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PubMed2005

Alkyl chain conformation and the electronic structure of octyl heavy chalcogenolate monolayers adsorbed on Au(111).

Adsorption states of dioctyl dichalcogenides (dioctyl disulfide, dioctyl diselenide, and dioctyl ditelluride) arranged on Au(111) have been studied by X-ray photoelectron spectroscopy (XPS), infrared-visible sum-frequency generation (SFG), and ultraviolet photoelectron spectroscopy (UPS). XPS measurements suggest that dioctyl dichalcogenides dissociatively adsorbed on Au(111) surfaces to form the corresponding monolayers having chalcogen-gold covalent bonds. The elemental compositions of octanechalcogenolates on Au(111) indicate that the saturation coverages of the octyl heavy chalcogenolate (OcSe, OcTe) monolayers are lower than that of the octanethiolate (OcS) self-assembled monolayers (SAMs). The SFG observations of the CH(2) vibrational bands for the heavy chalcogenolate monolayers strongly suggest that a discernible amount of gauche conformation exists in the monolayers, while OcS SAMs adopt highly ordered all-trans conformation. The intensity ratio of the symmetric and asymmetric CH(3) stretching vibration modes measured by SFG shows that the average tilt angle of the methyl group of the OcSe monolayers is greater than that of the OcS SAMs. The larger tilt angle of the methyl group and the existence of a discernible amount of gauche conformation in the OcSe monolayers are due to the lower surface coverage of the OcSe monolayers compared with the OcS SAMs. The smaller polarization dependence in the angle-resolved UPS (ARUPS) spectra of the OcSe monolayers than that of the OcS SAMs is caused by the more disordered structures of the alkyl chain in the former. XPS, SFG, and ARUPS measurements indicate a similar tendency for the OcTe monolayers. The density of states (DOS) observed by UPS at around 1.3 eV for OcS adsorbed on Au(111) is considered to be the antibonding state of the Au-sulfur bond. Similar DOS is also observed by UPS at around 1.0 eV for the OcSe monolayers and at approximately 1.6 eV for the OcTe monolayers on Au(111).

Journal Article↗
PubMed2005

Structure and bonding issues at the interface between gold and self-assembled conjugated dithiol monolayers.

Organic thiols have received extensive attention recently because of their relative stability and ease of examination compared to other potential molecular electronic materials. In this work, scanning probe microscopy (SPM) is used to study (i) the structural properties of self-assembled monolayers (SAMs) containing conjugated dithiols and (ii) the formation of the upper molecule-metal interface on dithiol SAMs. The top gold film is deposited either by thermal evaporation or by nano-transfer printing (nTP). Generally, the utility of thermal evaporation is limited because of Au diffusion through the SAMs. However, several dithiol SAMs are identified in this work that bond well to Au overlayers and act as satisfactory diffusion barriers. Coassembly of conjugated dithiols and alkanemonothiols is suggested as a route to obtain dithiols that are denser packed and more vertical (than is obtained from pure dithiol routes). High-yield nTP is demonstrated on coassembled SAMs. Advantages and limitations of different Au deposition and transfer techniques are compared on a variety of length scales.

Gold↗
PubMed2005

Orientational effect of surface-confined cyclodextrin on the inclusion of bisphenols.

The molecular recognition of various kinds of bisphenols (BPs) and a bisphenol A-polymer conjugate (BPA-polymer) by a self-assembled monolayer (SAM) of thiolated beta-cyclodextrin (CD) on a gold electrode was examined using cyclic voltammetry (CV). Based on the inhibitory effect of BPs on the inclusion of hydroquinone (HQ) as a probe by the surface-confined CD, the association constants (K(assoc)) of BPs with the immobilized beta-CD were estimated. The K(assoc) values for BPs with the SAM of 3-dithiobis(undecanoylamido)-3-deoxy-beta-cyclodextrin (DTUA-beta-CD) were smaller than those in the free beta-CD system reported previously. A similar tendency was obtained when 6-(lipoylamido)-6-deoxy-beta-cyclodextrin (LP-beta-CD) was used in place of DTUA-beta-CD. The K(assoc) values for all the BPs except for bisphenol B with the SAM of LP-beta-CD were always larger than those with the SAM of DTUA-beta-CD, due to a difference in the orientation of the beta-CD moiety in the SAMs. Furthermore, adsorption and desorption processes of the BPA-polymer from the surface-confined beta-CD was followed using local surface plasmon resonance spectroscopy.

