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PubMed2001

Hydrogen bond structural group constants.

The ability of functional groups to act as hydrogen bond acids and bases can be obtained from either equilibrium constants for 1:1 hydrogen bonding or overall hydrogen bond constants. Either method leads to structural constants for hydrogen bonding that in some way are analogous to substituent constants. Extensive lists of these functional group constants are reported. It is shown that those derived from overall hydrogen bond constants are the more useful in analyses of physicochemical and biochemical properties.

Journal Article↗
PubMed1980

The effect of surface curvature on the head-group structure and phase transition properties of phospholipid bilayer vesicles.

Proton nuclear magnetic resonance spectra at 360 MHz of small sonicated distearoyl phosphatidylcholine vesicles show easily distinguishable resonances due to choline N-methyl head-group protons located in the inner and outer bilayer halves. A study of the chemical shift of these resonances as a function of temperature reveals that the splitting between them increases below the phase transition. This occurs as a result of an upfield shift of the inner layer resonance at the phase transition. Consideration of the possible causes of this effect results in the conclusion that, at the phase transition, there is a change in the organization of the inner layer head-groups which does not occur for the outer layer head-groups.

Choline↗
PubMed1986

Role of head group structure in the phase behavior of amino phospholipids. 2. Lamellar and nonlamellar phases of unsaturated phosphatidylethanolamine analogues.

Three types of analogues of unsaturated phosphatidylethanolamines (PE) have been prepared: phosphatidyl-omega-amino-1-alkanols, N-alkyl-PE's, and C2-alkyl-PE's, with alkyl substitution of carbon-2 of the ethanolamine head group. The physical properties of dioleoyl, dielaidoyl, and 1-palmitoyl-2-oleoyl phospholipids with these head groups have been examined by calorimetry, 31P NMR, freeze-fracture electron microscopy, and X-ray diffraction. N-Alkylation of PE, or substitution of the ethanolamine moiety by 3-amino-1-propanol or 4-amino-1-butanol, decreases the transition temperature of the hydrated gel phase (Tc) and considerably increases the temperature of the lamellar to hexagonal II transition (TH). The pattern of these effects for various PE analogues suggests that head group size and hydrophobicity as well as hydrogen bonding are important determinants of the phase behavior of these lipids. C2-Alkylated PE analogues exhibit several rather surprising properties, notably the ready formation of a quasi-crystalline "high-melting" solid phase even for di-cis-unsaturated species and substantially lower TH values than are observed for the parent PE species. The behavior of these compounds suggests that "hydration forces" can be more important than considerations of lipid "dynamic shape" in predicting the relative stabilities of lamellar vs. nonlamellar phases for at least some zwitterionic phospholipids.

Calorimetry↗
PubMedDate not supplied

[Cholinomimetic activity of acetylcholine and sebacinyldicholine derivatives with differing cationic group structures].

The intrinsic alpha activities and the D2 (frog, m, rectus abdominalis) concentrations were estimated for different acetylcholine and sebacinylcholine derivatives. So were also the A2 values for antagonists and the affinity constants Kc for some partial agonists. The results obtained disprove Paton's "rate-theory". The relationship between the cholinergic activity and the volume of cationic groups was studied and it could not possibly be explained by the steric hindrance alone. It is suggested that certain hydrophobic radicals of the cationic groups contact the receptor surface outside the anionic centre. Such contacts prevent the cholinoreceptor to change its conformation and thus inhibit the depolarization of the membrane. An approximate estimation of the anionic site dimensions is given.

Abdominal Muscles↗
PubMed1985

The effect of head group structure on phase transition of phospholipid membranes as determined by differential scanning calorimetry.

The phase transition characteristics of cardiolipin and phosphatidylglycerol suspensions were investigated by differential scanning calorimetry. The phase transition temperatures for dimyristoylphosphatidylglycerol, tetramyristoylcardiolipin, dipalmitoylphosphatidylglycerol and tetrapalmitoylcardiolipin were 25.0, 47.0, 40.5 and 62.2 degrees C, respectively. The phase transition temperature for a mixture of two analogous phospholipids was higher than that for phosphatidylglycerol alone, but lower than that for cardiolipin alone. It increased along with cardiolipin content. The phase transition temperature for cardiolipin was increased in the presence of divalent cations, particularly Ca2+. The results indicate that the head group of cardiolipin by itself can increase the phase transition temperature.

