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

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

Yuichi Umegawa  ∗
a   Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan
,
Shiho Fukunaga
a   Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan
,
Tomokazu Yasuda
a   Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan
b   Forefront Research Center, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan
,
Michio Murata  ∗
a   Graduate School of Science, Osaka University, 1-1 Machikaneyama, Toyonaka, Osaka 560-0043, Japan
b   Forefront Research Center, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan
› Author AffiliationsThis work was supported by Grants-in-Aid for Scientific Research (Grants Nos. 20K05728, 21H04707, 23K04943, and 23K17373).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2210-1162.
  • Supporting Information


Publication History

Received: 26 October 2023

Accepted after revision: 13 November 2023

Accepted Manuscript online:
13 November 2023

Article published online:
15 December 2023

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