Amides↗
PubMed2004

Photochemical patterning of a self-assembled monolayer of 7-diazomethylcarbonyl-2,4,9-trithiaadmantane on gold films via Wolff rearrangement.

Photolithographic attachment of functional organic molecules via ester or amide linkages to self-assembled monolayers (SAMs) on gold thin films was achieved by employing a novel photoreactive surface anchor, 7-diazomethylcarbonyl-2,4,9-trithiaadmantane. The photoreactive SAM was prepared by the spontaneous physical adsorption of the photoreactive surface anchor onto gold surfaces. The alpha-diazo ketone moiety of the SAM was found to display the classical Wolff rearrangement reactivity to produce a ketene intermediate on the exposed area. Organic molecules such as alcohols and amines can thus be attached to the gold surfaces selectively by the facile in situ formation of ester or amide linkages. The structure and reactivity of the photoreactive surface anchor were characterized by real-time FT-IR, fluorescence, and polarization modulation infrared reflectance absorption spectroscopy (PM-IRRAS). The Wolff rearrangement reactivity of the SAM suggested that a "surface-isolated" carbonylcarbene may be generated when the SAM was exposed to 255-nm irradiation.

Adamantane↗
PubMed2004

Structure and electrochemistry of 4,4'-dithiodipyridine self-assembled monolayers in comparison with 4-mercaptopyridine self-assembled monolayers on Au(111).

4,4'-Dithiodipyridine (PySSPy) monolayers on Au(111) were investigated by cyclic voltammetry, X-ray photoelectron spectroscopy (XPS) and in situ scanning tunneling microscopy (STM). The studies were performed in solutions of different anions and pHs (0.1 M H2SO4, 0.1 M HClO4, 0.1 and 0.01 M Na2SO4, 0.1 and 0.01 M NaOH). The cyclic current-potential curves in H2SO4 show current peaks at about 0.4 V, which are absent for all other electrolytes at this potential. The XPS data suggest that PySSPy adsorbs via the S endgroup on the gold surface and the S-S bond breaks during adsorption. From the chemical shift of the N(ls) peak, it is concluded that in acidic media the self-assembled monolayer (SAM) is fully protonated, whereas in basic solution it is not. The pKa is estimated to be 5.3. STM studies reveal the existence of highly ordered superstructures for the SAM. In Na2SO4 and H2SO4, a (7 x mean square root of 3) structure is proposed. However, whereas in Na2SO4 solutions the superstructure does not change with potential, in 0.1 M H2SO4 the superstructure is observed only negative of the current peak at +0.4 V. At more positive potentials, the film becomes disordered. The results are compared to those for 4-mercaptopyridine (PyS) SAMs. XPS experiments and current-potential curves indicate that both molecules adsorb in the same manner on Au(111), that is, even in the case of PySSPy the adspecies is PyS. The STM results, however, call for a more subtle interpretation. While in Na2SO4 solutions the observed superstructures are the same for both SAMs, markedly different structures are found for PySSPy and PyS SAMs in 0.1 M H2SO4.

Journal Article↗
PubMed2006

Directed immobilization of protein-coated nanospheres to nanometer-scale patterns fabricated by electron beam lithography of poly(ethylene glycol) self-assembled monolayers.

Controlling the spatial organization of biomolecules on solid supports with high resolution is important for a wide range of scientific and technological problems. Here we report a study of electron beam lithography (EBL) patterning of a self-assembled monolayer (SAM) of the amide-containing poly(ethylene glycol) (PEG) thiol CH(3)O(CH(2)CH(2)O)(17)NHCO(CH(2))(2)SH on Au and demonstrate the patterning of biomolecular features with dimensions approaching 40 nm. The electron dose dependence of feature size and pattern resolution is studied in detail by atomic force microscopy (AFM), which reveals two distinct patterning mechanisms. At low doses, the pattern formation occurs by SAM ablation in a self-developing process where the feature size is directly dose-dependent. At higher doses, electron beam-induced deposition of material, so-called contamination writing, is seen in the ablated areas of the SAM. The balance between these two mechanisms is shown to depend on the geometry of the pattern. The patterned SAMs were backfilled with fluorescent 40-nm spheres coated with NeutrAvidin. These protein-coated spheres adhered to exposed areas in the SAM with high selectivity. This direct writing approach for patterning bioactive surfaces is a fast and efficient way to produce patterns with a resolution approaching that of single proteins.

