Title:
NOVEL FLUORESCENT SUBSTANCE FOR TRANSPORTER FUNCTION ANALYSIS
Document Type and Number:
WIPO Patent Application WO/2018/221479
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide a fluorescent substrate for a transporter, the fluorescent substrate maintaining high transport performance while being unlikely to be quenched and exhibiting strong fluorescent intensity. The present invention relates to a compound represented by formula (I). Formula (I): A-L-F [In the formula: A denotes cholic acid, chenodeoxycholic acid, deoxycholic acid, lithocholic acid, ursocholic acid, ursodeoxycholic acid, α-muricholic acid, β-muricholic acid, ω-muricholic acid, hyocholic acid, hyodeoxycholic acid, 7-oxo-deoxycholic acid, 7-oxo-lithocholic acid, 1-oxo-lithocholic acid, 2-oxo-lithocholic acid, or a derivative of these; L denotes a linker; and F denotes Tokyo Green (TG), Tokyo Magenta (TM), hydroxycoumarin (HC), or a derivative of these.]
More Like This:
Inventors:
YAMAGUCHI HIROAKI (JP)
MANO NARIYASU (JP)
YAMAGISHI YUTAKA (JP)
MANO NARIYASU (JP)
YAMAGISHI YUTAKA (JP)
Application Number:
PCT/JP2018/020440
Publication Date:
December 06, 2018
Filing Date:
May 29, 2018
Export Citation:
Assignee:
GORYO CHEMICAL INC (JP)
UNIV TOHOKU (JP)
UNIV TOHOKU (JP)
International Classes:
C07J9/00; C12Q1/02; G01N21/78; G01N33/15
Domestic Patent References:
| WO2014029756A1 | 2014-02-27 | |||
| WO2017035501A1 | 2017-03-02 | |||
| WO2002012267A1 | 2002-02-14 |
Foreign References:
| GB2459976A | 2009-11-18 | |||
| CN105541955A | 2016-05-04 | |||
| JPH072891A | 1995-01-06 |
Other References:
DE WAART, D. R . ET AL.: "Hepatic transport mechanisms of cholyl-L-lysyl-fluorescein", JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, vol. 334, no. 1, 2010, pages 78 - 86, XP055090728, ISSN: 0022-3565
DE MEY, C. ET AL.: "Effects of renal insufficiency on the elimination of fluorescein lisicol (NRL972), an investigational marker of hepatic transporter function", INTERNATIONAL JOURNAL OF CLINICAL PHARMACOLOGY AND THERAPEUTICS, vol. 53, no. 7, 2015, pages 523 - 530, ISSN: 0946-1965
BARBER, J. A. ET AL.: "Quantification of drug- induced inhibition of canalicular cholyl-1-lysyl- fluorescein excretion from hepatocytes by high content cell imaging", TOXICOLOGICAL SCIENCES, vol. 148, no. 1, 2015, pages 48 - 59, XP055570388, ISSN: 1096-0929
CANTORE, M. ET AL.: "The Src Family Kinase Fyn Mediates Hyperosmolarity-induced Mrp2 and Bsep Retrieval from Canalicular Membrane", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 286, no. 52, 2011, pages 45014 - 45029, XP055570395, ISSN: 0021-9258
MILKIEWICZ, P. ET AL.: "Visualization of the transport of primary and secondary bile acids across liver tissue in rats: In vivo study with fluorescent bile acids", JOURNAL OF HEPATOLOGY, vol. 34, no. 1, 2001, pages 4 - 10, XP027303116, ISSN: 0168-8278
MILLS, C. 0. ET AL.: "Different pathways of canalicular secretion of sulfated and non-sulfated fluorescent bile acids: A study in isolated hepatocyte couplets and TR - rats", JOURNAL OF HEPATOLOGY, vol. 31, no. 4, October 1999 (1999-10-01), pages 678 - 684, XP085003936, ISSN: 0168-8278
HOLZINGER, F. ET AL.: "Transport of fluorescent bile acids by the isolated perfused rat liver: kinetics, sequestration, and mobilization", HEPATOLOGY ( PHILADELPHIA), vol. 28, no. 2, 1998, pages 510 - 520, XP055570400, ISSN: 0270-9139
BAXTER, D. J. ET AL.: "Biliary lipid output by isolated perfused rat livers in response to cholyl- lysylfluorescein", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1256, no. 3, 1995, pages 374 - 380, XP000615216, ISSN: 0925-4439
