Factors affecting the uncaging efficiency of 500 nm light-activatable BODIPY caging group

Minoru Kawatani; Mako Kamiya; Hironori Takahashi; Yasuteru Urano

doi:10.1016/j.bmcl.2017.11.030

Factors affecting the uncaging efficiency of 500 nm light-activatable BODIPY caging group

Bioorg Med Chem Lett. 2018 Jan 1;28(1):1-5. doi: 10.1016/j.bmcl.2017.11.030. Epub 2017 Nov 16.

Authors

Minoru Kawatani¹, Mako Kamiya², Hironori Takahashi¹, Yasuteru Urano³

Affiliations

¹ Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
² Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; PRESTO, Japan Science and Technology Agency, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.
³ Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan; CREST, Japan Agency for Medicinal Research and Development, 1-7-1 Otemachi, Chiyoda-ku, Tokyo 100-0004, Japan. Electronic address: uranokun@m.u-tokyo.ac.jp.

PMID: 29239736
DOI: 10.1016/j.bmcl.2017.11.030

Abstract

Photoremovable protective groups, or caging groups, enable us to regulate the activities of bioactive molecules in living cells upon photoirradiation. Nevertheless, requirement of UV light for activating caging group is a significant limitation due to its cell toxicity and its poor tissue penetration. Our group previously reported a 500 nm light-activatable caging group based on BODIPY scaffold, however, its uncaging efficiency was lower than those of conventional caging groups. Here we show that the uncaging quantum yield (QY) of BODIPY caging group depends upon the driving force of photo-induced electron transfer (PeT). We also found that the uncaging QY increased in less polar solvents. We applied these findings to develop BODIPY-caged capsaicin, which is well localized to low-polarity intracellular compartments, as a tool to stimulate TRPV1 in live cells in response to blue-green light.

Keywords: BODIPY; Caged compound; Photo-induced electron transfer (PeT); TRPV1.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzylamines / chemical synthesis
Benzylamines / chemistry
Benzylamines / pharmacology*
Benzylamines / radiation effects
Boron Compounds / chemical synthesis
Boron Compounds / chemistry
Boron Compounds / pharmacology*
Boron Compounds / radiation effects
Calcium / metabolism
Capsaicin / analogs & derivatives*
Capsaicin / chemical synthesis
Capsaicin / pharmacology*
Capsaicin / radiation effects
Fatty Acids / chemical synthesis
Fatty Acids / chemistry
Fatty Acids / pharmacology*
Fatty Acids / radiation effects
HEK293 Cells
Humans
Hydrophobic and Hydrophilic Interactions
Light
Solvents / chemistry
TRPV Cation Channels / agonists

Substances

Benzylamines
Boron Compounds
Fatty Acids
Solvents
TRPV Cation Channels
TRPV1 protein, human
pelargonic acid vanillylamide
Capsaicin
Calcium