Relationship between the lipophilicity of gallic acid n-alquil esters' derivatives and both myeloperoxidase activity and HOCl scavenging.

Abstract:

:The gallic acid and several n-alkyl gallates, with the same number of hydroxyl substituents, varying only in the side carbonic chain length, with respective lipophilicity defined through the C log P, were studied. It evidenced the structure-activity relationship of the myeloperoxidase activity inhibition and the hypochlorous acid scavenger property, as well as its low toxicity in rat hepatic tissue. The gallates with C log P below 3.0 (compounds 2-7) were more active against the enzyme activity, what means that the addition of 1-6 carbons (C log P between 0.92 and 2.92) at the side chain increased approximately 50% the gallic acid effect. However, a relationship between the HOCl scavenging capability and the lipophilicity was not observed. With these results it is possible to suggest that the gallates protect the HOCl targets through two mechanisms: inhibiting its production by the enzyme and scavenging the reactive specie.

journal_name

Bioorg Med Chem

authors

Rosso R,Vieira TO,Leal PC,Nunes RJ,Yunes RA,Creczynski-Pasa TB

doi

10.1016/j.bmc.2006.05.038

subject

Has Abstract

pub_date

2006-09-15 00:00:00

pages

6409-13

issue

18

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(06)00413-5

journal_volume

14

pub_type

杂志文章
  • Synthesis and in vitro evaluation of aspartate transcarbamoylase inhibitors.

    abstract::The design, synthesis, and evaluation of a series of novel inhibitors of aspartate transcarbamoylase (ATCase) are reported. Several submicromolar phosphorus-containing inhibitors are described, but all-carboxylate compounds are inactive. Compounds were synthesized to probe the postulated cyclic transition-state of the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.09.045

    authors: Coudray L,Pennebaker AF,Montchamp JL

    更新日期:2009-11-15 00:00:00

  • Dose dependent actions of LCL521 on acid ceramidase and key sphingolipid metabolites.

    abstract::The function of acid ceramidase (ACDase), whose congenital deficiency leads to Farber disease, has been recognized to be vital to tumor cell biology, and inhibition of its activity may be beneficial in cancer therapy. Therefore, manipulation of the activity of this enzyme may have significant effect, especially on can...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.11.012

    authors: Bai A,Bielawska A,Rahmaniyan M,Kraveka JM,Bielawski J,Hannun YA

    更新日期:2018-12-15 00:00:00

  • 4,4'-Dihydroxy-trans-stilbene, a resveratrol analogue, exhibited enhanced antioxidant activity and cytotoxicity.

    abstract::Resveratrol (3,5,4'-trans-trihydroxystibene) is a natural phytoalexin present in grapes and red wine, which possesses a variety of biological activities including antioxidant activity. In order to find more active antioxidant with resveratrol as the lead compound we synthesized 4,4'-dihydroxy-trans-stilbene (4,4'-DHS)...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.02.014

    authors: Fan GJ,Liu XD,Qian YP,Shang YJ,Li XZ,Dai F,Fang JG,Jin XL,Zhou B

    更新日期:2009-03-15 00:00:00

  • Computer-aided discovery of aminopyridines as novel JAK2 inhibitors.

    abstract::The Janus kinase 2 (JAK2)-mediated signaling pathway plays an important role in controlling cell survival, proliferation, and differentiation. In recent years, genetic, biological, and physiological evidence has established JAK2 inhibitors as effective chemotherapeutic agents for the treatment of many different cancer...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.01.016

    authors: Zhao C,Yang SH,Khadka DB,Jin Y,Lee KT,Cho WJ

    更新日期:2015-03-01 00:00:00

  • Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides: synthesis, antitumor evaluation, and DNA photocleavage.

    abstract::A new heterocyclic family of (2-(dimethylamino)ethyl)-2-substituted phenylnaphtho[2,1-d]thiazole-5-carboxamides modified from naphthalimides was designed, synthesized, and quantitatively evaluated as antitumor agents and photonucleases. All these compounds were found to be more cytotoxic against P388 than against A549...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.02.045

    authors: Li Z,Yang Q,Qian X

    更新日期:2005-05-02 00:00:00

  • Structural optimization and in vitro profiling of N-phenylbenzamide-based farnesoid X receptor antagonists.

