[Synthesis of N-(solanesylpiperazine-alkyl)-9-anthracenemethylamines and its interaction with DNA].
Two novel N-solanesylpiperazine triamines (4a, 4b) were synthesized and their structures were characterized by 1H NMR, IR, MS, and elemental analysis. The preliminary in vitro tests revealed that the IC50 values of compound 4a and 4b on L1210 were 4.3 and 3.1 micromol respectively. The interaction of 4b with DNA was also investigated via UV and FL spectra with N1-(4-aminobutyl)-N4-(9-anthracenylmethyl) butane-1,4-diamine (5) as the reference compound. The results revealed that compound 5 could quench the fluorescence of DNA-EB system, while compound 4b had the opposite function. Further tests proved that the fluorescence of compound 5 and 4b could be both quenched by DNA. It was speculated that compound 4b, with the long chain and two tertiary nitrogens, interacted with DNA by the static attraction or was partially embedded into DNA, while compound 5 was typically inserted into DNA.
Wang
Jian-Hong
JH
Lab of Natural Products and Medicines, College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475001, China.
Cheng
Peng-Fei
PF
Sun
Xin-Qi
XQ
Zhao
Jin
J
Wang
Chao-Jie
CJ
D000873:Anthracenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D001667:Binding, Competitive; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D005029:Ethylenediamines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000873:Anthracenes; D005029:Ethylenediamines; D010879:Piperazines; D004247:DNA