pH Dependence of Sphingosine Aggregation
Sphingosine and sphingosine 1-phosphate (S1P) are sphingolipid metabolites that act as signaling messengers to activate or inhibit multiple downstream targets to regulate cell growth, differentiation, and apoptosis. The amphiphilic nature of these compounds leads to aggregation above their critical...
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| Published in | Biophysical journal Vol. 96; no. 7; pp. 2727 - 2733 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
United States
Elsevier Inc
08.04.2009
Biophysical Society The Biophysical Society |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Sphingosine and sphingosine 1-phosphate (S1P) are sphingolipid metabolites that act as signaling messengers to activate or inhibit multiple downstream targets to regulate cell growth, differentiation, and apoptosis. The amphiphilic nature of these compounds leads to aggregation above their critical micelle concentrations (CMCs), which may be important for understanding lysosomal glycosphingolipid storage disorders. We investigated the aggregation of sphingosine and S1P over a comprehensive, physiologically relevant range of pH values, ionic strengths, and lipid concentrations by means of dynamic light scattering, titration, and NMR spectroscopy. The results resolve discrepancies in literature reports of CMC and pK
a values. At physiological pH, the nominal CMCs of sphingosine and S1P are 0.99 ± 0.12
μM (pH 7.4) and 14.35 ± 0.08
μM (pH 7.2), respectively. We find that pH strongly affects the aggregation behavior of sphingosine by changing the ionic and hydrogen-bonding states; the nominal critical aggregation concentrations of protonated and deprotonated sphingosine are 1.71 ± 0.24
μM and 0.70 ± 0.02
μM, respectively. NMR measurements revealed that the NH
3
+–NH
2 transition of sphingosine occurs at pH 6.6, and that there is a structural shift in sphingosine aggregates caused by a transition in the predominant hydrogen-bonding network from intramolecular to intermolecular that occurs between pH 6.7 and 9.9. |
|---|---|
| AbstractList | Sphingosine and sphingosine 1-phosphate (S1P) are sphingolipid metabolites that act as signaling messengers to activate or inhibit multiple downstream targets to regulate cell growth, differentiation, and apoptosis. The amphiphilic nature of these compounds leads to aggregation above their critical micelle concentrations (CMCs), which may be important for understanding lysosomal glycosphingolipid storage disorders. We investigated the aggregation of sphingosine and S1P over a comprehensive, physiologically relevant range of pH values, ionic strengths, and lipid concentrations by means of dynamic light scattering, titration, and NMR spectroscopy. The results resolve discrepancies in literature reports of CMC and pK
a values. At physiological pH, the nominal CMCs of sphingosine and S1P are 0.99 ± 0.12
μM (pH 7.4) and 14.35 ± 0.08
μM (pH 7.2), respectively. We find that pH strongly affects the aggregation behavior of sphingosine by changing the ionic and hydrogen-bonding states; the nominal critical aggregation concentrations of protonated and deprotonated sphingosine are 1.71 ± 0.24
μM and 0.70 ± 0.02
μM, respectively. NMR measurements revealed that the NH
3
+–NH
2 transition of sphingosine occurs at pH 6.6, and that there is a structural shift in sphingosine aggregates caused by a transition in the predominant hydrogen-bonding network from intramolecular to intermolecular that occurs between pH 6.7 and 9.9. Sphingosine and sphingosine 1- phosphate (S1P) are sphingolipid metabolites that act as signaling messengers to activate or inhibit multiple downstream targets to regulate cell growth, differentiation, and apoptosis. The amphiphilic nature of these compounds leads to aggregation above their critical micelle concentrations (CMCs), which may be important for understanding lysosomal glycosphingolipid storage disorders. We investigated the aggregation of sphingosine and S1P over a comprehensive, physiologically relevant range of pH values, ionic strengths, and lipid concentrations by means of dynamic light scattering, titration, and NMR spectroscopy. The results resolve discrepancies in literature reports of CMC and pK... values. At physiological pH, the nominal CMCs of sphingosine and S1P are 0.99 0.12 ...M (pH 7.4) and 14.35 0.08 ...M (pH 7.2), respectively. We find that pH strongly affects the aggregation behavior of sphingosine by changing the ionic and hydrogen-bonding states; the nominal critical aggregation concentrations of protonated and deprotonated sphingosine are 1.71 0.24 ...M and 0.70 0.02 M, respectively. NMR measurements revealed that the ... transition of sphingosine occurs at pH 6.6, and that there is a structural shift in sphingosine aggregates caused by a transition in the predominant hydrogen-bonding network from intramolecular to intermolecular that occurs between pH 6.7 and 9.9. (ProQuest: ... denotes formulae/symbols