Diaminopropane Research Articles

Self-Catalytic Aminolysis of Aerosol-OT in Reverse Micelles by Diamines

Self-catalytic aminolysis of sodium bis(2-ethylhexyl)sulfosuccinate (AOT) induced by ethylenediamine (EDA) and by propylenediamine (PDA) solubilized in reverse AOT micelles in isooctane has been investigated. When decomposition of ester groups in AOT due to aminolysis reaches about 5-7%, the micellar solution suddenly becomes turbid. Reaction rates of the AOT aminolysis were studied in micellar and in nonmicellar solutions. This aminolysis process is analyzed in terms of a mechanism in which each ester group in AOT reacts with one of two amino groups in an EDA or PDA molecule by synergistic action with the other amino group. The rate constant for the aminolysis of AOT in micelles is about 360 times larger than in nonmicellar solution. This large difference in the rate constants appears to be based on the micelle effect for aminolysis. From the temperature dependency of the rate constants, the activation energy for aminolysis was determined to be 33.5 kJ mol -1 for the micellar system and 35.2 kJ mol -1 for the nonmicellar system. This slight difference indicates that essentially the same aminolysis mechanism applies in both systems. The magnitude of this micellar effect is explained by the idea that favorable proximity of a diamine molecule to ester groups of AOT in micelles accelerates the reaction rate of aminolysis. Such an effect is called "self-catalytic" because the aminolysis of AOT is promoted by AOT micellization.

Biofilm Development and Sanitizer Inactivation of Listeria monocytogenes and Salmonella typhimurium on Stainless Steel and Buna-n Rubber

Biofilm formation by seven strains of Listeria monocytogenes and one strain of Salmonella typhimurium on stainless steel and Buna-n rubber was examined under two nutrient conditions. The type of surface, nutrient level, and organism influenced biofilm development and production of extracellular materials. Buna-n had a strong bacteriostatic effect on L. monocytogenes, and biofilm formation on Buna-n under low nutrient conditions was reduced for four of the seven strains tested. Buna-n was less bacteriostatic toward S. typhimurium. It inhibited the growth of several other pathogens to varying degrees. An ethylene propylene diamine monomer rubber was less inhibitory than Buna-n, and Viton rubber had no effect. The effectiveness of sanitizers on biofilm bacteria was examined. Biofilms were challenged with four types of detergent and nondetergent sanitizers. Resistance to sanitizers was strongly influenced by the type of surface. Bacterial biofilm populations on stainless steel were reduced 3–5 log by all the sanitizers, but those on Buna-n were resistant to these sanitizers and were reduced less than 1–2 log. In contrast, planktonic (suspended) bacteria were reduced 7–8 log by these sanitizers. Chlorine and anionic acid sanitizers generally removed extracellular materials from biofilms better than iodine and quaternary ammonium detergent sanitizers. Scanning electron microscopy demonstrated that biofilm cells and extracellular matrices could remain on sanitized biofilm cells and extracellular matrices could remain surfaces from which no viable cells were recovered.

Relaxations in thermosets. XXV. Calorimetric studies of the curing kinetics of pure and rubber‐containing epoxy‐based thermosets

AbstractThe curing kinetics of diglycidyl ether of bisphenol‐A, with ethylene diamine, propylene diamine, and hexamethylene diamine, with 60 wt % amine‐terminated butadiene acrylonitrile (ATBN) and without, have been measured under both isothermal and ramp‐curing conditions. The phase separation of ATBN is undetectable by calorimetry, but has a significant effect on both the rate of curing and the extent of cure. In all cases, its presence decreases the extent of cure and lowers the Tg of the thermoset formed. The total heat of reaction for the curing is 445 ± 15 J/g and remains unaffected by both the presence of an elastomer and the increase in the molecular size of the curing agent. None of the formalisms available for the curing kinetics of epoxy‐based thermosets is consistent with the results for the neat thermosets. The average activation energy for the reactions increases from 107 to 150 kJ/mol when ethylene diamine is replaced by hexamethylene diamine, but curing reaches near completion in a shorter time with the latter than with the former. The Tg of the latter thermoset is lower than that of the former and follows a decreasing trend with increase in the molecular size of the curing agent—an effect that is related to the increase in the length of cross‐links in the network structure. © 1993 John Wiley & Sons, Inc.

Potentiometric determination of the protonation constants of N-methyl substituted ehtylene and propylene diamines in 1 mol/l KNO3

The acidity constant of 14 diammonium salts of N-methyl substituted ethylene and propylenediamines are determined potentiometrically in 1 mol/l KNO3 at 25°C. The sequence of the ΔpKA is a function of the number of substituted methyl groups.