SUN, J. ET AL.: "Biological deoxycholic acid- coumarin conjugates: photo-switchable structures and self-assembly morphology", TETRAHEDRON LETTERS, vol. 57, no. 19, 2016, pages 2125 - 2128, XP029512949, ISSN: 0040-4039
MAITRA, U. ET AL.: "Bile acid derived PET-based cation sensors: molecular structure dependence of their sensitivity", CHEMISTRY - AN ASIAN JOURNAL, vol. 4, no. 6, 2009, pages 989 - 997, XP055570434, ISSN: 1861-4728
DATABASE Registry CAS; 19 June 2018 (2018-06-19), Database accession no. 787542-95-4
GUO, H. ET AL.: "Competitive affinity-based proteome profiling and imaging to reveal potential cellular targets of betulinic acid", CHEMICAL COMMUNICATIONS, vol. 53, no. 69, 7 August 2017 (2017-08-07), Cambridge, United Kingdom, pages 9620 - 9623, XP055570447, ISSN: 1359-7345
DE MEY, C. ET AL.: "Effects of renal insufficiency on the elimination of fluorescein lisicol (NRL972), an investigational marker of hepatic transporter function", INTERNATIONAL JOURNAL OF CLINICAL PHARMACOLOGY AND THERAPEUTICS, vol. 53, no. 7, 2015, pages 523 - 530, ISSN: 0946-1965
BARBER, J. A. ET AL.: "Quantification of drug- induced inhibition of canalicular cholyl-1-lysyl- fluorescein excretion from hepatocytes by high content cell imaging", TOXICOLOGICAL SCIENCES, vol. 148, no. 1, 2015, pages 48 - 59, XP055570388, ISSN: 1096-0929
CANTORE, M. ET AL.: "The Src Family Kinase Fyn Mediates Hyperosmolarity-induced Mrp2 and Bsep Retrieval from Canalicular Membrane", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 286, no. 52, 2011, pages 45014 - 45029, XP055570395, ISSN: 0021-9258
MILKIEWICZ, P. ET AL.: "Visualization of the transport of primary and secondary bile acids across liver tissue in rats: In vivo study with fluorescent bile acids", JOURNAL OF HEPATOLOGY, vol. 34, no. 1, 2001, pages 4 - 10, XP027303116, ISSN: 0168-8278
MILLS, C. 0. ET AL.: "Different pathways of canalicular secretion of sulfated and non-sulfated fluorescent bile acids: A study in isolated hepatocyte couplets and TR - rats", JOURNAL OF HEPATOLOGY, vol. 31, no. 4, October 1999 (1999-10-01), pages 678 - 684, XP085003936, ISSN: 0168-8278
HOLZINGER, F. ET AL.: "Transport of fluorescent bile acids by the isolated perfused rat liver: kinetics, sequestration, and mobilization", HEPATOLOGY ( PHILADELPHIA), vol. 28, no. 2, 1998, pages 510 - 520, XP055570400, ISSN: 0270-9139
BAXTER, D. J. ET AL.: "Biliary lipid output by isolated perfused rat livers in response to cholyl- lysylfluorescein", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1256, no. 3, 1995, pages 374 - 380, XP000615216, ISSN: 0925-4439
SUN, J. ET AL.: "Biological deoxycholic acid- coumarin conjugates: photo-switchable structures and self-assembly morphology", TETRAHEDRON LETTERS, vol. 57, no. 19, 2016, pages 2125 - 2128, XP029512949, ISSN: 0040-4039
MAITRA, U. ET AL.: "Bile acid derived PET-based cation sensors: molecular structure dependence of their sensitivity", CHEMISTRY - AN ASIAN JOURNAL, vol. 4, no. 6, 2009, pages 989 - 997, XP055570434, ISSN: 1861-4728
DATABASE Registry CAS; 19 June 2018 (2018-06-19), Database accession no. 787542-95-4
GUO, H. ET AL.: "Competitive affinity-based proteome profiling and imaging to reveal potential cellular targets of betulinic acid", CHEMICAL COMMUNICATIONS, vol. 53, no. 69, 7 August 2017 (2017-08-07), Cambridge, United Kingdom, pages 9620 - 9623, XP055570447, ISSN: 1359-7345
Attorney, Agent or Firm:
NAKATANI Tomoko (JP)
Download PDF: