Basic Information

Affiliated programs (koza)

• Graduate School of Pharmaceutical Sciences, 薬科学専攻 生体機能化学講座, 助教

Professional Memberships

• 日本DDS学会
• 日本ペプチド学会
• 日本薬学会

Academic Degree

• 博士（薬科学）(京都大学)
• 修士（薬科学）(京都大学)

Research History

• From Aug. 2021, To Present

  京都大学化学研究所, 助教
• From Apr. 2016, To Jul. 2021

  塩野義製薬株式会社, 研究員
• From Apr. 2014, To Mar. 2016

  日本学術振興会, 特別研究員

ID,URL

• ORCID ID

  0000-0002-4180-7869

• J-Global ID

  202101020313207948

researchmap URL

• https://researchmap.jp/yoshimasa.kawaguchi

Research

Research Interests

• Protein Chemistry
• Biofunctional Chemistry
• Peptide Chemistry

Research Areas

• Life sciences, Pharmaceuticals - chemistry and drug development

Papers

• Physicochemical and cell biological aspects of microcondensate mediated intracellular infusion of antibodies

  Shiroh Futaki; Yoshimasa Kawaguchi; Megumi Kiyokawa; Daisuke Yamasaki; Mai Watabe; Shohei Shiomoto; Yuko Mimori-Kiyosue; Satoko Arakawa; Masaru Tanaka

  23 May 2025

  
• Lipidated macrocyclic peptide S-880008 as a broad-spectrum SARS-CoV-2 fusion inhibitor

  Takao Sanaki; Yoshimasa Kawaguchi; Yuki Anraku; Yoshifumi Kusumoto; Akihiko Sato; Shinsuke Toba; Keiichi Taniguchi; Atsuko Yamamoto; Yuki Maruyama; Tadashi Miyamoto; Shuhei Arita; Yuka Natsume; Hirotoshi Morita; Kei Mayumi; Takayo Haruna; Masaaki Izawa; Shunsuke Kita; Michihito Sasaki; Yasuko Orba; Takao Hashiguchi; Hirofumi Sawa; Hidenori Mikamiyama; Takao Shishido; Katsumi Maenaka

  14 Feb. 2025

  
• Covalent Plant Natural Product that Potentiates Antitumor Immunity.

  Misao Takemoto; Sara Delghandi; Masahiro Abo; Keiko Yurimoto; Minami Odagi; Vaibhav Pal Singh; Jun Wang; Reiko Nakagawa; Shin-Ichi Sato; Yasushi Takemoto; Asmaa M A S Farrag; Yoshimasa Kawaguchi; Kazuo Nagasawa; Tasuku Honjo; Kenji Chamoto; Motonari Uesugi

  Journal of the American Chemical Society, 22 Jan. 2025

  
• KCNN4 as a Genomic Determinant of Cytosolic Delivery by the Attenuated Cationic Lytic Peptide L17E

  Masashi Kuriyama; Hisaaki Hirose; Yoshimasa Kawaguchi; Junya Michibata; Masashi Maekawa; Shiroh Futaki

  Molecular Therapy, Jan. 2025

  
• Polysaccharide-Based Coacervate Microgel Bearing Cationic Peptides That Achieve Dynamic Cell-Membrane Structure Alteration and Facile Cytosolic Infusion of IgGs

  Junya Michibata; Yoshimasa Kawaguchi; Hisaaki Hirose; Akiko Eguchi; Sayaka Deguchi; Kazuo Takayama; Wei Xu; Takuro Niidome; Yoshihiro Sasaki; Kazunari Akiyoshi; Shiroh Futaki

  Bioconjugate Chemistry, 05 Nov. 2024

  
• An approach for the intracellular delivery of IgG via enzymatic ligation with a cell-permeable attenuated cationic amphiphilic lytic peptide.

  Yoshimasa Kawaguchi; Sakahiro Terada; Shiroh Futaki

  Bioorganic & medicinal chemistry, 24 Jul. 2024, Lead author, Corresponding author

  
• Finding ways into the cytosol: Peptide-mediated approaches for delivering proteins into cells.

