Both protection and sensitization of Mice C57Bl against 60Co gamma-rays by sulfur-containing amino acid derivatives--S-alkyl-L-cysteines, S-alkyl-2-methyl-DL-cysteines and their hydantoin derivatives, and sulfoxides of these compounds--were examined. DL-5 Allylthiomethyl-5-methylhydantoin (150 mg/kg body weight) had a remarkable radioprotective effect. The survival ratio was 4.3 or above two ti...

To obtain a rapid, efficient and mild synthesis of 5,5-diphenylhydantoin and 5,5-diphenyl-2-thiohydantoin derivatives, ultrasonic irradiation has been applied to the reaction mixtures containing substituted benzils and urea or thiourea derivatives catalyzed by KOH in DMSO/H(2)O, which allowed us to achieve products at room temperature in a good yield and short time without any side product. Thi...

Psammaplin F, an unsymmetrical disulfide bromotyrosine, was isolated from the sponge Pseudoceratina purpurea in 2003. We reported here the first total synthesis of psammaplin F in 12% overall yield by employing Cleland's reagent reduction as key step. The longest linear synthetic sequence starting from 3-bromo-4-hydroxybenzaldehyde and hydantoin was seven steps. In addition, a detailed X-ray cr...

The methylation and oxidative demethylation of cytosine in CpG dinucleotides plays a critical role in the regulation of genes during cell differentiation, embryogenesis and carcinogenesis. Despite its low abundance, 5-methylcytosine (5mC) is a hotspot for mutations in mammalian cells. Here, we measured five oxidation products of 5mC together with the analogous products of cytosine and thymine i...

G-quadruplex is a four-stranded G-rich DNA structure that is highly susceptible to oxidation. Despite the important roles that G-quadruplexes play in telomere biology and gene transcription, neither the impact of guanine lesions on the stability of quadruplexes nor their repair are well understood. Here, we show that the oxidized guanine lesions 8-oxo-7,8-dihydroguanine (8-oxoG), guanidinohydan...

The researches on D-hydantoinase activity and substrate specificity towards dihydropyrimidine and hydantoin derivatives have been carried out intensively over the last few decades. So far, the major efforts have focused on (R,S)-5-phenylhydantoin and (R,S)-5-(4-hydroxyphenyl)hydantoin, the most desirable D-hydantoinase substrates from pharmaceutical industry point of view. However, it was shown...

Hydantoin derivatives, including phenytoin (5,5-diphenylhydantoin), have recently gained attention as they possess a variety of important biochemical and pharmacological properties. Nevertheless, available information on anticancer activity of hydantoin derivatives is still scarce. Here, we evaluated possible antileukemic potential of four phenytoin analogs, namely: methyl 2-(2,4-dioxo-5,5-diph...

A number of structurally related hydantoins has been examined for their effects on the metabolic activities of Ehrlieh aseites carcinoma cells. 5-Ethylsulfinylmethylhydantoin [ESH] was a potent inhibitor of such activities. 5-Ethylsulfonylmethylhydantoin had less activity, and the other hydantoins tested were without effect. ESH was also a potent inhibitor of metabolism in Salk "altered" monkey...

Cisplatin is one of the most successful compounds in the fight against cancer. Recently, interest was directed towards the development of cisplatin analogues which possess Nheterocyclic carrier ligands, coordinated to the cytotoxic platinum(II) moiety, instead of one or both of the am(m)ines. Hydantoins form a large group of derivatives widely applied in medicine and pharmacy, especially as ant...