    abstract::Activation of the nuclear farnesoid X receptor (FXR) which acts as cellular bile acid sensor has been validated as therapeutic strategy to counter liver disorders such as non-alcoholic steatohepatitis by the clinical efficacy of obeticholic acid. FXR antagonism, in contrast, is less well studied and potent small molec...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.07.017

    authors: Schmidt J,Schierle S,Gellrich L,Kaiser A,Merk D

    更新日期:2018-08-07 00:00:00

  • Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1).

    abstract::Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His(10), to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their rates of transport in monolayers of mult...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.05.075

    authors: Orchard A,Schamerhorn GA,Calitree BD,Sawada GA,Loo TW,Claire Bartlett M,Clarke DM,Detty MR

    更新日期:2012-07-15 00:00:00

  • Active site mapping of trypsin, thrombin and matriptase-2 by sulfamoyl benzamidines.

    abstract::The benzamidine moiety, a well-known arginine mimetic, has been introduced in a variety of ligands, including peptidomimetic inhibitors of trypsin-like serine proteases. According to their primary substrate specificity, the benzamidine residue interacts with the negatively charged aspartate at the bottom of the S1 poc...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.08.042

    authors: Dosa S,Stirnberg M,Lülsdorff V,Häußler D,Maurer E,Gütschow M

    更新日期:2012-11-01 00:00:00

  • Synthesis and insecticidal activity of chromanone and chromone analogues of diacylhydrazines.

    abstract::Diacylhydrazine derivatives have been identified as one of the most important insect growth regulators. A variety of diacylhydrazine derivatives were designed and synthesized in recent years due to their unique action mechanism, simple structure, and environmental benign character. This paper describes the molecular d...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.01.008

    authors: Zhao PL,Li J,Yang GF

    更新日期:2007-03-01 00:00:00

  • A new class of non-thiazolidinedione, non-carboxylic-acid-based highly selective peroxisome proliferator-activated receptor (PPAR) γ agonists: design and synthesis of benzylpyrazole acylsulfonamides.

    abstract::Herein, we describe the design, synthesis, and structure-activity relationships of novel benzylpyrazole acylsulfonamides as non-thiazolidinedione (TZD), non-carboxylic-acid-based peroxisome proliferator-activated receptor (PPAR) γ agonists. Docking model analysis of in-house weak agonist 2 bound to the reported PPARγ ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.008

    authors: Rikimaru K,Wakabayashi T,Abe H,Imoto H,Maekawa T,Ujikawa O,Murase K,Matsuo T,Matsumoto M,Nomura C,Tsuge H,Arimura N,Kawakami K,Sakamoto J,Funami M,Mol CD,Snell GP,Bragstad KA,Sang BC,Dougan DR,Tanaka T,Katayama

    更新日期:2012-01-15 00:00:00

  • Optimization of thiazole analogues of resveratrol for induction of NAD(P)H:quinone reductase 1 (QR1).

    abstract::NAD(P)H:quinone reductase 1 (QR1) belongs to a class of enzymes called cytoprotective enzymes. It exhibits its cancer protective activity mainly by inhibiting the formation of intracellular semiquinone radicals, and by generating α-tocopherolhydroquinone, which acts as a free radical scavenger. It is therefore believe...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.10.006

    authors: Mayhoub AS,Marler L,Kondratyuk TP,Park EJ,Pezzuto JM,Cushman M

    更新日期:2012-12-15 00:00:00

  • 3- and 6-Substituted 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines as A1 adenosine receptor allosteric modulators and antagonists.

    abstract::A series of 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines were prepared and evaluated as potential allosteric modulators at the A(1) adenosine receptor. The structure-activity relationships of the 3- and 6-positions of a series of 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines were explored. Despite finding that ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.08.024

    authors: Aurelio L,Valant C,Figler H,Flynn BL,Linden J,Sexton PM,Christopoulos A,Scammells PJ