  Yoshimasa Kawaguchi; Shiroh Futaki

  Current opinion in chemical biology, 20 Jun. 2024, Lead author

  
• Light-controllable cell-membrane disturbance for intracellular delivery

  Wenting Huo; Koji Miki; Huiying Mu; Takashi Osawa; Harumi Yamaguma; Yuuya Kasahara; Satoshi Obika; Yoshimasa Kawaguchi; Hisaaki Hirose; Shiroh Futaki; Yusuke Miyazaki; Wataru Shinoda; Shuji Akai; Kouichi Ohe

  Journal of Materials Chemistry B, 2024

  
• E3MPH16: An efficient endosomolytic peptide for intracellular protein delivery.

  Yoshimasa Kawaguchi; Yuki Kawamura; Hisaaki Hirose; Megumi Kiyokawa; Momo Hirate; Tsuyoshi Hirata; Yuriko Higuchi; Shiroh Futaki

  Journal of Controlled Release, 30 Jan. 2024, Lead author, Corresponding author

  
• Liquid Droplet-Mediated Formulation of Lipid Nanoparticles Encapsulating Immunoglobulin G for Cytosolic Delivery

  Yusuke Hirai; Yoshimasa Kawaguchi; Chisato Kasahara; Hisaaki Hirose; Shiroh Futaki

  Molecular Pharmaceutics, 30 Jan. 2024

  
• Photoaffinity labeling methods to explore internalization mechanisms of arginine-rich cell-penetrating peptides

  Tanaka, G.; Kawaguchi, Y.; Kuwata, K.; Takeuchi, T.; Nakase, I.; Futaki, S.

  Photoaffinity Labeling for Structural Probing Within Protein, 2017

  
• Inkjet-Based Intracellular Delivery System that Effectively Utilizes Cell-Penetrating Peptides for Cytosolic Introduction of Biomacromolecules through the Cell Membrane

  Mika Omura; Kenta Morimoto; Yurina Araki; Hisaaki Hirose; Yoshimasa Kawaguchi; Yukiya Kitayama; Yuto Goto; Atsushi Harada; Ikuo Fujii; Tomoka Takatani-Nakase; Shiroh Futaki; Ikuhiko Nakase

  ACS Applied Materials & Interfaces, 04 Oct. 2023

  
• Structural Dissection of Epsin-1 N-Terminal Helical Peptide: The Role of Hydrophobic Residues in Modulating Membrane Curvature.

  Motoki Nishimura; Yoshimasa Kawaguchi; Kakeru Kuroki; Yuna Nakagawa; Toshihiro Masuda; Takayuki Sakai; Kenichi Kawano; Hisaaki Hirose; Miki Imanishi; Tomoka Takatani-Nakase; Sergii Afonin; Anne S Ulrich; Shiroh Futaki

  Chemistry (Weinheim an der Bergstrasse, Germany), 06 Mar. 2023

  Access this paper :

  
• Modular Redesign of a Cationic Lytic Peptide To Promote the Endosomal Escape of Biomacromolecules

  Yusuke Azuma; Haruka Imai; Yoshimasa Kawaguchi; Ikuhiko Nakase; Hiroshi Kimura; Shiroh Futaki

  Angewandte Chemie, 24 Sep. 2018, Peer-reviewed

  
• Hemopexin as a Potential Binding Partner of Arginine-Rich Cell-Penetrating Peptides in Serum

  Kayo Nomura; Kenichi Kawano; Yoshimasa Kawaguchi; Yuki Kawamura; Junya Michibata; Keiko Kuwata; Koji Sugiyama; Kenji Kusumoto; Shiroh Futaki

  ACS Pharmacology & Translational Science, 20 Jul. 2022, Lead author

  
• Split luciferase-based estimation of cytosolic cargo concentration delivered intracellularly via attenuated cationic amphiphilic lytic peptides

  Syusuke Okano; Yoshimasa Kawaguchi; Kenichi Kawano; Hisaaki Hirose; Miki Imanishi; Shiroh Futaki

  Bioorganic & Medicinal Chemistry Letters, Jul. 2022

  Access this paper :

  
• Stearylated Macropinocytosis-Inducing Peptides Facilitating the Cellular Uptake of Small Extracellular Vesicles.

