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PubMed1999

Preparation and pharmacological evaluation of novel glycoprotein (Gp) IIb/IIIa antagonists. 1. The selection of naphthalene derivatives.

The synthesis and design using molecular modeling techniques for non-peptide, low molecular weight novel fibrinogen receptor (glycoprotein IIb/IIIa: Gp IIb/IIIa) antagonists, is reported. We used a highly potent serine protease inhibitor, Nafamostat, having an amidinonaphthyl unit as the starting compound. The compounds 4-(6-amidino-2-naphthylaminocarbonyl)phenoxyacetic acid (5a) and 4-(6-amidino-2-naphthalenecarboxamido)phenoxyacetic acid (5b) inhibited adenosin-5'-diphospate (ADP)-induced aggregation of human platelet-rich plasma (PRP) with IC50 values of 0.05 and 0.07 microM, respectively, and had lost their ability to inhibit a variety of serine proteases, including thrombin, factor Xa, plasmin and trypsin.

Adenosine Diphosphate↗
PubMed1989

Uptake of phenylacetic acid by Penicillium chrysogenum Wis 54-1255: a critical regulatory point in benzylpenicillin biosynthesis.

The transport system of phenylacetic acid (PA) in Penicillium chrysogenum was studied. Kinetic measurements were carried out "in vivo" at 25 degrees C in 0.06 M phosphate buffer at pH 6.5. Uptake was a linear function of time over 3 minutes and the Km was 5.2 microM. PA uptake was inhibited by 2,4-dinitrophenol, 4-nitrophenol, sodium azide, potassium cyanide. N-ethylmaleimide, amino acids, xylose and fatty acids whereas lactose and ribose stimulated it. Benzylpenicillin, phenoxymethylpenicillin, penicillins DF, K and 6-aminopenicillanic acid did not modify uptake whereas phenoxyacetic acid and many phenyl derivatives strongly inhibited the incorporation of PA. PA transport is an inducible system that is strictly regulated by the carbon source used for P. chrysogenum growth. Uptake is not induced by phenoxyacetic acid and is repressed by L-lysine. The absence of the PA transport system when P. chrysogenum is grown in the presence of readily metabolized sugars and its repression by L-lysine suggests that this is a critical regulatory point in the control of benzylpenicillin biosynthesis.

Amino Acids↗
PubMed2002

Behavioral responses of the ciliated protozoan Paramecium caudatum to 2,4-dichlorophenoxyacetic acid and its analogues.

We found that the ciliated protozoan Paramecium caudatum ON-1 was repelled by 2,4-dichlorophenoxyacetic acid (2,4-D). P. caudatum was also repelled by phenoxyacetic acid, while it was attracted to benzoic acid. No significant behavioral response was detected with 2,4-dichlorophenol (2,4-DP) and phenol. These results suggested that the substitution of-OH of phenol with -OCH2COOH, but not the chlorination of phenol, was important for eliciting the avoiding response to 2,4-D in P. caudatum. Electrophysiological analysis revealed that 2,4-D and phenoxyacetic acid were able to trigger the action potential in P. caudatum, whereas 2,4-DP and phenol failed to elicit electrical responses in this organism. Well test assays suggested that the avoiding reactions allowed P. caudatum to escape from the harm caused by this herbicide.

Journal Article↗
PubMed1986

Agricultural herbicide use and risk of lymphoma and soft-tissue sarcoma.

A population-based case-control study of soft-tissue sarcoma (STS), Hodgkin's disease (HD), and non-Hodgkin's lymphoma (NHL) in Kansas found farm herbicide use to be associated with NHL (odds ratio [OR], 1.6; 95% confidence interval [CI], 0.9, 2.6). Relative risk of NHL increased significantly with number of days of herbicide exposure per year and latency. Men exposed to herbicides more than 20 days per year had a sixfold increased risk of NHL (OR, 6.0; 95% CI, 1.9, 19.5) relative to nonfarmers. Frequent users who mixed or applied the herbicides themselves had an OR of 8.0 (95% CI, 2.3, 27.9) for NHL. Excesses were associated with use of phenoxyacetic acid herbicides, specifically 2,4-dichlorophenoxyacetic acid. Neither STS nor HD was associated with pesticide exposure. This study confirms the reports from Sweden and several US states that NHL is associated with farm herbicide use, especially phenoxyacetic acids. It does not confirm the case-control studies or the cohort studies of pesticide manufacturers and Vietnam veterans linking herbicides to STS or HD.