Calorimetry, Differential Scanning↗
PubMedDate not supplied

[A theoretical conformational analysis of several substrates of cholinesterase having a cyclic ammonium group structure].

Conformational possibilities of pirrolidine analogues of acetylcholine beta-(N-methyl pirrolidinium)-ethyl ester of acetic acid and beta-(N-ethyl pirrolidinium)-ethyl ester of acetic acid and beta-(N-ethyl pirrolidinium)-ethyl ester of acetic acid were investigated by the method of atomic potentials. The conformational energy was considered as a sum of non-bonded and electrostatical interactions, torsional energy and distortions of bond angles. It has been shown that the replacement of the nitrogen methyl group to ethyl group results in decrease of the average barrier height between two gauche conformations of the O--C--C--N fragment. Comparison of conformational properties of some cholinesterase substrates permit to draw a suggestion that the barrier height influences the rate of the enzymatic hydrolysis.

Acetylcholine↗
PubMed1999

Effects of tail alkyl chain length (n), head group structure and junction (Z) on amphiphilic properties of 1-Z-R-D,L-xylitol compounds (R = CnH2n+1).

In the family of 1-Z-R-D,L-xylitol, we have determined the main amphiphilic properties of esters (Z = OCO) as a function of alkyl chain length (R = CnH2n+1, n = 4-17). A classical decrease of critical micelle concentration with the increase in the alkyl chain has been found. With water, esters displayed lamellar phases at temperatures of 25 degrees C or higher. The extent of hydrophilic/lipophilic balance range obtained by emulsification method can be proven to be of interest for pharmaceutical applications. The results were compared with those obtained in previous investigations, i.e. for alkyl-substituted xylitol, with thioether (Z=S) and ether (Z=O) linking groups in order to discuss the role of the junction nature. Likewise, they were compiled with the results related to their D-glucose homologues, in order to put forward the effects of the head group configuration, cyclic or acyclic.

Crystallization↗
PubMed1975

Identification of drugs and other toxic compounds from their ultraviolet spectra. Part II: Ultraviolet absorption properties of thirteen structural groups.

The ultraviolet absorption spectra of 13 different chemical classes of drugs and toxic organic compounds were studied. A classification system has been developed in which compounds with the same conjugated molecular system and auxochrome substituents are grouped together. Each of these groups has characteristic absorption spectra, showing similarities in the number of major bands, position of maximum absorbance, pH effects, and solvent effects. The absorption maxima and molecular absorptivities are tabulated for approximately 100 compounds, and characteristic spectra of each designated group are illustrated. Classes of drugs included in this study are pyridine derivatives, hydrazines, pyridylamine derivatives, variously substituted phenols, barbiturates, ureides, imides, hydantoins, and conjugted ketones (enones).

Amines↗
PubMed2004

Biphenyl derived Schiff-base vanadium(V) complexes with pendant OH-groups--structure, characterization and hydrogen peroxide mediated sulfide oxygenation.

A series of mononuclear oxovanadium(v) complexes of tridentate Schiff bases HL(1)-HL(4) and H(2)L(5)-H(2)L(8) derived from 6-phenylsalicylaldehyde and 6-(2-hydroxyphenyl)salicylaldehyde and four different amines was synthesized. The systematically selected ligands contain aliphatic or aromatic nitrogen, or alkoxy- and phenoxy-oxygen as third donor atom. The complexes were characterised by spectroscopic methods in solution and the solid state. Single-crystal X-ray analyses were performed with VO(2)L(1)(), VO(2)L(3)x1/2EtOH (), VO(2)L(4)(), VO(OiPr)L(7)xiPrOH, VO(OiPr)L(8) and H(2)L(8). For all compounds the vanadium(v) cores contain distorted tetragonal pyramidal geometry around the dioxo- and oxovanadium site at which the N(2)O- and NO(2)-donor ligands bind equatorially. Complexes and display intramolecular hydrogen bonding of the pendant hydroxyphenyl group to a coordinated oxygen trans to a nitrogen atom and therefore serve as suitable models for the native site of vanadium dependent haloperoxidases. Variable-temperature (1)H NMR spectra revealed significant hydrogen bond interaction in acetonitrile solution. In situ prepared catalysts are active for hydrogen peroxide mediated oxygenation of ethyl phenyl sulfide and showed complete conversion of the substrate to ethyl phenyl sulfoxide, together with small amounts of the corresponding sulfone, as detected by GC/MS after 10 min. The complex of H(2)L(7) turned out to be most efficient while HL(1) and HL(2) were completely inactive. Catalysis is supported by the pendant OH group in the complex of HL(3), the catalyst is twice as active as the complex of HL(4).

