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Mar. Drugs 2017, 15(12), 352; doi:10.3390/md15120352

Liposomal Circular Dichroism (L-CD) of Arenoyl Derivatives of Sphingolipids. Amplification of Cotton Effects in Ordered Lipid Bilayers

1
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive MC0358, La Jolla, CA 92093, USA
2
Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, 9500 Gilman Drive MC0358, La Jolla, CA 92093, USA
Present address, Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543, Singapore.
*
Author to whom correspondence should be addressed.
Received: 13 October 2016 / Revised: 4 December 2017 / Accepted: 6 December 2017 / Published: 20 December 2017
(This article belongs to the Special Issue Structural Techniques in Natural Products Drug Discovery)
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Abstract

Liposomal circular dichroism (L-CD) of acyclic amino alcohols exhibit amplification of Cotton effects when measured in highly uniform, unilamellar liposomes. The effect is likely due to intermolecular associations—H-aggregates—that self-assemble spontaneously within the lipid bilayer, and persists over long time scales. L-CD spectra of N,O,O′-tri-(6′methoxy-2′-naphthoyl)-d-erythro-sphingosine, or the corresponding dihydro-derivative (sphinganine), shows ~10-fold amplification of magnitudes of Cotton effects over conventional CD spectra recorded in isotropic solution. View Full-Text
Keywords: marine natural product; circular dichroism; exciton coupling; absolute configuration; liposome; sphingosine; sphingolipid marine natural product; circular dichroism; exciton coupling; absolute configuration; liposome; sphingosine; sphingolipid
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MDPI and ACS Style

Molinski, T.F.; Broaddus, C.D.; Morinaka, B.I. Liposomal Circular Dichroism (L-CD) of Arenoyl Derivatives of Sphingolipids. Amplification of Cotton Effects in Ordered Lipid Bilayers. Mar. Drugs 2017, 15, 352.

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