Adult↗
PubMed1984

Effect of phenoxy acids on rat liver regeneration.

Phenoxy-acids incorporated in a basal region on a weight basis, were fed to male rats from which two-thirds of the liver had been removed and the extent of regeneration or the liver increment was ascertained over a period of 10 days p.o. Stimulatory responses occurred with the hypolipidemic drugs, ethyl clofibrate, at levels of 0.25% higher or by gavage over the 1st 8 days p.o. at an overall dosage of 1275 mg/kg, 2-(p-chlorophenoxy)propionic acid (0.50, 1.0%), the corresponding o-chloro-acids (0.20 and 0.50%, respectively) and several other with branching of the acid side-chain. The latter included phenoxyisobutyric acid (0.50%), 2-phenoxypropionic acid (1.0%), 2-phenoxybutyric acid (1.0%), the phenoxydimethyl-pentanoic acid, gemfibrozil (0.40%), the herbicide, 2-(2,4,5-trichlorophenoxy)propionic acid (0.10%) and as screened on a few males, possibly, halofenate (0.20%). The liver increments were in the control range for compounds containing straight chain acid substituents as 4-(p-chlorophenoxy)-butyric acid (0.35%), 3-phenoxypropionic acid (0.75%), 3-(p-chlorophenoxy)-1,2-propanediol (0.50%) and phenoxyacetic acid derivatives, including p-chloroacetic acid and the herbicides 2,4-dichlorophenoxy-, 2-methyl-4-chlorophenoxy- and 2,4,5-trichlorophenoxyacetic acids at levels of up to about 0.50%. Where effects resulted with the phenoxyacetic acids, these were in the direction of inhibition of the regenerative process. The response of the female rat to clofibrate either by diet or gavage was rather poor or equivocal but was more definite with 2-(2,4,5-trichlorophenoxy)propionic acid (0.10%). However, intact females were more consistent in eliciting wet and dry liver enlargement with clofibrate (0.25%) as noted earlier by others and with gemfibrizol (0.040%) and the trichlorophenoxypropionic acid (0.10%) but not with 2,4,5-trichlorophenoxyacetic acid at 0.10%.

Animals↗
PubMed2004

Combinatorial formulation of biocatalyst preparations for increased activity in organic solvents: salt activation of penicillin amidase.

A combinatorial experimental technique was used to identify salts and salt mixtures capable of activating penicillin amidase in organic solvents for the transesterification of phenoxyacetate methyl ester with 1-propanol. Penicillin amidase was lyophilized in the presence of various chloride and acetate salts within 96-deep-well plates and catalytic rates measured to determine lead candidates for highly salt-activated preparations. The kinetics of the most active formulations were then further evaluated. These studies revealed that a formulation consisting of 98% (w/w) of a 1:1 KAc:CsCl salt mixture, 1% (w/w) enzyme, and 1% (w/w) potassium phosphate buffer was approximately 35,000-fold more active than the salt-free formulation in hexane, as reflected in values of V(max)/K(m). This extraordinary activation could be extended to more polar solvents, including tert-amyl alcohol, and to formulations with lower total salt contents. A correlation was found between the kosmotropic/chaotropic behavior of the salts (as measured by the Jones-Dole B coefficients) and the observed activation. Strongly chaotropic cations combined with strongly kosmotropic anions yielded the greatest activation, and this is likely due to the influence of the ions on protein-water and protein-salt interactions.

1-Propanol↗
PubMed2005

Determination of dissociation constants of compounds with potential cognition enhancing activity by capillary zone electrophoresis.

