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At least 19 recordsLinked to original sources
PubMed1987

The role of biotransformation in the genotoxicity of allylic compounds.

Allylic compounds exert direct genotoxic activities which depend on the chemical nature of the leaving group and on further substituents. Besides the direct genotoxic effects, metabolic activation mechanisms are also conceivable. Epoxidation seems to play a minor role in bioactivation, whereas the metabolic formation of strongly mutagenic alpha, beta-unsaturated carbonyl compounds is obviously of great importance for the indirect genotoxicity of allylic compounds. Only in the case of 2,3-dichloro-1-propene is an epoxide formed which is extremely unstable and immediately rearranges to the strong mutagen, 1,3-dichloroacetone.

Allyl Compounds↗
PubMed1983

Induction of unscheduled DNA synthesis in HeLa cells by allylic compounds.

Thirteen allylic compounds, mostly with close structural relationship, were tested for their ability to induce unscheduled DNA synthesis (UDS) in HeLa cells and mutations in the Ames test; 11 induced UDS in dose dependence. Allyl isothiocyanate was negative in UDS (borderline in the Ames test) and acrolein (positive in the Ames test) proved toxic to HeLa cells, therefore UDS measurement was excluded. In general, positive qualitative and quantitative correlation between UDS, Ames test and alkylating properties (as measured in the 4-nitrobenzyl-pyridine test, NBP) were found. Among structural analogs and typical allylic compounds with various leaving groups, the amount of induced DNA repair at equimolar concentrations decreased in the same order as the mutagenic and alkylating activities in the other 2 test systems: 1,3-dichloropropene (cis) greater than 1,3-dichloropropene (trans) greater than 2,3-dichloro-1-propene; 1-chloro-2-butene greater than 3-chloro-1-butene greater than 3-chloro-2-methyl-1-propene greater than allyl chloride; allyl-methane-sulfonate greater than -iodide greater than -bromide greater than -chloride.

Allyl Compounds↗
PubMed1987

Allylic compounds bind directly to DNA: investigation of the binding mechanisms in vitro.

The in vitro binding of three allyl compounds, allyl methanesulphonate, allyl bromide and allyl chloride to DNA from salmon sperm was investigated. Kinetic DNA-alkylation measurements revealed significant differences between the strongly alkylating allyl methanesulphonate and allyl bromide with half-life values of 1.5 h and 8.1 h, respectively and the weakly alkylating allyl chloride with a half-life value of 360 h. Five alkylated nucleic bases, 3-allyladenine, N6-allyladenine, N2-allylguanine, 7-allylguanine and O6-allylguanine, could be identified after DNA-alkylation with all three allyl compounds.

Alkylating Agents↗
PubMed1993

Allyl compounds selectively killed human immunodeficiency virus (type 1)-infected cells.

Various allyl compounds were tested as anti-HIV reagents. Of all the allyl compounds tested, allyl disulfide (CH2 = CH-CH2-S-S-CH2-CH = CH2), allyl alcohol (CH2 = CH-CH2-OH), and its ester strongly depressed cell proliferation of HIV-1-infected cells. KC50 (50% killing concentration) of the allyl disulfide and the allyl alcohol were 34 microM and 10 microM, respectively. The allyl alcohol, in particular, completely inhibited cell growth of HIV-1-infected cells by a single injection at a concentration of 40 microM, ultimately killing the viable CEM/LAV-1 cells within 96 hr cultivation. No effect of the allyl alcohol and its esters on cell proliferation of CEM cells, which are a HIV-1 noninfected human T-cell cell line, was observed at the concentration range of 20 to 200 microM under the same experimental conditions. The results suggest that the effect of the allyl alcohol and its esters resulted in remarkable promotion of the cytopathic effect induced by HIV-1 virus.

1-Propanol↗
PubMed1982

Correlation of alkylating and mutagenic activities of allyl and allylic compounds: standard alkylation test vs. kinetic investigation.

Thirty-nine allylic and non-allylic compounds have been tested in the standard 4-(p-nitrobenzyl)pyridine (NBP) alkylating procedure and the Salmonella typhimurium mutagenicity assay. Fourteen of these were found directly mutagenic (without addition of S-9 mix activating enzyme system). With twelve of these compounds, a good correlation of alkylating and mutagenic potencies was established; the remaining two do not meet the chemical conditions of the NBP procedure on account of HCl elimination with these two compounds. The other 25 substances were inactive in both systems. The quantitative correlation proved to be almost linear in the lower activity ranges (E approximately 2; revertants/muml approximately 600). The reasons for some deviations from the linear relationship have been analyzed and discussed on the basis of structural features. In addition to the standard alkylation test, a modified NBP-test was performed in order to obtain kinetic data and activation energy values. The results with 6 representative allylic compounds show that the overall correlation is not substantially improved above that of the standard procedure: nonetheless, additional information on reaction characteristics is obtained with some substances.

Alkylating Agents↗
PubMedDate not supplied

Genotoxicity of allyl compounds--a quick screening strategy based on structure-activity relationships and a battery of prescreening tests.

A proposed strategy for the rapid screening of the genotoxic activities of allylic compounds is based on structure-activity relationships elaborated by a battery of quick screening tests. The procedure facilitates the selection of appropriate representatives of this class of compound for subsequent testing, so that both expensive and time-consuming assays and the use of animals can be drastically reduced. The studies have yielded several important results. Allylic compounds with suitable leaving groups have been shown to exert direct genotoxic activity. In the metabolic activation of these compounds the formation of epoxides is clearly of minor importance, playing a role only in the case of 2,3-dichloro-1-propene and some of its homologues, whereas all reactive allylic compounds can be activated to genotoxic alpha,beta-unsaturated carbonyl compounds (acrolein). The most significant factors for genotoxicity are the leaving groups and halogen substituents. Alkyl substituents increase the direct genotoxicity while decreasing the indirect activity (via acroleins).