    更新日期:2009-10-15 00:00:00

  • General synthesis and biological evaluation of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides).

    abstract::A general synthesis of alpha-1-C-substituted derivatives of fagomine (2-deoxynojirimycin-alpha-C-glycosides) by ring-opening reactions of an aziridine with various heteroatomic nucleophiles, including thiol, amine, alcohol, carboxylate and phosphate, is described. The nine-step reaction sequence proceeded in an overal...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.12.043

    authors: Goujon JY,Gueyrard D,Compain P,Martin OR,Ikeda K,Kato A,Asano N

    更新日期:2005-03-15 00:00:00

  • A novel sesquiterpenoid dimer parviflorene F induces apoptosis by up-regulating the expression of TRAIL-R2 and a caspase-dependent mechanism.

    abstract::Parviflorene F (1), a novel sesquiterpenoid dimer isolated from Curcuma parviflora Wall, is a cytotoxic compound. In this study, we examined the mechanism of its cytotoxic effect in HeLa cells. Treatment with 1 enhanced the mRNA and protein expression of TRAIL-R2 (tumor necrosis factor alpha-related apoptosis inducing...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.11.022

    authors: Ohtsuki T,Tamaki M,Toume K,Ishibashi M

    更新日期:2008-02-15 00:00:00

  • Synthesis and biological evaluations of A-ring isomers of 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3.

    abstract::The activated vitamin D3 derivative 26,27-F6-1alpha,25(OH)2D3 (2a), its three A-ring diastereomers (2b, 2c, 2d), and 5,6-trans isomer (2e) were prepared. Two analogues (2b, 2c) of these isomers were synthesized by a palladium catalyzed coupling reaction using vinyl bromide 5 and enynes (6a, 6b), which were derived fro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00142-5

    authors: Ikeda M,Takahashi K,Dan A,Koyama K,Kubota K,Tanaka T,Hayashi M

    更新日期:2000-08-01 00:00:00

  • Novel 4-acetamide-2-alkylthio-N-acetanilides resembling nimesulide: Synthesis, cell viability evaluation and in silico studies.

    abstract::Since nimesulide, a nonsteroidal anti-inflammatory drug, is known to be a selective inhibitor of cyclooxygenase-2 and shows activity against cancer cells, there has been much interest in developing related molecules with enhanced anticancer properties. Taking in consideration structural features of nimesulide analogue...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.06.009

    authors: Catarro M,Serrano J,Cavalheiro E,Ramos S,Santos AO,Silvestre S,Almeida P

    更新日期:2017-08-15 00:00:00

  • Structural design, synthesis and pharmacological evaluation of 4-thiazolidinones against Trypanosoma cruzi.

    abstract::Chagas disease is an infection caused by protozoan Trypanosoma cruzi, which affects approximately 8-10million people worldwide. Benznidazole is the only drug approved for treatment during the acute and asymptomatic chronic phases of Chagas disease; however, it has poor efficacy during the symptomatic chronic phase. Th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.10.048

    authors: de Oliveira Filho GB,de Oliveira Cardoso MV,Espíndola JW,Ferreira LF,de Simone CA,Ferreira RS,Coelho PL,Meira CS,Magalhaes Moreira DR,Soares MB,Lima Leite AC

    更新日期:2015-12-01 00:00:00

  • Lead identification and optimization of bacterial glutamate racemase inhibitors.

    abstract::Mycobacterium tuberculosis glutamate racemase is an essential enzyme involved in peptidoglycan synthesis and conserved in most bacteria. Small molecule inhibitors were reported on other bacterial species whereas in M. tuberculosis it wasn't explored much. In this study we have screened in house compound library using ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.11.031

    authors: Malapati P,Siva Krishna V,Nallangi R,Meda N,Reshma Srilakshmi R,Sriram D

