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PubMed2004

Antimicrobial activities of some amino derivatives of 5, 7-dibromo-2-methyl-8-benzoyloxyquinoline.

In an attempt to design and synthesize more potent quinoline-based chemotherapeutic agents structural modifications of 5, 7-Dibromo-2-methyl-8-benzoyloxyqinoline was carried out. The replacement of the bromine atoms with the requisite alkylamino compound gave four amino-derivatives viz: bis(dipropylamino)-dipyrrolidino-, dipiperidino- and dipiperazino derivatives. The antimicrobial activities of these compounds were investigated against selected Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Escherichin coli, Pseudomonas aeruginosa and Klebsiella spp) and yeast (Candida albicans). All the compounds showed broad or significant antimicrobial activity, which varied from two to ninety times that of the parent compound. The dipyrrolidino derivative was the most effective against Gram-positive bacteria and yeast while the dipiperidino derivative was the most effective against Gram-negative bacteria. No correlation has been established between the minimum inhibitory, (MIC) concentrations of the derivatives and the structural modifications.

Anti-Infective Agents↗
PubMed2005

[A study on the ultraviolet spectra of halogenated benzoylferrocenes].

The ultraviolet spectra of all of the o, m, p-halogenated benzoylferrocenes have been studied the following rules obtained: 1. The lambdamax of the ultraviolet spectrum R band and K band for the isomers is lambdamax(m-X) > lambdamax(p-X) > lambdamax(o-X). 2. With the same substituted positions of the different halogen on the benzene ring, the lambdamax of the ultraviolet spectrum K band is lambdamax(C1) > lambdamax(Br) > lambdamax(I) > lambdamax(F), then, the lambdamax of ultraviolet spectrum R band is lambdamax(I) > lambdamax(Br) > lambdamax(Cl) > lambdamax(F).

Benzene↗
PubMed1988

The effects of cetrimide and potassium bromate on the potassium ion concentration in the inner ear fluid of the guinea-pig.

The mammalian inner ear is located deep within the temporal bone. The organ of Corti, the delicate sensory system for sound, is surrounded by two fluid systems; the potassium-rich endolymph and the sodium-rich perilymph. The pathogenesis of inner ear deafness is thought to be largely due to an imbalance of potassium and sodium ions in the inner ear fluids. Dynamic changes in K+ in the endolymph and perilymph were studied in the guinea-pig following cetrimide (cetrimonium bromide, a powerful cationic detergent which shows ototoxicity) applications on the round window membrane, intramuscular injection of potassium bromate (bread whitener, known to cause renal damage and permanent deafness in animals and man). Maximum fall in K+ concentration in the endolymoh (mM/min) and maximum K+ conductance (mM/min/mV) were 3.54 +/- 1.65 and 0.036 +/- 0.02 in cetrimide, and 1.85 +/- 0.35 and 0.021 +/- 0.009 in potassium bromate, respectively. In view of these findings, the influence of the active transport mechanism to K+ concentrations are discussed in comparison with dynamic changes in endolymph K+ induced by asphyxia and ethacrynic acid.

Animals↗
PubMed1997

Loading and localization of Fluo-3 and Fluo-3/AM calcium indicators in sinapis alba root tissue.

Stimulus-induced changes in free cytosolic Ca2+ in different types of plant cells have been monitored with the aid of fluorescent calcium indicator dyes. However, there is no simple and convenient method for introducing these dyes into the plant cell cytoplasm. This paper reports tests of different procedures for loading either free fluorescent dyes or their acetoxymethyl esters (Fluo-3 and Fluo-3/AM, respectively) into Sinapis alba root tissue. Loading of Fluo-3 was pH and temperature dependent. Moreover, in the presence of beta-escin (saponin) in the loading medium very high fluorescent signals in root tissues were observed. The highest signals were recorded when tissue was loaded in a medium containing 0.1% beta-escin, at pH 5.0 and 30 degrees C. Only very weak fluorescence signals were found in mustard roots loaded with Fluo-3/AM. Acidity and temperature of the medium had no significant effect on the process. However, addition of eserine, a cholinesterase inhibitor led to a dramatic increase in fluorescence in the root cells. On the basis of these observations rapid and efficient methods of loading both Fluo-3 and Fluo-3/AM into mustard root tissues are proposed.

Acetylcholinesterase↗
PubMed2006

Identification of highly brominated analogues of Q1 in marine mammals.

Three novel halogenated organic compounds (HOCs) have been identified in the blubber of marine mammals from coastal New England with the molecular formulae C(9)H(3)N(2)Br(6)Cl, C(9)H(3)N(2)Br(7), and C(9)H(4)N(2)Br(5)Cl. They were identified using high and low resolution gas chromatography mass spectrometry (GCMS) and appear to be highly brominated analogues of Q1, a heptachlorinated HOC suspected to be naturally produced. These compounds were found in Atlantic white sided dolphin (Lagenorhynchus acutus), bottlenose dolphin (Tursiops truncatus), common dolphin (Delphinus delphis), Risso's dolphin (Grampus griseus), harbor porpoise (Phocoena phocoena), beluga whale (Delphinapterus leucas), fin whale (Balaenoptera physalus), grey seal (Halichoerus grypus), harp seal (Phoca groenlandica) and a potential food source (Loligo pealei) with concentrations as high as 2.7 microg/g (lipid weight). The regiospecificity of C(9)H(3)N(2)Br(6)Cl is suggestive of a biogenic origin. Debromination of C(9)H(3)N(2)Br(6)Cl may be significant in the formation of C(9)H(4)N(2)Br(5)Cl.

