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Communication | Regular issue | Vol 48, No. 12, 1998, pp.2477-2480
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8330
Synthesis of β-Carboline Derivatives and Their Interaction with Duplex-DNA

Sanae Tamura, Takeo Konakahara,* Harunobu Komatsu, Tomokazu Ozaki, Yuichi Ohta, and Hiroki Takeuchi

*Department of Industrial Chemistry, Faculty of Science and Technology, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan

Abstract

3-Amino-9-N-(2-aminoethyl)carbamoylethyl-β-carboline (3) was synthesized from 3-methoxycarbonyl-β-carboline through successive cyanoethylation, Curtius rearrangement, and addition reaction of ethylenediamine in 45% overall yield. The terminal aliphatic amino group of 3 was transformed to a N’-methylureido group with succinimidyl N-methylcarbamate to afford a compound 4 in 80% yield. Affinity of 3, 4, β-carboline (1), and 3-amino-β-carboline (2) to a DNA oligomer or calf thymus DNA was spectrophotometrically studied. Optical spectroscopy of these β-carbolines showed 25 ~ 65 nm bathochromic shifts of the light absorption bands upon binding to the nucleic acids, which suggests binding by intercalation. Scatchard plots, obtained by fluorescence titration, gave the corresponding binding constants KD to the DNA oligomer; 7.45 x 103, 5.13 x 105, 7.34 x 105, and 7.01x 105, respcetively. The terminal aliphatic amino group considerably decreases the intercalating ability of 3 to DNA.