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Water-soluble photochromic molecules

外国特許コード F160008904
整理番号 92US
掲載日 2016年11月14日
出願国 アメリカ合衆国
出願番号 201314427635
公報番号 20150307541
出願日 平成25年9月6日(2013.9.6)
公報発行日 平成27年10月29日(2015.10.29)
国際出願番号 JP2013074052
国際公開番号 WO2014042087
国際出願日 平成25年9月6日(2013.9.6)
国際公開日 平成26年3月20日(2014.3.20)
優先権データ
  • 特願2012-199292 (2012.9.11) JP
  • 2013JP074052 (2013.9.6) WO
発明の名称 (英語) Water-soluble photochromic molecules
発明の概要(英語) A diarylethene compound having high water-solubility is provided, and the compound is a diarylethene compound of formula (I) wherein, Sg is a monovalent sugar-type residue consisting of a sugar-type compound (in which some of hydroxyl groups may be protected) selected from a group consisting of a six-membered ring sugar, a five-membered ring sugar, cyclitol and oligosaccharides containing a six-membered ring sugar, a five-membered ring sugar, or cyclitol and excluding an hydroxyl group; U is —(CH2)n-, —CH2—U′—, or —C(═O)— (wherein, n is an integer of 1 to 5, U′ is a C1-C10 alkyl group binding to Ar); and Ar is a group represented by formula (A1) or (A2); wherein, X is S, SO2, NR3 (R3 is a C1-C3 alkyl group) or O, R is C1-C4 alkyl group, R1 and R2 are independently a C1-C3 alkyl group, a is 0 or 1, b is an integer of 0-3, and * represents a bond with U); Y is a hydrogen atom or a halogen atom; m is an integer of 5-7.
従来技術、競合技術の概要(英語) BACKGROUND ART
[0002]Photochromic molecules are molecules that reversibly transform between two isomers with different absorption spectra while maintaining the same molecular weight when irradiated with appropriate wavelength of light.
The diarylethene compound is known to exhibit excellent photochromic performance (Non-Patent Document 1).
The diarylethene has a following structure, and it undergoes cyclization/cycoreversion reactions upon irradiation with light as shown in the following scheme.
[0000]
[0003]Ext ensive studies have been carried out to apply the photochromic molecules as optical memory media that can optically store information (Patent Document 1, etc.).
In such use, the media were prepared by dissolving photochromic molecules in an organic solvent, then spreading the resulting solution over a substrate.
[0004]Recently, bioimaging using fluorescent microscope, which is a method to observe an image by binding fluorochrome molecules to biomolecules, has been actively studied.
Bioimaging that employs green fluorescent proteins (GFP) is frequently used, but this method is disadvantageous in that the label molecule is large, and the protein-protein interaction affects the target biomolecule.
Diarylethenes are expected to achieve bioimaging with high resolution, since they are low molecular weight compounds.
However, it is indispensable to provide water-solubility to the compounds for the application to biological samples.
[0005]In the studies of optical memory media mentioned above, the diarylethene compound did not need to be dissolved in water, so Patent Document 1 does not mention anything about a water-soluble diarylethene compound.
Concerning water-solubility, Non-Patent Documents 3, 4 teach diarylethene compounds that have ionic groups or amphiphilic groups.
However, these compounds tend to be aggregated in water, and would excessively affect the target molecule due to their strong ionic interaction, so they are hardly applied to bioimaging.
Under such situation, a highly water-soluble diarylethene compound obtained by a different means was desired.

CITATION LIST

Patent Documents
[0006]Patent Document 1: Japanese Publication No. 2005-325087

Non-Patent Documents
[0007]Non-Patent Document 1: M. Irie et al., Nature, 420, 759 (2002)
[0008]Non-Patent Document 2: K. H. Jones and J. A. Senft, J. Histochem. Cytochem., 33, 77 (1985)
[0009]Non-Patent Document 3: M. Takeshita, et al., J. Org. Chem., 63, 9306 (1998)
[0010]Non-Patent Document 4: M. Matsuda, et al., Chem. Lett. 32, 1178 (2003)
[0011]Non-Patent Document 5: S. Kobatake, et al., J. Am. Chem. Soc. 121, 2380 (1999)
[0012]Non-Patent Document 6: T. Yamaguchi, et al., J. Photochem. Photobio. A, 178, 162 (2006)

特許請求の範囲(英語) [claim1]
1. A diarylethene compound represented by formula (I):

wherein, Sg is a monovalent sugar-type residue consisting of a sugar-type compound (in which some of hydroxyl groups may be protected) selected from a group consisting of a six-membered ring sugar, a five-membered ring sugar, cyclitol and oligosaccharides containing a six-membered ring sugar, a five-membered ring sugar, or cyclitol and excluding a hydroxyl group; U is -- (CH2)n-, -- CH2 -- U' -- , or -- C(.dbd.O) -- (wherein, n is an integer of 1 to 5, U' is a C1-C10 alkyl group binding to Ar);
Ar is a group represented by formula (A1) or (A2);

wherein, X is S, SO2, NR3 (R3 is a C1-C3 alkyl group) or O,
R is C1-C4 alkyl group,
R1 and R2 are independently a C1-C3 alkyl group,
a is 0 or 1, b is an integer of 0-3, and
* represents a bond with U;
Y is a hydrogen atom or a halogen atom; and
m is an integer of 5-7.00031
[claim2]
2. The compound according to claim 1, wherein the Sg is a monovalent sugar-type residue of pyranose excluding a hydroxyl group.
[claim3]
3. The compound according to claim 1, wherein the Sg is a monovalent sugar-type residue of pyranose excluding a hydroxyl group on a position-1 carbon.
[claim4]
4. The compound according to claim 1, wherein the Sg is a monovalent sugar-type residue of cyclitol excluding a hydroxyl group.
[claim5]
5. The compound according to claim 1, wherein the X is S or SO2.
[claim6]
6. A method for producing a diarlyethene compound according to claim 1, comprising: (1) a step of preparing a halogenated sugar derivative derived from a sugar-type compound selected from a group consisting of a six-membered ring sugar, a five-membered ring sugar, cyclitol and oligosaccharides containing a six-membered ring sugar, a five-membered ring sugar, or cyclitol, and having 1 hydroxyl group substituted with a halogen atom, and all other hydroxyl groups protected by protection groups;
(2) an etherification step of reacting the halogenated sugar derivative with the compound represented by formula (a) to generate a compound represented by formula (b)
wherein, U, Ar, Y and m are as defined above;
wherein, U, Ar, Y and m are as defined above, and PSg shows a group in which all hydroxyl groups of the Sg are protected; and
(3) a deprotection step of removing a protection group of the compound represented by formula (b).
[claim7]
7. The method according to claim 6, wherein the step (1) is performed under a presence of Ag2O.
[claim8]
8. The method according to claim 6, wherein the halogen atom in the halogenated sugar derivative is bromine atom.
[claim9]
9. The method according to claim 6, wherein a protection group in the halogenated sugar derivative is an acyl group.
  • 発明者/出願人(英語)
  • TOKIWA HIROAKI
  • IRIE MASAHIRO
  • IKEDA KIYOSHI
  • OTSUBO TADAMUNE
  • RIKKYO EDUCATIONAL
  • JOSHO GAKUEN EDUCATIONAL FOUNDATION
国際特許分類(IPC)
米国特許分類/主・副
  • 536/18.1
  • 549/53
  • 549/59
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