Inhibition of HIV proliferation in MT-4 cells by antisense oligonucleotide conjugated to lipophilic groups

Anti-HIV activity of antisense oligonucleotide derivatives conjugated to lipophilic groups has been investigated. Aliphatic linear structures and cholesterol were coupled to the 5′-terminal phosphate of oligonucleotides via glycin or propylene diamine spacers. The oligonucleotides were targeted to a conserved sequence of the viral gene env, to a sequence in the negative sense viral RNA, to the 5′-terminus of the gene rev and to poly(A) sequences. The conjugation with lipophilic groups stimulated binding of oligonucleotides to cells and protected the oligonucleotides against cellular nucleases. The lipophilic derivatives of oligonucleotides containing an ester bond in the linker structure were cleaved by cellular esterases yielding oligonucleotides protected from 5′-nuclease degradation by the glycin residue. Antiviral activity of the derivatives exceeded that of the corresponding unmodified oligonucleotides. The virus suppression was sequence-specific and most pronounced in the case of the cholesteryl conjugated oligonucleotides.

Analysis of the polyphosphate-accumulating microflora in phosphorus-eliminating, anaerobic-aerobic activated sludge systems by using diaminopropane as a biomarker for rapid estimation of Acinetobacter spp

Polyphosphate-accumulating gram-negative bacteria were isolated from different anaerobic-aerobic activated sludge systems with diverse processes for enhanced biological phosphorus (P) elimination. Of 22 isolates, 10 were allocated to the genus Acinetobacter by using multiple-test systems and soluble protein and polyamine patterns. As diaminopropane (DAP) appears to be the characteristic main polyamine compound produced by Acinetobacter spp., it was used as a biomarker for the genus. The high DAP contents of representative samples from municipal wastes with enhanced biological P elimination indicated that Acinetobacter spp. can be dominant organisms in sewage treatment plants with low organic loading and nitrification and denitrification steps. Contrary to accepted opinion, sludge from treatment plants with efficient P removal and high organic loading had a low DAP content, indicating that bacteria other than Acinetobacter spp. are responsible for enhanced biological P elimination in these plants.

Potential Metabolic Targets in Chemotherapy for Acanthamoeba Infections: Polyamine Metabolism

Reports of infections with protozoan parasites are increasing. Polyamine metabolism in protozoa is dissimilar from that in the eukaryotic host and could be exploited for therapy [1]. Using high-pressure liquid chromatography, we determined that diaminopropane (DAP) is the principal polyamine of Acanthamoeba culbertsoni, while spermidine is present in smaller quantities [2]. During cultivation of A. culbertsoni on peptone medium, the DAP and spermidine content of amebas increased with growth, reaching a maximal level in the postexponential phase. At the peak period of growth, the concentration of DAP in cells was 10-12 mM, while that of spermidine was 1.5-2.0 mM. Appreciable activity of certain polyamine biosynthetic enzymes-ornithine decarboxylase (ODC) and S-adenosylmethionine decarboxylase (SAM-DC)-was found, while no activities of lysine decarboxylase, arginine decarboxylase, and diaminobutyrate decarboxylase were detected. Maximal ODC activity was observed in younger cells. An inhibitor of ornithine decarboxylase, o-difluoromethylornithine (DFMO), had no effect

The use of modified sporopollenin from Lycopodium clavatum as a novel ion- or ligand-exchange medium

The outer coat (exine) of plant pollen grains and many related microspores derived from algae or fungi is composed of the material sporopollenin, probably produced biochemically by an enzyme-controlled oxidative polymerisation of carotenoids. Sporopollenin is exceptionally resistant to chemical and physical attack. The material from the commercially available Lycopodium clavatum retains the full morphology of the original spore grain after processing. It may also be functionalised without any change in microscopic appearance by direct amination with ethylene or propylene diamine, sulphonation with chlorosulphonic acid and carboxyalkylation of the former aminoethylsporopollenin which produces a carboxymethylsporopollenin. These materials have been used as column materials for the successful separation of a selection of nucleosides, nucleotides, α-amino acids and transition metals. The advantages of sporopollenin over conventional ion-exchange materials are discussed.

Electrochemical Behaviour Study of Mixed Ligand Complexes of Diaminopropane and Phthalate with Cd(II) Using Differential Pulse Polarography and Cyclic Voltammetry Techniques

Abstract Differential pulse(d. p.)polarography has been used to study the simple and mixed ligand complexes of 1, 3 diaminopropane (DAMP) and phthalate(PHLT) with Cd(II) at constant ionic strength (u= 1.0 M NaNO3) at 25°C The overall formation constants of simple and mixed complexes were calculated. The reduction of the simple and mixed species is reversible and diffusion controlled. The postive values of the mixing constants for the mixed-ligand complexes indicate that the mixed-ligand complexes are more stable than simple binary complexes. The equilibria between the various mixed-ligand species in the solution and their equilibrium are given.