Biphenyl Compounds↗
PubMed1998

Resource distribution, female home range dispersion and male spatial interactions: group structure in a solitary carnivore.

We monitored 74 (41 male, 33 female) radiocollared raccoons (Procyon lotor) from February 1990 to July 1992 on the Welder Wildlife Refuge, Texas, to relate male and female space use to each other and to the spatial distribution of water, a critical resource for raccoons. Female home ranges were spatially aggregated early in the study, when standing water occurred in only a few, widely separated patches on the study site, but were randomly distributed during seasons when water was more widely distributed. Adult females generally foraged and rested independently of other adults. Most adult males were arranged in spatial groups whose home ranges overlapped little with those of adjacent groups. These groups were usually composed of three to four individuals; Doncaster's (1990, J. theor. Biol., 143, 431-443) test for dynamic interaction and visual observations showed that group members tended to associate positively during resting and foraging activities in all seasons. Among raccoons, as among many other mammals, female spatial patterns are apparently determined primarily by resource distribution, whereas male patterns are influenced by the distribution of females. Copyright 1998 The Association for the Study of Animal Behaviour. Copyright 1998 The Association for the Study of Animal Behaviour.

Journal Article↗
PubMed1993

Recent advances in molecular and genetic analysis of Rh blood group structures.

The Rh antigens are carried by 30-32 kDa integral proteins of the red cell membrane. The Rh locus is composed of two genes: RhD, which encodes the major D antigen and is present only in Rh-positive genomes, and RhCcEe, which encodes both the Cc and Ee polypeptides, most likely by alternative splicing events. The D and non-D Rh mRNAs have been cloned. Their sequence homology suggest that the two Rh genes have evolved by duplication of a common ancestor.

Amino Acid Sequence↗
PubMed1991

Effect of head-group structure and counterion condensation on phase equilibria in anionic phospholipid-water systems studied by 2H, 23Na, and 31P NMR and X-ray diffraction.

The phase equilibria, hydration, and sodium counterion association for the systems DOPA-2H2O, DOPS-2H2O, DOPG-2H2O, and DPG-2H2O were investigated with 2H, 23Na, and 31P NMR and X-ray diffraction. The following one-phase regions were found in the DOPA-water system: a reversed hexagonal liquid-crystalline (HII) phase up to about 35 wt % water and a lamellar liquid-crystalline (L alpha) phase between about 55 and 98 wt % water. The area per DOPA molecule was 36-65 A2 in the HII phase (10-40 wt % water) and 69 A2 in the L alpha phase (60 wt % water). DOPS and DOPG with 10-98 wt % water, and DPG with 20-95 wt % water formed an L alpha phase at temperatures between 25 and 55 degrees C. At temperatures above 55 degrees C, DPG with 20 and 30 wt % water formed a mixture of L alpha, HII, and cubic liquid-crystalline phases, the mole percent of lipid forming nonlamellar phases being smaller at 30 wt % water than at 20 wt % water. DPG with 10 wt % water probably formed a mixture of an L alpha phase and at least one nonlamellar liquid-crystalline phase at 25 and 35 degrees C, and a pure HII phase at 45 degrees C and higher temperatures. At water concentrations above about 50 wt % the 23Na quadrupole splitting was constant for all four lipid-water systems studied, implying that the counterion association to the charged lipid aggregates did not change upon dilution. These experimental observations can be described with an ion condensation model but not with a simple equilibrium model. The fraction of counterions located close to the lipid-water interface was calculated to be greater than 95%. The 2H and 23Na NMR quadrupole splittings of 2H2O and sodium counterions, respectively, indicate that the molecular order in the polar head-group region decreases for the L alpha phase in the order DOPA approximately DPG greater than DOPS greater than DOPG.

Deuterium↗