SYNTHETIC STUDIES OF NEW BITHIAZOLE-AMINO ACID CONJUGATES AS DNA CLEAVERS

点击翻译按钮获取中文摘要

1. SynthesisNew bithiazole-amino acid conjugates containing 2,3-diaminopropanoic acid, 2,4-diaminobutanoic acid, 2,5-diaminopentanoic acid, 2,6-diaminohexanoic acid, arginine, histidine, alanine, β-alanine, glycine, and aminoalkanoic acid as amino acid residues were readily synthesized. The thirteen synthesized conjugates are N-substituted derivatives at one of aminoethyl group of 2,2'-bis (aminoethyl)-4,4'-bithiazole and other six conjugates are N-substituted derivatives at both aminoethyl groups. Also, two conjugates possessing 2,4'-bithiazole ring as a recognition site for DNA were also synthesized.2. DNA cleavage reactionsDNA cleavage reactions of the all obtained conjugates occurred only in the presence of Co (II) ion. Also, the reactions of DNA cleavage are dependent on pH of reaction solution. The conjugates having one or two amino acid substituent such as 2,3-diaminopropanoic acid possess strong DNA cleaving ability. The conjugates having one amino acid substituent are more pow … More erful DNA cleavers than those having two substituents. On the other hand, the conjugates having one or two 2,3-diaminopropanoic acid residues as a substituent are almost same cleaving ability.3. Interaction with DNAThe conjugates having one substituent such as diaminoalkanoic acid except for 2,3-diaminopropanoic acid possess a strong affinity for DNA because they have more amino groups as a cationic center than those of 2,2'-bis (aminoethyl)-4,4'-bithiazole. Furthermore, the conjugates having two lysine residues indicated the strongest affinity for DNA among those having two substituents.A number and the ionization of α-amino groups of the obtained bithiazole-amine acid conjugates play an important role in the ability of the DNA cleavage and the affinity for DNA.4. New 2,4'-bithiazole-4-carboxamide derivativesFive new 2,4'-bithiazole4-carboxamide derivatives possessing aminoalkyl groups were synthesized and investigated their affinity for DNA.It was considered that not only a number of the ionized amino groups but also the presence of 2,4'-bithiazole ring are strongly affected the affinity for DNA. Less