A Fluorescent Probe for C24 Fatty Acids to Report the Deep Interior of Lipid Bilayers

Yuichi Umegawa; Shiho Fukunaga; Tomokazu Yasuda; Michio Murata

doi:10.1055/a-2210-1162

Synlett, Table of Contents

Synlett 2024; 35(11): 1269-1272
DOI: 10.1055/a-2210-1162

cluster

Japan/Netherlands Gratama Workshop

A Fluorescent Probe for C₂₄ Fatty Acids to Report the Deep Interior of Lipid Bilayers

Yuichi Umegawa ∗

^aGraduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan

,

Shiho Fukunaga

^aGraduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan

,

Tomokazu Yasuda

^aGraduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan

^bForefront Research Center, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan

,

Michio Murata ∗

^aGraduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan

^bForefront Research Center, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan

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Abstract

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Abstract

To investigate the interdigitation and the resulting fluctuation of lipid chains in the deep part of biomembranes, we aimed to develop a new fluorescent probe based on the well-known trans-parinaric acid (t-PA), but with a tetraene near the end of the C₂₄ chain. The probe, tetracosa-16,18,20,22-tetraenoic acid (TCTEA), synthesized mainly by means of reported strategies, was found to better reflect the behavior of lipids in the deeper interior of bilayers than did t-PA. TCTEA could serve as a useful probe for studying the plasma-membrane dynamics of very-long-chain fatty acids, which have recently elicited significant attention in relation to necroptosis.

Key words

long-chain fatty acids - fatty acids - fluorescent probes - teteraenes - lipid bilayers - interdigitation

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References

References and Notes
1 Y. Umegawa has relocated to another position at the same university: Office of Management and Planning, Osaka University, 1–3, Machikaneyama, Toyonaka, Osaka 560-8531, Japan.

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