Title:
STABLE-ISOTOPE-LABELED COMPOUND
Document Type and Number:
WIPO Patent Application WO/2019/098179
Kind Code:
A1
Abstract:
Provided are: a novel internal standard substance that is useful for measuring androgen; a highly selective and sensitive (accurate) method for measuring androgen which is capable of simplifying pretreatment and uses liquid chromatography mass spectrometry; and a method for identifying a disease using the method for measuring androgen. A novel stable-isotope-labeled compound is synthesized by performing reduction reaction with a specific solvent. Androgen is measured by using this novel stable-isotope-labeled compound as the internal standard substance.
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Inventors:
MINATO KOICHI (JP)
ITO YUSUKE (JP)
ITO YUSUKE (JP)
Application Number:
PCT/JP2018/041947
Publication Date:
May 23, 2019
Filing Date:
November 13, 2018
Export Citation:
Assignee:
ASKA PHARM CO LTD (JP)
International Classes:
C07J1/00; G01N27/62
Other References:
DU TOIT, T. ET AL.: "Profiling adrenal 11beta- hydroxyandrostenedione metabolites in prostate cancer cells, tissue and plasma: UPC2-MS/MS quantification of 11beta-hydroxytestosterone, 11keto- testosterone and llketo-dihydrotestosterone", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, vol. 166, 21 June 2016 (2016-06-21), pages 54 - 67, XP029865494, ISSN: 0960-0760
IMAMICHI, Y. ET AL.: "11-Ketotestosterone is a major androgen produced in human gonads", JOURNAL OF CLINICAL ENDOCRINOLOGY AND METABOLISM, vol. 101, no. 10, 18 July 2016 (2016-07-18) - October 2016 (2016-10-01), pages 3582 - 3591, XP055609438, ISSN: 0021-972X
PRETORIUS, E. ET AL.: "11-ketotestosterone and 11- ketodihydrotestosterone in castration resistant prostate cancer: potent androgens which can no longer be ignored", PLOS ONE, vol. 11, no. 7, 21 July 2016 (2016-07-21), pages e0159867/l - e0159867/17, XP055609441, ISSN: 1932-6203
SWART, A. C. ET AL.: "IIbeta-Hydroxyandrostenedione, the product of androstenedione metabolism in the adrenal, is metabolized in LNCaP cells by 5 a- reductase yielding 11beta-hydroxy-5alpha-androstanedione", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, vol. 138, 2013, pages 132 - 142, XP028766172, ISSN: 0960-0760, DOI: doi:10.1016/j.jsbmb.2013.04.010
PRETORIUS, E ET AL.: "Anew dawn for androgens: Novel lessons from 11-oxygenated C19 steroids", MOLECULAR AND CELLULAR ENDOCRINOLOGY, vol. 441, 9 August 2016 (2016-08-09), pages 76 - 85, XP029879229, ISSN: 0303-7207, DOI: doi:10.1016/j.mce.2016.08.014
QUANSON, J. L. ET AL.: "High-throughput analysis of 19 endogenous androgenic steroids by ultra- performance convergence chromatography tandem mass spectrometry", JOURNAL OF CHROMATOGRAPHY B, vol. 1031, 18 July 2016 (2016-07-18), pages 131 - 138, XP055609442, ISSN: 1570-0232
SHOPPEE, C. W. ET AL.: "Line widths of nuclear magnetic resonance signals of tertiary methyl groups", TETRAHEDRON, vol. 22, no. 8, 1966, pages 421 - 442, XP028086921, ISSN: 0563-2072, DOI: doi:10.1016/S0040-4020(01)90952-4
J. STEROID BIOCHEM MOL. BIOL., vol. 166, 2017, pages 54 - 67
J CLIN ENDOCRINOL METAB., vol. 101, no. 10, 2016, pages 3582 - 3591
PLOS ONE, vol. 11, no. 7, pages eO 159867
J. STEROID BIOCHEM MOL. BIOL., vol. 138, 2013, pages 312 - 142
MOLECULAR AND CELLULAR ENDOCRINOLOGY, vol. 441, 2017, pages 76 - 85
J. CHROMATOGRAPHY B, vol. 1013, 2016, pages 131 - 138
J. CLIN. ENDOCRINOL METAB., vol. 98, 2013, pages 1182 - 1188
See also references of EP 3725795A4
IMAMICHI, Y. ET AL.: "11-Ketotestosterone is a major androgen produced in human gonads", JOURNAL OF CLINICAL ENDOCRINOLOGY AND METABOLISM, vol. 101, no. 10, 18 July 2016 (2016-07-18) - October 2016 (2016-10-01), pages 3582 - 3591, XP055609438, ISSN: 0021-972X
PRETORIUS, E. ET AL.: "11-ketotestosterone and 11- ketodihydrotestosterone in castration resistant prostate cancer: potent androgens which can no longer be ignored", PLOS ONE, vol. 11, no. 7, 21 July 2016 (2016-07-21), pages e0159867/l - e0159867/17, XP055609441, ISSN: 1932-6203
SWART, A. C. ET AL.: "IIbeta-Hydroxyandrostenedione, the product of androstenedione metabolism in the adrenal, is metabolized in LNCaP cells by 5 a- reductase yielding 11beta-hydroxy-5alpha-androstanedione", JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, vol. 138, 2013, pages 132 - 142, XP028766172, ISSN: 0960-0760, DOI: doi:10.1016/j.jsbmb.2013.04.010
PRETORIUS, E ET AL.: "Anew dawn for androgens: Novel lessons from 11-oxygenated C19 steroids", MOLECULAR AND CELLULAR ENDOCRINOLOGY, vol. 441, 9 August 2016 (2016-08-09), pages 76 - 85, XP029879229, ISSN: 0303-7207, DOI: doi:10.1016/j.mce.2016.08.014
QUANSON, J. L. ET AL.: "High-throughput analysis of 19 endogenous androgenic steroids by ultra- performance convergence chromatography tandem mass spectrometry", JOURNAL OF CHROMATOGRAPHY B, vol. 1031, 18 July 2016 (2016-07-18), pages 131 - 138, XP055609442, ISSN: 1570-0232
SHOPPEE, C. W. ET AL.: "Line widths of nuclear magnetic resonance signals of tertiary methyl groups", TETRAHEDRON, vol. 22, no. 8, 1966, pages 421 - 442, XP028086921, ISSN: 0563-2072, DOI: doi:10.1016/S0040-4020(01)90952-4
J. STEROID BIOCHEM MOL. BIOL., vol. 166, 2017, pages 54 - 67
J CLIN ENDOCRINOL METAB., vol. 101, no. 10, 2016, pages 3582 - 3591
PLOS ONE, vol. 11, no. 7, pages eO 159867
J. STEROID BIOCHEM MOL. BIOL., vol. 138, 2013, pages 312 - 142
MOLECULAR AND CELLULAR ENDOCRINOLOGY, vol. 441, 2017, pages 76 - 85
J. CHROMATOGRAPHY B, vol. 1013, 2016, pages 131 - 138
J. CLIN. ENDOCRINOL METAB., vol. 98, 2013, pages 1182 - 1188
See also references of EP 3725795A4
Attorney, Agent or Firm:
TSUKUNI & ASSOCIATES et al. (JP)
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