Accurate determination of pK(a) values is important for proper characterization of newly synthesized molecules. In this work we have used CZE for determination of pK(a) values of new compounds prepared from intermediates, 2, 3 and 4-(2-chloro-acetylamino)-phenoxyacetic acids, by substituting chloride for 2-oxo-pyrrolidine, 2-oxo-piperidine or 2-oxo-azepane. These substances are expected to have a cognition enhancing activity and free radicals scavenging effect. Measurements were performed in a polyacrylamide-coated fused-silica capillary of 0.075 mm ID using direct UV detection at 254 nm. Three electrolyte systems were used for measurements to eliminate effects of potential interactions between tested compounds and components of the BGE. In the pH range 2.7-5.4, chloride, formate, acetate and phosphate were used as BGE co-ions, and sodium, beta-alanine and epsilon-aminocaproate as counterions. Mobility standards were measured simultaneously with the tested compounds for calculations of correct electrophoretic mobilities. Several approaches for the calculation of the pK(a) values were used. The values of pK(a) were determined by standard point-to-point calculation using Henderson-Hasselbach equation. Mobility and pH data were also evaluated by using nonlinear regression. Three parameter sigmoidal function fitted the experimental data with correlation coefficients higher than 0.99. Results from CZE measurements were compared with spectrophotometric measurements performed in sodium formate buffer solutions and evaluated at wavelength where the highest absorbance difference for varying pH was recorded. The experimental pK(a) values were compared with corresponding values calculated by the SPARC online calculator. Results of all three used methods were in good correlation.

Aminocaproic Acid↗
PubMed1993

A colorimetric assay for penicillin-V amidase.

The hydrolysis of penicillin-V to phenoxyacetic acid and 6-aminopenicillanic acid by the fungal enzyme penicillin-V amidase is of industrial importance since the 6-aminopenicillanic acid produced is an intermediate for semisynthetic penicillins. A rapid colorimetric assay of penicillin-V amidase was developed which uses 2-nitro-5-(phenoxyacetamido)-benzoic acid as a substrate. The released chromophore, 2-amino-5-nitrobenzoic acid, was detected at 405 nm. Using penicillin-V amidase from the fungus Fusarium oxysporum, the KM and Vmax for this substrate were 0.89 mM and 2.6 mumol/min/mg enzyme, respectively. Hydrolysis could be competitively inhibited by penicillin-V with a Ki of 4 mM. The change in the initial velocity of hydrolysis of 2-nitro-5-(phenoxyacetamido)-benzoic acid at 500 microM was linear over the range of 0.5 to 10 micrograms/ml enzyme. These results show that this new compound is useful in determining the presence and levels of penicillin-V amidase.

Colorimetry↗
PubMed1994

Utilization of side-chain precursors for penicillin biosynthesis in a high-producing strain of Penicillium chrysogenum.

Utilization of the side-chain precursors phenoxyacetic acid (POA) and phenylacetic acid (PA) for penicillin biosynthesis by Penicillium chrysogenum was studied in shake flasks. Precursor uptake and penicillin production were followed by HPLC analysis of precursors and products in the medium and in the cells. P. chrysogenum used both POA and PA as precursors, producing phenoxymethylpenicillin (penicillin V) and benzylpenicillin (penicillin G), respectively. If both precursors were present simultaneously, the formation of penicillin V was blocked and only penicillin G was produced. When PA was added at different times to cells that were induced initially for POA utilization and were producing penicillin V, the POA utilization and penicillin V formation were blocked, whereas the cells started utilizing PA and produced penicillin G. The blocking of the POA turnover lasted for as long as PA was present in the medium. If POA was added to cultures induced initially for PA utilization and producing penicillin G, this continued irrespective of the presence of POA. Utilization of POA increased concomitant with depletion of PA from the medium. Analysis of cellular pools from a growing cell system with POA as precursor to which PA was added after 48 h showed that the cellular concentration of POA was kept high without production of penicillin V and at a concentration comparable to the concentration in the medium. The cellular concentration of POA was higher than the concentration of PA that was utilized for penicillin G production.

Biotechnology↗
PubMed1991

Characteristics of induction of peroxisomal fatty acid oxidation-related enzymes in rat liver by drugs. Relationships between structure and inducing activity.

