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


: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.


Bioorg Med Chem


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




Has Abstract


2006-09-15 00:00:00














  • Design and structure-activity relationship of thrombin inhibitors with an azaphenylalanine scaffold: potency and selectivity enhancements via P2 optimization.

    abstract::Theoretical and structural studies followed by the directed synthesis and in vitro biological tests lead us to novel noncovalent thrombin pseudopeptide inhibitors. We have incorporated an azapeptide scaffold into the central part of the classical tripeptide D-Phe-Pro-Arg inhibitor structure thus eliminating one stereo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zega A,Mlinsek G,Sepic P,Golic Grdadolnik S,Solmajer T,Tschopp TB,Steiner B,Kikelj D,Urleb U

    更新日期:2001-10-01 00:00:00

  • 6-amino-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl derivatives as a new class of potent inhibitors of Interleukin-8-induced neutrophil chemotaxis.

    abstract::A series of 6-amino-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl derivatives was synthesized. The compounds demonstrated to be novel, potent and selective inhibitors of Interleukin-8-induced human neutrophil chemotaxis. A SAR study was performed by varying the carbonyl function at position 5 and...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Cesarini S,Spallarossa A,Ranise A,Bruno O,Arduino N,Bertolotto M,Dallegri F,Tognolini M,Gobbetti T,Barocelli E

    更新日期:2009-05-15 00:00:00

  • Facile preparation of deuterium-labeled N-acylhomoserine lactones as internal standards for isotope dilution mass spectrometry.

    abstract::N-Acylhomoserine lactones (AHLs) are widely conserved signal molecules that mediate quorum sensing in Gram-negative bacteria. In this study, deuterium-labeled AHLs were prepared for use as internal standards for isotope dilution mass spectrometry. Their utility in the sensitive and precise quantification of AHLs in cu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kai K,Tani A,Hayashi H

    更新日期:2010-06-01 00:00:00

  • Structure-activity relationships of amide-phosphonate derivatives as inhibitors of the human soluble epoxide hydrolase.

    abstract::Structure-activity relationships of amide-phosphonate derivatives as inhibitors of the human soluble epoxide hydrolase (sEH) were investigated. First, a series of alkyl or aryl groups were substituted on the carbon alpha to the phosphonate function in amide compounds to see whether substituted phosphonates can act as ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kim IH,Park YK,Nishiwaki H,Hammock BD,Nishi K

    更新日期:2015-11-15 00:00:00

  • Advances in inhibition of protein-protein interactions targeting hypoxia-inducible factor-1 for cancer therapy.

    abstract::Hypoxia is a common characteristic of many types of solid tumors and is associated with tumor propagation, malignant progression, and resistance to anti-cancer therapy. HIF-1 pathway is one of the survival pathways activated in tumor in response to hypoxia. In hypoxic condition, hypoxia-inducible factor-1α (HIF-1α) is...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Li J,Xi W,Li X,Sun H,Li Y

    更新日期:2019-04-01 00:00:00

  • Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists: relationship between absolute configuration and subtype selectivity.

    abstract::Introduction of an alkylcarboxylic acid unit, which is a partial structure of endogenous peroxisome proliferator-activated receptor (PPAR) ligands, into a phenethylphenylphthalimide skeleton, which possesses liver X receptor (LXR) antagonistic activity, afforded novel PPAR ligands. The results of structure-activity re...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Motoshima K,Ishikawa M,Hashimoto Y,Sugita K

    更新日期:2011-05-15 00:00:00

  • Visual observation of G-quadruplex DNA with the label-free fluorescent probe silole with aggregation-induced emission.

    abstract::AIE molecule silole 1 could be used to detect G-quadruplex formation using an exonuclease I hydrolysis assay. This visual observation of G-quadruplexes has been successfully used in investigating multiple G-quadruplexes, including the one-stranded telomeric, c-myc, c-kit, VEGF G-quadruplexes, and a d(G(4)T(4)G(4)) int...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Huang J,Wang M,Zhou Y,Weng X,Shuai L,Zhou X,Zhang D

    更新日期:2009-11-15 00:00:00

  • Cytotoxicity mechanisms of pyrazino[1,2-b]isoquinoline-4-ones and SAR studies.

    abstract::The cytotoxicity showed by 1b, an interesting representant of the title compounds, for HT-29 human colon cancer cells (CI(50) value of 1.95 x 10(-7)M) has been related to the induced cell death at the G2 phase and not to DNA damage. This compound promotes the degradation of components of the G2/M checkpoint machinery,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ortín I,González JF,Cuesta Ede L,Manguan-García C,Perona R,Avendaño C

