title: Highly sensitive naphthalene-based two-photon fluorescent probe for in situ real-time bioimaging of ultratrace cyclooxygenase-2 in living biosystems.
abstract: Detecting and imaging of ultratrace cyclooxygenase-2 in living biosystems could provide much important valuable information for the diagnosis and intervention of cancer. Molecular probes, whose fluorescent signals are generated by cyclooxygenase-2, hold great potential for identification and enumeration of cyclooxygenase-2 in living biosystems. Although quite a few fluorescent probes have been reported for cyclooxygenase-2, the use fluorogenic probe with the excellent two-photon properties for the determination of ultratrace cyclooxygenase-2 has been scarce. Herein, an "off-on" fluorescence probe (BTDAN-COX-2), able to report and image the presence of ultratrace cyclooxygenase-2 in living biosystems, has been designed and evaluated. In order to improve sensitivity and specific selectivity of probe for ultratrace cyclooxygenase-2, BTDAN-COX-2 employed cyclooxygenase-2's inhibitor as recognition group, because it is a classical and efficient recognition group for cyclooxygenase-2. A polarity-sensitive naphthalene derivative (BTDAN) as fluorophore was introduced into the molecule to enhance two-photon properties of BTDAN-COX-2. In the absent of cyclooxygenase-2, BTDAN-COX-2 mainly exists in a folded conformation where probe fluorescence is quenched through photoinduced electron transfer between the fluorophore and the recognition group. Under the condition of existence of cyclooxygenase-2, fluorescence of probe is turned on, because photoinduced electron transfer between the fluorophore and the recognition group is restrained. BTDAN-COX-2 provides high signal-to-background staining for the ultratrace cyclooxygenase-2 and has been successfully used to rapidly detect and image ultratrace cyclooxygenase-2 in living biosystems.
authors.affiliation: School of Chemistry and Chemical Engineering, Henan Normal University , 46 Jianshe Road, Muye Zone, Xinxiang 453007, P.R. China.
authors.forename: Hua
authors.initials: H
authors.lastname: Zhang
authors.forename: Jiangli
authors.initials: J
authors.lastname: Fan
authors.forename: Kui
authors.initials: K
authors.lastname: Wang
authors.forename: Jing
authors.initials: J
authors.lastname: Li
authors.forename: Caixia
authors.initials: C
authors.lastname: Wang
authors.forename: Yamin
authors.initials: Y
authors.lastname: Nie
authors.forename: Tao
authors.initials: T
authors.lastname: Jiang
authors.forename: Huiying
authors.initials: H
authors.lastname: Mu
authors.forename: Xiaojun
authors.initials: X
authors.lastname: Peng
authors.forename: Kai
authors.initials: K
authors.lastname: Jiang
mesh_terms: D000818:Animals; D002351:Carrageenan / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D051546:Cyclooxygenase 2 / Q000032:analysis*; D004797:Enzyme-Linked Immunosorbent Assay; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000633:toxicity; D057809:HEK293 Cells; D006367:HeLa Cells; D006801:Humans; D007249:Inflammation / Q000139:chemically induced / Q000175:diagnosis; D061986:MCF-7 Cells; D051379:Mice; D008856:Microscopy, Fluorescence; D009281:Naphthalenes / Q000737:chemistry* / Q000633:toxicity; D017785:Photons; D011789:Quantum Theory; D013050:Spectrometry, Fluorescence; D013844:Thiazoles / Q000737:chemistry* / Q000633:toxicity
chemical_list: C000600671:BTDAN-COX-2; D005456:Fluorescent Dyes; D009281:Naphthalenes; D013844:Thiazoles; C031721:naphthalene; D002351:Carrageenan; D051546:Cyclooxygenase 2