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REAGENT FOR FLUORESCENCE IMAGING OF LIPID DROPLETS IN CELL AND TISSUE NEW

外国特許コード F200010246
整理番号 (S2019-0343-N0)
掲載日 2020年10月30日
出願国 世界知的所有権機関(WIPO)
国際出願番号 2020JP012002
国際公開番号 WO2020189721
国際出願日 令和2年3月18日(2020.3.18)
国際公開日 令和2年9月24日(2020.9.24)
優先権データ
  • 特願2019-051368 (2019.3.19) JP
発明の名称 (英語) REAGENT FOR FLUORESCENCE IMAGING OF LIPID DROPLETS IN CELL AND TISSUE NEW
発明の概要(英語) The present invention addresses the problem of providing a fluorescent reagent with which it is possible to perform high-sensitivity imaging of lipid droplets at a scale from the cultured cell level to the individual level. The present invention provides a reagent that contains a compound represented by general formula (I) and that is for detecting lipid droplets. (In the formula, m is an integer between 0 and 5; n is an integer between 0 and 5; X is selected from the group consisting of a sulfur atom, an oxygen atom, and a group indicated by NR; R is a hydrogen atom or a group indicated by -(CH2)yCH3; and y is an integer between 0 and 5.)
従来技術、競合技術の概要(英語) BACKGROUND ART
Lipid drop (fat drop) is a spherical intracellular organelle in which neutral lipids such as triacylglycerol and cholesterol ester are surrounded by a monolayer phospholipid membrane. Most of them are found in adipocytes, but they are universally present in any cells. In recent years, lipid droplets are involved in the regulation of lipid metabolism in cells. In addition, studies on lipid droplets and autophagy have been reported. On the other hand, excessive accumulation of fat in tissue (individuals) leads to tissue dysfunction, causing diabetes, arteriosclerosis, and the like. In recent years, the development of non-alcoholic steatohepatitis (NASH), which is 1 species of hepatitis, has rapidly increased. If NASH is left to stand, there is a risk of progressing to liver cirrhosis or liver cancer. Therefore, it is important to elucidate the mechanism of formation, growth and degradation of lipid droplets in cells and tissues not only in cell biology but also in diagnosis and treatment of these diseases. Therefore, it is necessary to develop a molecular probe for real-time imaging of lipid droplets in living cells or tissues with high sensitivity.
Fluorescence imaging is a convenient method for imaging cells and tissues in living state, and is widely used in biological and medical studies. Many fluorescent reagents for imaging lipid droplets have been reported at the scientific level, but the reagent used for practical use is limited to several kinds. Fig.1 shows currently commercially available lipid drop fluorescence imaging reagents. BODIPY493/503, Nile Red are used by many researchers. BODIPY493/503 shows green fluorescence near 500 nm and has high lipid droplet selectivity. However, there are problems such as the leakage of excitation light caused by the fact that the light stability is not high, the retention of lipid droplets is low, and the energy difference) between the Stokes shift (absorption maximum wavelength and the fluorescence maximum wavelength is small. Further, since Nile red is distributed in many subcellular organelles other than lipid droplets, lipid droplet selectivity is low. Furthermore, since absorption and fluorescence spectra greatly change depending on the surrounding microenvironment, it is difficult to perform multiple dyeing with other fluorescent reagents. In addition, Patent Document 1 reports an oil droplet staining agent using a ring-fused thiophene compound, however, since the peak of excitation light is widely present from blue to green, imaging is overlapped and multicolor imaging is difficult. To solve these problems, LipiDye and Lipi series (Lipi-Blue , Lipi-Green , Lipi-Red) have been developed. Although these reagents are capable of selectively imaging intracellular lipid droplets, there is no knowledge about lipid droplet imaging in living tissue.
For lipid droplet imaging in living tissues, a Nile Blue derivative with nitrobenzenes substituted, (MNs-NB , Fig. 2) is reported as Japanese Patent Document 2. In MNs-NB, a photoinduced electron transfer reaction occurs between the nitrobenzene unit and Nile blue in a polar solvent. On the other hand, in a low-polarity solvent, photoinduced electron transfer reaction is less likely to occur, and red fluorescence is exhibited. Although MNs-NB is a reagent capable of imaging lipid droplets in tissue, there are problems such as) in (0.21: chloroform having a small fluorescence quantum yield and a small Stokes shift.
  • 出願人(英語)
  • ※2012年7月以前掲載分については米国以外のすべての指定国
  • GUNMA UNIVERSITY
  • 発明者(英語)
  • YOSHIHARA, Toshitada
  • MARUYAMA, Ryo
  • TOBITA, Seiji
国際特許分類(IPC)
指定国 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 ST SV SY TH TJ TM TN TR TT TZ UA UG US UZ VC VN WS 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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