Title:
MODIFIED AMINO ACIDS AND APPLICATION THEREOF IN ADC
Document Type and Number:
WIPO Patent Application WO/2022/199237
Kind Code:
A1
Abstract:
Provided are modified amino acids and an application thereof in ADC. The modified amino acids are phosphorylcholine group-modified amino acids represented by R1-L1-N(R2)-R3, wherein R1, L1, N, R2 and R3 are as defined herein. Further provided are peptides containing the modified amino acids. ADCs made by using such modified amino acids or modified peptides have significantly improved solubility.
Inventors:
GUO MAOJUN (CN)
LI HUI (CN)
LI HAIHONG (CN)
XU ZHE (CN)
WANG WEIWEI (CN)
ZHAO LEI (CN)
LIU HAIDONG (CN)
QI WENKE (CN)
LI HUI (CN)
LI HAIHONG (CN)
XU ZHE (CN)
WANG WEIWEI (CN)
ZHAO LEI (CN)
LIU HAIDONG (CN)
QI WENKE (CN)
Application Number:
PCT/CN2022/072943
Publication Date:
September 29, 2022
Filing Date:
January 20, 2022
Export Citation:
Assignee:
LEVENA BIOPHARMA CO LTD (CN)
International Classes:
C07F9/09; A61K45/00; A61K47/64; A61K47/68; C07K5/062; C07K5/083; C07K5/103; C07K7/06
Domestic Patent References:
| WO2013032643A2 | 2013-03-07 | |||
| WO2012108990A2 | 2012-08-16 | |||
| WO2021050917A1 | 2021-03-18 | |||
| WO2014009774A1 | 2014-01-16 |
Foreign References:
| CN114106088A | 2022-03-01 | |||
| CN113816990A | 2021-12-21 | |||
| US20170240576A1 | 2017-08-24 | |||
| CN111499685A | 2020-08-07 | |||
| CN108026123A | 2018-05-11 |
Other References:
OBANDO, D. WIDMER, F. WRIGHT, L.C. SORRELL, T.C. JOLLIFFE, K.A.: "Synthesis, antifungal and antimicrobial activity of alkylphospholipids", BIOORGANIC & MEDICINAL CHEMISTRY, ELSEVIER, AMSTERDAM, NL, vol. 15, no. 15, 8 June 2007 (2007-06-08), AMSTERDAM, NL, pages 5158 - 5165, XP022110118, ISSN: 0968-0896, DOI: 10.1016/j.bmc.2007.05.028
HANABUSA KENJI, NAKASHIMA MASASHI, FUNATSU ERIKO, KISHI SACHIYO, SUZUKI MASAHIRO: "A Safe, Simple, and Facile Staining Method Using Polysiloxanes for High-Contrast Visualization of Gelator Aggregates by Transmission Electron Microscopy", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 91, no. 7, 15 July 2018 (2018-07-15), JP , pages 1176 - 1185, XP055970068, ISSN: 0009-2673, DOI: 10.1246/bcsj.20180072
TADASHI, N. ET AL.: "ε-N-trimethyl-L-δ-hydroxylysine phosphate and its nonphosphorylated compound in diatom cell walls", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 39, no. 1, 31 December 1970 (1970-12-31), pages 28 - 33, XP024831137, ISSN: 0006-291X, DOI: 10.1016/0006-291X(70)90752-7
XU XIEJUN, XIAO XINGQING, WANG YIMING, XU SHOUHONG, LIU HONGLAI: "Modulation of phase transition of thermosensitive liposomes with leucine zipper-structured lipopeptides", PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 20, no. 23, 1 January 2018 (2018-01-01), pages 15916 - 15925, XP055970064, ISSN: 1463-9076, DOI: 10.1039/C8CP01464G
ALBERS MICHAEL F., HEDBERG CHRISTIAN: "Amino Acid Building Blocks for Fmoc Solid-Phase Synthesis of Peptides Phosphocholinated at Serine, Threonine, and Tyrosine", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 78, no. 6, 15 March 2013 (2013-03-15), pages 2715 - 2719, XP055970063, ISSN: 0022-3263, DOI: 10.1021/jo302587g
KANG, J. H. ET AL.: "Self-assembling Lipid-Peptide Hybrid Nanoparticles of Phospholipid-Nonaarginine Conjugates for Enhanced Delivery of Nucleic Acid Therapeutics", BIOMACROMOLECULES, vol. 18, no. 11, 27 September 2017 (2017-09-27), pages 3733 - 3741, XP055794024, ISSN: 1525-7797, DOI: 10.1021/acs.biomac.7b01084
