当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Iromycins from Streptomyces sp. and from synthesis: new inhibitors of the mitochondrial electron transport chain.

Iromycins from Streptomyces sp. and from synthesis: new inhibitors of the mitochondrial electron transport chain.

Abstract：

:Two new alpha-pyridone metabolites, iromycins E and F, were isolated from cultures of strain Streptomyces sp. Dra 17, thus expanding the recently discovered iromycin family. The inhibitory potential on the mitochondrial respiratory chain was examined and revealed that iromycin metabolites block NADH oxidation in beef heart submitochondrial particles with different efficacy, yet remarkably show only very low cytotoxicity. Difference spectroscopic studies indicated that iromycins inhibit the electron transport at the site of complex I (NADH-ubiquinone oxidoreductase). Derivatives of the natural products were semisynthetically prepared and provided detailed insights into structure-activity relationships. Drawn from these results, there are strong similarities with the piericidins, which are among the most potent complex I inhibitors of the mitochondrial electron transport chain. Furthermore, total synthesis afforded new analogues, and the non-natural iromycin S (IC50 = 58 ng/mL) emerged as the most active compound, thus opening avenues of future studies with the iromycins as new valuable biochemical tools.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Surup F,Shojaei H,von Zezschwitz P,Kunze B,Grond S

doi

10.1016/j.bmc.2007.11.023

subject

Has Abstract

pub_date

2008-02-15 00:00:00

pages

1738-46

issue

4

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(07)00992-3

journal_volume

16

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • Click approach to the discovery of 1,2,3-triazolylsalicylamides as potent Aurora kinase inhibitors.

    abstract：:A series of 1,2,3-triazolylsalicylamide derivatives has been developed from the antiproliferative agent 7 and was evaluated for their Aurora kinase inhibitory activity. The novel 1,2,3-triazolylsalicylamide scaffold could be readily assembled by Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition, allowing rapid ac...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.06.047

    authors： Song D,Park Y,Yoon J,Aman W,Hah JM,Ryu JS

    更新日期：2014-09-01 00:00:00

  • Synthesis and cytotoxic activities of goniothalamins and derivatives.

    abstract：:Substituted goniothalamins containing cyclopropane-groups were efficiently prepared in high yields and good selectivity. Antiproliferative activity was measured on three human cancer cell lines (A549, MCF-7, HBL-100), to show which of the structural elements of goniothalamins is mandatory for cytotoxicity. We found th...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.02.004

    authors： Weber A,Döhl K,Sachs J,Nordschild ACM,Schröder D,Kulik A,Fischer T,Schmitt L,Teusch N,Pietruszka J

    更新日期：2017-11-15 00:00:00

  • Syntheses and receptor-binding studies of derivatives of the opioid antagonist naltrexone.

    abstract：:Naltrexone (1), which is a member of the group of competitive opioid antagonists, shows a strong affinity for mu-receptors and its derivatives have been notable as novel receptor antagonists. In this paper, the preparation of several naltrexone derivatives is described; these were used to investigate the role of the o...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2003.10.039

    authors： Uwai K,Uchiyama H,Sakurada S,Kabuto C,Takeshita M

    更新日期：2004-01-15 00:00:00

  • Proteasome inhibition by peptide-semicarbazones.

    abstract：:Peptide-semicarbazones derived from Z-Trp-Trp-Phe-aldehyde inhibit the chymotryptic activity of the human proteasome at nanomolar concentrations, but are less active in a NFkappaB reporter gene assay. Cyclic semicarbazones, in contrast, combine a strong inhibitory effect on the enzyme with an inhibition of NFkappaB si...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.02.042

    authors： Leban J,Blisse M,Krauss B,Rath S,Baumgartner R,Seifert MH

    更新日期：2008-04-15 00:00:00

  • Transdermal penetration behaviour of drugs: CART-clustering, QSPR and selection of model compounds.

    abstract：:A set of 116 structurally very diverse compounds, mainly drugs, was characterized by 1630 molecular descriptors. The biological property modelled in this study was the transdermal permeability coefficient logK(p). The main objective was to find a limited set of suitable model compounds for skin penetration studies. Th...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.07.050

    authors： Baert B,Deconinck E,Van Gele M,Slodicka M,Stoppie P,Bodé S,Slegers G,Vander Heyden Y,Lambert J,Beetens J,De Spiegeleer B

