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PubMed1997

Heparinization of gas plasma-modified polystyrene surfaces and the interactions of these surfaces with proteins studied with surface plasmon resonance.

Polystyrene surfaces obtained by spin-coating a solution of polystyrene in toluene on a gold layer were functionalized with carboxylic acid groups by preadsorption of the sodium salt of undecylenic acid, followed by an argon plasma treatment. A conjugate of albumin and heparin (alb-hep) was covalently immobilized onto the functionalized surface via preactivation of carboxylic acid groups with a water-soluble carbodiimide. The immobilization of alb-hep conjugate and the subsequent interactions of the heparinized surface with antithrombin III (ATIII, a heparin cofactor) and thrombin were monitored with surface plasmon resonance (SPR). The surface concentration of conjugate as determined with SPR deviated quantitatively from the results obtained with radiolabelled conjugate. The difference in surface concentrations of conjugate obtained with the two methods probably originates from the uncertainty of the refractive index of the alb-hep conjugate in the SPR technique. ATIII could be bound to the surface modified with alb-hep conjugate but not to a polystyrene surface modified with albumin. Rabbit anti-human ATIII did bind to the alb-hep surface previously exposed to ATIII, confirming the presence of surface bound ATIII. The alb-hep immobilized surface was able to bind much more thrombin than ATIII, which is probably due to the less specific heparin-thrombin interaction as compared to the heparin-ATIII interaction. This study shows that SPR is a technique that can be used to study, in real time, both the modification of polymer surfaces and the subsequent interactions of the modified surfaces with proteins.

Albumins↗
PubMed2004

Structure-activity relationship of conjugated linoleic acid and its cognates in inhibiting heparin-releasable lipoprotein lipase and glycerol release from fully differentiated 3T3-L1 adipocytes.

Conjugated linoleic acid (CLA) reduces body fat in part by inhibiting the activity of heparin-releasable lipoprotein lipase (HR-LPL) activity in adipocytes, an effect that is induced by the trans-10,cis-12 CLA isomer. In this study we used a series of compounds that are structurally related to CLA (i.e., CLA cognates) to investigate the structural basis for this phenomenon. None of the 18:1 CLA cognates that were tested, nor trans-9,cis-12 18:2, cis-12-octadecen-10-ynoic acid (10y,cis-12) or 11-(2'-(n-pentyl)phenyl)-10-undecylenic acid (designated P-t10), exhibited any significant effect on HR-LPL activity. Among the CLA derivatives (alcohol, amide, and chloride) that were tested, only the alcohol form inhibited HR-LPL activity, although to a lesser extent than CLA itself. In addition, intracellular TG was reduced only by trans-10,cis-12 CLA and the alcohol form of CLA. Hence it appears that the trans-10,cis-12 conjugated double bond in conjunction with a carboxyl group at C-1 is required for inhibition of HR-LPL activity, and that an alcohol group can partially substitute for the carboxyl group. We also studied glycerol release from the cells, observing that this was enhanced by trans-10 18:1, trans-13 18:1, cis-12 18:1, cis-13 18:1, P-t10 but was reduced by cis-9 18:1, the alcohol and amide forms of CLA or 10y,cis-12. Accordingly the structural feature or features involved in regulating lipolysis appear to be more complex. Despite enhancing lipolysis in cultured 3T3-L1 adipocytes, trans-10 18:1 did not reduce body fat gain when fed to mice.

3T3-L1 Cells↗
PubMed2002

Antioxidant and cyclooxygenase activities of fatty acids found in food.

Several commercially available C-8 to C-24 saturated and unsaturated fatty acids (1-29) were assayed for cyclooxygenase-I (COX-I) and cyclooxygenase-II (COX-II) inhibitory and antioxidant activities. Among the saturated fatty acids tested at 60 microg mL(-1), there was an increase in antioxidant activity with increasing chain length from octanoic acid to myristic acid (C-8-C-14) and a decrease thereafter. All unsaturated fatty acids tested at 60 microg mL(-1) showed good antioxidant activity except for undecylenic acid (12), cis-5-dodecenoic acid (13), and nervonic acid (29). The highest inhibitory activities among the saturated fatty acids tested on cyclooxygenase enzymes COX-I and COX-II were observed for decanoic acid to lauric acid (3-5) at 100 microg mL(-1). Similarly, among the unsaturated fatty acids tested, the highest activities were observed for cis-8,11,14-eicosatrienoic acid (25) and cis-13,16-docosadienoic acid (27) at 100 microg mL(-1).