  Yuna Nakagawa; Jan Vincent V Arafiles; Yoshimasa Kawaguchi; Ikuhiko Nakase; Hisaaki Hirose; Shiroh Futaki

  Bioconjugate chemistry, 04 May 2022

  Access this paper :

  
• Grafting Hydrophobic Amino Acids Critical for Inhibition of Protein-Protein Interactions on a Cell-Penetrating Peptide Scaffold.

  Yuki Nagano; Jan Vincent V Arafiles; Keiko Kuwata; Yoshimasa Kawaguchi; Miki Imanishi; Hisaaki Hirose; Shiroh Futaki

  Molecular pharmaceutics, 27 Dec. 2021

  
• Dipicolylamine/Metal Complexes that Promote Direct Cell-Membrane Penetration of Octaarginine.

  Yoshimasa Kawaguchi; Shoko Ise; Yusuke Azuma; Toshihide Takeuchi; Kenichi Kawano; Toan Khanh Le; Junko Ohkanda; Shiroh Futaki

  Bioconjugate chemistry, 20 Feb. 2019, Lead author

  
• Modular Redesign of a Cationic Lytic Peptide To Promote the Endosomal Escape of Biomacromolecules.

  Yusuke Azuma; Haruka Imai; Yoshimasa Kawaguchi; Ikuhiko Nakase; Hiroshi Kimura; Shiroh Futaki

  Angewandte Chemie (International ed. in English), 24 Sep. 2018

  
• Cytosolic antibody delivery by lipid-sensitive endosomolytic peptide.

  Misao Akishiba; Toshihide Takeuchi; Yoshimasa Kawaguchi; Kentarou Sakamoto; Hao-Hsin Yu; Ikuhiko Nakase; Tomoka Takatani-Nakase; Fatemeh Madani; Astrid Gräslund; Shiroh Futaki

  Nature chemistry, Aug. 2017

  
• Cholesterol-Lowering Effect of Octaarginine-Appended β-Cyclodextrin in Npc1-Trap-CHO Cells.

  Keiichi Motoyama; Rena Nishiyama; Yuki Maeda; Taishi Higashi; Yoshimasa Kawaguchi; Shiroh Futaki; Yoichi Ishitsuka; Yuki Kondo; Tetsumi Irie; Takumi Era; Hidetoshi Arima

  Biological & pharmaceutical bulletin, 01 Nov. 2016

  
• Syndecan-4 Is a Receptor for Clathrin-Mediated Endocytosis of Arginine-Rich Cell-Penetrating Peptides.

  Yoshimasa Kawaguchi; Toshihide Takeuchi; Keiko Kuwata; Junya Chiba; Yasumaru Hatanaka; Ikuhiko Nakase; Shiroh Futaki

  Bioconjugate chemistry, 20 Apr. 2016, Lead author

  
• Identification of cellular proteins interacting with octaarginine (R8) cell-penetrating peptide by photo-crosslinking.

  Yoshimasa Kawaguchi; Gen Tanaka; Ikuhiko Nakase; Miki Imanishi; Junya Chiba; Yasumaru Hatanaka; Shiroh Futaki

  Bioorganic & medicinal chemistry letters, 01 Jul. 2013, Lead author

  
• CXCR4 stimulates macropinocytosis: implications for cellular uptake of arginine-rich cell-penetrating peptides and HIV.

  Gen Tanaka; Ikuhiko Nakase; Yasunori Fukuda; Ryo Masuda; Shinya Oishi; Kazuya Shimura; Yoshimasa Kawaguchi; Tomoka Takatani-Nakase; Ulo Langel; Astrid Gräslund; Katsuya Okawa; Masao Matsuoka; Nobutaka Fujii; Yasumaru Hatanaka; Shiroh Futaki

  Chemistry & biology, 21 Nov. 2012

  

Misc.

