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Highly sensitive naphthalene-based two-photon fluorescent probe for in situ real-time bioimaging of ultratrace cyclooxygenase-2 in living biosystems.

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.