    更新日期:2009-12-01 00:00:00

  • Teixobactin as a scaffold for unlimited new antimicrobial peptides: SAR study.

    abstract::It looks that a new era of antimicrobial peptides (AMPs) started with the discovery of teixobactin, which is a "head to side-chain" cyclodepsipeptide. It was isolated from a soil gram-negative b-proteobacteria by means of a revolutionary technique. Since there, several groups have developed synthetic strategies for ef...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Abdel Monaim SAH,Jad YE,El-Faham A,de la Torre BG,Albericio F

    更新日期:2018-06-01 00:00:00

  • Reactivity of dimethyl fumarate and methylhydrogen fumarate towards glutathione and N-acetyl-L-cysteine--preparation of S-substituted thiosuccinic acid esters.

    abstract::Dimethyl fumarate (DMF) is used successfully to treat psoriasis. In spite of its proven clinical efficacy, the mode of metabolism and the pharmacodynamics of DMF are still not completely understood. Some previous studies have indicated that orally applied DMF for a considerable part is quickly hydrolysed to methylhydr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Schmidt TJ,Ak M,Mrowietz U

    更新日期:2007-01-01 00:00:00

  • A new dihydroxanthenone from a plant-associated strain of the fungus Chaetomium globosum demonstrates anticancer activity.

    abstract::Bioassay-guided fractionation of a cytotoxic EtOAc extract of the fungal strain, Chaetomium globosum, inhabiting the rhizosphere of the Christmas cactus, Opuntia leptocaulis, of the Sonoran desert afforded a new dihydroxanthenone, globosuxanthone A (1), a new tetrahydroxanthenone, globosuxanthone B (2), two new xantho...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wijeratne EM,Turbyville TJ,Fritz A,Whitesell L,Gunatilaka AA

    更新日期:2006-12-01 00:00:00

  • Synthesis of a novel potent cyclic peptide MC4-ligand by ring-closing metathesis.

    abstract::The synthesis of a novel potent cyclic peptide MC4-ligand by ring-closing metathesis (RCM) is described. Based on the Ac-Nle-Gly-Lys-D-Phe-Arg-Trp-Gly-NH2-MC4 ligand, Ac-Nle-Alg-Lys-D-Phe-Arg-Trp-Alg-NH2 was designed and synthesized followed by cyclization using RCM. Both compounds are high affinity and selective MC4-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wels B,Kruijtzer JA,Garner K,Nijenhuis WA,Gispen WH,Adan RA,Liskamp RM

    更新日期:2005-07-01 00:00:00

  • Toward the development of chemoprevention agents (III): synthesis and anti-inflammatory activities of a new class of 5-glycylamino-2-substituted-phenyl-1,3-dioxacycloalkanes.

    abstract::A new series of 5-glycylamino-2-substituted-phenyl-1,3-dioxacycloalkanes were designed and synthesized. The anti-inflammatory activities of these compounds were tested using the xylene-induced mouse ear edema model. Sixteen of these new compounds exhibited comparable or better anti-inflammatory activities than aspirin...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Bi L,Zhao M,Gu K,Wang C,Ju J,Peng S

    更新日期:2008-02-15 00:00:00

  • Synthesis and biological activity of semipeptoid farnesyltransferase inhibitors.

    abstract::Semipeptoids derived from the Ras farnesyl transferase inhibitor, CVFM, were synthesized by the Simultaneous Multiple Analogue Peptide Synthesis methodology. The semipeptoids were screened for their in vitro inhibition potency towards farnesyl transferase and geranylgeranyl transferase. Structure-activity relationship...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Reuveni H,Gitler A,Poradosu E,Gilon C,Levitzki A

    更新日期:1997-01-01 00:00:00

  • [1,2,4]Triazole derivatives as 5-HT(1A) serotonin receptor ligands.

    abstract::A series of new 4-amino-3-[3-[4-(2-methoxy or nitro phenyl)-1-piperazinyl] propyl]thio]-5-(substitutedphenyl)[1,2,4]triazoles 11a-t was synthesized in order to obtain compounds with high affinity and selectivity for 5-HT(1A) receptor over the alpha(1)-adrenoceptor. A series of isomeric 4-amino-2-[3-[4-(2-methoxy or ni...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sarvà MC,Romeo G,Guerrera F,Siracusa M,Salerno L,Russo F,Cagnotto A,Goegan M,Mennini T

