Synthesis of naphthalenediimide having two beta-cyclodextrins at both of its substituent termini.
Naphthalenediimide (1) carrying two beta-cyclodextrins (beta CDs) was successfully synthesized by click chemistry between pentynylnaphthalenediimide and azido beta CD. Absorption spectra of 1 showed hypochromic and red shifts upon addition of sonicated calf thymus DNA as a double stranded DNA. Kinetic studies showed its slow association with and dissociation from calf thymus DNA. These results suggested that 1 can bind to double stranded DNA by the threading mode, where one of the beta CD is required to go through adjacent base pairs of double stranded DNA. If this is proven, beta CD is one of the largest groups ever reported which can go through a DNA duplex for threading.
Ohtsuka
Keiichi
K
Department of Applied Chemistry, Kyushu Institute of Technology, Kitakyushu 804-8550, Japan.
Sato
Shinobu
S
Watanabe
Sadayoshi
S
Komizo
Kohei
K
Takenaka
Shigeori
S
D002851:Chromatography, High Pressure Liquid; D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D007094:Imides / Q000138:chemical synthesis* / Q000737:chemistry; D007364:Intercalating Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D047392:beta-Cyclodextrins / Q000737:chemistry*
D003505:Cyclodextrins; D007094:Imides; D007364:Intercalating Agents; D047392:beta-Cyclodextrins; D004247:DNA; C427203:calf thymus DNA