Adhesiveness↗
PubMed2006

Ferrocenylalkylthiolates as a probe of heterogeneity in binary self-assembled monolayers on gold.

The oft-cited complexity of tethered ferrocene electrochemistry in single component (FcRS-) or binary (FcRS-/CH3R'S-) self-assembled monolayers (SAMs) on gold has been investigated. The complex voltammetry is shown to be linked to local electrostatics caused by the formation of the ferrocenium ion. This conclusion is reached by studying model effects in binary SAMs, where a cationic alkylthiolate (H3N+ C11S-Au) is mixed with FcC12S-Au. A fitting procedure involving both a Gaussian and a Lorentzian distribution is used for deconvolution of the two peaks which are consistently observed in the SAMs when chi(Fc)surf > or = 0.2. The lower-potential (E degrees ' = 250 mV) and higher-potential (E degrees ' = 350 mV) voltammetric peaks are assigned to Fc moieties in "isolated" and "clustered" states, respectively. Use of this method to better understand SAM structure is demonstrated by distinguishing the degree of homogeneity in two binary SAMs of similar composition.

Journal Article↗
PubMed2006

Assembly dynamics and detailed structure of 1-propanethiol monolayers on Au(111) surfaces observed real time by in situ STM.

1-Propanethiol is chosen as a model alkanethiol to probe detailed mechanisms of the self-assembled monolayer (SAM) formation at aqueous/Au(111) interfaces. The assembly processes, including initial physi- and chemisorption, pit formation, and domain growth, were recorded into movies in real-time with high resolution by in situ scanning tunneling microscopy (STM) under potential control. Two major adsorption steps were disclosed in the propanethiol SAM formation. The first step involves weak interactions accompanied by the lift of the Au(111) surface reconstruction, which depends reversibly on the electrochemical potentials. The second step is chemisorption to form a dense monolayer, accompanied by formation of pits as well as structural changes in the terrace edges. Pits emerged at the stage of the reconstruction lift and increased to a maximum surface coverage of 4.0 +/- 0.4% at the completion of the SAM formation. Well-defined triangular pits in the SAM were found on the large terraces (more than 300 nm wide), whereas few and small pinholes appeared at the terrace edge areas. Smooth edges were converted into saw-like structural features during the SAM formation, primarily along the Au(111) atomic rows. These observations suggest that shrinking and rearrangement of gold atoms are responsible for both formation of the pits and the shape changes of the terrace edges. STM images disclose a (2 square root 3 x 3)R30 degrees periodic lattice within the ordered domains. Along with electrochemical measurements, each lattice unit is assigned to contain four propanethiol molecules exhibiting different electronic contrasts, which might originate in different surface orientations of the adsorbed molecules.

Journal Article↗
PubMed2006

Globotriose- and oligo(ethylene glycol)-terminated self-assembled monolayers: surface forces, wetting, and surfactant adsorption.

A set of oligo(ethylene glycol)-terminated and globotriose-terminated self-assembled monolayers (SAMs) has been prepared on gold substrates. Such model surfaces are well defined and have good stability due to the strong binding of thiols and disulfides to the gold substrate. They are thus very suitable for addressing questions related to effects of surface composition on wetting properties, surface interactions, and surfactant adsorption. These issues are addressed in this report. Accurate wetting tension measurements have been performed as a function of temperature using the Wilhelmy plate technique. The results show that the nonpolar character of oligo(ethylene glycol)-terminated SAMs increases slightly but significantly with temperature in the range 20-55 degrees C. On the other hand, globotriose-terminated SAMs are fully wetted by water at room temperature. Surface forces measurements have been performed and demonstrated that the interactions between oligo(ethylene glycol)-terminated SAMs are purely repulsive and similar to those determined between adsorbed surfactant layers with the same terminal headgroup. On the other hand, the interactions between globotriose-terminated SAMs include a short-range attractive force component that is strongly affected by the packing density in the layer. In some cases it is found that the attractive force component increases with contact time. Both these observations are rationalized by an orientation- and conformation-dependent interaction between globotriose headgroups, and it is suggested that hydrogen-bond formation, directly or via bridging water molecules, is the molecular origin of these effects.

