Top > Search of International Patents > Water-soluble photochromic molecule

Water-soluble photochromic molecule

Foreign code F160008905
File No. 92EP
Posted date Nov 17, 2016
Country EPO
Application number 13837714
Gazette No. 2902402
Date of filing Sep 6, 2013
Gazette Date Aug 5, 2015
International application number JP2013074052
International publication number WO2014042087
Date of international filing Sep 6, 2013
Date of international publication Mar 20, 2014
Priority data
  • P2012-199292 (Sep 11, 2012) JP
  • 2013JP74052 (Sep 6, 2013) WO
Title Water-soluble photochromic molecule
Abstract 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 -(CH 2 )n-, -CH 2 -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, SO 2 , NR 3 (R 3 is a C1-C3 alkyl group) or O, R is C1-C4 alkyl group, R 1 and R 2 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.
Outline of related art and contending technology BACKGROUND ART
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.
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.
Recently, bioimaging using fluoresnent 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.
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.
Scope of claims [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(=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.
[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 either Claim 1 or 2, 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 either Claim 1 or 2, wherein the Sg is a monovalent sugar-type residue of cyclitol excluding a hydroxyl group.
[claim5]
5. The compound according to any one of Claims 1 to 4, wherein the X is S or SO2.
[claim6]
6. A method for producing a diarlyethene compound according to any one of Claims 1 to 5, 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 either Claim 6 or 7, wherein the halogen atom in the halogenated sugar derivative is bromine atom.
[claim9]
9. The method according to any of Claims 6 to 8, wherein a protection group in the halogenated sugar derivative is an acyl group.
  • Applicant
  • JOSHO GAKUEN EDUCATIONAL FOUNDATION
  • RIKKYO EDUCATIONAL CORPORATION
  • Inventor
  • TOKIWA, Hiroaki
  • IRIE, Masahiro
  • IKEDA, Kiyoshi
  • OTSUBO, Tadamune
IPC(International Patent Classification)
Specified countries Contracting States: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
Please contact us by E-mail or facsimile if you have any interests on this patent.

PAGE TOP

close
close
close
close
close
close