Animals↗
PubMed2006

Synthesis and HPLC evaluation of carboxylic acid phases on a hydride surface.

Three organic moieties containing carboxylic acid functional groups are attached to a particulate silica surface through silanization/hydrosilation. Two compounds (undecylenic acid and 10-undecynoic acid) have 11 carbon chains and the other is a five-carbon acid (pentenoic acid). Bonding is confirmed through carbon elemental analysis, diffuse reflectance infrared fourier transform spectroscopy, and carbon-13 and silicon-29 CP-MAS NMR spectroscopy. The bonded phases are tested by HPLC using PTH amino acids, nucleic acids, theophylline-related compounds, anilines, benzoic acid compounds, choline, and tobramycin. The latter two compounds are used to investigate the aqueous normal phase properties of the three bonded materials.

Amino Acids↗
PubMed2006

Controlling electroosmotic flow in poly(dimethylsiloxane) separation channels by means of prepolymer additives.

The electroosmotic flow (EOF) in a poly(dimethylsiloxane) (PDMS) separation channel can be altered and controlled by adding a carboxylic acid to the prepolymer prior to curing. When the prepolymer is doped with 0.5 wt % undecylenic acid (UDA), the electroosmotic mobility in a modified PDMS channel rises to (7.6 +/- 0.2) x 10(-4) cm(2) V(-1) s(-1) (in HEPES buffer at pH 8.5), which is nearly twice that in the native PDMS channel. Because this modification does not significantly change the hydrophobicity of the PDMS surface, it is possible to combine the modified PDMS with a dynamic coating of n-dodecyl beta-d-maltoside (DDM), which prevents protein sticking (see Huang, B.; Wu, H. K.; Kim, S.; Zare, R. N. Lab Chip 2005, 5, 1005-1007). The modified PDMS channel with a dynamic coating of DDM generates an electroosmotic mobility of (5.01 +/- 0.09) x 10(-4) cm(2) V(-1) s(-1), which shows excellent reproducibility both in successive runs and during storage in water. Combining this surface modification and the dynamic coating of DDM is an effective means for both providing stable EOF in the PDMS channels and preventing protein adsorption on the channel walls. To demonstrate these effects, we show that the electrophoretic separation of immunocomplexes in free solution can be readily accomplished in a microfluidic chip made of UDA-doped (0.5 wt %) PDMS with a dynamic coating of DDM.

Dimethylpolysiloxanes↗
PubMed2004

Formation, characterization, and chemistry of undecanoic acid-terminated silicon surfaces: patterning and immobilization of DNA.

This paper describes a simple strategy for DNA immobilization on chemically modified and patterned silicon surfaces. The photochemical modification of hydrogen-terminated Si(111) with undecylenic acid leads to the formation of an organic monolayer covalently attached to the surface through Si-C bonds without detectable reaction of the carboxylic acid group, providing indirect support of a free radical mechanism. Chemical activation of the acid function was achieved by a simple chemical route using N-hydroxysuccinimide (NHS) in the presence of N-ethyl-N'-(3-dimethylaminopropyl) carbodiimide hydrochloride. Single strand DNA with a 5'-dodecylamine group was then coupled to the NHS-activated surface by amide bond formation. Using a previously reported chemical patterning approach, we have shown that DNA can be immobilized on silicon surfaces in spatially well-resolved domains. Methoxytetraethyleneglycolamine was used to inhibit nonspecific adsorption. The resulting DNA-modified surfaces have shown good specificity and chemical and thermal stability under hybridization conditions. The sequential reactions on the surface were monitored by ATR-FTIR, X-ray Photoelectron Spectroscopy, and fluorescence spectroscopy.

DNA↗
PubMed2004

Surface functionalization of silicon nanoparticles produced by laser-driven pyrolysis of silane followed by HF-HNO3 etching.

