

    abstract::To determine if both the Ca2+-calmodulin system and the cyclic AMP system may regulate tyrosine hydroxylase (TH) activity in situ, rat striatal tissue slices that contain all of the components of the TH, cyclic AMP and Ca2+-calmodulin systems were subjected to experimental manipulations. Incubation of striatal tissue ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(85)90560-x

    authors: Hirata Y,Nagatsu T

    更新日期:1985-08-01 00:00:00

  • Aspirin attenuates vinorelbine-induced endothelial inflammation via modulating SIRT1/AMPK axis.

    abstract::Vinorelbine (VNR), a semisynthetic vinca alkaloid acquired from vinblastine, is frequently used as the candidate for intervention of solid tumors. Nevertheless, VNR-caused endothelial injuries may lead a mitigative effect of clinical treatment efficiency. A growing body of evidence reveals that aspirin is a potent ant...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2013.12.005

    authors: Tsai KL,Huang PH,Kao CL,Leu HB,Cheng YH,Liao YW,Yang YP,Chien Y,Wang CY,Hsiao CY,Chiou SH,Chen JW,Lin SJ

    更新日期:2014-03-15 00:00:00

  • Lipocortin 1 and the control of cPLA2 activity in A549 cells. Glucocorticoids block EGF stimulation of cPLA2 phosphorylation.

    abstract::Epidermal growth factor (EGF) rapidly stimulates the release of arachidonic acid in A549 cells by a mechanism that is sensitive to pertussis toxin [1]. We show that EGF treatment of A549 cells stimulates phosphorylation of cytosolic phospholipase A2 (cPLA2) through a mechanism that is similarly inhibited by pertussis ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(95)02442-5

    authors: Croxtall JD,Choudhury Q,Newman S,Flower RJ

    更新日期:1996-07-26 00:00:00

  • Involvement of all-trans-retinoic acid in the breakdown of retinoic acid receptors alpha and gamma through proteasomes in MCF-7 human breast cancer cells.

    abstract::Most studies have reported an up-regulation of retinoic acid receptor (RAR) mRNA expression by all-trans retinoic acid (RA). We aimed to study the effect of RA on RAR protein levels in MCF-7 human breast cancer cells. Incubation of these cells with 10(-6) M RA induced a rapid breakdown of both RARalpha and RARgamma in...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(01)00600-1

    authors: Tanaka T,Rodríguez de la Concepción ML,De Luca LM

    更新日期:2001-06-01 00:00:00

  • Implications of selective type II IMP dehydrogenase (IMPDH) inhibition by the 6-ethoxycarbonyl-3,3-disubstituted-1,5-diazabicyclo[3.1.0]hexane-2,4-diones on tumor cell death.

    abstract::It was shown previously that three 1,5-diazabicyclo[3.1.0]hexane-2,4-diones selectively inhibited human Type II IMP dehydrogenase (IMPDH) from Tmolt4 cell leukemia [Barnes et al., Biochemistry 2000;39:13641-50]. The agents acted as competitive inhibitors of this isoform, yet when tested against human Type I at concent...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(01)00649-9

    authors: Barnes BJ,Eakin AE,Izydore RA,Hall IH

    更新日期:2001-07-01 00:00:00

  • The acetaminophen-derived bioactive N-acylphenolamine AM404 inhibits NFAT by targeting nuclear regulatory events.

    abstract::AM404 is a synthetic TRPV1/CB(1) hybrid ligand with inhibitory activity on the anandamide transporter and is used for the pharmacological manipulation of the endocannabinoid system. It has been recently described that acetaminophen is metabolised in the brain to form the bioactive N-acylphenolamine AM404 and therefore...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2006.12.001

    authors: Caballero FJ,Navarrete CM,Hess S,Fiebich BL,Appendino G,Macho A,Muñoz E,Sancho R

    更新日期:2007-04-01 00:00:00

  • Inhibition of S-nitrosation of reduced glutathione in aerobic solutions of nitric oxide by phosphate and other inorganic anions.

    abstract::Reduced glutathione is nitrosated in aerobic solutions of nitric oxide under physiological conditions; however, the extent of S-nitrosation was found to be dependent on the inorganic anions present. Of nine anions tested, the bifunctional anions, arsenate, phosphate, and pyrophosphate (40 mM), inhibited the S-nitrosat...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(96)00825-8

    authors: DeMaster EG,Quast BJ,Mitchell RA

    更新日期:1997-02-21 00:00:00

  • Snake three-finger α-neurotoxins and nicotinic acetylcholine receptors: molecules, mechanisms and medicine.

    abstract::Snake venom three-finger α-neurotoxins (α-3FNTx) act on postsynaptic nicotinic acetylcholine receptors (nAChRs) at the neuromuscular junction (NMJ) to produce skeletal muscle paralysis. The discovery of the archetypal α-bungarotoxin (α-BgTx), almost six decades ago, exponentially expanded our knowledge of membrane rec...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/j.bcp.2020.114168

    authors: Nirthanan S

    更新日期:2020-11-01 00:00:00

  • Effect of pretreatment with sodium phenobarbital on the toxicity of soman in mice.

