Synthesis of naphthalenediimide having two -cyclodextrins at both of its substituent termini | Zendy

Keiichi Ohtsuka | Zendy; Shinichi Sato | Zendy; S. Watanabe | Zendy; Kohei Komizo | Zendy; Shigeori Takenaka | Zendy

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Synthesis of naphthalenediimide having two -cyclodextrins at both of its substituent termini

Author(s) -

Keiichi Ohtsuka,

Shinichi Sato,

S. Watanabe,

Kohei Komizo,

Shigeori Takenaka

Publication year - 2008

Publication title -

nucleic acids symposium series

Language(s) - English

Resource type - Journals

eISSN - 1746-8272

pISSN - 0261-3166

DOI - 10.1093/nass/nrn362

Subject(s) - dna , chemistry , substituent , double stranded , base pair , duplex (building) , threading (protein sequence) , stereochemistry , crystallography , biochemistry , protein structure

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.

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