CO2 laser induced pyrolysis of silane was used to produce silicon nanoparticles with an average diameter as small as 5 nm at high rates (up to 200 mg/h). Etching these particles with a mixture of hydrofluoric acid (HF) and nitric acid (HNO3) reduces their size and passivates their surface such that they exhibit bright visible photoluminescence (PL). This paper describes the attachment of organic molecules to hydrogen-terminated and hydroxyl-terminated surfaces of these nanoparticles. Stable particle dispersions in various solvents were obtained by treatment of hydrogen-terminated surfaces with octadecene or undecylenic acid and by treatment of hydroxyl-terminated surfaces with octadecyltrimethoxysilane. Transmission electron microscopy showed that the surface-functionalized particles were well dispersed and crystalline. FTIR spectroscopy confirmed the expected reactions of the organic molecules with the particle surfaces. Photoluminescence measurements showed that surface treatment significantly stabilized the PL properties of the nanoparticles against degradation. Size selective precipitation was applied to particle dispersions and allowed some narrowing and tuning of the PL spectrum.

Journal Article↗
PubMed1979

Bioavailability of oral testosterone in males.

Twenty-six male volunteers received a single oral dose of testosterone as free crystals or as the undecanoate ester. The latter was given either in crystalline form or in arachis oil. All preparations were tested three times in the same individual, whilst fasting on 2 days and on one day together with a breakfast rich in fat. Serum testosterone concentration was measured at intervals for up to 6--24 h after the dose. A significant and reproducible rise in serum testosterone level was found after ingestion of free testosterone. Testosterone esterified with undecylenic acid was only effective when administered in arachis oil. The meal increased the bioavailability of the ester, but had hardly any effect on that of the free hormone. It is concluded that bioavailability of oral testosterone can be improved by pharmaceutical means to an extent sufficient to produce adequate blood levels in substitution therapy.

Administration, Oral↗
PubMed2006

Novel stimuli-responsive micelle self-assembled from Y-shaped P(UA-Y-NIPAAm) copolymer for drug delivery.

A new amphiphilic Y-shaped copolymer, comprised of hydrophobic poly(undecylenic acid) (PUA) and hydrophilic poly(N-isopropylacrylamide) (PNIPAAm), was designed and synthesized. A cytotoxicity study revealed that P(UA-Y-NIPAAm) copolymers did not exhibit apparent inhibition impact on the proliferation of cells when the concentration of the copolymer was below 1000 mg/L. Characterization demonstrated that the P(UA-Y-NIPAAm) copolymer is thermosensitive with a lower critical solution temperature (LCST) of 31 degrees C. In water, the P(UA-Y-NIPAAm) copolymer would self-assemble into micelles with a critical micelle concentration (CMC) of 20 mg/L. Self-assembled P(UA-Y-NIPAAm) micelles exhibited a nanospherical morphology of 40 to approximately 80 nm in size. The controlled drug release behavior of the P(UA-Y-NIPAAm) micelles was further investigated, and self-assembled micelles exhibited improved properties in controlled drug release.

3T3 Cells↗
PubMed2006

Grazing angle mirror-backed reflection (GMBR) for infrared analysis of monolayers on silicon.

An easy handling infrared measurement, grazing angle mirror-backed reflection (GMBR), has been established to analyze the silicon-based organic monolayer. Theoretical prediction gave the optimal configuration with p-polarized irradiation near a grazing angle 78.1 degrees of incidence. Experimental measurement of hydrogen-terminated, undecylenic acid (UA) and N-hydroxysuccinimide (NHS) functionalized silicon (111) surfaces showed good signal peaks and reproducibility.

Letter↗
PubMed2004

X-ray studies of self-assembled organic monolayers grown on hydrogen-terminated Si(111).