omitted.) Sphingosine and sphingosine 1-phosphate (S1P) are sphingolipid metabolites that act as signaling messengers to activate or inhibit multiple downstream targets to regulate cell growth, differentiation, and apoptosis. The amphiphilic nature of these compounds leads to aggregation above their critical micelle concentrations (CMCs), which may be important for understanding lysosomal glycosphingolipid storage disorders. We investigated the aggregation of sphingosine and S1P over a comprehensive, physiologically relevant range of pH values, ionic strengths, and lipid concentrations by means of dynamic light scattering, titration, and NMR spectroscopy. The results resolve discrepancies in literature reports of CMC and pK(a) values. At physiological pH, the nominal CMCs of sphingosine and S1P are 0.99 +/- 0.12 microM (pH 7.4) and 14.35 +/- 0.08 microM (pH 7.2), respectively. We find that pH strongly affects the aggregation behavior of sphingosine by changing the ionic and hydrogen-bonding states; the nominal critical aggregation concentrations of protonated and deprotonated sphingosine are 1.71 +/- 0.24 microM and 0.70 +/- 0.02 microM, respectively. NMR measurements revealed that the NH3+-NH2 transition of sphingosine occurs at pH 6.6, and that there is a structural shift in sphingosine aggregates caused by a transition in the predominant hydrogen-bonding network from intramolecular to intermolecular that occurs between pH 6.7 and 9.9. Sphingosine and sphingosine 1-phosphate (S1P) are sphingolipid metabolites that act as signaling messengers to activate or inhibit multiple downstream targets to regulate cell growth, differentiation, and apoptosis. The amphiphilic nature of these compounds leads to aggregation above their critical micelle concentrations (CMCs), which may be important for understanding lysosomal glycosphingolipid storage disorders. We investigated the aggregation of sphingosine and S1P over a comprehensive, physiologically relevant range of pH values, ionic strengths, and lipid concentrations by means of dynamic light scattering, titration, and NMR spectroscopy. The results resolve discrepancies in literature reports of CMC and pK a values. At physiological pH, the nominal CMCs of sphingosine and S1P are 0.99 ± 0.12 μ M (pH 7.4) and 14.35 ± 0.08 μ M (pH 7.2), respectively. We find that pH strongly affects the aggregation behavior of sphingosine by changing the ionic and hydrogen-bonding states; the nominal critical aggregation concentrations of protonated and deprotonated sphingosine are 1.71 ± 0.24 μ M and 0.70 ± 0.02 μ M, respectively. NMR measurements revealed that the NH 3 + –NH 2 transition of sphingosine occurs at pH 6.6, and that there is a structural shift in sphingosine aggregates caused by a transition in the predominant hydrogen-bonding network from intramolecular to intermolecular that occurs between pH 6.7 and 9.9. |
| Author | Cocco, Melanie J. White, Stephen H. Sasaki, Hirotaka Arai, Hiromi |
| AuthorAffiliation | Department of Physiology and Biophysics, Center for Biomembrane Systems, University of California, Irvine, California Department of Molecular Biology and Biochemistry, University of California, Irvine, California |
| AuthorAffiliation_xml | – name: Department of Molecular Biology and Biochemistry, University of California, Irvine, California – name: Department of Physiology and Biophysics, Center for Biomembrane Systems, University of California, Irvine, California |
| Author_xml | – sequence: 1 givenname: Hirotaka surname: Sasaki fullname: Sasaki, Hirotaka organization: Department of Physiology and Biophysics, Center for Biomembrane Systems, University of California, Irvine, California – sequence: 2 givenname: Hiromi surname: Arai fullname: Arai, Hiromi organization: Department of Physiology and Biophysics, Center for Biomembrane Systems, University of California, Irvine, California – sequence: 3 givenname: Melanie J. surname: Cocco fullname: Cocco, Melanie J. organization: Department of Molecular Biology and Biochemistry, University of California, Irvine, California – sequence: 4 givenname: Stephen H. surname: White fullname: White, Stephen H. email: stephen.white@uci.edu organization: Department of Physiology and Biophysics, Center for Biomembrane Systems, University of California, Irvine, California |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/19348755$$D View this record in MEDLINE/PubMed |
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| SubjectTerms | Apoptosis Cell growth Hydrogen Bonding Hydrogen-Ion Concentration Light Lysophospholipids - metabolism Magnetic Resonance Spectroscopy Membrane Micelles NMR Nuclear magnetic resonance Scattering Scattering, Radiation Signal transduction Spectrum analysis Sphingosine - analogs & derivatives Sphingosine - chemistry Sphingosine - metabolism Titrimetry |
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| Title | pH Dependence of Sphingosine Aggregation |
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