US 11,988,667 B2
Fluorescent compound and fluorescent labeled biological substance using the same
Hiyoku Nakata, Kanagawa (JP); Kousuke Watanabe, Kanagawa (JP); Akihiro Asakura, Kanagawa (JP); Keiko Makita, Kanagawa (JP); Yoshinori Kanazawa, Kanagawa (JP); and Kazuhei Kaneko, Kanagawa (JP)
Assigned to FUJIFILM Corporation, Tokyo (JP)
Filed by FUJIFILM Corporation, Tokyo (JP)
Filed on Nov. 27, 2020, as Appl. No. 17/105,638.
Application 17/105,638 is a continuation of application No. PCT/JP2019/021770, filed on May 31, 2019.
Claims priority of application No. 2018-106460 (JP), filed on Jun. 1, 2018; and application No. 2019-025958 (JP), filed on Feb. 15, 2019.
Prior Publication US 2021/0088526 A1, Mar. 25, 2021
Int. Cl. C09K 11/06 (2006.01); C09B 23/06 (2006.01); G01N 21/64 (2006.01); G01N 33/58 (2006.01)
CPC G01N 33/582 (2013.01) [C09B 23/06 (2013.01); C09K 11/06 (2013.01); G01N 21/6428 (2013.01); C09K 2211/1029 (2013.01); G01N 2021/6439 (2013.01)] 18 Claims
 
1. A fluorescent compound represented by Formula (1) or Formula (4),

OG Complex Work Unit Chemistry
in the formula, X represents CR5 or N,
R1 to R6 represent a halogen atom, a cyano group, or a group represented by Formula (A),
R7 represents an alkyl group, a cycloalkyl group, an aliphatic heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxyl group, a mercapto group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, an aryl group, a heteroaryl group, or a halogen atom, where R6 and R7 do not bond to each other to form a ring,
Q1 and Q2 represent a group represented by any one of Formulae (1-1) to (1-3),
L1 and L2 represent an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, a cycloalkylene group, a cycloalkenylene group, a divalent aliphatic heterocyclic group, or a group represented by any one of Formulae (1-1) to (1-8), or a linking group formed by combining two to four of these groups, and
a ring β1 and a ring β2 are a 5- to 8-membered ring,
provided that at least one of R1 to R7, L1, L2, Q1, or Q2 has at least one of a carboxy group or a salt thereof, a sulfo group or a salt thereof, a phosphono group or a salt thereof, an onio group selected from the group consisting of an ammonio group, a sulfonio group and a phosphonio group, or a polyamino acid residue,
in a case where X is CR5, where R5 is a group represented by Formula (A), the ring pi and the ring β2 are a 6-membered ring, and L1 and L2 are an arylene group, (a) there is no case in which L3 is a single bond and Rill is an aryl group having a linear alkyl group having 18 or more carbon atoms, as a substituent, and (b) there is no case in which L3 is arylene group and R111 is a linear alkyl group having 18 or more carbon atoms, and
in a case where X is CR5, where R5 is a group represented by Formula (A), the ring pi and the ring β2 are a 6-membered ring, L1 and L2 are an arylene group, and R111 has a substituent having a dipyrromethene boron complex structure, the dipyrromethene boron complex structure has a structure in which a dipyrromethene skeleton is coordinately bonded to a boron atom in a tridentate or tetradentate coordination,
*L3-R111  Formula (A)
in the formula, L3 represents a single bond or a linking group formed by combining one or two or more of an alkylene group, an arylene group, and a group represented by any one of Formulae (1-1) to (1-8),
R11 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, or a monovalent aliphatic heterocyclic group, and
* represents a bonding portion,

OG Complex Work Unit Chemistry
in the formula, R11 and R12 represent a hydrogen atom or a substituent, and
* represents a bonding portion.