The structure of self-assembled monolayers (SAMs) of undecylenic acid methyl ester (SAM-1) and undec-10-enoic acid 2-bromo-ethyl ester (SAM-2) grown on hydrogen-passivated Si(111) were studied by X-ray reflectivity (XRR), X-ray standing waves (XSW), X-ray fluorescence (XRF), atomic force microscopy, and X-ray photoelectron spectroscopy (XPS). The two different SAMs were grown by immersion of H-Si(111) substrates into the two different concentrated esters. UV irradiation during immersion was used to create Si dangling bond sites that act as initiators of the surface free-radical addition process that leads to film growth. The XRR structural analysis reveals that the molecules of SAM-1 and SAM-2 respectively have area densities corresponding to 50% and 57% of the density of Si(111) surface dangling bonds and produce films with less than 4 angstroms root-mean-square roughness that have layer thicknesses of 12.2 and 13.2 angstroms. Considering the molecular lengths, these thicknesses correspond to a 38 degrees and 23 degrees tilt angle for the respective molecules. For SAM-2/Si(111) samples, XRF analysis reveals a 0.58 monolayer (ML) Br total coverage. Single-crystal Bragg diffraction XSW analysis reveals (unexpectedly) that 0.48 ML of these Br atoms are at a Si(111) lattice position height that is identical to the T1 site that was previously found by XSW analysis for Br adsorbed onto Si(111) from a methanol solution and from ultrahigh vacuum. From the combined XPS, XRR, XRF, and XSW evidence, it is concluded that Br abstraction by reactive surface dangling bonds competes with olefin addition to the surface.

Hydrogen↗
PubMed1991

Protein-ubiquinone interaction in bovine heart mitochondrial succinate-cytochrome c reductase. Synthesis and biological properties of fluorine substituted ubiquinone derivatives.

To investigate the protein-ubiquinone interaction in the bovine heart mitochondrial succinate-cytochrome c reductase region of the respiratory chain, three fluorine substituted ubiquinone derivatives, 2,3-dimethoxy-6-(9'-fluorodecyl)-1,4-benzoquinone (9FQ), 2-methoxy-5-trifluoromethyl-6-decyl-1,4-benzoquinone (TFQ), and 2-methoxy-5-trifluoromethyl-6-(9'-fluorodecyl)-1,4-benzoquinone (9FTFQ), were synthesized. 9FQ was synthesized by radical coupling of Q0 and bis(10-fluoroundecanoyl)peroxide. The latter was prepared by fluorination of undecylenic acid followed by thionylchloride treatment and peroxidation. TFQ was synthesized from 2,2,2-trifluoro-p-cresol by methylation, nitration, reduction, acetylation, nitration, reduction, oxidation, and radical alkylation. 9FTFQ was prepared by the radical alkylation of 2-methoxy-5-trifluoromethyl-1,4-benzoquinone with bis(10-fluoroundecanoyl)peroxide. All three fluoro-Q derivatives are active (greater than 50% the activity of 2,3-dimethoxy-5-methyl-6-decyl-1,4-benzoquinone) when used as electron acceptors for succinate-ubiquinone reductase. However, only 9FQ is active when used as an electron donor for ubiquinol-cytochrome c reductase or as an electron mediator for succinate-cytochrome c reductase. Both TFQ and 9FTFQ are competitive inhibitors for ubiquinol-cytochrome c reductase. A 19FNMR peak-broadening effect was observed for 9FQ when it was reconstituted with ubiquinone-depleted ubiquinol-cytochrome c reductase. A drastic up-field chemical shift was observed for TFQ when it was reconstituted with ubiquinone-depleted reductase. These results indicate that the binding environments of the benzoquinone ring and the alkyl side chain of the Q molecule are different. The strong up-field chemical shift for TFQ, and lack of significant chemical shift for 9FQ, suggest that the benzoquinone ring is bound near the paramagnetic cytochrome b heme.

Animals↗
PubMed1996

Topical antifungal agents: an update.

So many topical antifungal agents have been introduced that it has become very difficult to select the proper agent for a given infection. Nonspecific agents have been available for many years, and they are still effective in many situations. These agents include Whitfield's ointment, Castellani paint, gentian violet, potassium permanganate, undecylenic acid and selenium sulfide. Specific antifungal agents include, among others, the polyenes (nystatin, amphotericin B), the imidazoles (metronidazole, clotrimazole) and the allylamines (terbinafine, naftifine). Although the choice of an antifungal agent should be based on an accurate diagnosis, many clinicians believe that topical miconazole is a relatively effective agent for the treatment of most mycotic infections. Terbinafine and other newer drugs have primary fungicidal effects. Compared with older antifungal agents, these newer drugs can be used in lower concentrations and shorter therapeutic courses. Studies are needed to evaluate the clinical efficacies and cost advantages of both newer and traditional agents.

Administration, Topical↗