    更新日期：2007-11-15 00:00:00

  • Ensemble-based docking: From hit discovery to metabolism and toxicity predictions.

    abstract：:This paper describes and illustrates the use of ensemble-based docking, i.e., using a collection of protein structures in docking calculations for hit discovery, the exploration of biochemical pathways and toxicity prediction of drug candidates. We describe the computational engineering work necessary to enable large ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.07.064

    authors： Evangelista W,Weir RL,Ellingson SR,Harris JB,Kapoor K,Smith JC,Baudry J

    更新日期：2016-10-15 00:00:00

  • Design, synthesis and biological evaluation of isochroman-4-one hybrids bearing piperazine moiety as antihypertensive agent candidates.

    abstract：:7,8-Dihydroxy-3-methyl-isochromanone-4 (XJP), is a polyphenolic natural product with moderate antihypertensive activity. To obtain new agents with stronger potency and safer profile, we employed XJP and naftopidil as the lead compounds to design and synthesize a novel class of hybrids as antihypertensive agent candida...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.05.004

    authors： Xie S,Li X,Yu H,Zhang P,Wang J,Wang C,Xu S,Wu Z,Liu J,Zhu Z,Xu J

    更新日期：2019-07-01 00:00:00

  • Dolichylpyrophosphate oligosaccharides: large-scale isolation and evaluation as oligosaccharyltransferase substrates.

    abstract：:Oligosaccharyltransferase (OST) catalyzes the transfer of a branched oligosaccharide from a dolichylpyrophosphate oligosaccharide (Dol-PP-OS) to the asparagine of a nascent polypeptide chain in vivo and peptide substrates in vitro. Here we report the isolation and purification of Dol-PP-OS from bovine pancreas and thy...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00268-5

    authors： Gibbs BS,Coward JK

    更新日期：1999-03-01 00:00:00

  • A novel assay revealed that ribonucleotide reductase is functionally important for interstrand DNA crosslink repair.

    abstract：:Cells have evolved complex biochemical pathways for DNA interstrand crosslink (ICL) removal. Despite the chemotherapeutic importance of ICL repair, there have been few attempts to identify which mechanistic DNA repair inhibitor actually inhibits ICL repair. To identify such compounds, a new and robust ICL repair assay...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.09.045

    authors： Fujii N,Evison BJ,Actis ML,Inoue A

    更新日期：2015-11-01 00:00:00

  • Studies on 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole/2-hydroxypropyl-β-cyclodextrin association: Characterization, molecular modeling studies, and in vivo anthelminthic activity.

    abstract：:The purpose of this work is to study the molecular association that occurs between 2-hydroxypropyl-β-cyclodextrin (HPβCD) and 6-chloro-5-(1-naphthyloxy)-2-(trifluoromethyl)-1H-benzimidazole (RCB20), an antiparasitic compound recently found by our research group, with poor aqueous solubility. The complex stability cons...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.12.015

    authors： Rojas-Aguirre Y,Yépez-Mulia L,Castillo I,López-Vallejo F,Soria-Arteche O,Hernández-Campos A,Castillo R,Hernández-Luis F

    更新日期：2011-01-15 00:00:00

  • New highly active taxoids from 9beta-dihydrobaccatin-9,10-acetals. Part 4.

    abstract：:It was shown that a new taxane analogue 3, which exhibited both in vitro antitumor activity and in vivo efficacy by both i.v. and p.o. administration, was prone to be metabolized by human liver microsomes. We identified a major metabolite, M-1, generated by human liver microsomes as 20a, a hydroxylated compound at the...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(03)00454-1

    authors： Takeda Y,Uoto K,Chiba J,Horiuchi T,Iwahana M,Atsumi R,Ono C,Terasawa H,Soga T

    更新日期：2003-10-01 00:00:00

  • Design, synthesis, radiolabeling and in vivo evaluation of potential positron emission tomography (PET) radioligands for brain imaging of the 5-HT₇ receptor.

