Interplay of long-chain tetrazine derivatives and biomembrane components at the air-water interface

Hiromichi Nakahara; Masayori Hagimori; Takahiro Mukai; Osamu Shibata

doi:10.1063/5.0083352

Interplay of long-chain tetrazine derivatives and biomembrane components at the air-water interface

Biophys Rev (Melville). 2022 Apr 28;3(2):021303. doi: 10.1063/5.0083352. eCollection 2022 Jun.

Authors

Hiromichi Nakahara¹, Masayori Hagimori², Takahiro Mukai³, Osamu Shibata⁴

Affiliations

¹ Department of Industrial Pharmacy, Faculty of Pharmaceutical Sciences, Daiichi University of Pharmacy, 22-1 Tamagawa-cho, Minami-ku Fukuoka 815-8511, Japan.
² Laboratory of Analytical Chemistry, Faculty of Pharmaceutical Sciences, Mukogawa Women's University, 11-68 Koshien Kyubancho, Nishinomiya 663-8179, Japan.
³ Laboratory of Biophysical Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyama Kitamachi, Higashinada-ku, Kobe 658-8558, Japan.
⁴ Department of Biophysical Chemistry, Graduate School of Pharmaceutical Sciences, Nagasaki International University, 2825-7 Huis Ten Bosch, Sasebo, Nagasaki 859-3298, Japan.

Abstract

Tetrazine (Tz) is an emerging bioorthogonal ligand that is expected to have applications (e.g., bioimaging) in chemistry and chemical biology. In this review, we highlight the interactions of reduced tetrazine (rTz) derivatives insoluble in aqueous media with biological membrane constituents or their related lipids, such as dipalmitoyl-phosphatidylcholine, dipalmitoyl-phosphatidylethanolamine, dipalmitoyl-phosphatidylglycerol, palmitoyl-sphingomyelin, and cholesterol in the Langmuir monolayer state at the air-water interface. The two-component interaction was thermodynamically elucidated by measuring the surface pressure (π) and molecular area (A) isotherms. The monolayer miscibility between the two components was analyzed using the excess Gibbs energy of mixing and two-dimensional phase diagram. The phase behavior of the binary monolayers was studied using the Brewster angle, fluorescence, and atomic force microscopy. This study discusses the affinities of the rTz moieties for the hydrophilic groups of the lipids used.

Publication types

Review