Fluorescent polyene ceramide analogues as membrane probes
Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl...
Ausführliche Beschreibung
Gespeichert in:
| Autor*in: |
Montes, L Ruth [verfasserIn] |
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| Format: |
Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
2015 |
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| Schlagwörter: |
Fluorescent Dyes - chemical synthesis |
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| Systematik: |
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| Übergeordnetes Werk: |
Enthalten in: Langmuir - Washington, DC : ACS Publ., 1985, 31(2015), 8, Seite 2484 |
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| Übergeordnetes Werk: |
volume:31 ; year:2015 ; number:8 ; pages:2484 |
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| 520 | |a Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid-water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel-fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes. | ||
| 650 | 4 | |a Fluorescent Dyes - chemistry | |
| 650 | 4 | |a Ceramides - chemistry | |
| 650 | 4 | |a Polyenes - chemical synthesis | |
| 650 | 4 | |a Fluorescent Dyes - chemical synthesis | |
| 650 | 4 | |a Ceramides - chemical synthesis | |
| 650 | 4 | |a Polyenes - chemistry | |
| 700 | 1 | |a Nieves, Ingrid |4 oth | |
| 700 | 1 | |a Goñi, Félix M |4 oth | |
| 700 | 1 | |a Alonso, Alicia |4 oth | |
| 700 | 1 | |a Delgado, Antonio |4 oth | |
| 700 | 1 | |a Busto, Jon V |4 oth | |
| 700 | 1 | |a Abad, José Luis |4 oth | |
| 700 | 1 | |a Artetxe, Ibai |4 oth | |
| 700 | 1 | |a Fajarí, Lluís |4 oth | |
| 700 | 1 | |a Sot, Jesús |4 oth | |
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PQ20160211 (DE-627)OLC1969926422 (DE-599)GBVOLC1969926422 (PRQ)p472-51eb9e9050362cc9106106a0e9ca04fa85fb092ff61bdf7dda1927843ab0c3bf0 (KEY)0138429520150000031000802484fluorescentpolyeneceramideanaloguesasmembraneprobe DE-627 ger DE-627 rakwb eng 670 540 DNB VA 5760 AVZ rvk 35.18 bkl Montes, L Ruth verfasserin aut Fluorescent polyene ceramide analogues as membrane probes 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid-water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel-fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes. Fluorescent Dyes - chemistry Ceramides - chemistry Polyenes - chemical synthesis Fluorescent Dyes - chemical synthesis Ceramides - chemical synthesis Polyenes - chemistry Nieves, Ingrid oth Goñi, Félix M oth Alonso, Alicia oth Delgado, Antonio oth Busto, Jon V oth Abad, José Luis oth Artetxe, Ibai oth Fajarí, Lluís oth Sot, Jesús oth Enthalten in Langmuir Washington, DC : ACS Publ., 1985 31(2015), 8, Seite 2484 (DE-627)129170690 (DE-600)50983-8 (DE-576)01445520X 0743-7463 nnns volume:31 year:2015 number:8 pages:2484 http://www.ncbi.nlm.nih.gov/pubmed/25658138 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_23 GBV_ILN_70 GBV_ILN_2006 GBV_ILN_2007 VA 5760 35.18 AVZ AR 31 2015 8 2484 |
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PQ20160211 (DE-627)OLC1969926422 (DE-599)GBVOLC1969926422 (PRQ)p472-51eb9e9050362cc9106106a0e9ca04fa85fb092ff61bdf7dda1927843ab0c3bf0 (KEY)0138429520150000031000802484fluorescentpolyeneceramideanaloguesasmembraneprobe DE-627 ger DE-627 rakwb eng 670 540 DNB VA 5760 AVZ rvk 35.18 bkl Montes, L Ruth verfasserin aut Fluorescent polyene ceramide analogues as membrane probes 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid-water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel-fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes. Fluorescent Dyes - chemistry Ceramides - chemistry Polyenes - chemical synthesis Fluorescent Dyes - chemical synthesis Ceramides - chemical synthesis Polyenes - chemistry Nieves, Ingrid oth Goñi, Félix M oth Alonso, Alicia oth Delgado, Antonio oth Busto, Jon V oth Abad, José Luis oth Artetxe, Ibai oth Fajarí, Lluís oth Sot, Jesús oth Enthalten in Langmuir Washington, DC : ACS Publ., 1985 31(2015), 8, Seite 2484 (DE-627)129170690 (DE-600)50983-8 (DE-576)01445520X 0743-7463 nnns volume:31 year:2015 number:8 pages:2484 http://www.ncbi.nlm.nih.gov/pubmed/25658138 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_23 GBV_ILN_70 GBV_ILN_2006 GBV_ILN_2007 VA 5760 35.18 AVZ AR 31 2015 8 2484 |
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PQ20160211 (DE-627)OLC1969926422 (DE-599)GBVOLC1969926422 (PRQ)p472-51eb9e9050362cc9106106a0e9ca04fa85fb092ff61bdf7dda1927843ab0c3bf0 (KEY)0138429520150000031000802484fluorescentpolyeneceramideanaloguesasmembraneprobe DE-627 ger DE-627 rakwb eng 670 540 DNB VA 5760 AVZ rvk 35.18 bkl Montes, L Ruth verfasserin aut Fluorescent polyene ceramide analogues as membrane probes 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid-water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel-fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes. Fluorescent Dyes - chemistry Ceramides - chemistry Polyenes - chemical synthesis Fluorescent Dyes - chemical synthesis Ceramides - chemical synthesis Polyenes - chemistry Nieves, Ingrid oth Goñi, Félix M oth Alonso, Alicia oth Delgado, Antonio oth Busto, Jon V oth Abad, José Luis oth Artetxe, Ibai oth Fajarí, Lluís oth Sot, Jesús oth Enthalten in Langmuir Washington, DC : ACS Publ., 1985 31(2015), 8, Seite 2484 (DE-627)129170690 (DE-600)50983-8 (DE-576)01445520X 0743-7463 nnns volume:31 year:2015 number:8 pages:2484 http://www.ncbi.nlm.nih.gov/pubmed/25658138 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_23 GBV_ILN_70 GBV_ILN_2006 GBV_ILN_2007 VA 5760 35.18 AVZ AR 31 2015 8 2484 |