    abstract：:Here we describe the design, synthesis, and pharmacological evaluation of a set of compounds structurally related to the high affinity serotonin 5-HT7 receptor agonist N-(4-cyanophenylmethyl)-4-(2-diphenyl)-1-piperazinehexanamide (6, LP-211). Specific structural modifications were performed in order to maintain affini...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.01.016

    authors： Lacivita E,Niso M,Hansen HD,Di Pilato P,Herth MM,Lehel S,Ettrup A,Montenegro L,Perrone R,Berardi F,Colabufo NA,Leopoldo M,Knudsen GM

    更新日期：2014-03-01 00:00:00

  • Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines.

    abstract：:In vitro evaluation of the halogenated pyrrolo[3,2-d]pyrimidines identified antiproliferative activities in compounds 1 and 2 against four different cancer cell lines. Upon screening of a series of pyrrolo[3,2-d]pyrimidines, the 2,4-Cl compound 1 was found to exhibit antiproliferative activity at low micromolar concen...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.06.025

    authors： Temburnikar KW,Ross CR,Wilson GM,Balzarini J,Cawrse BM,Seley-Radtke KL

    更新日期：2015-08-01 00:00:00

  • d(G3T4G4) forms unusual dimeric G-quadruplex structure with the same general fold in the presence of K+, Na+ or NH4+ ions.

    abstract：:We have recently communicated that DNA oligonucleotide d(G(3)T(4)G(4)) forms a dimeric G-quadruplex in the presence of K(+) ions [J. Am. Chem. Soc.2003, 125, 7866-7871]. The high-resolution NMR structure of d(G(3)T(4)G(4))(2) G-quadruplex exhibits G-quadruplex core consisting of three stacked G-quartets. The two overh...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.08.009

    authors： Sket P,Crnugelj M,Plavec J

    更新日期：2004-11-15 00:00:00

  • Chemical synthesis of tetracyclic terpenes and evaluation of antagonistic activity on endothelin-A receptors and voltage-gated calcium channels.

    abstract：:A class of tetracyclic terpenes was synthesized and evaluated for antagonistic activity of endothelin-1 (ET-1) induced vasoconstriction and inhibitory activity of voltage-activated Ca(2+) channels. Three repeated Robinson annulation reactions were utilized to construct the tetracyclic molecules. A stereoselective redu...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.06.055

    authors： Lu J,Aguilar A,Zou B,Bao W,Koldas S,Shi A,Desper J,Wangemann P,Xie XS,Hua DH

    更新日期：2015-09-01 00:00:00

  • Chemical and biological effects of substitution of the 2-position of ring-expanded ('fat') nucleosides containing the imidazo[4,5-e][1,3]diazepine-4,8-dione ring system: the role of electronic and steric factors on glycosidic bond stability and anti-HCV a

    abstract：:The attempted removal of the aralkyl group of 2-bromo-1-p-methoxybenzyl-6-octylimidazo[4,5-e][1,3]diazepine (ZP-33) with trifluoroacetic acid resulted in replacement of the bromo group with a carbonyl at position-2 in addition to the desired deprotection at the 1-position. 2'-Deoxynucleosides of 2-bromo-substituted-im...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.04.043

    authors： Zhang P,Zhang N,Buckwold VE,Hosmane RS

    更新日期：2007-07-15 00:00:00

  • Synthesis of novel 7-oxo and 7-hydroxy trifluoroallocolchicinoids with cytotoxic effect.

    abstract：:The synthesis of 7-oxo and 7-hydroxy trifluoroallocolchicinoids was achieved through the intramolecular cyclization of o-phenyl-β-phenylalanines. The resulting compounds were evaluated for their cytotoxic activity against KB cells and their inhibitory effect towards the polymerization of tubulin. The results yielded s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.02.043

    authors： Chosson E,Santoro F,Rochais C,Santos JS,Legay R,Thoret S,Cresteil T,Sinicropi MS,Besson T,Dallemagne P

