Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties

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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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Autor principal: Vignoni, M.
Otros Autores: Walalawela, N., Bonesi, S.M, Greer, A., Thomas, A.H
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: American Chemical Society 2018
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024 7 |2 scopus  |a 2-s2.0-85043253365 
024 7 |2 cas  |a pterin, 2236-60-4; pterin derivative, 948-60-7 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a MPOHB 
100 1 |a Vignoni, M. 
245 1 0 |a Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties 
260 |b American Chemical Society  |c 2018 
270 1 0 |m Greer, A.; Department of Chemistry, Brooklyn College, City University of New YorkUnited States; email: agreer@brooklyn.cuny.edu 
506 |2 openaire  |e Política editorial 
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520 3 |a 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.  |l eng 
536 |a Detalles de la financiación: Universidad Nacional de La Plata, UNLP 
536 |a Detalles de la financiación: Universidad Nacional de La Plata, UNLP 
536 |a Detalles de la financiación: City University of New York 
536 |a Detalles de la financiación: National Science Foundation, CHE-1464975 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: PIP 112-200901-00425 
536 |a Detalles de la financiación: Universidad Nacional de La Plata, UNLP, UNLP-Grant X712 
536 |a Detalles de la financiación: PICT-2012−0508 
536 |a Detalles de la financiación: †Instituto de Investigaciones Fisicoquímicas Teoricaś 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, 1900 La Plata, Argentina ‡Department of Chemistry, Brooklyn College, City University of New York, Brooklyn, New York 11210, United States §Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, 365 Fifth Avenue, New York, New York 10016, United States ∥CIHIDECAR-CONICET, Departamento de Química Orgańica, FCEyN, Universidad de Buenos Aires, Pabelloń 2, 3er Piso, Ciudad Universitaria, Buenos Aires, Argentina 
536 |a Detalles de la financiación: The authors thank the Consejo Nacional de Investigaciones Cientifí cas y Tećnicas (CONICET) and the National Science Foundation (NSF) for supporting their collaboration through a Bilateral Cooperation ProgrammeLevel I (PCB-I, Res. 2172). N.W. and A.G. acknowledge support from the NSF (CHE-1464975). A.G. acknowledges support from the Tow Professorship at Brooklyn College. M.V. and A.H.T. acknowledge support from CONICET (Grant PIP 112-200901-00425), Agencia de Promocioń Cientifí ca y Tecnologicá (ANPCyT-Grant PICT-2012−0508), and Universidad Nacional de La Plata (UNLP-Grant X712). The authors gratefully acknowledge Dr. Mariá Noel Urrutia for her contribution. M.V., S.M.B., and A.H.T. are research members of CONICET. 
593 |a 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 
593 |a Department of Chemistry, Brooklyn College, City University of New York, Brooklyn, NY 11210, United States 
593 |a Ph.D. Program in Chemistry, Graduate Center of the City University of New York, 365 Fifth Avenue, New York, NY 10016, United States 
593 |a CIHIDECAR-CONICET, Departamento de Química Orgánica, FCEyN, Universidad de Buenos Aires, Pabellón 2, 3er Piso, Ciudad Universitaria, Buenos Aires, Argentina 
690 1 0 |a FLUORESCENCE 
690 1 0 |a LIPOPHILIC PTERINS 
690 1 0 |a LUVS 
690 1 0 |a SINGLET OXYGEN 
690 1 0 |a SYNTHESIS 
690 1 0 |a 2 AMINO 3 DECYLPTERIDIN 4(3H) ONE 
690 1 0 |a 4 (DECYLOXY)PTERIDIN 2 AMINE 
690 1 0 |a ALKYL GROUP 
690 1 0 |a N' (3 DECYL 4 OXO 3,4 DIHYDROPTERIDIN 2 YL) N,N DIMETHYLFORMIMIDAMIDE 
690 1 0 |a N' [4 (DECYLOXY)PTERIDIN 2 YL] N,N DIMETHYLFORMIMIDAMIDE 
690 1 0 |a PHOTOSENSITIZING AGENT 
690 1 0 |a PTERIN 
690 1 0 |a PTERIN DERIVATIVE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ALKYLATION 
690 1 0 |a ARTICLE 
690 1 0 |a COMPARATIVE STUDY 
690 1 0 |a CONJUGATE 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a DRUG SOLUBILITY 
690 1 0 |a DRUG STRUCTURE 
690 1 0 |a DRUG SYNTHESIS 
690 1 0 |a FLUORESCENCE 
690 1 0 |a LIPOPHILICITY 
690 1 0 |a NUCLEOPHILICITY 
690 1 0 |a PHOSPHOLIPID MEMBRANE 
690 1 0 |a PHOTODEGRADATION 
690 1 0 |a PHOTOSENSITIZATION 
690 1 0 |a PHOTOTHERMAL THERAPY 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a QUANTUM YIELD 
690 1 0 |a REGIOSELECTIVITY 
690 1 0 |a SUBSTITUTION REACTION 
700 1 |a Walalawela, N. 
700 1 |a Bonesi, S.M. 
700 1 |a Greer, A. 
700 1 |a Thomas, A.H. 
773 0 |d American Chemical Society, 2018  |g v. 15  |h pp. 798-807  |k n. 3  |p Mol. Pharm.  |x 15438384  |t Molecular Pharmaceutics 
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856 4 0 |u https://doi.org/10.1021/acs.molpharmaceut.7b00136  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_15438384_v15_n3_p798_Vignoni  |y Handle 
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999 |c 78027 

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