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PHOSPHA-RHODAMINE COMPOUND OR SALT THEREOF, AND FLUORESCENT DYE USING SAME

Foreign code F180009366
File No. (S2016-1019-N0)
Posted date Apr 19, 2018
Country WIPO
International application number 2017JP031203
International publication number WO 2018043579
Date of international filing Aug 30, 2017
Date of international publication Mar 8, 2018
Priority data
  • P2016-168882 (Aug 31, 2016) JP
Title PHOSPHA-RHODAMINE COMPOUND OR SALT THEREOF, AND FLUORESCENT DYE USING SAME
Abstract A phospha-rhodamine compound represented by general formula (1) (in the formula, R1 to R4 are the same or different and each represent a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted (hetero)aryl group; R5 represents a substituted or unsubstituted aryl group; R6 and R7 represent a hydrogen atom; R1 and R6 may be bonded to each other to form a substituted or unsubstituted alkylene group, and/or R3 and R7 may be bonded to each other to form a substituted or unsubstituted alkylene group; R8 represents a substituted or unsubstituted aryl group; and X represents a counterion) or salt thereof can provide a maximum fluorescence wavelength at a longer wavelength than conventional near-infrared fluorescent dyes and can do so without extending the conjugated system of the phospha-rhodamine skeleton.
Outline of related art and contending technology BACKGROUND ART
Having a high light stability is the development of a near infrared fluorescent dye, as well as life science research, also very interested in the medical field are provided. In fact, a near infrared fluorescent dye indocyanine green (ICG) which is representative of the surgical procedure is used, a relatively recent and has been increased, is expected to continue to grow in the future. However, poor in light stability is ICG, limiting applications.
Is a near infrared fluorescent dye, the current is thus poor in light stability, and limited applications, the near-infrared to the development of compounds represented by the strong fluorescence, non-invasive imaging of a living body from the viewpoint of the depth of the very important research issue. In addition, also in the imaging of the plants, chloroplast of the auto-fluorescence in the wavelength region of a long-wavelength region is extremely useful for fluorescent compound.
Such as a near infrared fluorescent dye, for example, Patent Document 1 and Non-Patent Document 1 is disclosed. Patent Document 1 shown is a near infrared fluorescent dye, xanthene skeleton having a 9 at a location P on a phosphorus atom (O-) =Ophospharodamine compound having a structure. In addition, non-patent document 1 shown in the near infrared fluorescent dye, xanthene skeleton having a 9 at a location P on a phosphorus atom (CH3) =Ophospharodamine compound having a structure. Such a conventional near-infrared fluorescent dye, a fluorescence maximum wavelength is not only about 710nm. In this case, the transmission from the viewpoints of the depth of the body not sufficient, further, a chloroplast fluorescence is in the range cannot be ignored. The fluorescence maximum wavelength to a longer wavelength is several tens of nm, the depth of the transparent body can be increased as well, the effect of the autofluorescence of the chloroplast completely ignore a region that can be very important.
Patent Document 1 is described above, the conjugated backbone phospharodamine further extended to the left as the compound of the aromatic ring,
Of the compound represented by the maximum fluorescence wavelength is 732nm has been described. However, the complexity of synthesis, water-soluble, non-specific adsorption takes place at the time of imaging from the viewpoint of the ease, phospharodamine skeleton itself can be changed with a fluorescence maximum wavelength is demanded a method capable of a longer wavelength.
Scope of claims (In Japanese)[請求項1]
一般式(1):
[化1]
[式中、R1~R4は同一又は異なって、水素原子、置換若しくは非置換アルキル基、又は置換若しくは非置換(ヘテロ)アリール基を示す。R5は置換若しくは非置換アリール基を示す。R6及びR7は水素原子を示す。R1とR6、及び/又はR3とR7は、互いに結合して置換若しくは非置換アルキレン基を構成してもよい。R8は置換若しくは非置換アリール基を示す。Xは対イオンを示す。]
で表されるホスファローダミン化合物又はその塩。
[請求項2]
前記R6及びR7がいずれも水素原子である、請求項1に記載のホスファローダミン化合物又はその塩。
[請求項3]
前記R6が、一般式(2):
[化2]
[式中、R9及びR10は同一又は異なって、水素原子、置換若しくは非置換アルキル基、又は置換若しくは非置換アルコキシ基を示す。R11は水素原子又は反応性基を示す。]
で表される、請求項1又は2に記載のホスファローダミン化合物又はその塩。
[請求項4]
前記R9及びR10がいずれも置換若しくは非置換アルキル基、又は置換若しくは非置換アルコキシ基である、請求項3に記載のホスファローダミン化合物又はその塩。
[請求項5]
前記R11が、アミン反応性基又はチオール反応性基である、請求項3又は4に記載のホスファローダミン化合物又はその塩。
[請求項6]
前記アミン反応性基又はチオール反応性基が、一般式(3A)~(3E):
[化3]
[式中、R12は水素原子又はスルホ基を示す。R13は置換若しくは非置換アルキル基を示す。実線と破線で示される結合は、単結合又は二重結合である。]
で表される構造を末端に有する基である、請求項5に記載のホスファローダミン化合物又はその塩。
[請求項7]
請求項1~6のいずれかに記載のホスファローダミン化合物又はその塩からなる蛍光色素。
[請求項8]
請求項5又は6に記載のホスファローダミン化合物又はその塩を用いたタンパク質標識剤。
[請求項9]
請求項8に記載のタンパク質標識剤を含有する、タンパク質標識化キット。
[請求項10]
請求項8に記載のタンパク質標識剤と、タンパク質とを反応させる工程
を備える、タンパク質標識化方法。
  • Applicant
  • ※All designated countries except for US in the data before July 2012
  • NAGOYA UNIVERSITY
  • Inventor
  • YAMAGUCHI, Shigehiro
  • TAKI, Masayasu
  • SATO, Yoshikatsu
  • NAKA, Aiko
  • GRZYBOWSKI, Marek Grzegorz
IPC(International Patent Classification)
Specified countries National States: AE AG AL AM AO AT AU AZ BA BB BG BH BN BR BW BY BZ CA CH CL CN CO CR CU CZ DE DJ DK DM DO DZ EC EE EG ES FI GB GD GE GH GM GT HN HR HU ID IL IN IR IS JO JP KE KG KH KN KP KR KW KZ LA LC LK LR LS LU LY MA MD ME MG MK MN MW MX MY MZ NA NG NI NO NZ OM PA PE PG PH PL PT QA RO RS RU RW SA SC SD SE SG SK SL SM ST SV SY TH TJ TM TN TR TT TZ UA UG US UZ VC VN ZA ZM ZW
ARIPO: BW GH GM KE LR LS MW MZ NA RW SD SL SZ TZ UG ZM ZW
EAPO: AM AZ BY KG KZ RU TJ TM
EPO: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
OAPI: BF BJ CF CG CI CM GA GN GQ GW KM ML MR NE SN ST TD TG
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