• Promotion of membrane permeation of biopharmaceuticals using coacervates

  川口祥正; 二木史朗

  日本薬学会年会要旨集(Web), 2025

  
• Cytosolic delivery of anion-tagged antibodies via coacervates and the physicochemical properties of coacervates

  清川めぐみ; 川口祥正; 二木史朗

  日本薬学会年会要旨集(Web), 2025

  
• Inkjet-based cytosolic delivery technology using cell-penetrating peptides: evaluation and application

  二宮蒼平; 大村美香; 川口祥正; 藤原大佑; 藤原大佑; 道上雅孝; 道上雅孝; 中瀬朋夏; 藤井郁雄; 藤井郁雄; 二木史朗; 中瀬生彦; 中瀬生彦

  日本薬学会年会要旨集(Web), 2025

  
• Enhancement of intracellular delivery of mRNA using coacervates

  吉川あゆみ; 川口祥正; 二木史朗

  日本薬学会年会要旨集(Web), 2025

  
• 細胞外小胞を基盤とした感染症治療に向けた薬物送達キャリア

  川口祥正; 中川優奈; 二木史朗

  日本生化学会大会(Web), 2024, Invited

  
• Screening of G-quadruplex (G4) structure-specific peptide probes

  井田南加; 川口祥正; 二木史朗; 今西未来

  日本薬学会年会要旨集(Web), 2024

  
• Evaluation of an inkjet-based technology for cytosolic delivery of therapeutic molecules using cell-penetrating peptides

  大村美香; 二宮蒼平; 川口祥正; 藤原大佑; 藤原大佑; 道上雅孝; 道上雅孝; 中瀬朋夏; 藤井郁雄; 藤井郁雄; 二木史朗; 中瀬生彦; 中瀬生彦

  日本薬学会年会要旨集(Web), 2024

  
• Development of an Efficient Endosomolytic Peptide for Cytosolic Protein Delivery

  川口祥正; 川村優貴; 清川めぐみ; 広瀬久昭; 樋口ゆり子; 二木史朗

  日本薬学会年会要旨集(Web), 2024

  
• Cell-Specific and Efficient Delivery By SARS-CoV-2 Spike Protein-Loaded Extracellular Vesicles

  中川優奈; 川口祥正; 広瀬久昭; 橋口隆生; 二木史朗

  日本薬学会年会要旨集(Web), 2024

  
• Cytosolic Delivery of Antibodies through L17ER4 Conjugation

  寺田旺之; 川口祥正; 二木史朗

  日本薬学会年会要旨集(Web), 2024

  
• Engineering Extracellular Vesicles for Drug Delivery Carrier Development

  Kawaguchi Yoshimasa

  MEMBRANE, 2024

  
• 安全かつ効率的な細胞質送達ペプチドの開発

  川口 祥正

  Drug Delivery System, Jan. 2024

  
• ペプチドによる細胞内送達の効率と遺伝子発現の相関解析

  栗山 理志; 広瀬 久昭; 川口 祥正; 二木 史朗

  日本生化学会大会プログラム・講演要旨集, Oct. 2023

  
• SARS-CoV-2S protein搭載による細胞外小胞の膜融合促進

  中川優奈; 川口祥正; 橋口隆生; 二木史朗

  生体膜と薬物の相互作用シンポジウム講演要旨集, 2023

  
• The mechanism of action of intracellular delivery peptide L17E

  栗山理志; 広瀬久昭; 川口祥正; 二木史朗

  日本薬学会年会要旨集(Web), 2023

  
• 生理活性物質の細胞内送達に向けたMelittin誘導体の創製

  川口祥正; 為本尚樹; 麓昌高; 二木史朗

  生体膜と薬物の相互作用シンポジウム講演要旨集, 2022

  
• "DDSの「ちょっとした」技術・知識"(第19回) ポリアクリルアミドゲル電気泳動 タンパク質の電気泳動 SDS-PAGE

  川口 祥正

  Drug Delivery System, Mar. 2023

  
• Quantitative evaluation system for cytosolic delivery of peptide and protein-based drugs