To clarify the mechanism of induction of hepatic peroxisome-associated enzymes by drugs, we examined the interrelationship between the structures of fifteen drugs of two types (phenoxyacetic acid derivatives and perfluorinated compounds) and their inducing activities. Male Wistar rats were given the drugs at 150 mg/kg body weight daily for 2 weeks, and then hepatic activities of fatty acid metabolism-related enzymes were determined. The activity of the cyanide-insensitive fatty acyl-CoA oxidizing system located in peroxisomes was increased significantly in the following order: 2,4,5-trichlorophenoxypropionic acid (12.5-fold) greater than 2,4-dichlorophenoxypropionic acid (6.6-fold) greater than clofibrate (4.5-fold) greater than 2-methyl-4-chlorophenoxyacetic acid (2.6-fold) greater than 2,4,5-trichlorophenoxyacetic acid (2.5-fold) greater than p-chlorophenoxypropionic acid (2.4-fold) greater than 2,4-dichlorophenoxyacetic acid (1.7-fold). Treatment with perfluorinated compounds, perfluorobutyric acid, perfluorooctanoic acid, perfluorodecanoic acid and perfluorooctanol, also induced the activity by 2-, 4.3-, 3.1- and 2.0-fold respectively. The profile of the induction of carnitine acetyltransferase by these compounds was quite similar to that of cyanide-insensitive fatty acyl-CoA oxidizing system. Lipophilicity of these drugs was determined by the octanol-water partition method. Among these drugs, 2,4,5-trichlorophenoxypropionic acid showed the largest octanol/water partition coefficient (log P = 0.39). These results show a strong correlation among the number of chlor-substitutions on the phenyl moiety, the methyl-group on the alpha position of the acetic acid moiety, lipophilicity and the inducibility of peroxisomal fatty acid oxidation-related enzymes.

Animals↗
PubMed1996

The acid metabolite of ZD7114 is a partial agonist of lipolysis mediated by the rat beta 3-adrenoceptor.

Experiments were performed to characterise the lipolytic effects of the acid metabolite, ZM215001, ((S)-4-[2-hydroxy-3-phenoxy-propylamino-ethoxy] phenoxyacetic acid) of the putative beta 3-adrenoceptor agonist, ZD7114 ((S)-4-[2-hydroxy-3-phenoxy-propylamino-ethoxy]-N-(2-methoxyethyl) phenoxyacetamide) on isolated rat white adipocytes. ZM215001 was used for these studies since it is the predominant moiety after in vivo administration of ZD7114. The agonist properties of ZM215001 were assessed in comparison to the standard nonselective beta-adrenoceptor agonist (+/-)-isoprenaline and the beta 3-adrenoceptor-selective agonist BRL 37344. Isoprenaline, BRL 37344 and ZM215001 all stimulated the rate of free fatty acid release from isolated adipocytes with the order of potency being BRL > isoprenaline > ZM215001. The maximum effect of BRL 37344 was equivalent to that of isoprenaline, but ZM215001 achieved only 30% of the maximum isoprenaline response. ZM215001 competitively antagonised the lipolytic response to BRL 37344 (pA2 = 7.26), whereas the agonist effects of BRL 37344 were not antagonised competitively by the selective antagonists ICI 118551 and CGP 20712A, at concentrations which would be expected to block beta 1- and beta 2-adrenoceptors respectively. These results indicate that ZM215001 has low intrinsic activity at the rat adipocyte beta 3-adrenoceptor, and is a partial agonist of lipolysis in rat white adipocytes.

Adipocytes↗
PubMed1996

Pharmacological study of atypical beta-adrenoceptors in rat esophageal smooth muscle.