Influence of dehydroepiandrosterone, diaminopropane and butylated hydroxyanisole treatment during the induction phase of rat liver nodular lesions in a short-term system.

The effects of concomitant treatment with dehydroepiandrosterone, an inhibitor of glucose-6-phosphate dehydrogenase (G6PD), diaminopropane (DAP), an inhibitor of ornithine decarboxylase or the microsomal drug detoxifying enzyme inducer butylated hydroxyanisole (BHA) during the induction phase of rat liver nodular lesion development were investigated. Clear reductions in both number and size of foci and nodules as assayed quantitatively with the aid of marker enzymes G6PD, glutathione S-transferase P form or gamma-glutamyl transpeptidase were established for treatment with either DHEA or BHA. DAP in contrast did not exert influence on the number of lesions, but brought about a significant reduction in size. The quantitative data taken together with the finding that increased labelling of tritiated thymidine occurred in extrafocal hepatocyte populations in BHA-treated animals, give direct support to the view that alteration in enzyme phenotype within putative pre-neoplastic lesions plays a central role in their generation with this short-term model. In particular, a physiological adaptive significance of G6PD elevation is suggested.

4376635 Novel gasohol or ethanol fuel composition containing as a corrosion inhibitor the reaction product of benzothiazole, formaldehyde and an N-alkyl propylene diamine: Rodney L. Sung, assigned to Texaco Inc

4376635 Novel gasohol or ethanol fuel composition containing as a corrosion inhibitor the reaction product of benzothiazole, formaldehyde and an N-alkyl propylene diamine: Rodney L. Sung, assigned to Texaco Inc

Studies on amoebicidal and bactericidal activity of iron, cobalt and copper complexes with various amines.

Many coordination complexes of iron(II) oxalate, cobalt(II) oxalate, copper(II) oxalate, cobalt tetrathiocyanatomercurate(II), copper tetrathiocyanatomercurate(II) and iron tetrathiocyanatomercurate(II) with various aliphatic, aromatic, and heterocyclic amines have been synthesized and tested for their toxicity on mice, amoebicidal activity against E. histolytica and antibacterial activity against S. aureus. Three complexes CoC2O4 (orthophenylenediamine)2, Cu[Hg(SCN)4] (ethylenediamine)2 and Cu[Hg(SCN)4] (propylene diamine)2 exhibited pronounced antiamoebic activity whereas all thiocyanate complexes and CoC2O4 (ethylenediamine)2 showed significant antibacterial action against S. aureus. Possible structure-activity relationship has been postulated, and it has been noticed that toxicity and the amoebicidal and bactericidal activities of the metal complexes increased with a decrease in the ionic radius of the metal ion.

Inhibition of rat heart hypertrophy by 1-3 diaminopropane (DAP)

Inhibition of rat heart hypertrophy by 1-3 diaminopropane (DAP)

Ornithine decarboxylase activity in retinal explants of goldfish undergoing optic nerve regeneration.

Retinal explants cultured in the presence of fetal calf serum (FCS) exhibit an increase in the activity of ornithine decarboxylase which is maximal several hours after explantation. The measured activity of this enzyme is higher in explants of retinas whose optic nerve had been crushed several days previously (post-crush, PC) than in control (normal, N) retinas. The addition of rabbit antibodies against nerve growth factor (NGF) to the incubation medium does not block this stimulatory effect of FCS, a result suggesting that factors other than NGF present in FCS are responsible for the observed stimulation. An inhibitor of ODC synthesis, diaminopropane (DAP), and an irreversible inhibitor of ODC activity, alpha-DL-difluoromethylornithine (alpha-DFMO), each suppressed the FCS-stimulated ODC activity when added to the culture medium. Since FCS addition also promotes neuritic outgrowth from PC goldfish retinal explants, we explored the possible relationship of the stimulated ODC activity and the ability of explants to extend neurites. Concentrations of DAP or alpha-DFMO that block ODC activity also suppress neuritic outgrowth. Possible non-specific actions of the drugs unrelated to the block of ODC are examined. While the increases in OCD activity seen in PC and N goldfish retinas explanted into FCS-containing medium may be a requisite, they cannot be sufficient to support neuritic outgrowth. Intrinsic changes in the retinal explant secondary to crush of its optic nerve as well as factor(s) present in FCS that may be unrelated to the stimulation of ODC activity also appear necessary for neuritic outgrowth.