Allyl Compounds↗
PubMed2005

A phosphine-catalyzed [3+6] annulation reaction of modified allylic compounds and tropone.

A novel phosphine-catalyzed reaction of modified allylic compounds, including acetates, bromides, chlorides, or tert-butyl carbonates derived from the Morita-Baylis-Hillman (MBH) reaction with tropone to yield [3+6] annulation products in excellent yields was developed. It offers a simple and convenient method for constructing bridged nine-membered carbocycles.

Journal Article↗
PubMed2003

Palladium-catalyzed benzannulation from alkynes and allylic compounds.

Various alkynes reacted with allyl tosylates in the presence of palladium catalysts, giving polysubstituted benzenes with good to high regioselectivity. Pentasubstituted and trisubstituted benzenes were readily prepared by reaction of internal alkynes and terminal alkynes, respectively. The combination of allyl alcohols and p-toluenesulfonic anhydride could be utilized in place of isolated allyl tosylates. The cyclization of diynes with allyl tosylate afforded bicyclic compounds containing an aromatic ring.

Journal Article↗
PubMed1995

Pemphigus and dietary factors. In vitro acantholysis by allyl compounds of the genus Allium.

BACKGROUND: Today it is generally accepted that every drug that possesses an active thiol group in its molecule is capable of inducing pemphigus in vivo and provoking acantholysis in vitro. We therefore suggested that plants, in particular those belonging to the Allium group, that contain several active compounds with stable disulfide and thiol groups in their molecule may cause the same. OBJECTIVE: To verify this hypothesis by investigating the in vitro acantholytic effect of three compounds of garlic. METHODS: Skin samples from donors were cultured in the presence of three compounds of garlic (i.e. allylmercaptan, allylmethylsulfide and allylsulfide) for 3 days. The skin samples were then processed for microscopic control for acantholysis. RESULTS: Results indicate that, indeed, the three garlic compounds tested are capable of inducing acantholysis in vitro. Focal and diffuse acantholysis was observed in the specimens from 4 out of 7 donors cultured in the presence of 6 and 9 mM of each of the allyl compounds for 3 days. Interestingly, tissues from a DR4+ donor proved to be more acantholysis prone than others, showing large blistering due to diffuse acantholysis, thus indicating that individual susceptibility plays a crucial role also in vitro. CONCLUSION: Garlic compounds with stable disulfide and thiol groups in their molecule are capable of inducing acantholysis in vitro. These findings lend further support to the theory that 'harmless' nutritional factors are capable of inducing acantholysis in vitro and possibly also in vivo. In view of these findings, it is suggested that nutritional factors should be added to the ever-growing list of exogenous factors capable of inducing pemphigus.

Acantholysis↗
PubMed2005

On the [2,3] sigmatropic rearrangement of allylic nitro compounds.

Allylic nitro compounds undergo relatively clean [2,3] sigmatropic rearrangement upon heating in refluxing 1,2-dichlorobenzene in the presence of DABCO to give the corresponding allylic alcohols via the intermediate allylic nitrite. [reaction: see text]

Journal Article↗
PubMed2006

The antioxidant properties of garlic compounds: allyl cysteine, alliin, allicin, and allyl disulfide.

Garlic and garlic extracts, through their antioxidant activities, have been reported to provide protection against free radical damage in the body. This study investigated antioxidant properties of garlic compounds representing the four main chemical classes, alliin, allyl cysteine, allyl disulfide, and allicin, prepared by chemical synthesis or purification. Alliin scavenged superoxide, while allyl cysteine and allyl disulfide did not react with superoxide. Allicin suppressed the formation of superoxide by the xanthine/xanthine oxidase system, probably via a thiol exchange mechanism. Alliin, allyl cysteine, and allyl disulfide all scavenged hydroxyl radicals; the rate constants calculated based on deoxyribose competitive assay were 1.4-1.7 x 10(10), 2.1-2.2 x 10(9), and 0.7-1.5 x 10(10) M (1) second(1), respectively. Contrary to previous reports, allicin did not exhibit hydroxyl radical scavenging activity in this study. Alliin, allicin, and allyl cysteine did not prevent induced microsomal lipid peroxidation, but both alliin and allyl cysteine were hydroxyl scavengers, and allyl disulfide was a lipid peroxidation terminator. In summary, our findings indicated that allyl disulfide, alliin, allicin, and allyl cysteine exhibit different patterns of antioxidant activities as protective compounds against free radical damage.

Allyl Compounds↗
PubMed1976

The effect of allyl compounds on hepatic microsomal mixed function oxidation and porphyrogenesis.

The activities of 5-aminolaevulinate (5-ALA) synthetase and of various microsomat drug-metabolising enzymes have been determined in the livers of rats pretreated with different drugs and chemicals containing the allyl group. Safrole, isosafrole and secobarbital gave rise to slight increases in 5-ALA synthetase, whereas alclophenac and triallyl cyanurate almost doubled the enzyme activity and the known porphyrogenic agents, allylisopropylacetamide (AIA) and allobarbital caused increases of 1.5- and 2.5-fold, respectively. Allobarbital induced the microsomal drug-metabolising enzymes while secobarbital had only a weak effect and alclophenac and triallyl cyanurate had no effect at all. From these results it is suggested that induction of the synthesis of cytochrome P-450 is not rate dependent on the synthesis haem and induction of porphyrin biosynthesis.

5-Aminolevulinate Synthetase↗