The chemical specificity for the beta-adrenoceptor mediated relaxation of rat esophageal smooth muscle was evaluated using selective and non-selective beta-adrenoceptor agonists and antagonists. Pindolol, ICI 89,406, ICI 118551 [erythro-1-(7-methylindan-4-yloxy)-3-(isopropylamine)-but an-2-ol] and the beta-adrenoceptor alkylating agent, pindobind, produced only small rightward shifts in the concentration-response curves of (-)-isoprenaline and (-)-trimetoquinol in this preparation. Rank order potency (pD2 values) of agonists was: (+/-)-trimetoquinol [1-(3',4',5'-trimethoxybenzyl)-6,7-dihydroxy-1,2,3, 4-tetrahydroisoquinoline] (8.34) = (-)-trimetoquinol (8.26) = BRL 37344 [(R* R*)-(+/-)-4-[2'-2-hydroxy 2-(3-chlorophenyl)ethylamino]propyl] phenoxyacetic acid] (8.16) = ICID7114 [(S)-4-(2-hydroxy- 3-phenoxy-propylamino-ethoxy)-N-(2-methoxyethyl) phenoxyacetamide] (8.03) > or = (-)-isoprenaline (7.82) > 3',5'-diiodotrimetoquinol [1-(3',5'-diiodo-4'-methoxybenzyl)-6, 7-dihydroxy-1,2,3,4-tetrahydroisoquinoline] (7.28) > 3'-iodotrimetoquinol [1-(3'-iodo-4',5'-dimethoxybenzyl)-6, 7-dihydroxy-1,2,3,4-tetrahydroisoquinoline] (7.04) > ractopamine (6.84) = 5,8-difluorotrimetoquinol [5,8-difluoro-6,7-dihydroxy-1- (3',4',5'-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline] (6.82) > 8-fluorotrimetoquinol [6,7-dihydroxy-8-fluoro-1-(3',4',5'- trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline] (6.56) > or = (-)-noradrenaline (6.46) > or = (-)-adrenaline (6.36) > (+/-)-noradrenaline (6.24) > (+/-)-adrenaline (6.00) > clenbuterol (5.83) > (-)-1-benzyl-6, 7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (5.75). Isomeric activity ratios of trimetoquinol isomers [(-)-(S)- > > (+)-(R)-] in esophageal smooth muscle in the presence and absence of 1 microM pindolol were 1995- and 2951-fold, respectively; and were much greater than those in rat atria (282-fold) and rat trachea (107-fold). The atypical beta/beta 3-adrenoceptor partial agonist, ICI D7114, produced concentration-dependent rightward shifts of the concentration-response curves of (-)-isoprenaline, (-)-trimetoquinol and the reference atypical beta/beta 3-adrenoceptor agonist, BRL 37344. Schild plot analysis of ICI D7114 against trimetoquinol gave slope and pA2 values of 0.91 and of 7.9, respectively. These results clearly demonstrate that the relaxant effects of these agonists in rat esophageal smooth muscle are primarily mediated through the activation of atypical beta/beta 3-adrenoceptors. (-)-Trimetoquinol was as potent as (-)- isoprenaline and BRL 37344, and was the most stereoselective agonist evaluated in this tissue system.

Adrenergic beta-1 Receptor Antagonists↗
PubMed1981

Angiotensin I recovery from plasma incubated with organic reagents.

(1) In order to explore the possible mechanism that organic reagents used in the incubation step of the plasma renin activity (PRA) analysis act as a angiotensinase inhibitors we did angiotensin I (AI) recovery studies from plasma with such reagents. The organic acids and their mean difference in percent recovery of AI as compared to that for hydrochloric acid (HCI) are respectively as follows for one and a three hour incubation time: maleic (0.7%, 4.5%); and potassium hydrogen phthalate (KHphthalate) (7.2%, 9.6%). The tris(hydroxymethyl)aminomethane (Tris) organic acid salts and their mean difference in percent recovery of AI as compared to that for Tris-HCl are as follows for a one hour incubation: Tris-acetylsalicylate (3.6%), Tris-phenoxyacetate (3.6%), Tris-benzoate (2.6%), and Tris-salicylate (4.9%). (2) Of the reagents studied KHphthalate after a three hour incubation produced a statistically significant difference from the HCl reagent. The recovery data for all the organic reagents suggested that the primary mechanism of action was not that of an angiotensinase inhibitory one.

Angiotensin I↗
PubMed1999

Polymer water-soluble derivatives of polypeptide antibiotic, gramicidin-S based on reactive copolymers of N-(2-hydroxypropyl) methacrylamide.

Copolymers of N-(2-hydroxypropyl)methacrylamide with p-nitrophenyl esters of unsaturated phenoxyacetic acids and N-methacryloylglycylleucine and with acrylic acid were synthesized as polymer carriers for obtaining water-soluble polymer forms of an antibiotic gramicidin-S. The kinetics of the aminolysis of copolymers of N-(2-hydroxypropyl) methacrylamide (HPMA) which contain reactive p-nitrophenoxycarbonyl groups by gramicidin-S were investigated. It was established that aminolysis rate depends on the structure of the bridge group which binds p-nitrophenoxycarbonyl group to the main chain of the copolymer. On the basis of these copolymers of HPMA polymer amide and salt derivatives of gramicidin-S were obtained and their composition was determined. It was shown, that the antibacterial activity of these polymer derivatives of gramicidin-S depends on the bond type of the antibiotic with the polymer and attains a relatively high level for polymer salts of gramicidin-S.

