Short Photoswitchable Ceramides Enable Optical Control of Apoptosis

Johannes Morstein; Matthijs Kol; Alexander J.E. Novak; Suihan Feng; Shadi Khayyo; Konstantin Hinnah; Nasi Li-Purcell; Grace Pan; Benjamin M. Williams; Howard Riezman; G. Ekin Atilla-Gokcumen; Joost C.M. Holthuis; Dirk Trauner

doi:10.1021/acschembio.0c00823

Short Photoswitchable Ceramides Enable Optical Control of Apoptosis

Johannes Morstein
, Matthijs Kol
, Alexander J.E. Novak
, Suihan Feng
, Shadi Khayyo
, Konstantin Hinnah
, Nasi Li-Purcell
, Grace Pan
, Benjamin M. Williams
, Howard Riezman
, G. Ekin Atilla-Gokcumen
, Joost C.M. Holthuis
, Dirk Trauner

Chemistry

New York University
Osnabrück University
University of Geneva
SUNY Buffalo
Ludwig Maximilian University of Munich

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

We report short ceramide analogs that can be activated with light and further functionalized using azide-alkyne click chemistry. These molecules, termed scaCers, exhibit increased cell permeability compared to their long-chain analogs as demonstrated using mass spectrometry and imaging. Notably, scaCers enable optical control of apoptosis, which is not observed with long-chain variants. Additionally, they function as photoswitchable substrates for sphingomyelin synthase 2 (SMS2), exhibiting inverted light-dependence compared to their extended analogs.

Original language	English
Pages (from-to)	452-456
Number of pages	5
Journal	ACS Chemical Biology
Volume	16
Issue number	3
DOIs	https://doi.org/10.1021/acschembio.0c00823
State	Published - Mar 19 2021

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title = "Short Photoswitchable Ceramides Enable Optical Control of Apoptosis",

abstract = "We report short ceramide analogs that can be activated with light and further functionalized using azide-alkyne click chemistry. These molecules, termed scaCers, exhibit increased cell permeability compared to their long-chain analogs as demonstrated using mass spectrometry and imaging. Notably, scaCers enable optical control of apoptosis, which is not observed with long-chain variants. Additionally, they function as photoswitchable substrates for sphingomyelin synthase 2 (SMS2), exhibiting inverted light-dependence compared to their extended analogs.",

author = "Johannes Morstein and Matthijs Kol and Novak, \{Alexander J.E.\} and Suihan Feng and Shadi Khayyo and Konstantin Hinnah and Nasi Li-Purcell and Grace Pan and Williams, \{Benjamin M.\} and Howard Riezman and Atilla-Gokcumen, \{G. Ekin\} and Holthuis, \{Joost C.M.\} and Dirk Trauner",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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day = "19",

doi = "10.1021/acschembio.0c00823",

language = "English",

volume = "16",

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T1 - Short Photoswitchable Ceramides Enable Optical Control of Apoptosis

AU - Morstein, Johannes

AU - Kol, Matthijs

AU - Novak, Alexander J.E.

AU - Feng, Suihan

AU - Khayyo, Shadi

AU - Hinnah, Konstantin

AU - Li-Purcell, Nasi

AU - Pan, Grace

AU - Williams, Benjamin M.

AU - Riezman, Howard

AU - Atilla-Gokcumen, G. Ekin

AU - Holthuis, Joost C.M.

AU - Trauner, Dirk

PY - 2021/3/19

Y1 - 2021/3/19

N2 - We report short ceramide analogs that can be activated with light and further functionalized using azide-alkyne click chemistry. These molecules, termed scaCers, exhibit increased cell permeability compared to their long-chain analogs as demonstrated using mass spectrometry and imaging. Notably, scaCers enable optical control of apoptosis, which is not observed with long-chain variants. Additionally, they function as photoswitchable substrates for sphingomyelin synthase 2 (SMS2), exhibiting inverted light-dependence compared to their extended analogs.

AB - We report short ceramide analogs that can be activated with light and further functionalized using azide-alkyne click chemistry. These molecules, termed scaCers, exhibit increased cell permeability compared to their long-chain analogs as demonstrated using mass spectrometry and imaging. Notably, scaCers enable optical control of apoptosis, which is not observed with long-chain variants. Additionally, they function as photoswitchable substrates for sphingomyelin synthase 2 (SMS2), exhibiting inverted light-dependence compared to their extended analogs.

UR - https://www.scopus.com/pages/publications/85101594381

U2 - 10.1021/acschembio.0c00823

DO - 10.1021/acschembio.0c00823

M3 - Article

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AN - SCOPUS:85101594381

SN - 1554-8929

VL - 16

SP - 452

EP - 456

JO - ACS Chemical Biology

JF - ACS Chemical Biology

IS - 3

ER -

Short Photoswitchable Ceramides Enable Optical Control of Apoptosis

Abstract

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