    更新日期：2012-04-15 00:00:00

  • A new and efficient synthesis of substituted 6-[(2'-dialkylamino)ethyl] pyrimidine and 4-N,N-dialkyl-6-vinyl-cytosine derivatives and evaluation of their anti-rubella activity.

    abstract：:New 6-[(2'-dialkylamino)ethyl]-4(3H)-pyrimidinones were prepared by a multistep procedure starting from acetone dicarboxylic acid diethyl ester and urea derivatives. These compounds were used as starting materials to obtain 4-N,N-dialkyl-6-vinyl-pyrimidine derivatives by an unprecedented tandem C-6 side chain Hofmann-...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00077-9

    authors： Saladino R,Ciambecchini U,Maga G,Mastromarino P,Conti C,Botta M

    更新日期：2002-07-01 00:00:00

  • Synthesis and biological activities of quinazoline derivatives with ortho-phenol-quaternary ammonium salt groups.

    abstract：:One phenol-quaternary ammonium salt derivative with a flexible linker and three derivatives with a quinazoline moiety are present. Their binding affinities for DNA are discussed and it is clearly demonstrated that this class of phenol-quaternary ammonium salt derivatives could inhibit DNA transcription effectively. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.07.053

    authors： Zhang L,Ren L,Bai M,Weng L,Huang J,Wu L,Deng M,Zhou X

    更新日期：2007-11-15 00:00:00

  • Synthesis and biological properties of 2-methylene-19-nor-25-dehydro-1alpha-hydroxyvitamin D(3)-26,23-lactones--weak agonists.

    abstract：:In a continuing effort to explore the 2-methylene-1alpha-hydroxy-19-norvitamin D(3) class of pharmacologically important vitamin D compounds, two novel 2-methylene-19-nor-25-dehydro-1alpha-hydroxyvitamin D(3)-26,23-lactones, GC-3 and HLV, were synthesized and biologically tested. Based on reports of similarly structur...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.08.011

    authors： Chiellini G,Grzywacz P,Plum LA,Barycki R,Clagett-Dame M,DeLuca HF

    更新日期：2008-09-15 00:00:00

  • 5-demethylovalicin, as a methionine aminopeptidase-2 inhibitor produced by Chrysosporium.

    abstract：:5-Demethylovalicin was isolated from the fermentation broth Chrysosporium lucknowense and the structure was identified by spectroscopic methods. 5-Demethylovalicin inhibited the recombinant human MetAP-2 (IC(50)=17.7 nM) and the growth of human umbilical vein endothelial cells (HUVEC; IC(50)=100 nM) in cell proliferat...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00268-1

    authors： Son KH,Kwon JY,Jeong HW,Kim HK,Kim CJ,Chang YH,Choi JD,Kwon BM

    更新日期：2002-01-01 00:00:00

  • Carbon-carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria.

    abstract：:In an effort to expand the spectrum of activity of the oxazolidinone class of antibacterial agents to include Gram-negative bacteria, a series of new carbon-carbon linked pyrazolylphenyl analogues has been prepared. The alpha-N-substituted methyl pyrazole (10alpha) in the C3-linked series exhibited very good Gram-posi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00233-4

    authors： Lee CS,Allwine DA,Barbachyn MR,Grega KC,Dolak LA,Ford CW,Jensen RM,Seest EP,Hamel JC,Schaadt RD,Stapert D,Yagi BH,Zurenko GE,Genin MJ

    更新日期：2001-12-01 00:00:00

  • Synthesis, biological assays and QSAR studies of N-(9-benzyl-2-phenyl-8-azapurin-6-yl)-amides as ligands for A1 adenosine receptors.

    abstract：:2-Phenyl-9-benzyl-8-azapurines, bearing at the 6 position an amido group interposed between the 8-azapurine moiety and an alkyl or a substituted phenyl group, have been synthesised and assayed as ligands for adenosine receptors. All the compounds show high affinity for the A(1) adenosine receptor, and many of them als...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.01.060

    authors： Giorgi I,Leonardi M,Pietra D,Biagi G,Borghini A,Massarelli I,Ciampi O,Bianucci AM

    更新日期：2009-03-01 00:00:00

  • Synthesis of beta-substituted naphth-1-yl ethylamido derivatives as new melatoninergic agonists.