    更新日期:2018-01-01 00:00:00

  • Development of a liposomal delivery system for temperature-triggered release of a tumor targeting agent, Ln(III)-DOTA-phenylboronate.

    abstract::Liposomes, capable of temperature-triggered content release at the site of interest, can be of great importance for imaging and therapy of tumors. The delivery of imaging agents or therapeutics can be improved by application of liposomes with a gel-to-liquid phase-transition temperature suitable for mild hyperthermia ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.06.036

    authors: Djanashvili K,ten Hagen TL,Blangé R,Schipper D,Peters JA,Koning GA

    更新日期:2011-02-01 00:00:00

  • Cell surface biotinylation by azaelectrocyclization: easy-handling and versatile approach for living cell labeling.

    abstract::Versatile method for living cell labeling has been established. Cell surfaces are initially biotinylated by azaelectrocyclization, and then treated with the fluorescence-labeled avidin or the anti-biotin antibody. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.12.043

    authors: Tanaka K,Yokoi S,Morimoto K,Iwata T,Nakamoto Y,Nakayama K,Koyama K,Fujiwara T,Fukase K

    更新日期:2012-03-15 00:00:00

  • Synthesis and in vivo evaluation of [O-methyl-11C] N-[3,5-dichloro-2-(methoxy)phenyl]-4-(methoxy)-3-(1-piperazinyl)benzenesulfonamide as an imaging probe for 5-HT6 receptors.

    abstract::The serotonin receptor 6 (5-HT(6)) is implicated in the pathophysiology of cognitive diseases, schizophrenia, anxiety and obesity and in vivo studies of this receptor would be of value for studying the pathophysiology of these disorders. Therefore, N-[3,5-dichloro-2-(methoxy)phenyl]-4-(methoxy)-3-(1-piperazinyl)benzen...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.06.090

    authors: Liu F,Majo VJ,Prabhakaran J,Milak MS,John Mann J,Parsey RV,Kumar JS

    更新日期:2011-09-01 00:00:00

  • Design, synthesis and biological evaluation of (E)-3,4-dihydroxystyryl 4-acylaminophenethyl sulfone, sulfoxide derivatives as dual inhibitors of HIV-1 CCR5 and integrase.

    abstract::Aiming at the limited effectiveness of current clinical therapeutic effect of AIDS, novel series of compounds bearing (E)-3,4-dihydroxystyryl sulfone (or sulfoxide) and anilide fragments were designed and synthesized as dual inhibitors of HIV-1 CCR5/IN. The biological results indicated that several target compounds sh...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.12.035

    authors: Sun Y,Xu W,Fan N,Sun X,Ning X,Ma L,Liu J,Wang X

    更新日期:2017-02-01 00:00:00

  • Chemical identification, electrophysiological and behavioral activities of the pheromone of Metamasius hemipterus (Coleoptera: Curculionidae).

    abstract::Five hydroxylated aliphatic molecules were identified as the pheromone produced by male West Indian Sugarcane Borer (WISB): 4-methyl-5-nonanol (1), 2-methyl-4-heptanol (2), 2-methyl-4-octanol (3), 5-nonanol (4) and 3-hydroxy-4-methyl-5-nonanone (5). Electroantennographic recordings revealed antennal responses to compo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(96)00009-0

    authors: Ramirez-Lucas P,Malosse C,Ducrot PH,Lettere M,Zagatti P

    更新日期:1996-03-01 00:00:00

  • Antioxidant activity of benzoxazolinonic and benzothiazolinonic derivatives in the LDL oxidation model.

    abstract::A series of benzazolone compounds were synthesized utilizing benzoxazolinonic and benzothiazolinonic heterocycles as the building unit. The antioxidant activity of these compounds was determined by inhibition of lipid peroxidation. The oxidation of LDL was induced in the presence of CuSO(4) or 2,2'-azobis(2-amidinopro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.09.016

    authors: Yekini I,Hammoudi F,Martin-Nizard F,Yous S,Lebegue N,Berthelot P,Carato P

    更新日期:2009-11-15 00:00:00

  • Synthesis and trypanocidal activity of ent-kaurane glycosides.

    abstract::Novel ent-kaurane glucosides were synthezised by a Koenigs-Knorr reaction between C17 and C19 alcohols derived from kaurenoic acid and 2,3,4,6-tetra-O-acetyl-glucopyranosyl bromide, followed by the hydrolysis of the acetates. Main products were assayed in vitro and in vivo against blood trypomastigote forms of Trypano...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.09.048

    authors: Batista R,Humberto JL,Chiari E,de Oliveira AB

    更新日期:2007-01-01 00:00:00

  • Synthesis and structure activity relationships of novel non-peptidic metallo-aminopeptidase inhibitors.

    abstract::Racemic derivatives of 3-amino-2-tetralone were synthesised and evaluated for their ability to inhibit metallo-aminopeptidase activities. New compounds substituted in position 2 by methyl ketone, substituted oximes or hydroxamic acids as well as heterocyclic derivatives were evaluated against representative members of...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.06.050

    authors: Albrecht S,Defoin A,Salomon E,Tarnus C,Wetterholm A,Haeggström JZ

    更新日期:2006-11-01 00:00:00

  • Polyvalent saccharide-functionalized generation 3 poly(amidoamine) dendrimer-methotrexate conjugate as a potential anticancer agent.

    abstract::A saccharide-terminated generation 3 (G3) polyamidoamine (PAMAM) dendrimer was synthesized as a drug carrier. Utilizing this dendritic platform, we have successfully synthesized polyvalent conjugates (G3-MTX) containing the drug methotrexate (MTX). Surface Plasmon Resonance (SPR) results showed that G3-MTX presented t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.03.019

    authors: Zhang Y,Thomas TP,Lee KH,Li M,Zong H,Desai AM,Kotlyar A,Huang B,Holl MM,Baker JR Jr

    更新日期:2011-04-15 00:00:00

  • A novel sesquiterpene lactone from Centaurea pullata: structure elucidation, antimicrobial activity, and prediction of pharmacokinetic properties.

    abstract::A novel elemanolide with an alpha-methyl-gamma-lactone moiety, 8alpha-O-(4-hydroxy-2-methylenebutanoyloxy)melitensine, in addition to four known sesquiterpene lactones also bearing the same lactone ring, melitensin, 11beta,13 dihydrosalonitenolide, 8alpha-hydroxy-11beta,13-dihydro-4-epi-sonchucarpolide, and 8alpha-hyd...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.01.056

    authors: Djeddi S,Karioti A,Sokovic M,Koukoulitsa C,Skaltsa H

    更新日期:2008-04-01 00:00:00

  • Participation of the conjugated diene part for potent cytotoxicity of callystatin A, a spongean polyketide.

    abstract::5-epi, 10-epi, 8-Deethyl, and 10-demethyl analogues of callystatin A, a potent cytotoxic spongean polyketide, were synthesized to elucidate structure-requirement for cytotoxic potency. Inversion of the asymmetric center at C-10 in callystatin A minimally affected the activity, while lack of the 10-methyl group in call...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(00)00199-1

    authors: Murakami N,Sugimoto M,Nakajima T,Kawanishi M,Tsutsui Y,Kobayashi M

    更新日期:2000-11-01 00:00:00

  • Antimicrobial and cytotoxic arylazoenamines. Part III: antiviral activity of selected classes of arylazoenamines.

    abstract::Eighty-five arylazoenamines, characterized by different types of aryl and basic moieties, have been synthesized and evaluated in cell-based assays for cytotoxicity and antiviral activity against a panel of ten RNA and DNA viruses. The most commonly affected viruses were, in decreasing order, CVB-2, RSV, BVDV, YFV, and...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.08.028

    authors: Tonelli M,Boido V,Canu C,Sparatore A,Sparatore F,Paneni MS,Fermeglia M,Pricl S,La Colla P,Casula L,Ibba C,Collu D,Loddo R

    更新日期:2008-09-15 00:00:00