Adsorption↗
PubMed2006

Thiol-mediated anchoring of ligands to self-assembled monolayers for studies of biospecific interactions.

We report a method to immobilize thiol-containing ligands onto self-assembled monolayers (SAMs) of alkanethiolates presenting chloracetylated hexa(ethylene glycol) groups. The chloroacetyl groups react with thiols under mild basic conditions, enabling the stable immobilization of biologically active ligands in a well-defined orientation. These SAMs on gold are well suited for studies of biospecific interactions of immobilized ligands with proteins and cells. As a demonstration, we functionalized these SAMs with thiol-containing derivatives of biotin and benzene sulfonamide and observed the specific binding of neutravidin and carbonic anhydrase, respectively. We also used this method to generate mixed SAMs presenting the Arg-Gly-Asp (RGD) peptide sequence and demonstrated the integrin-mediated adhesion of fibroblast cells to these SAMs. This approach would allow the immobilization of proteins and other sensitive biomolecules and ligands for a wide variety of applications in biotechnology.

Alkanes↗
PubMed2007

Study of the packing density and molecular orientation of bimolecular self-assembled monolayers of aromatic and aliphatic organosilanes on silica.

Bimolecular self-assembled monolayers (SAMs) of aromatic and aliphatic chlorosilanes were self-assembled onto silica, and their characteristics were established by contact angle measurement, near-edge X-ray absorption fine structure spectroscopy, and Fourier transform infrared spectroscopy. Three aromatic constituents (phenyltrichlorosilane, benzyltrichlorosilane, and phenethyltrichlorosilane) were studied in combination with four aliphatic coadsorbates (butyltrichlorosilane, butyldimethylchlorosilane, octadecyltrichlorosilane, and octadecyldimethylchlorosilane). Our results demonstrate that whereas SAMs made of trichlorinated organosilanes are densely packed, SAMs prepared from monochlorinated species are less dense and poorly ordered. In mixed systems, trichlorinated aromatics and trichlorinated aliphatics formed SAMs with highly tunable compositions; their surfaces were compositionally homogeneous with no large-scale domain separation. The homogeneous nature of the resulting SAM was a consequence of the formation of in-plane siloxane linkages among neighboring molecules. In contrast, when mixing monochlorinated aliphatics with trichlorinated aromatics, molecular segregation occurred. Although the two shortest aromatic species did not display significant changes in orientation upon mixing with aliphatics, the aromatic species with the longest polymethylene spacer, phenethyltrichlorosilane, displayed markedly different orientation behavior in mixtures of short- and long-chain aliphatics.

Journal Article↗
PubMedDate not supplied

Proteomic profiling of erythrocyte proteins by proteolytic digestion chip and identification using two-dimensional electrospray ionization tandem mass spectrometry.

Self-assembled monolayers (SAMs) on coinage metal provide versatile modeling systems for studies of interfacial electron transfer, biological interactions, molecular recognition, and other interfacial phenomena. The bonding of enzyme to SAMs of alkanethiols onto gold surfaces is exploited to produce an enzyme chip. In this work, the attachment of trypsin to a SAMs surface of 11-mercaptoundecanoic acid was achieved using water soluble N-ethyl-N'-(3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinimide as coupling agent. A two-dimensional liquid-phase separation scheme coupled with mass spectrometry is presented for proteomic analysis of erythrocyte proteins. The application of proteomics, particularly with reference to analysis of proteins, will be described. Surface analyses have revealed that the X-ray Photoelectron Spectroscopy (XPS) C1s and N1s core levels illustrate the immobilization of trypsin. These data are also in good agreement with Fourier Transformed Infrared Reflection-Attenuated Total Reflection (FTIR-ATR) spectra for the peaks at Amide I and Amide II. Using two-dimensional nano-high performance liquid chromatography electrospray ionization tandem mass spectrometry (2D nano-HPLC-ESI-MS/MS) system observations, analytical results have demonstrated the erythrocyte proteins digestion of the immobilized trypsin on the functionalized SAMs surface. For such surfaces, it also shows the enzyme digestion ability of the immobilized trypsin. The experiment results revealed the identification of 272 proteins from erythrocyte protein sample. The terminal groups of the SAMs structure can be further functionalized with biomolecules or antibodies to develop surface-base diagnostics, biosensors, or biomaterials.

