Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties
A new series of decyl chain [-(CH2)9CH3] pterin conjugates have been investigated by photochemical and photophysical methods, and with theoretical solubility calculations. To synthesize the pterins, a nucleophilic substitution (SN2) reaction was used for the regioselective coupling of the alkyl chai...
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2018
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15438384_v15_n3_p798_Vignoni http://hdl.handle.net/20.500.12110/paper_15438384_v15_n3_p798_Vignoni |
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paper:paper_15438384_v15_n3_p798_Vignoni2023-06-08T16:21:09Z Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties fluorescence lipophilic pterins LUVs singlet oxygen synthesis 2 amino 3 decylpteridin 4(3h) one 4 (decyloxy)pteridin 2 amine alkyl group n' (3 decyl 4 oxo 3,4 dihydropteridin 2 yl) n,n dimethylformimidamide n' [4 (decyloxy)pteridin 2 yl] n,n dimethylformimidamide photosensitizing agent pterin pterin derivative unclassified drug alkylation Article comparative study conjugate controlled study drug solubility drug structure drug synthesis fluorescence lipophilicity nucleophilicity phospholipid membrane photodegradation photosensitization photothermal therapy priority journal quantum yield regioselectivity substitution reaction A new series of decyl chain [-(CH2)9CH3] pterin conjugates have been investigated by photochemical and photophysical methods, and with theoretical solubility calculations. To synthesize the pterins, a nucleophilic substitution (SN2) reaction was used for the regioselective coupling of the alkyl chain to the O site over the N3 site. However, the O-alkylated pterin converts to N3-alkylated pterin under basic conditions, pointing to a kinetic product in the former and a thermodynamic product in the latter. Two additional adducts were also obtained from an N-amine condensation of DMF solvent molecule as byproducts. In comparison to the natural product pterin, the alkyl chain pterins possess reduced fluorescence quantum yields (F) and increased singlet oxygen quantum yields (-). It is shown that the DMF-condensed pterins were more photostable compared to the N3- and O-alkylated pterins bearing a free amine group. The alkyl chain pterins efficiently intercalate in large unilamellar vesicles, which is a good indicator of their potential use as photosensitizers in biomembranes. Our study serves as a starting point where the synthesis can be expanded to produce a wider series of lipophilic, photooxidatively active pterins. © Copyright 2017 American Chemical Society. 2018 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15438384_v15_n3_p798_Vignoni http://hdl.handle.net/20.500.12110/paper_15438384_v15_n3_p798_Vignoni |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
fluorescence lipophilic pterins LUVs singlet oxygen synthesis 2 amino 3 decylpteridin 4(3h) one 4 (decyloxy)pteridin 2 amine alkyl group n' (3 decyl 4 oxo 3,4 dihydropteridin 2 yl) n,n dimethylformimidamide n' [4 (decyloxy)pteridin 2 yl] n,n dimethylformimidamide photosensitizing agent pterin pterin derivative unclassified drug alkylation Article comparative study conjugate controlled study drug solubility drug structure drug synthesis fluorescence lipophilicity nucleophilicity phospholipid membrane photodegradation photosensitization photothermal therapy priority journal quantum yield regioselectivity substitution reaction |
| spellingShingle |
fluorescence lipophilic pterins LUVs singlet oxygen synthesis 2 amino 3 decylpteridin 4(3h) one 4 (decyloxy)pteridin 2 amine alkyl group n' (3 decyl 4 oxo 3,4 dihydropteridin 2 yl) n,n dimethylformimidamide n' [4 (decyloxy)pteridin 2 yl] n,n dimethylformimidamide photosensitizing agent pterin pterin derivative unclassified drug alkylation Article comparative study conjugate controlled study drug solubility drug structure drug synthesis fluorescence lipophilicity nucleophilicity phospholipid membrane photodegradation photosensitization photothermal therapy priority journal quantum yield regioselectivity substitution reaction Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties |
| topic_facet |
fluorescence lipophilic pterins LUVs singlet oxygen synthesis 2 amino 3 decylpteridin 4(3h) one 4 (decyloxy)pteridin 2 amine alkyl group n' (3 decyl 4 oxo 3,4 dihydropteridin 2 yl) n,n dimethylformimidamide n' [4 (decyloxy)pteridin 2 yl] n,n dimethylformimidamide photosensitizing agent pterin pterin derivative unclassified drug alkylation Article comparative study conjugate controlled study drug solubility drug structure drug synthesis fluorescence lipophilicity nucleophilicity phospholipid membrane photodegradation photosensitization photothermal therapy priority journal quantum yield regioselectivity substitution reaction |
| description |
A new series of decyl chain [-(CH2)9CH3] pterin conjugates have been investigated by photochemical and photophysical methods, and with theoretical solubility calculations. To synthesize the pterins, a nucleophilic substitution (SN2) reaction was used for the regioselective coupling of the alkyl chain to the O site over the N3 site. However, the O-alkylated pterin converts to N3-alkylated pterin under basic conditions, pointing to a kinetic product in the former and a thermodynamic product in the latter. Two additional adducts were also obtained from an N-amine condensation of DMF solvent molecule as byproducts. In comparison to the natural product pterin, the alkyl chain pterins possess reduced fluorescence quantum yields (F) and increased singlet oxygen quantum yields (-). It is shown that the DMF-condensed pterins were more photostable compared to the N3- and O-alkylated pterins bearing a free amine group. The alkyl chain pterins efficiently intercalate in large unilamellar vesicles, which is a good indicator of their potential use as photosensitizers in biomembranes. Our study serves as a starting point where the synthesis can be expanded to produce a wider series of lipophilic, photooxidatively active pterins. © Copyright 2017 American Chemical Society. |
| title |
Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties |
| title_short |
Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties |
| title_full |
Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties |
| title_fullStr |
Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties |
| title_full_unstemmed |
Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties |
| title_sort |
lipophilic decyl chain-pterin conjugates with sensitizer properties |
| publishDate |
2018 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15438384_v15_n3_p798_Vignoni http://hdl.handle.net/20.500.12110/paper_15438384_v15_n3_p798_Vignoni |
| _version_ |
1768544150779592704 |