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PQ20160211 (DE-627)OLC1969926422 (DE-599)GBVOLC1969926422 (PRQ)p472-51eb9e9050362cc9106106a0e9ca04fa85fb092ff61bdf7dda1927843ab0c3bf0 (KEY)0138429520150000031000802484fluorescentpolyeneceramideanaloguesasmembraneprobe DE-627 ger DE-627 rakwb eng 670 540 DNB VA 5760 AVZ rvk 35.18 bkl Montes, L Ruth verfasserin aut Fluorescent polyene ceramide analogues as membrane probes 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid-water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel-fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes. Fluorescent Dyes - chemistry Ceramides - chemistry Polyenes - chemical synthesis Fluorescent Dyes - chemical synthesis Ceramides - chemical synthesis Polyenes - chemistry Nieves, Ingrid oth Goñi, Félix M oth Alonso, Alicia oth Delgado, Antonio oth Busto, Jon V oth Abad, José Luis oth Artetxe, Ibai oth Fajarí, Lluís oth Sot, Jesús oth Enthalten in Langmuir Washington, DC : ACS Publ., 1985 31(2015), 8, Seite 2484 (DE-627)129170690 (DE-600)50983-8 (DE-576)01445520X 0743-7463 nnns volume:31 year:2015 number:8 pages:2484 http://www.ncbi.nlm.nih.gov/pubmed/25658138 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_23 GBV_ILN_70 GBV_ILN_2006 GBV_ILN_2007 VA 5760 35.18 AVZ AR 31 2015 8 2484 |
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PQ20160211 (DE-627)OLC1969926422 (DE-599)GBVOLC1969926422 (PRQ)p472-51eb9e9050362cc9106106a0e9ca04fa85fb092ff61bdf7dda1927843ab0c3bf0 (KEY)0138429520150000031000802484fluorescentpolyeneceramideanaloguesasmembraneprobe DE-627 ger DE-627 rakwb eng 670 540 DNB VA 5760 AVZ rvk 35.18 bkl Montes, L Ruth verfasserin aut Fluorescent polyene ceramide analogues as membrane probes 2015 Text txt rdacontent ohne Hilfsmittel zu benutzen n rdamedia Band nc rdacarrier Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid-water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel-fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes. Fluorescent Dyes - chemistry Ceramides - chemistry Polyenes - chemical synthesis Fluorescent Dyes - chemical synthesis Ceramides - chemical synthesis Polyenes - chemistry Nieves, Ingrid oth Goñi, Félix M oth Alonso, Alicia oth Delgado, Antonio oth Busto, Jon V oth Abad, José Luis oth Artetxe, Ibai oth Fajarí, Lluís oth Sot, Jesús oth Enthalten in Langmuir Washington, DC : ACS Publ., 1985 31(2015), 8, Seite 2484 (DE-627)129170690 (DE-600)50983-8 (DE-576)01445520X 0743-7463 nnns volume:31 year:2015 number:8 pages:2484 http://www.ncbi.nlm.nih.gov/pubmed/25658138 GBV_USEFLAG_A SYSFLAG_A GBV_OLC SSG-OLC-TEC SSG-OLC-CHE SSG-OLC-PHA SSG-OLC-DE-84 GBV_ILN_23 GBV_ILN_70 GBV_ILN_2006 GBV_ILN_2007 VA 5760 35.18 AVZ AR 31 2015 8 2484 |
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Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid-water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel-fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes. |
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Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid-water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel-fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes. |
| abstract_unstemmed |
Three ceramide analogues have been synthesized, with sphingosine-like chains containing five conjugated double bonds. Pentaene I has an N-palmitoyl acyl chain, while the other two pentaenes contain also a doxyl radical, respectively, at C5 (Penta5dox) and at C16 (Penta16dox) positions of the N-acyl chain. Pentaene I maximum excitation and emission wavelengths in a phospholipid bilayer are 353 and 478 nm, respectively. Pentaene I does not segregate from the other lipids in the way natural ceramide does, but rather mixes with them in a selective way according to the lipid phases involved. Fluorescence confocal microscopy studies show that when lipid domains in different physical states coexist, Pentaene I emission is higher in gel than in fluid domains, and in liquid-ordered than in liquid-disordered areas. Electron paramagnetic resonance of the pentaene doxyl probes confirms that these molecules are sensitive to the physical state of the bilayer. Calorimetric and fluorescence quenching experiments suggest that the lipids under study orient themselves in lipid bilayers with their polar moieties located at the lipid-water interface. The doxyl radical in the N-acyl chain quenches the fluorescence of the pentaene group when in close proximity. Because of this property, Penta16dox can detect gel-fluid transitions in phospholipids. The availability of probes for lipids in the gel phase is important in view of novel evidence for the existence of gel microdomains in cell membranes. |
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