Acrylates↗
PubMed1989

Synthesis and investigation of effects of 2-[4- [[(arylamino)carbonyl]amino]phenoxy]-2-methylpropionic acids on the affinity of hemoglobin for oxygen: structure-activity relationships.

A series of 2-[4-[[[(substituted-phenyl)amino]carbonyl]amino]phenoxy]-2- methylpropionic acids and other substituted phenoxyacetic acids were synthesized and tested for their ability to reduce the affinity of hemoglobin for oxygen. 2-[4-[[[(3,4,5-trichlorophenyl)amino]carbonyl]amino]phenoxy]-2- methylpropionic acid was found to be the most potent compound known. Structure-activity relationships of the compounds synthesized are discussed.

Erythrocytes↗
PubMed2006

Novel selective orally active CRTH2 antagonists for allergic inflammation developed from in silico derived hits.

Hits from an in silico derived focused library for CRTH2 were transformed into highly selective antagonists with favorable ADME properties. Oral administration of 4-bromo-2-(1-phenyl-1H-pyrazole-4-carbonyl)phenoxyacetic acid (19) inhibited peribronchial eosinophilia and mucus cell hyperplasia in a mouse model of allergic asthma, supporting the therapeutic potential of this novel compound class. In addition, this selective pharmacological tool compound provides further evidence for CRTH2 as a relevant therapeutic target for treatment of Th2- and eosinophil-related inflammation.

Acetates↗
PubMed1996

Estrogenic triarylethylene acetic acids: effect of structural variation on estrogen receptor affinity and estrogenic potency and efficacy in MCF-7 cells.

Triarylethylenecarboxylic acids exemplified by (E,Z)-2-{4-[1-(p-hydroxyphenyl)-2-phenyl]-1-butenyl}phenoxyacetic acid (8) are a new class of estrogen receptor (ER) ligands capable of tissue selective estrogen agonist and antagonist effects. We report the syntheses of 8 and of analogues incorporating structural features known or anticipated to facilitate ER affinity in triarylethylenes. These studies revealed that the p-hydroxyphenyl moiety, ethylenic bond, and ether oxygen of 8 were all critical for high ER affinity. Although a 1,1-bisphenolic analogue bearing the p-(oxyacetic acid) moiety on its 2-phenyl ring, 12, had low ER affinity, it exhibited estrogenic potency approaching that of 8 in MCF-7 cells. Unlike 8 which was a partial agonist with weak antagonist potency, 12 was a full agonist. A similar profile of potency/efficacy in MCF-7 cells was seen in 9, an ethylenic bond saturated analogue of 8. Growth-promoting effects of 8, 9, and 12 were fully antagonized by the antiestrogen tamoxifen, suggesting that such effects were mediated solely via ER. Thus, our studies in MCF-7 cells have confirmed the estrogenicity of 8 and have enabled identification of two analogues with favorable estrogenic potency and full estrogen efficacy. On this basis, these three (triarylethylene)acetic acids have been selected for more intensive animal studies of their extrareproductive tract estrogenic effects.

Animals↗
PubMed1997

Anionic- and lipophilic-mediated surface binding inhibitors of human leukocyte elastase.

We report the synthesis of a series of diphenylmethane-based oligomers containing anionic and lipophilic functionalities that are potent inhibitors of human leukocyte elastase (HLE). The enzyme inhibition is regulated by the size of the oligomer, as well as, the number of charges. Lipophilicity is an important element in determining potency and specificity against other basic enzymes. Compounds whose scaffolds contain three phenoxyacetic acid groups and three alkyl ethers are competitive and specific inhibitors of HLE with Ki = 20 nM. The mechanism of action of this class of compounds is believed to involve multidendate interactions with the surface of HLE near the active site which prevents substrate access to the catalytic site.

Benzhydryl Compounds↗