Adult↗
PubMed1998

Differential induction by methyl jasmonate of genes encoding ornithine decarboxylase and other enzymes involved in nicotine biosynthesis in tobacco cell cultures.

A cDNA of tobacco BY-2 cells corresponding to an mRNA species which was rapidly induced by methyl jasmonate (MeJA) in the presence of cycloheximide (CHX) was found to encode ornithine decarboxylase (ODC). Another cDNA from a MeJA-inducible mRNA encoded S-adenosylmethionine synthase (SAMS). Although these enzymes could be involved in the biosynthesis of polyamines, the level of putrescine, a reaction product of ODC, increased slowly and while the levels of spermidine and spermine did not change following treatment of cells with MeJA. However, N-methylputrescine, which is a precursor of pyrrolidine ring of nicotine, started to increase shortly after MeJA-treatment of cells and the production of nicotine occured thereafter. The levels of mRNA for arginine decarboxylase (ADC), an alternative enzyme for putrescine synthesis, and that for S-adenosylmethionine decarboxylase (SAMDC), required for polyamine synthesis, were not affected by MeJA. In addition to mRNAs for ODC and SAMS, mRNA for putrescine N-methyltransferase (PMT) was also induced by MeJA. Unlike the MeJA-induction of ODC mRNA, MeJA-induction of SAMS and PMT mRNAs were blocked by CHX. The level of ODC mRNA declined after 1 to 4 h following MeJA treatment, while the levels of mRNAs for SAMS and PMT continued to increase. Auxin significantly reduced the MeJA-inducible accumulation of mRNAs for ODC, SAMS and PMT. These results indicate that MeJA sequentially induces expression of a series of genes involved in nicotine biosynthesis by multiple regulatory mechanisms.

Acetates↗
PubMed2000

Monitoring of isoflurane and desflurane breakdown: interfering gases and infrared detection.

OBJECTIVE: The reaction of isoflurane, enflurane or desflurane with dried CO2 absorbents produces carbon monixide (CO), a highly toxic gas which cannot be detected by gas monitors typically available in the operating room. Trifluoromethane (CHF3) is produced along with CO when this reaction occurs with isoflurane and desflurane, and can be detected by gas monitors. This study will determine the ability of a modified SAM module (Smart Anesthesia Multigas Module, GE/Marquette Medical Systems, Milwaukee, WI) to identify the presence of CHF3, and provide a clinically useful indirect warning of CO production. METHODS: Isoflurane (1.5%) and desflurane (7.5%) were reacted under clinical conditions with desiccated absorbents resulting in CO production. CO and CHF3 concentrations were measured using gas chromatography. The CHF3 concentrations measured by a modified SAM monitor were compared with the measurements obtained by gas chromatography. Alarm limits set on the SAM monitor were used to warn of the presence of CHF3. RESULTS: A concentration of 0.25% CHF3, as measured by the SAM monitor, corresponds to an average CO concentration of 780 ppm for isoflurane and 1700 ppm for desflurane. Lowering the threshold to 0.05% CHF3 would result in an average CO concentration of 155 ppm CO for isoflurane and 345 ppm CO for desflurane. CONCLUSIONS: We have shown that the SAM module is capable of measuring CHF3 due to anesthetic breakdown. With appropriate changes in the display programming and reference cell spectra the monitor would be able to provide an early warning of CO exposure, although the amount of CO would not be reported.

Anesthesia, General↗
PubMed2004

Comparison of scan-angle method and convective cloud differential method in retrieving tropospheric ozone from TOMS.