    更新日期:2002-02-01 00:00:00

  • Use of a deoxynojirimycin-fluorophore conjugate as a cell-specific imaging probe targeting α-glucosidase on cell membranes.

    abstract::Molecules designed for cell-specific imaging were studied, taking advantage of an enzyme-inhibitor interaction. 1-Deoxynojirimycin (DNJ) can be actively captured by cells which express the surface membrane protein α-glucosidase. New probes composed of DNJ for recognition linked to a fluorophore signal portion were pre...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Hatano A,Kanno Y,Kondo Y,Sunaga Y,Umezawa H,Fukui K

    更新日期:2019-03-01 00:00:00

  • Design and synthesis of novel androgen receptor antagonists with sterically bulky icosahedral carboranes.

    abstract::Carboranes (dicarba-closo-dodecaboranes) are a class of carbon-containing polyhedral boron-cluster compounds having remarkable chemical and thermal stability, and hydrophobic character. These features may allow application of carboranes as a new hydrophobic core structure in biologically active molecules that interact...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Goto T,Ohta K,Suzuki T,Ohta S,Endo Y

    更新日期:2005-12-01 00:00:00

  • Variations in the C-unit of bedaquiline provides analogues with improved biology and pharmacology.

    abstract::Analogues of the anti-tuberculosis drug bedaquiline, bearing a 3,5-dimethoxy-4-pyridyl C-unit, retain high anti-bacterial potency yet exert less inhibition of the hERG potassium channel, in vitro, than the parent compound. Two of these analogues (TBAJ-587 and TBAJ-876) are now in preclinical development. The present s...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sutherland HS,Tong AST,Choi PJ,Blaser A,Franzblau SG,Cooper CB,Upton AM,Lotlikar M,Denny WA,Palmer BD

    更新日期:2020-01-01 00:00:00

  • Induction of potent cell growth inhibition by schizophyllan/K-ras antisense complex in combination with gemcitabine.

    abstract::Antisense oligonucleotides (AS-ODNs) specifically hybridize with target mRNAs, resulting in interference with the splicing mechanism or the regulation of protein translation. In our previous reports, we demonstrated that β-glucan schizophyllan (SPG) can form a complex with AS-ODNs attached with oligo deoxyadenosine dA...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sasaki S,Izumi H,Morimoto Y,Sakurai K,Mochizuki S

    更新日期:2020-09-15 00:00:00

  • Structural insights into binding of inhibitors to soluble epoxide hydrolase gained by fragment screening and X-ray crystallography.

    abstract::Soluble epoxide hydrolase (sEH) is a component of the arachidonic acid cascade and is a candidate target for therapies for hypertension or inflammation. Although many sEH inhibitors are available, their scaffolds are not structurally diverse, and knowledge of their specific interactions with sEH is limited. To obtain ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Amano Y,Yamaguchi T,Tanabe E

    更新日期:2014-04-15 00:00:00

  • Synthesis and biological evaluation of pyrimidine derivatives as novel human Pin1 inhibitors.

    abstract::Pin1 (Protein interacting with NIMA1) is a cis-trans isomerase and promotes the amide bond rotation of phosphoSer/Thr-Pro motifs in its substrates. Inhibition of Pin1 might be a novel strategy for developing anticancer agents. Herein, a series of pyrimidine derivatives were synthesized and their Pin1 inhibitory activi...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Cui G,Jin J,Chen H,Cao R,Chen X,Xu B

    更新日期:2018-05-01 00:00:00

  • 1-Benzazepin-2-one calcium channel blockers--VI. Receptor-binding model and possible relationship to desmethoxyverapamil.

    abstract::We have prepared a series of potent antihypertensive 1-benzazepin-2-one calcium channel blockers (CCBs) 1 that are structurally related to diltiazem 2. Structural studies and the preparation of conformationally constrained analogs of 1-benzazepin-2-ones have led us to postulate a receptor-bound conformation for both 1...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kimball SD,Hunt JT,Barrish JC,Das J,Floyd DM,Lago MW,Lee VG,Spergel SH,Moreland S,Hedberg SA

    更新日期:1993-10-01 00:00:00

  • Activity landscape modeling of PPAR ligands with dual-activity difference maps.

