title: A Programmed DNA Marker Based on Bis(4-ethynyl-1,8-naphthalimide) and Three-Methane-Bridged Thiazole Orange.
abstract: Two large conjugated naphthalimide derivatives with or without three-methane-bridged thiazole orange (TO3; i.e., compounds 1 a and 2 a, respectively) were designed and synthesized. The fluorescence of the naphthalimide group in compound 1 a at λ=532 nm initially decreased and that for the TO3 group at λ=655 nm increased sequentially upon adding Salmon testes (St) DNA. In contrast, without the TO3 group, the fluorescence intensity of compound 2 a monotonously decreased in response to the addition of DNA. The non-monotonic change in the fluorescence for compound 1 a could be divided into two linear sections with two different wavelengths in the range of 0<Rb/1 a <1.2 and 1.2 <Rb/1 a <6.0 (Rb/1 a =[base pair]/[1 a]). Thus, compound 1 a can be regarded as a programmed responding molecule for DNA, which can semi-quantitatively determine the concentration of DNA over a large concentration range from the standard fluorescence curve of compound 1 a at different wavelengths when bound with DNA. Furthermore, the binding modes of compounds 1 a and 2 a with StDNA were studied by using CD spectroscopy and melting temperature (Tm ) testing. The results showed that compound 1 a interacts with StDNA through multi-interactions including weak intercalation, weak minor groove binding, and inter-dye interactions, whereas compound 2 a bound with DNA through simultaneous intercalation and minor groove binding.
authors.affiliation: Department of Chemistry and, Collaborative Innovation Center of Chemistry for Energy Materials, Fudan University, 220 Handan Road, Shanghai 200433 (P.R. China).
authors.forename: Yueyuan
authors.initials: Y
authors.lastname: Mao
authors.affiliation: Department of Chemistry and, Collaborative Innovation Center of Chemistry for Energy Materials, Fudan University, 220 Handan Road, Shanghai 200433 (P.R. China).
authors.forename: Keyin
authors.initials: K
authors.lastname: Liu
authors.affiliation: Department of Chemistry and, Collaborative Innovation Center of Chemistry for Energy Materials, Fudan University, 220 Handan Road, Shanghai 200433 (P.R. China).
authors.forename: Liang
authors.initials: L
authors.lastname: Chen
authors.affiliation: Department of Chemistry and, Collaborative Innovation Center of Chemistry for Energy Materials, Fudan University, 220 Handan Road, Shanghai 200433 (P.R. China).
authors.forename: Xinhua
authors.initials: X
authors.lastname: Cao
authors.affiliation: Department of Chemistry and, Collaborative Innovation Center of Chemistry for Energy Materials, Fudan University, 220 Handan Road, Shanghai 200433 (P.R. China). yitao@fudan.edu.cn.
authors.forename: Tao
authors.initials: T
authors.lastname: Yi
mesh_terms: D000818:Animals; D020029:Base Pairing; D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D005453:Fluorescence; D005819:Genetic Markers; D008297:Male; D008697:Methane / Q000737:chemistry*; D053644:Naphthalimides / Q000138:chemical synthesis* / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D012487:Salmonidae
chemical_list: D052160:Benzothiazoles; D005819:Genetic Markers; D053644:Naphthalimides; D011804:Quinolines; C000608193:bis(4-ethynyl-1,8-naphthalimide); C051000:thiazole orange; D004247:DNA; D008697:Methane
keywords: DNA; fluorescence; naphthalimides; programmed molecules; thiazole orange