Tropospheric ozone, derived from the Scan-Angle Method (SAM) and the Convective Cloud Differential (CCD) method, exhibits a noticeable abundance over the South Atlantic, where it is associated with biomass-burning in the austral spring. This feature is also seen in the distribution of carbon monoxide observed from Measurements Of Pollution In The Troposphere (MOPITT). In the boreal burning season, however, the distribution of the results from SAM and MOPITT-CO present an enhancement related to the biomass-burning over North Africa that does not appear in the CCD results. The relationship of the results from SAM and MOPITT-CO is better than those of the results from the CCD and MOPITT-CO for the December-February period. Conversely, the latter relationship is better than the former for the October-November period. The two methods, SAM and CCD, show higher correlation in the southern burning season, but lower correlation in the northern burning season. The influence of biomass burning on ozone amounts is clearly seen in the SAM results of the elevated ozone over northern equatorial Africa during the northern burning season, but is not present in the CCD results.

Africa↗
PubMed2004

SUMO modification is required for in vivo Hox gene regulation by the Caenorhabditis elegans Polycomb group protein SOP-2.

Post-translational modification of proteins by the ubiquitin-like molecule SUMO (sumoylation) regulates their subcellular localization and affects their functional properties in vitro, but the physiological function of sumoylation in multicellular organisms is largely unknown. Here, we show that the C. elegans Polycomb group (PcG) protein SOP-2 interacts with the SUMO-conjugating enzyme UBC-9 through its evolutionarily conserved SAM domain. Sumoylation of SOP-2 is required for its localization to nuclear bodies in vivo and for its physiological repression of Hox genes. Global disruption of sumoylation phenocopies a sop-2 mutation by causing ectopic Hox gene expression and homeotic transformations. Chimeric constructs in which the SOP-2 SAM domain is replaced with that derived from fruit fly or mammalian PcG proteins, but not those in which the SOP-2 SAM domain is replaced with the SAM domains of non-PcG proteins, confer appropriate in vivo nuclear localization and Hox gene repression. These observations indicate that sumoylation of PcG proteins, modulated by their evolutionarily conserved SAM domain, is essential to their physiological repression of Hox genes.

Animals↗
PubMed1996

Recording condylar movement with two facebow systems.

Two different articulator systems are commonly used by orthodontists to reveal the maxillomandibular relationship for improved diagnosis and treatment planning. The purposes of the study were: (1) to compare the SAM and the Panadent articulator systems when recording condylar discrepancies for the same patient; (2) to evaluate the interchangeability of the SAM estimated facebow when mounting to the Panadent articulator; and (3) to evaluate the direction of condylar movement between centric relation (CR) and centric occlusion (CO). Maxillary and mandibular impressions, CO and CR bite registrations, and SAM and Panadent facebow recordings were taken for 37 patients. There were no statistically significant differences between the SAM and the Panadent systems (p > 0.05). However, the SAM facebow should not be used when mounting to the Panadent articulator. In most cases, the condyle moves down and back when the subject bites into maximum intercuspation.

Centric Relation↗
PubMed2001

Subaortic membrane excision: mid-term results.

BACKGROUND: Subaortic membrane (SAM) is a form of fixed subaortic obstruction in which a fibrous membrane is located below the aortic valve. AIM: To determine the role of surgical treatment for patients with a discrete SAM. PATIENTS AND METHODS: The hospital records of 45 patients (age range: 2-23 years; median 8 years) undergoing surgery for SAM between 1990 and 1998 at the All India Institute of Medical Sciences, New Delhi, India, were analysed. Preoperative echocardiographically calculated gradients across the left ventricular outflow tract ranged from 50 to 154 mmHg (mean: 86.5 +/- 33.2 mmHg). Nine patients had trivial aortic regurgitation (AR), 10 had mild AR and five had moderate-severe AR. The left ventricular ejection fraction (LVEF) ranged from 20 to 68% (mean 48 +/- 15%). Nineteen patients had significant left ventricular dysfunction (LVEF <50%). Transaortic resection of SAM was done in all patients along with excision of a wedge-shaped segment of septal muscle underlying the membrane. RESULTS: There were no early or late postoperative deaths. On follow up (up to 113 months), only four patients had gradients >30 mmHg. LVEF improved to 45-70% (mean 58 +/- 7.7%). AR reduced to mild in four patients and trivial in four patients, and did not progress further. CONCLUSION: Resection of SAM carries long-term benefits. Routine septal myectomy appears to be associated with a low risk of recurrence.

Journal Article↗