    abstract：:Naphthalene melatoninergic ligands with alkyl groups (Me, Et, Pr, Bz) in the beta position of the ethylamido chain were synthesised. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[125I]-iodomelatonin as the radioligand. An increase in the affinity was observed with the beta-...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(99)00236-9

    authors： Mathé-Allainmat M,Le Gall M,Jellimann C,Andrieux J,Langlois M

    更新日期：1999-12-01 00:00:00

  • Design, synthesis and preliminary biological evaluation of zatebradine analogues as potential blockers of the hyperpolarization-activated current.

    abstract：:A series of zatebradine analogues, differing in the basic moiety and in the methylene spacer, have been synthesized; their negative chronotropic activity has been determined in guinea pig atria. The most active compounds have been studied for their blocking properties on the hyperpolarization-activated current If (whi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.11.017

    authors： Romanelli MN,Cerbai E,Dei S,Guandalini L,Martelli C,Martini E,Scapecchi S,Teodori E,Mugelli A

    更新日期：2005-02-15 00:00:00

  • Studies of TAK1-centered polypharmacology with novel covalent TAK1 inhibitors.

    abstract：:Targeted polypharmacology provides an efficient method of treating diseases such as cancer with complex, multigenic causes provided that compounds with advantageous activity profiles can be discovered. Novel covalent TAK1 inhibitors were validated in cellular contexts for their ability to inhibit the TAK1 kinase and f...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.11.034

    authors： Tan L,Gurbani D,Weisberg EL,Jones DS,Rao S,Singer WD,Bernard FM,Mowafy S,Jenney A,Du G,Nonami A,Griffin JD,Lauffenburger DA,Westover KD,Sorger PK,Gray NS

    更新日期：2017-02-15 00:00:00

  • Inhibitors of human tyrosyl-DNA phospodiesterase (hTdp1) developed by virtual screening using ligand-based pharmacophores.

    abstract：:Human tyrosyl-DNA phosphodiesterase (hTdp1) inhibitors have become a major area of drug research and structure-based design since they have been shown to work synergistically with camptothecin (CPT) and selectively in cancer cells. The pharmacophore features of 14 hTdp1 inhibitors were used as a filter to screen the C...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.11.008

    authors： Weidlich IE,Dexheimer T,Marchand C,Antony S,Pommier Y,Nicklaus MC

    更新日期：2010-01-01 00:00:00

  • Antitumor activity and COMPARE analysis of bis-indole derivatives.

    abstract：:This paper reports the synthesis of new derivatives (formed by two indole systems separated by a central moiety) analogous of potent antitumor agents previously described. The activity of the bis-indoles bearing a pyridine core confirms the good result described in the previous paper and compound 4c was chosen for the...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.03.063

    authors： Andreani A,Burnelli S,Granaiola M,Leoni A,Locatelli A,Morigi R,Rambaldi M,Varoli L,Landi L,Prata C,Dalla Sega FV,Caliceti C,Shoemaker RH

    更新日期：2010-05-01 00:00:00

  • Tailoring structure-function and targeting properties of ceramides by site-specific cationization.

    abstract：:In the course of our studies on compartment-specific lipid-mediated cell regulation, we identified an intimate connection between ceramides (Cers) and the mitochondria-dependent death-signaling pathways. Here, we report on a new class of cationic Cer mimics, dubbed ceramidoids, designed to act as organelle-targeted sp...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.07.016

    authors： Szulc ZM,Bielawski J,Gracz H,Gustilo M,Mayroo N,Hannun YA,Obeid LM,Bielawska A

    更新日期：2006-11-01 00:00:00

  • Amino derivatives of glycyrrhetinic acid as potential inhibitors of cholinesterases.

    abstract：:The development of remedies against the Alzheimer's disease (AD) is one of the biggest challenges in medicinal chemistry nowadays. Although not completely understood, there are several strategies fighting this disease or at least bringing some relief. During the progress of AD, the level of acetylcholine (ACh) decreas...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.04.046

    authors： Schwarz S,Lucas SD,Sommerwerk S,Csuk R

    更新日期：2014-07-01 00:00:00