    abstract::Pretreatment with sodium phenobarbital induces hepatic microsomal enzymes which are responsible for the metabolic breakdown of a large number of endogenous and exogenous chemical compounds. A previous study [K. P. DuBois and F. K. Kinoshita, Proc. Soc. exp. Biol. Med. 129, 699 (1968)] reported that phenobarbital pretr...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(83)90455-0

    authors: Clement JG

    更新日期:1983-04-15 00:00:00

  • Comparative effects of englitazone and glyburide on gluconeogenesis and glycolysis in the isolated perfused rat liver.

    abstract::Englitazone (CP 68,722, Pfizer) is a member of a family of drugs known as thiazolidinediones. One member of this family, troglitazone (Rezulin), is currently utilized in the treatment of Type 2 diabetes. Previous studies have focused on the ability of englitazone to increase insulin sensitivity in various tissues. How...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(98)00052-5

    authors: Adams MD,Raman P,Judd RL

    更新日期:1998-06-01 00:00:00

  • Genetic expression of aflatoxin metabolism. Effects of 3-methylcholanthrene and beta-naphthoflavone on hepatic microsomal metabolism and mutagenic activation of aflatoxins.

    abstract::The effects of pretreatment with 3-methylcholanthrene (MC) and beta-naphthoflavone (beta NF) on the hepatic microsome-mediated mutagenesis of aflatoxin B1 (AFB1) and benzo[a]pyrene, and on the metabolism of aflatoxins B1 and B2, were investigated in inbred mouse strains. The inbred strains of mice studied included Ah ...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(83)90146-6

    authors: Raina V,Williams CJ,Gurtoo HL

    更新日期:1983-12-15 00:00:00

  • Role of sodium in intracellular calcium elevation and leukotriene B4 formation by receptor-mediated activation of human neutrophils.

    abstract::The role of Na(+) and Na(+) exchangers in intracellular Ca(2+) elevation and leukotriene B(4) (LTBs) formation was investigated in granulocyte macrophage colony-stimulating factor (GM-CSF)-primed, fMLP-stimulated human neutrophils. Isotonic substitution of extracellular Na(+) with N-methyl-D-glucamine(+) (NMDG(+)) res...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2003.09.019

    authors: Tedeschi A,Ciceri P,Zarini S,Lorini M,Di Donato M,Nicosia S,Miadonna A,Sala A

    更新日期:2004-01-15 00:00:00

  • Covalent binding of the anticancer drug ellipticine to DNA in V79 cells transfected with human cytochrome P450 enzymes.

    abstract::Ellipticine is a potent antineoplastic agent whose mechanism of action is considered to be based mainly on DNA intercalation and/or inhibition of topoisomerase II. Recently, we found that ellipticine also forms covalent DNA adducts and that the formation of the major adduct is dependent on the activation of ellipticin...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/s0006-2952(02)01072-9

    authors: Frei E,Bieler CA,Arlt VM,Wiessler M,Stiborová M

    更新日期:2002-07-15 00:00:00

  • Resveratrol inhibits BK-induced COX-2 transcription by suppressing acetylation of AP-1 and NF-κB in human rheumatoid arthritis synovial fibroblasts.

    abstract::Bradykinin (BK) induces inflammation in rheumatoid arthritis (RA). Resveratrol is a potent activator of Sirt1 which could modulate inflammation through deacetylating histones of transcription factors. Here, we investigated the mechanisms underlying BK-induced COX-2 expression which is modulated by resveratrol/Sirt1 in...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2017.03.003

    authors: Yang CM,Chen YW,Chi PL,Lin CC,Hsiao LD

    更新日期:2017-05-15 00:00:00

  • The effect of metformin in EML4-ALK+ lung cancer alone and in combination with crizotinib in cell and rodent models.

    abstract::Cell based studies have suggested that the diabetes drug metformin may combine with the anaplastic lymphoma kinase receptor (ALK) inhibitor crizotinib to increase ALK positive lung cancer cell killing and overcome crizotinib resistance. We therefore tested metformin alone and in combination with crizotinib in vivo, by...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/j.bcp.2020.114345

    authors: Bland AR,Shrestha N,Bower RL,Rosengren RJ,Ashton JC

    更新日期:2021-01-01 00:00:00

  • In vivo and in vitro studies on the effects of some phenothiazines and sulpiride on kynurenine metabolism.

    abstract::The effect of 5 consecutive daily i.p. doses of CPZ (5 mg/kg), PZ (10 mg/kg) and PMZ (10 mg/kg) on the activity of kynurenine hydrolase and kynurenine aminotransferase in mouse liver was studied. All three phenothiazines effected an increase in the activity of kynurenine hydrolase per unit weight of liver with CPZ sho...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章

    doi:10.1016/0006-2952(82)90105-8

    authors: Mostafa MH,El-Sewedy SM,El-Bassiouni EA,Abdel-Tawab GA

    更新日期:1982-07-01 00:00:00

  • The forgotten Gram-negative bacilli: what genetic determinants are telling us about the spread of antibiotic resistance.

    abstract::Gram-negative bacilli have become increasingly resistant to antibiotics over the past 2 decades due to selective pressure from the extensive use of antibiotics in the hospital and community. In addition, these bacteria have made optimum use of their innate genetic capabilities to extensively mutate structural and regu...

    journal_title:Biochemical pharmacology

    pub_type: 杂志文章,评审

    doi:10.1016/j.bcp.2005.11.006

    authors: Gootz TD

    更新日期:2006-03-30 00:00:00