On the importance of chain branching in tear film lipid layer wax and cholesteryl esters

被引:8
作者
Viitaja, Tuomo [1 ,2 ,3 ]
Raitanen, Jan-Erik [1 ,3 ]
Hynynen, Antti [1 ,3 ]
Moilanen, Jukka [2 ,3 ]
Svedstrom, Kirsi [3 ]
Paananen, Riku O. [1 ,2 ,3 ]
Ekholm, Filip S. [1 ,3 ]
机构
[1] Univ Helsinki, Dept Chem, POB 55, FI-00014 Helsinki, Finland
[2] Univ Helsinki, Ophthalmol, Haartmaninkatu 8, FI-00290 Helsinki, Finland
[3] Helsinki Univ Hosp, Haartmaninkatu 8, FI-00290 Helsinki, Finland
基金
芬兰科学院;
关键词
Biophysics; Chemical synthesis; Structural elucidation; Tear film lipid layer; X-RAY-DIFFRACTION; HYDROXY FATTY-ACIDS; MEIBOMIAN GLAND; PHYSICAL-PROPERTIES; SURFACE PHASE; HUMAN MEIBUM; WATER; EVAPORATION; MONOLAYERS; BEHAVIOR;
D O I
10.1016/j.colsurfb.2022.112429
中图分类号
Q6 [生物物理学];
学科分类号
071011 ;
摘要
The tear film lipid layer (TFLL) is important to the maintenance of ocular surface health. Surprisingly, information on the individual roles of the myriad of unique lipids found therein is limited. The most abundant lipid species are the wax esters (WE) and cholesteryl esters (CE), and, especially their branched analogs. The isolation of these lipid species from the TFLL has proved to be tedious, and as a result, insights on their biophysical profiles and role in the TFLL is currently lacking. Herein, we circumvent these issues by a total synthesis of the most abundant iso-methyl branched WEs and CEs found in the TFLL. Through a detailed characterization of the biophysical properties, by the use of Langmuir monolayer and wide-angle X-ray scattering techniques, we demonstrate that chain branching alters the behavior of these lipid species on multiple levels. Taken together, our results fill an important knowledge gap concerning the structure and function of the TFLL on the whole.
引用
收藏
页数:10
相关论文
共 81 条
[1]   INFRARED SPECTRA AND POLYMORPHISM OF LONG CHAIN ESTERS .4. SOME ESTERS FROM TETRADECANOL, HEXADECANOL, OCTADECANOL, EICOSANOL, DOCOSANOL AND DODECANOIC, TETRADECANOIC, HEXADECANOIC, OCTADECANOIC AND EICOSANOIC ACID [J].
ALEBY, S ;
FISCHMEISTER, I ;
IYENGAR, BTR .
LIPIDS, 1971, 6 (06) :421-+
[2]   Self-assembly of crystalline films of interdigitated long-chain cholesteryl esters at the air-water interface [J].
Alonso, C ;
Kuzmenko, I ;
Jensen, TR ;
Kjaer, K ;
Lahav, M ;
Leiserowitz, L .
JOURNAL OF PHYSICAL CHEMISTRY B, 2001, 105 (36) :8563-8568
[3]   HUMAN TEAR FILM LIPIDS .1. COMPOSITION OF PRINCIPAL NON-POLAR COMPONENT [J].
ANDREWS, JS .
EXPERIMENTAL EYE RESEARCH, 1970, 10 (02) :223-&
[4]   Regiocontrolled syntheses of FAHFAs and LC-MS/MS differentiation of regioisomers [J].
Balas, Laurence ;
Bertrand-Michel, Justine ;
Viars, Fanny ;
Faugere, Julien ;
Lefort, Corinne ;
Caspar-Bauguil, Sylvie ;
Langin, Dominique ;
Durand, Thierry .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (38) :9012-9020
[5]   SYNTHESIS OF FLUORESCENT-PROBES FOR LOCALIZED MEMBRANE FLUIDITY MEASUREMENTS [J].
BECK, A ;
HEISSLER, D ;
DUPORTAIL, G .
TETRAHEDRON, 1991, 47 (08) :1459-1472
[6]   Investigating the Role of Specific Tear Film Lipids Connected to Dry Eye Syndrome: A Study on O-Acyl-ω-hydroxy Fatty Acids and Diesters [J].
Bland, Helena C. ;
Moilanen, Jukka A. ;
Ekholm, Filip S. ;
Paananen, Riku O. .
LANGMUIR, 2019, 35 (09) :3545-3552
[7]   Human meibum chain branching variability with age, gender and meibomian gland dysfunction [J].
Borchman, Douglas ;
Ramasubramanian, Aparna .
OCULAR SURFACE, 2019, 17 (02) :327-335
[8]   Lubricating and waxy esters, I. Synthesis, crystallization, and melt behavior of linear monoesters [J].
Bouzidi, Laziz ;
Li, Shaojun ;
Di Biase, Steve ;
Rizvi, Syed Q. ;
Narine, Suresh S. .
CHEMISTRY AND PHYSICS OF LIPIDS, 2012, 165 (01) :38-50
[9]   TFOS DEWS II pathophysiology report [J].
Bron, Anthony J. ;
de Paiva, Cintia S. ;
Chauhan, Sunil K. ;
Bonini, Stefano ;
Gabison, Eric E. ;
Jain, Sandeep ;
Knop, Erich ;
Markoulli, Maria ;
Ogawa, Yoko ;
Perez, Victor ;
Uchino, Yuichi ;
Yokoi, Norihiko ;
Zoukhri, Driss ;
Sullivan, David A. .
OCULAR SURFACE, 2017, 15 (03) :438-510
[10]   A Comparison of Patient Matched Meibum and Tear Lipidomes [J].
Brown, Simon H. J. ;
Kunnen, Carolina M. E. ;
Duchoslav, Eva ;
Dolla, Naveen K. ;
Kelso, Michael J. ;
Papas, Eric B. ;
de la Jara, Percy Lazon ;
Willcox, Mark D. P. ;
Blanksby, Stephen J. ;
Mitchell, Todd W. .
INVESTIGATIVE OPHTHALMOLOGY & VISUAL SCIENCE, 2013, 54 (12) :7417-7423