NDLI: Synthesis of the diacetylenic phospholipids 1,2-(10',12'-heptadecadiynoyl)-sn-glycero-3-phophatidylcholine and 1,2-(4',6'-tricosadiynoyl)-sn-glycero-3-phophatidylcholine

Content Provider	Scientific Electronic Library Online (SciELO)
Author	Hennies, Paulo T. Santana, Maria H. C. Correia, Carlos R. D.
Abstract	Diacetylenic phosphatidylcholines are synthetic compounds analogous to natural phospholipids. These molecules can be hydrated to form bilayered aggregates known as liposomes in a manner similar to natural phosphatidylcholines. A particular feature of these liposomes is their capability of undergoing polymerization when submitted to ultraviolet (UV) light irradiation. This process allows the construction of polymerized liposomes possessing interesting physical properties making these vesicles appropriate for slow-release drug delivering systems. In this article we describe the total syntheses of diacetylenic phosphatidylcholines 1,2-bis(10',12'-heptadecadiynoyl)-sn-glycero-3-phosphatidylcholine (1a), 1,2-bis(10',12'-tricosadiynoyl)-sn-glycero-3-phosphatidylcholine (1b) and 1,2-bis(4',6'-tricosadiynoyl)-sn-glycero-3-phosphatidylcholine (1c). Phospholipids 1a and 1c, displaying the butadiinyl chromophores closer to the chain terminus, or closer to the polar heads respectively, have not been reported before. Noteworthy was the observation that liofilization of the diacetylenic alcohols and acids intermediates significantly reduced undesired polymerization, allowing to stock these compounds for a short period of time (~24 h).
Related Links	http://www.scielo.br/scielo.php?script=sci_abstract&pid=S0103-50532001000100009&lng=en&nrm=iso http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532001000100009&lng=en&nrm=iso
Starting Page	64
Ending Page	72
Page Count	9
File Format	PDF
ISSN	01035053
DOI	10.1590/S0103-50532001000100009
Journal	Journal of the Brazilian Chemical Society
Issue Number	1
Volume Number	12
Language	English
Publisher	Sociedade Brasileira de Química
Publisher Date	2001-01-01
Publisher Institution	Universidade Estadual de Campinas Faculdade de Engenharia Química Departamento de Processos Biotecnológicos Universidade Estadual de Campinas Instituto de Química Departamento de Química Orgânica
Publisher Place	Brazil
Access Restriction	Open
Subject Keyword	Diacetylenic phospholipids Liposomes Polymerizable phospholipid
Content Type	Text
Resource Type	Article
Subject	Chemistry

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