Title:
SAPONIN CONJUGATE AND VACCINE OR PHARMACEUTICAL COMPOSITION COMPRISING THE SAME
Document Type and Number:
WIPO Patent Application WO/2020/244483
Kind Code:
A1
Abstract:
Provided are novel chemical compounds in which a lipophilic moiety such as a lipid, fatty acid, polyethylene glycol or terpene is covalently attached to a non-acylated or desacylated triterpene saponin via a carboxyl group present on the 3-O-glucuronic acid of the triterpene saponin. The attachment of a lipophile moiety to the 3-O-glucuronic acid of a saponin such as Quillaja desacylsaponin, lucyoside P, or saponin from Gypsophila, Saponaria and Acanthophyllum enhances their adjuvant effects on humoral and cell mediated immunity. Additionally, the attachment of a lipophile moiety to the 3-O-glucuronic acid residue of non-or des-acylsaponin yields a saponin analog that is easier to purify, less toxic, chemically more stable, and possesses equal or better adjuvant properties than the original saponin.
Inventors:
LIANG PI-HUI (CN)
LAI YEN-HSUN (CN)
CHANG CHUN-KAI (CN)
CHAW CHEE-WAI (CN)
LAI YEN-HSUN (CN)
CHANG CHUN-KAI (CN)
CHAW CHEE-WAI (CN)
Application Number:
PCT/CN2020/093784
Publication Date:
December 10, 2020
Filing Date:
June 01, 2020
Export Citation:
Assignee:
LIANG PI HUI (CN)
International Classes:
C07H15/20; A61K31/704; C07J9/00
Domestic Patent References:
| WO2019183159A1 | 2019-09-26 |
Other References:
X.-F. ZHOU, X.-Y. ZHAO, L. TANG, H.-L. RUAN, Y.-H. ZHANG, H.-F. PI, W.-L. XIAO, H.-D. SUN, J.-Z. WU: "Three new triterpenoid saponins from the rhizomes of Impatiens pritzellii var. hupehensis", JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, GORDON AND BREACH, CHUR, CH, vol. 9, no. 4, 1 June 2007 (2007-06-01), CH, pages 379 - 385, XP055765275, ISSN: 1028-6020, DOI: 10.1080/10286020600781019
PENGFEI WANG, DATTATRAY A. DEVALANKAR, QIPU DAI, PING ZHANG, SUZANNE M. MICHALEK: "Synthesis and Evaluation of QS-21-Based Immunoadjuvants with a Terminal-Functionalized Side Chain Incorporated in the West Wing Trisaccharide", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, vol. 81, no. 20, 21 October 2016 (2016-10-21), Washington, pages 9560 - 9566, XP055765276, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b00922
LIU, G. ET AL.: "QS-21 structure/function studies: effect of acylation on adjuvant activity.", VACCINE, vol. 20, no. 21-22, 21 June 2002 (2002-06-21), pages 2808 - 2815, XP004357805, DOI: 1-19
XUE-FENG ZHOUA, LAN TANGC , PENG ZHANGB, XIAO-YA ZHAOD, HUI-FANG PIB , YONG-HUI ZHANGB , HAN-LI RUANB , YONGHONG LIUA, JI-ZHOU WU: "The interleukin-18 inhibitory activities of echinocystic acid and its saponins from impatiens pritzellii var. hupehensis.", ZEITSCHRIFT FÜR NATURFORSCHUNG C, vol. 64, no. 5-6, 2 June 2014 (2014-06-02), pages 369 - 372, XP055765280
S. M. BERGE ET AL., J. PHARMACEUTICAL SCIENCES, vol. 66, 1977, pages 1 - 19
See also references of EP 3976627A4
PENGFEI WANG, DATTATRAY A. DEVALANKAR, QIPU DAI, PING ZHANG, SUZANNE M. MICHALEK: "Synthesis and Evaluation of QS-21-Based Immunoadjuvants with a Terminal-Functionalized Side Chain Incorporated in the West Wing Trisaccharide", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, vol. 81, no. 20, 21 October 2016 (2016-10-21), Washington, pages 9560 - 9566, XP055765276, ISSN: 0022-3263, DOI: 10.1021/acs.joc.6b00922
LIU, G. ET AL.: "QS-21 structure/function studies: effect of acylation on adjuvant activity.", VACCINE, vol. 20, no. 21-22, 21 June 2002 (2002-06-21), pages 2808 - 2815, XP004357805, DOI: 1-19
XUE-FENG ZHOUA, LAN TANGC , PENG ZHANGB, XIAO-YA ZHAOD, HUI-FANG PIB , YONG-HUI ZHANGB , HAN-LI RUANB , YONGHONG LIUA, JI-ZHOU WU: "The interleukin-18 inhibitory activities of echinocystic acid and its saponins from impatiens pritzellii var. hupehensis.", ZEITSCHRIFT FÜR NATURFORSCHUNG C, vol. 64, no. 5-6, 2 June 2014 (2014-06-02), pages 369 - 372, XP055765280
S. M. BERGE ET AL., J. PHARMACEUTICAL SCIENCES, vol. 66, 1977, pages 1 - 19
See also references of EP 3976627A4
Attorney, Agent or Firm:
PACIFIC CHINA PATENT AGENT CO., LTD. (CN)
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