Animals↗
PubMed2001

Synthesis and molluscicidal structure-activity relationships of some novel 1,2,4-triazole N-methyl carbamates.

A new series of 1,2,4-triazole derivatives and their corresponding carbamates have been synthesized and screened for their molluscicidal activity against two types of terrestrial snail, Helix aspersa and Theba pisana, by two methods of application, either as contact or as bran baits. Several of the tested compounds exhibited good molluscicidal activity, and T pisana was more sensitive than H aspersa. Substitution at the o- and/or p-positions of the phenyl ring with chlorine or bromine gave higher molluscicidal activity than the unsubstituted compound, with o,p-dichloro substitution being optimum. In addition, compounds containing two triazole moieties showed higher molluscicidal activity, particularly as stomach poisons, than the contact toxic effect of the corresponding compound with one triazole ring. In general, carbamate derivatives were more active than their corresponding 1,2,4-triazole derivatives.

Animals↗
PubMed1998

5'-Substituted thalidomide analogs as modulators of TNF-alpha.

The synthesis of 5'-substituted thalidomide analogs is described. The amino acids 2 necessary to synthesize the target compounds were prepared by Michael reaction. Condensation of 2 with phthalic anhydrides followed by reaction with urea yielded 4 as diastereomeric mixtures. Furthermore glutethimide (5) was brominated by an improved method and the resulting compound 6 was reacted in several steps with sodium azide, hydrogen, and phthalic anhydride to give 8. In a similar manner, 6 was reacted with sodium azide and various phthalic anhydrides to give 9, 10, and 11. All final compounds were tested in vitro for their inhibitory activity on the release of TNF-alpha, using stimulated peripheral mononuclear blood cells (PBMCs). Compounds with an additional aromatic substituent in position 5' of the thalidomide molecule were more active than thalidomide. Compound 11 was able to reduce increased levels of IL-2 in vitro.

Humans↗
PubMed2004

Vapour pressures, aqueous solubilities, Henry's Law constants, and octanol/water partition coefficients of a series of mixed halogenated dimethyl bipyrroles.

Basic physical-chemical properties of five bromine and chlorine containing mixed halogenated dimethyl bipyrroles (HDBPs) were determined using established methods. Subcooled liquid vapour pressures (P(o)(L,25)), aqueous solubilities (S(w,25)), and octanol/water partition coefficients (K(ow)) were determined using the gas chromatography-retention time, generator column, and slow-stirring methods, respectively. Henry's Law constants (H25) were estimated using experimentally-derived P(o)(L) and S(w,25) data. Values of all four properties were generally similar to those reported for other polyhalogenated aromatic compounds [P(o)(L,25) = (7.55-191) x 10(-6) Pa; S(w,25) = (1.0-1.9) x 10(-5) g/l; log K(ow) = 6.4-6.7; H25 = 0.0020-0.14 Pa m3/mol]. The effect of replacing a chlorine with a bromine atom significantly decreased P(o)(L,25) (log P(o)(L,25) = -0.4197 (# bromine atoms) - 2.643, p<0.01) and H25 (log H25 = -0.508 (# bromine atoms) + 0.394, p<0.02). There were no significant effects of bromine/chlorine substitution on S(w,25) or K(ow). A simple Level I equilibrium partitioning model predicted the environmental behaviour of HDBPs to be similar to a tetrabrominated diphenyl ether. Only slight differences in behaviour amongst HDBP congeners were predicted since substitution of a bromine for a chlorine (Cl/Br substitution) atom had less effect than H/Cl or H/Br substitution on P(o)(L,25), S(w,25), H25, and K(ow).

Bromine Compounds↗
PubMed1990

Comparison of the DNA-alkylating properties and mutagenic responses of a series of S-(2-haloethyl)-substituted cysteine and glutathione derivatives.

The mutagenicity of 1,2-dibromoethane is highly dependent upon its conjugation to glutathione by the enzyme glutathione S-transferase. The conjugates thus formed can react with DNA and yield almost exclusively N7-guanyl adducts. We have synthesized the S-haloethyl conjugates of cysteine and glutathione, as well as selected methyl ester and N-acetyl derivatives, and compared them for ability to produce N7-guanyl adducts with calf thymus DNA. The cysteine compounds were found to be more reactive toward calf thymus DNA and yielded higher adduct levels than did the glutathione compounds. Adduct levels tended to be suppressed when there was a net charge on the compound and were not affected by substitution of bromine for chlorine, as expected for a mechanism known to involve an intermediate episulfonium ion. Sequence-selective alkylation of fragments of pBR322 DNA was investigated. The compounds produced qualitatively similar patterns of alkylation, with higher levels of alkylation at runs of guanines. The compounds were also tested for their ability to act as direct mutagens in Salmonella typhimurium TA98 and TA100. None of the compounds caused mutations in the TA98 frameshift mutagenesis assay. In the strain TA100, where mutation of a specific guanine by base-pair substitution produces reversion, all compounds were found to produce mutations, but the levels of mutagenicity did not correlate at all with the levels of DNA alkylation. The ratio of mutations to adducts varied at least 14-fold among the various N7-guanyl adducts examined.(ABSTRACT TRUNCATED AT 250 WORDS)

Alkylating Agents↗