TURNER WILLIAM W., HARTVIGSEN KARSTEN, BOULLIER AGNES, MONTANO ERICA N., WITZTUM JOSEPH L., VANNIEUWENHZE MICHAEL S.: "Design and Synthesis of a Stable Oxidized Phospholipid Mimic with Specific Binding Recognition for Macrophage Scavenger Receptors", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 55, no. 18, 27 September 2012 (2012-09-27), US , pages 8178 - 8182, XP055970062, ISSN: 0022-2623, DOI: 10.1021/jm300685s
SREEKANTH VEDAGOPURAM, MEDATWAL NIHAL, KUMAR SANDEEP, PAL SANJAY, VAMSHIKRISHNA MALYLA, KAR ANIMESH, BHARGAVA PRIYANSHU, NAAZ AALI: "Tethering of Chemotherapeutic Drug/Imaging Agent to Bile Acid-Phospholipid Increases the Efficacy and Bioavailability with Reduced Hepatotoxicity", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 28, no. 12, 20 December 2017 (2017-12-20), US , pages 2942 - 2953, XP055970057, ISSN: 1043-1802, DOI: 10.1021/acs.bioconjchem.7b00564
HANABUSA KENJI, NAKASHIMA MASASHI, FUNATSU ERIKO, KISHI SACHIYO, SUZUKI MASAHIRO: "A Safe, Simple, and Facile Staining Method Using Polysiloxanes for High-Contrast Visualization of Gelator Aggregates by Transmission Electron Microscopy", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 91, no. 7, 15 July 2018 (2018-07-15), JP , pages 1176 - 1185, XP055970068, ISSN: 0009-2673, DOI: 10.1246/bcsj.20180072
TADASHI, N. ET AL.: "ε-N-trimethyl-L-δ-hydroxylysine phosphate and its nonphosphorylated compound in diatom cell walls", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 39, no. 1, 31 December 1970 (1970-12-31), pages 28 - 33, XP024831137, ISSN: 0006-291X, DOI: 10.1016/0006-291X(70)90752-7
XU XIEJUN, XIAO XINGQING, WANG YIMING, XU SHOUHONG, LIU HONGLAI: "Modulation of phase transition of thermosensitive liposomes with leucine zipper-structured lipopeptides", PHYSICAL CHEMISTRY CHEMICAL PHYSICS, vol. 20, no. 23, 1 January 2018 (2018-01-01), pages 15916 - 15925, XP055970064, ISSN: 1463-9076, DOI: 10.1039/C8CP01464G
ALBERS MICHAEL F., HEDBERG CHRISTIAN: "Amino Acid Building Blocks for Fmoc Solid-Phase Synthesis of Peptides Phosphocholinated at Serine, Threonine, and Tyrosine", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 78, no. 6, 15 March 2013 (2013-03-15), pages 2715 - 2719, XP055970063, ISSN: 0022-3263, DOI: 10.1021/jo302587g
KANG, J. H. ET AL.: "Self-assembling Lipid-Peptide Hybrid Nanoparticles of Phospholipid-Nonaarginine Conjugates for Enhanced Delivery of Nucleic Acid Therapeutics", BIOMACROMOLECULES, vol. 18, no. 11, 27 September 2017 (2017-09-27), pages 3733 - 3741, XP055794024, ISSN: 1525-7797, DOI: 10.1021/acs.biomac.7b01084
TURNER WILLIAM W., HARTVIGSEN KARSTEN, BOULLIER AGNES, MONTANO ERICA N., WITZTUM JOSEPH L., VANNIEUWENHZE MICHAEL S.: "Design and Synthesis of a Stable Oxidized Phospholipid Mimic with Specific Binding Recognition for Macrophage Scavenger Receptors", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 55, no. 18, 27 September 2012 (2012-09-27), US , pages 8178 - 8182, XP055970062, ISSN: 0022-2623, DOI: 10.1021/jm300685s
SREEKANTH VEDAGOPURAM, MEDATWAL NIHAL, KUMAR SANDEEP, PAL SANJAY, VAMSHIKRISHNA MALYLA, KAR ANIMESH, BHARGAVA PRIYANSHU, NAAZ AALI: "Tethering of Chemotherapeutic Drug/Imaging Agent to Bile Acid-Phospholipid Increases the Efficacy and Bioavailability with Reduced Hepatotoxicity", BIOCONJUGATE CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 28, no. 12, 20 December 2017 (2017-12-20), US , pages 2942 - 2953, XP055970057, ISSN: 1043-1802, DOI: 10.1021/acs.bioconjchem.7b00564
Attorney, Agent or Firm:
SUZHOU RUNSUN INTELLECTUAL PROPERTY AGENCY (CN)
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