An HBT-based fluorescent dye with enhanced quantum yield in water system and its application for constructing NQO1 fluorescent probe

NAD(P)H Quinone Oxidoreductase-1 in Organ and Tumor Tissues: Distinct Activity Levels Observed with a Benzo-rosol-Based Dual-Excitation and Dual-Emission Probe

“…In 2011, McCarley and coworkers disclosed the first fluorescent probe for NQO1, which contains an enzyme substrate quinone linked by way of a self-immolative “trimethyl lock” acid to a fluorophore (Scheme ). Subsequently, other groups − used the sensing scheme to develop different activatable probes by changing the fluorophore, leading to a few tens of NQO1 probes so far (Table S1 in the Supporting Information). Most of them, however, signal a turn-on type fluorescence change because the quinone is apt to quench fluorescence through photoinduced electron transfer (PET).…”

Optical substrates for drug-metabolizing enzymes: Recent advances and future perspectives

“…Consequently, McCarley group and his team 67 , 68 , 69 have developed several QPA-based fluorescent substrates for highly selective imaging of NQO1 in cancer cells (NQO1-F1-F3). Other fluorophores include naphthalimide (NQO1-F4,F11 ) 70 , 71 , acedan (NQO1-F5,F6) 72 , 73 , coumarin (NQO1-F7) 74 , hemicyanine (NQO1-F8,F10) 75 , 76 , cyanine 7 amine (NQO1-F9) 75 , 2-hydroxyphenyl substituted benzimidazole (HBI)/benzoxazole (HBO)/benzothiazole (HBT) (NQO1-F12) 77 , 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran (TCF) (NQO1-F13) 78 , dicyanoisophorone (NQO1-F14) 79 , and 7-nitro-2,1,3-benzoxadiazole (NBD) (NQO1-F15) 80 were also used in designing NQOs triggered sensors. Some chemists add some self-leaving groups to the above strategy, upon NQOs treatment, the linking group leaves and releases the fluorescent group ( Fig.…”

“… N.A. 670/710 75 NQO1 NQO1-F9 1.42 ± 0.18 1.89 730/800 75 NQO1 NQO1-F10 3.73 1.22 680/704 76 NQO1 NQO1-F11 1.80 ± 0.37 0.267 345/540 70 NQO1 NQO1-F12 3.79 V max =0.126 μmol/min/L 397/600 77 NQO1 NQO1-F13 N.A. N.A.…”

A bioluminescent probe for NQO1 overexpressing cancer cell imagingin vitroandin vivo

“…14,15 NAD(P)H: quinone oxidoreductase-1 (NQO1), a cytosolic flavin two-electron reductase which catalyses the reduction of quinones to the corresponding hydroquinones with NADH or NADPH as the auxiliary electron donors, plays essential roles in cellular detoxification of quinone derivatives, protection against oxidative stress, stabilization of metabolic functions, regulation of tumor suppressors ( p53, p33) and so on. [16][17][18] NQO1 is constitutively expressed at a low level in normal tissues but highly expressed in a variety of cancers such as lung cancer, prostate cancer, colon cancer, pancreatic cancer, brain cancer, breast cancer, and head and neck cancer and thus can be recognized as an attractive cancer biomarker. [18][19][20][21][22] In addition, its elevated activity is also closely associated with tumor progression, aggressiveness, resistance to chemotherapy, and poor prognosis.…”