Artículo

Vignoni, M.; Walalawela, N.; Bonesi, S.M.; Greer, A.; Thomas, A.H. "Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties" (2018) Molecular Pharmaceutics. 15(3):798-807
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Abstract:

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.

Registro:

Documento: Artículo
Título:Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties
Autor:Vignoni, M.; Walalawela, N.; Bonesi, S.M.; Greer, A.; Thomas, A.H.
Filiación:Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas (INIFTA), Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de la Plata (UNLP), CCT la Plata-CONICET, Casilla de Correo 16, Sucursal 4, La Plata, 1900, Argentina
Department of Chemistry, Brooklyn College, City University of New York, Brooklyn, NY 11210, United States
Ph.D. Program in Chemistry, Graduate Center of the City University of New York, 365 Fifth Avenue, New York, NY 10016, United States
CIHIDECAR-CONICET, Departamento de Química Orgánica, FCEyN, Universidad de Buenos Aires, Pabellón 2, 3er Piso, Ciudad Universitaria, Buenos Aires, Argentina
Palabras clave: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
Año:2018
Volumen:15
Número:3
Página de inicio:798
Página de fin:807
DOI: http://dx.doi.org/10.1021/acs.molpharmaceut.7b00136
Título revista:Molecular Pharmaceutics
Título revista abreviado:Mol. Pharm.
ISSN:15438384
CODEN:MPOHB
CAS:pterin, 2236-60-4; pterin derivative, 948-60-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15438384_v15_n3_p798_Vignoni

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Citas:

---------- APA ----------
Vignoni, M., Walalawela, N., Bonesi, S.M., Greer, A. & Thomas, A.H. (2018) . Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties. Molecular Pharmaceutics, 15(3), 798-807.
http://dx.doi.org/10.1021/acs.molpharmaceut.7b00136
---------- CHICAGO ----------
Vignoni, M., Walalawela, N., Bonesi, S.M., Greer, A., Thomas, A.H. "Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties" . Molecular Pharmaceutics 15, no. 3 (2018) : 798-807.
http://dx.doi.org/10.1021/acs.molpharmaceut.7b00136
---------- MLA ----------
Vignoni, M., Walalawela, N., Bonesi, S.M., Greer, A., Thomas, A.H. "Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties" . Molecular Pharmaceutics, vol. 15, no. 3, 2018, pp. 798-807.
http://dx.doi.org/10.1021/acs.molpharmaceut.7b00136
---------- VANCOUVER ----------
Vignoni, M., Walalawela, N., Bonesi, S.M., Greer, A., Thomas, A.H. Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties. Mol. Pharm. 2018;15(3):798-807.
http://dx.doi.org/10.1021/acs.molpharmaceut.7b00136