US 7,524,974 B2
Fluorescent probe
Tetsuo Nagano, 1-28-15, Amanuma, Suginami-ku, Tokyo 167-0032 (Japan); Yasuteru Urano, Kanagawa (Japan); Suguru Kenmoku, Tokyo (Japan); and Kohjiro Kanda, Saitama (Japan)
Assigned to Tetsuo Nagano, Tokyo (Japan); and Daiichi Pure Chemicals Co., Ltd., Tokyo (Japan)
Appl. No. 10/519,682
PCT Filed Jul. 07, 2003, PCT No. PCT/JP03/08585
§ 371(c)(1), (2), (4) Date Aug. 15, 2005,
PCT Pub. No. WO2004/005917, PCT Pub. Date Jan. 15, 2004.
Claims priority of application No. 2002-198197 (JP), filed on Jul. 08, 2002; and application No. 2003-20295 (JP), filed on Jan. 29, 2003.
Prior Publication US 2006/0030054 A1, Feb. 09, 2006
Int. Cl. C07D 311/90 (2006.01)
U.S. Cl. 549—224 17 Claims
 
1. A fluorescent probe which is represented by the following formula (I):

OG Complex Work Unit Drawing
wherein,
R1 and R2 each independently represents hydrogen atom, or a substituent for trapping proton, a metal ion, or an active oxygen species, provided that both of R1 and R2 do not simultaneously represent hydrogen atoms, or R1 and R2 may combine to each other to form a ring structure for trapping proton, a metal ion, or active oxygen species;
R3 is a lower alkyl group or a lower alkoxy group;
R4 and R5 each independently represents hydrogen atom or a halogen atom;
R6 represents hydrogen atom, an alkylcarbonyl group, or an alkylcarbonyloxymethyl group, provided that a combination of R1, R2, and R3 provides:
(1) substantially high electron density of the benzene ring to which said groups bind so that the compound represented by the formula (I) is substantially no fluorescent before the trapping of proton, a metal ion, or an active oxygen species, and
(2) substantially reduced electron density of the benzene ring to which said groups bind so that a compound after the trapping, which is derived from the compound represented by the formula (I), is substantially highly fluorescent after the trapping of proton, a metal ion, or an active oxygen species.