  岡野秀亮; 川口祥正; 河野健一; 二木史朗

  日本薬学会年会要旨集(Web), Mar. 2022

  
• Ni(II)/Dipicolylamine modification of octaarginine to promote the cell penetration

  川口祥正; 伊勢祥子; 二木史朗

  日本薬学会年会要旨集(Web), Mar. 2022

  
• CELL PENETRATION OF DIPICOLYLAMINE-MODIFIED R8 FACILITATED BY METAL COMPLEX FORMATION

  S. Ise; Y. Kawaguchi; T. Takeuchi; K. Kawano; S. Futaki

  JOURNAL OF PEPTIDE SCIENCE, Sep. 2016

  
• An Approach to Explore Proteins Involved in the Internalization of Arginine-Rich Peptides Using Photocrosslinking

  KAWAGUCHI Yoshimasa; TANAKA Gen; FUKUDA Yasunori; NAKASE Ikuhiko; HATANAKA Yasumaru; FUTAKI Shiroh

  Peptide science : proceedings of the ... Japanese Peptide Symposium, 01 Mar. 2012

  
• DEVELOPMENT OF PEPTIDE TOOLS FOR INTRACELLULAR DELIVERY OF ANTIBODIES

  M. Akishiba; T. Takeuchi; Y. Kawaguchi; K. Sakamoto; I. Nakase; S. Futaki

  JOURNAL OF PEPTIDE SCIENCE, Sep. 2016

  
• PHOTOCROSSLINKING APPROACHES TO IDENTIFY CELLULAR-UPTAKE RECEPTORS OF ARGININE-RICH CELL-PENETRATING PEPTIDES

  S. Futaki; Y. Kawaguchi; T. Takeuchi; K. Kuwata

  JOURNAL OF PEPTIDE SCIENCE, Sep. 2016

  
• ポストゲノム時代の創薬を目指して〜タンパク質にできること・タンパク質ならできること〜 エンドソーム不安定化ペプチドを用いた細胞内への機能性タンパク質の導入

  秋柴 美沙穂; 武内 敏秀; 川口 祥正; 坂本 健太郎; 中瀬 生彦; 二木 史朗

  日本薬学会年会要旨集, Mar. 2018

  
• ニーマンピック病C型治療薬としての新規膜透過性シクロデキストリンの可能性評価

  西山 怜奈; 本山 敬一; 前田 有紀; 東 大志; 川口 祥正; 二木 史朗; 石塚 洋一; 近藤 悠希; 入江 徹美; 江良 択実; 有馬 英俊

  日本薬学会年会要旨集, Mar. 2017

  
• エンドソーム膜を不安定化する新規ペプチドの開発と抗体の細胞内送達

  秋柴 美沙穂; 武内 敏秀; 川口 祥正; 坂本 健太郎; 二木 史朗

  日本薬学会年会要旨集, Mar. 2017

  
• オクタアルギニンを介した細胞内タンパク質送達法の細胞質輸送効率を評価するためのMALDI-TOF型質量分析計を用いた分析法(A MALDI-TOF mass spectroscopy-based approach to evaluate the cytosolic translocation efficiency of octaarginine-mediated intracellular protein delivery)

  Arafiles Jan Vincent; 川口 祥正; Cherine Bechara; Erancoise Illien; 河野 健一; Fabienne Burlina; Sandrine Sagan; 二木 史朗

