Title:
NOVEL SUGAR DERIVATIVE USEFUL IN FREEZING OF CELLS
Document Type and Number:
WIPO Patent Application WO/2021/095741
Kind Code:
A1
Abstract:
Provided is a cryoprotectant capable of inhibiting cytotoxicity, even in the presence of a cryoprotectant such as DMSO. Specifically provided is a compound represented by formula I-1 or I-2, or a salt or a solvate thereof. [In the formulas, n is 0 or 1; R1 and R2 are both H, or R1 and R2 together form =O; R3and R4 are both H, or R3 and R4 together form a bond; R5 is a saturated or unsaturated aliphatic hydrocarbon group having 1-30 carbons; R6 is H or -CH2OH, with the caveat that if R6 is -CH2OH, n is 0; R7 is H or a C1-6alkyl, or is selected from the group consisting of the structures defined in the description; R8 is H or -NR9R10; R9 and R10 are each independently H, a C1-6alkyl or -COR11; and R11 is -OH or a C1-6alkyl.]
Inventors:
IJIMA HIROYUKI (JP)
ONO FUMIYASU (JP)
YOSHIDA KOZUE (JP)
CHOUNO TAKEHIRO (JP)
SHIRAKIGAWA NANA (JP)
ONO FUMIYASU (JP)
YOSHIDA KOZUE (JP)
CHOUNO TAKEHIRO (JP)
SHIRAKIGAWA NANA (JP)
Application Number:
PCT/JP2020/041967
Publication Date:
May 20, 2021
Filing Date:
November 10, 2020
Export Citation:
Assignee:
UNIV KYUSHU NAT UNIV CORP (JP)
NISSAN CHEMICAL CORP (JP)
NISSAN CHEMICAL CORP (JP)
International Classes:
A01N1/02; C07H9/04; C12N5/071
Domestic Patent References:
| WO2017034004A1 | 2017-03-02 | |||
| WO2012067240A1 | 2012-05-24 |
Foreign References:
| JPH093087A | 1997-01-07 | |||
| JPH01128994A | 1989-05-22 | |||
| JP2017537924A | 2017-12-21 | |||
| JP2019501158A | 2019-01-17 | |||
| JPH01128992A | 1989-05-22 | |||
| US20040067480A1 | 2004-04-08 |
Other References:
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JOEL T. SMITH, ZIAD EL RASSI: "Micellar electrokinetic capillary chromatography with in situ charged micelles: II. Evaluation and comparison of octylmaltoside and octylsucrose surfactants as anionic borate complexes in the separation of herbicides", JOURNAL OF MICROCOLUMN SEPARATIONS, vol. 6, no. 2, March 1994 (1994-03-01), pages 127 - 138, DOI: 10.1002/mcs.1220060206
HOLMQUIST LEIF: "Synthesis of Some 4,6-O-Alkylidene and 4,6-O-Arylidene Derivatives of 2-Acetamido-2-deoxy-D-glucose.", ACTA CHEMICA SCANDINAVICA, vol. 24, no. 1, 1970, pages 173 - 178, XP055823897, DOI: 10.3891/acta.chem.scand.24-0173
OGAWA, S. OSANAI, S.: "Inhibition effect of sugar-based amphiphiles on eutectic formation in the freezing-thawing process of aqueous NaCl solution", CRYOBIOLOGY, ACADEMIC PRESS INC, US, vol. 54, no. 2, 6 April 2007 (2007-04-06), US, pages 173 - 180, XP022020087, ISSN: 0011-2240, DOI: 10.1016/j.cryobiol.2007.01.005
BUREK MAŁGORZATA, WAŚKIEWICZ SYLWIA, LALIK ANNA, STUDENT SEBASTIAN, BIEG TADEUSZ, WANDZIK ILONA: "Thermoresponsive microgels containing trehalose as soft matrices for 3D cell culture", BIOMATERIALS SCIENCE, R S C PUBLICATIONS, GB, vol. 5, no. 2, 1 January 2017 (2017-01-01), GB, pages 234 - 246, XP055823884, ISSN: 2047-4830, DOI: 10.1039/C6BM00624H
REACTIVE AND FUNCTIONAL POLYMERS, vol. 119, 2017, pages 105 - 115, DOI: 10.1016/j.reactfunctpolym.2017.09.009
HOLY, ANTONIN; KOENIG, JOACHIM; VESELY, JIRI; CECH, DIETER; VOTRUBA, IVAN; DE CLERCQ, ERIK: "5'-O-Alkyl-5-fluorouridines: synthesis and biological activity", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY, ACADEMY OF SCIENCES OF THE CZECH REPUBLIC, CZ, vol. 52, no. 6, 1 January 1987 (1987-01-01), CZ, pages 1589 - 1608, XP009110618, ISSN: 0010-0765, ISBN: 978-80-86241-25-8
JOEL T. SMITH, ZIAD EL RASSI: "Micellar electrokinetic capillary chromatography with in situ charged micelles: II. Evaluation and comparison of octylmaltoside and octylsucrose surfactants as anionic borate complexes in the separation of herbicides", JOURNAL OF MICROCOLUMN SEPARATIONS, vol. 6, no. 2, March 1994 (1994-03-01), pages 127 - 138, DOI: 10.1002/mcs.1220060206
HOLMQUIST LEIF: "Synthesis of Some 4,6-O-Alkylidene and 4,6-O-Arylidene Derivatives of 2-Acetamido-2-deoxy-D-glucose.", ACTA CHEMICA SCANDINAVICA, vol. 24, no. 1, 1970, pages 173 - 178, XP055823897, DOI: 10.3891/acta.chem.scand.24-0173
OGAWA, S. OSANAI, S.: "Inhibition effect of sugar-based amphiphiles on eutectic formation in the freezing-thawing process of aqueous NaCl solution", CRYOBIOLOGY, ACADEMIC PRESS INC, US, vol. 54, no. 2, 6 April 2007 (2007-04-06), US, pages 173 - 180, XP022020087, ISSN: 0011-2240, DOI: 10.1016/j.cryobiol.2007.01.005
Attorney, Agent or Firm:
TSUKUNI & ASSOCIATES et al. (JP)
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