    abstract::Activation of peroxisome proliferator-activated receptor (PPAR) subtypes offers a promising strategy for the treatment of diabetes mellitus and metabolic diseases. Selective and dual PPAR agonists have been developed and the systematic characterization of their structure-activity relationships (SAR) is of major signif...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Méndez-Lucio O,Pérez-Villanueva J,Castillo R,Medina-Franco JL

    更新日期:2012-06-01 00:00:00

  • Benzanilides with spasmolytic activity: chemistry, pharmacology, and SAR.

    abstract::The following study describes the synthesis of new benzanilide derivatives and their pharmacological investigation on smooth muscle preparations of guinea pigs. All compounds were synthesized in good yields and showed a spasmolytic activity without significant effect on vascular smooth muscles and heart muscle prepara...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Brunhofer G,Handler N,Leisser K,Studenik CR,Erker T

    更新日期:2008-06-01 00:00:00

  • Evaluation of 1,2,5-thiadiazoles as modulators of M₁/M₅ muscarinic receptor subtypes.

    abstract::Studies have demonstrated the presence of allosteric binding sites on each of the muscarinic acetylcholine receptor (mAChR) subtypes. Since most drugs targeting muscarinic receptors bind to the highly conserved orthosteric binding site, they fail to achieve appreciable subtype selectivity. Targeting non-conserved allo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Maheshwari A,Rao PS,Messer WS Jr

    更新日期:2014-03-15 00:00:00

  • Synthesis and anticonvulsant activity of aromatic tetramethylcyclopropanecarboxamide derivatives.

    abstract::As part of our ongoing research on potential new antiepileptic drugs (AEDs), a series of tetramethylcyclopropanecarboxamide derivatives containing benzene ring were designed, synthesized, and evaluated for anticonvulsant activities in the murine maximal electroshock (MES) and subcutaneous pentylenetetrazole (scMet) se...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Shimshoni JA,Bialer M,Yagen B

    更新日期:2008-06-01 00:00:00

  • Synthesis, biological evaluation and molecular modeling study of 2-amino-3,5-disubstituted-pyrazines as Aurora kinases inhibitors.

    abstract::Serine/threonine protein kinases Aurora A, B, and C play essential roles in cell mitosis and cytokinesis, and a number of Aurora kinase inhibitors have been evaluated in the clinic. Herein we report the synthesis and their antiproliferation of 3,5-disubstituted-2-aminopyrazines as kinases inhibitors. Amongst, 4-((3-am...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Bo YX,Xiang R,Xu Y,Hao SY,Wang XR,Chen SW

    更新日期:2020-03-01 00:00:00

  • The role of dicarbonyl compounds in non-enzymatic crosslinking: a structure-activity study.

    abstract::The Maillard reaction is a complex network of reactions that has been shown to result in the non-enzymatic crosslinking of proteins. Recent attention has focussed on the role of alpha-dicarbonyl compounds as important in vivo contributors to protein crosslinking but, despite extensive research, the molecular mechanism...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Meade SJ,Miller AG,Gerrard JA

    更新日期:2003-03-20 00:00:00

  • Synthesis and antibacterial activity of novel 4-pyrrolidinylthio carbapenems Part IV. 2-Alkyl substituents containing cationic heteroaromatics linked via a C-C bond.

    abstract::The synthesis and biological activity of a novel series of 2-alkyl-4-pyrrolidinylthio-beta-methylcarbapenems containing a variety of cationic heteroaromatic substituents linked via a C-C bond is described. As a result of these studies, we selected FR21818 (In) as a candidate compound for development. FR21818 exhibited...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zam HA,Barrett D,Tanaka A,Sasaki H,Matsuda K,Sakurai M,Terasawa T,Shirai F,Chiba T,Matsumoto Y,Tawara S

    更新日期:2001-04-01 00:00:00

  • Identification of selective inhibitors of sphingosine kinases 1 and 2 through a structure-activity relationship study of 4-epi-jaspine B.

    abstract::We recently reported that 4-epi-jaspine B exhibits potent inhibitory activity towards sphingosine kinases (SphKs). In this study, we investigated the effects of modifying the 2-alkyl group, as well as the functional groups on the THF ring of 4-epi-jaspine B using a diversity-oriented synthesis approach based on a late...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ohno H,Honda M,Hamada N,Miyagaki J,Iwata A,Otsuki K,Maruyama T,Nakamura S,Nakanishi I,Inuki S,Fujii N,Oishi S

    更新日期:2017-06-15 00:00:00