  日本薬学会年会要旨集, Mar. 2017

  
• オクタアルギニンと血清タンパク質の相互作用

  野村 佳世; 河野 健一; 川口 祥正; 桑田 啓子; 二木 史朗

  日本薬学会年会要旨集, Mar. 2017

  
• ニーマンピック病C型様細胞の細胞内コレステロール量に及ぼすオクタアルギニン修飾シクロデキストリンの影響

  西山 怜奈; 本山 敬一; 東 大志; 石塚 洋一; 近藤 悠希; 入江 徹美; 江良 択実; 川口 祥正; 二木 史朗; 有馬 英俊

  日本DDS学会学術集会プログラム予稿集, Jun. 2016

  
• ジピコリルアミン修飾オクタアルギニンと金属の錯体形成による膜透過促進

  伊勢 祥子; 川口 祥正; 武内 敏秀; 二木 史朗

  日本薬学会年会要旨集, Mar. 2016

  
• グルタミン酸を導入した毒素ペプチド変異体による抗体の細胞内送達

  秋柴 美沙穂; 川口 祥正; 武内 敏秀; 二木 史朗

  日本生化学会大会・日本分子生物学会年会合同大会講演要旨集, Dec. 2015

  
• Cellular Uptake of Arginine-Rich Cell-Penetrating Peptides and the Contribution of Membrane-Associated Proteoglycans

  Ikuhiko Nakase; Yoshimasa Kawaguchi; Motoyoshi Nomizu; Shiroh Futaki

  TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, May 2015

  
• オクタアルギニン-ユビキチンコンジュゲートを利用したR8の細胞内在化量の定量

  川口 祥正; Bechara Cherine; Yu Hao-Hsin; 中瀬 生彦; 今西 未来; 武内 敏秀; Burlina Fabienne; Sagan Sandrine; 二木 史朗

  日本薬学会年会要旨集, Mar. 2015

  
• 天然由来の膜傷害ペプチドを用いた高分子生理活性物質の細胞内送達法の開発

  秋柴 美沙穂; 武内 敏秀; 川口 祥正; 二木 史朗

  日本薬学会年会要旨集, Mar. 2015

  
• 光架橋法によるオクタアルギニンペプチドの細胞内移行関連タンパク質の同定

  川口 祥正; 田中 弦; 中瀬 生彦; 武内 敏秀; 畑中 保丸; 二木 史朗

  日本薬学会年会要旨集, Mar. 2014

  
• CXCR4によるマクロピノサイトーシスの誘導とHIV-1感染

  川口 祥正; 田中 弦; 中瀬 生彦; 大石 真也; 藤井 信孝; 志村 和也; 松岡 雅雄; 二木 史朗

  日本薬学会年会要旨集, Mar. 2013

  
• フォトクロスリンカーを用いたアルギニンペプチドの取り込みに関与する細胞表面蛋白質の探索

  川口 祥正; 田中 弦; 福田 保則; 中瀬 生彦; 畑中 保丸; 二木 史朗

  日本薬学会年会要旨集, Mar. 2012

  

Presentations

• Attenuated cationic lytic peptides for intracellular delivery of antibodies

  Yoshimasa Kawaguchi

  pre-ISBC2024 symposium, 22 Apr. 2024, Invited

  
• Development of cytosolic delivery peptides by attenuated membrane lytic activity

  Yoshimasa Kawaguchi

  The 61th Annual Meeting of the Biophysical Society of Japan, 16 Nov. 2023, Invited

  
• Development of a Novel Endosomolytic Peptide for Cytosolic Delivery of Proteins

  Yoshimasa Kawaguchi

  Satellite Symposium of the 60th Japanese Peptide Symposium, 11 Nov. 2023, Invited

  

Industrial Property Rights

• 特許第6617930号, WO2016-052442, 特願2016-552026, 細胞質送達ペプチド

  二木 史朗; 秋柴 美沙穂; 川口 祥正; 武内 敏秀

  

Awards

• 13 Sep. 2024

  バイオ関連化学シンポジウム講演賞(日本化学会生体機能関連化学部会)
• 28 Oct. 2022

  The Japanese Peptide Society, Excellent Poster Presentation Award

Education

Teaching subject(s)

• From 01 Apr. 2023, To 31 Mar. 2024

  Fundamental Chemical Experiments

  N308, Fall, Institute for Liberal Arts and Sciences, 2

Administration

Faculty management (title, position)

• From 01 Apr. 2022, To 31 Mar. 2023

  化学研究所広報委員会委員