Mixed Ligand Complexes of Co(II) with Ethylene diamine & Propylene diamine

Mixed Ligand Complexes of Co(II) with Ethylene diamine & Propylene diamine

Some Thiocyanato, Cyanato and Selenocyanato Complexes of Copper(II) with Propylene Diamine and Diethylenediamine

Some Thiocyanato, Cyanato and Selenocyanato Complexes of Copper(II) with Propylene Diamine and Diethylenediamine

アルミナ触媒充填層反応装置によるエチレンジアミンとエチレングリコールの気相反応 その2 反応機構の考察

Several pyrazine derivatives were synthesized by using 1, 2-propylenediamine and 1, 2-propylene glycol as the starting material. 2, 6-Dimethyl-(I), 2, 5-dimethyl-(II), 2, 5-dimethyl-3-n-propyl-(IV), and 2, 6-dimethyl-3-n-propyl-pyrazines (V) were thereby obtained. At a lower temperature of 350° and a molar ratio of propylene glycol to propylene diamine of 3, the main products were IV and V, while at a higher temperature of 400° nearly the same amount of I, II, IV, and V was obtained. It was concluded from these experimental results that both the condensation and deaminocyclization occurred in this method of synthesis, as was suggested earlier. At a temperature below 370°, only the condensation reaction progresses whereas both condensation and deaminocyclization progress at above 370°. When the molar ratio of the starting materials is lower than 0.5, deaminocyclization is predominant.

Biocidal and Biostatic Activity of Aliphatic Amines Against Southern House Mosquito Larvae and Pupae1

About 120 aliphatic, fatty, and alkyl amines were evaluated against larvae and pupae of the southern house mosquito, Culex pipiens quinquefasciatus Say. The lower alkyl amines and their salts showed low level of activity. In the homologous series of primary long chain alkyl amines (R-NH2), the activity generally increased as the length of the alkyl chain increased. Against larvae, oleyl, tall oil, coco oil and tallow amines showed considerable activity. In the secondary amines (R2 NH), dicoco (mostly dilauryl) amine was more effective against larvae than dilauryl and dioleyl-linoleyl amine. They were not effective against pupae. Two tertiary amines (trilauryl and tricapryl) showed little activity. Fatty imidazolines and diethanol amides generally were ineffective against larvae, but they showed some activity. against pupae. The former group, however, was more active than the latter. Three fatty propylene diamines showed considerable activity against both larvae and pupae. These were com and tallow propylene diamines. In the homologous series of primary beta-amines, the biological activity was correlated with the length of the alkyl chain. Maximum activity was obtained when the alkyl side chain contained 15 carbon atoms. This was true for both the larvae and the pupae. Their salts were less effective. In the homologous monoquarternaries, high larvicidal activity was manifested by dimethyl-dilauryl, and dimethyl dicoco ammonium salts. In general the dimethyl dialkyl ammonium chlorides were more effective against pupae than larvae. One compound, namely dimethyl dialkyl ammonium bromide, also was quite effective against larvae and pupae. The remaining quaternaries showed slight to moderate activity. Alkyl imidazolinium and isoquinolinium bromides showed slight to moderate activity. The imidazolinium halides were generally more effective. Ethoxylated adducts of aliphatic amines showed slight to moderate activity. Among these the ethoxylated adducts of β-mono amines and β-diamines were more effective. The overall level of activity of these compounds was lower than that of the parent compounds.

A further study of Cu++ chelate of kanamycin.

In the previous paper (1), it was reported that kanamycin (KM), an antibiotic found by Umezawa et al. (2), formed a chelate with Cu++ at a molar ratio of 2:1. The structure shown in Fig. 1-a was proposed for this chelate where the propylene diamine moiety of KM took part in the formation of the chelation compound. To confirm this structure, deoxystreptamine (DOSA) was prepared by hydrolysis of KM and a comparative study of Cu++ chelates of DOSA and ethylene diamine (EDA) with that of KM was made by infrared spectroscopy and polarography.

Some new acido (thiosulphato or chlorothiosulphato)‐amino (propylenediamine or ethylene‐bis‐biguanide) cobalt(III) complexes

AbstractThe preparations and properties of the thiosulphatocobalt(III) co‐ordination compounds Na[Co(Pn)2(S2O3)2], [Co(Pn)2(S2O3)Cl] and [Co2{Et(BigH) 2}2(S2O3)3] as well as of the cyanosalt [Co(Pn)2(CN)2]2S2O3 are described (Pn = propylene diamine; Et(BigH)2 = ethylene‐bis‐biguanide).