Mono- and Bis-Alkylated Lumazine Sensitizers: Synthetic, Molecular Orbital Theory, Nucleophilic Index and Photochemical Studies.
Journal
Photochemistry and photobiology
ISSN: 1751-1097
Titre abrégé: Photochem Photobiol
Pays: United States
ID NLM: 0376425
Informations de publication
Date de publication:
01 2021
01 2021
Historique:
received:
27
04
2020
revised:
08
06
2020
accepted:
29
06
2020
pubmed:
7
7
2020
medline:
7
7
2020
entrez:
7
7
2020
Statut:
ppublish
Résumé
Mono- and bis-decylated lumazines have been synthesized and characterized. Namely, mono-decyl chain [1-decylpteridine-2,4(1,3H)-dione] 6a and bis-decyl chain [1,3-didecylpteridine-2,4(1,3H)-dione] 7a conjugates were synthesized by nucleophilic substitution (S
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
80-90Informations de copyright
© 2020 American Society for Photobiology.
Références
Kappock, T. J. and J. P. Caradonna (1996) Pterin-dependent amino acid hydroxylases. Chem. Rev. 96, 2659-2756.
Rembold, H. and W. L. Gyure (1972) Biochemistry of the Pteridines. Angew. Chem. Int. Ed. Engl. 11, 1061-1072.
Rembold, H., V. Chandrashekar and P. Sudershan (1971) Catabolism of pteridine cofactors: IV. In vivo catabolism of reduced pterins in rats. Biochim. Biophys. Acta 237, 365-368.
Kis, K., K. Kugelbrey and A. Bacher (2001) Biosynthesis of Riboflavin. The reaction catalyzed by 6,7-dimethyl-8-ribityllumazine synthase can proceed without enzymatic catalysis under physiological conditions. J. Org. Chem. 66, 2555-2559.
Brown, D. J. (1988) Introduction to the Pteridines. In The Chemistry of Heterocyclic Compounds, Part 3, Volume 24, Fused Pyrimidines: Pteridines, Vol. 6 (Edited by D. J. Brown), Ch. 6, pp. 1-42. John Wiley and Sons, New York.
Serrano, M. P., M. Vignoni, M. L. Dántola, E. Oliveros, C. Lorente and A. H. Thomas (2011) Emission properties of dihydropterins in aqueous solutions. Phys. Chem. Chem. Phys. 13, 7419-7425.
Lorente, C. and A. H. Thomas (2006) Photophysics and photochemistry of pterins in aqueous solution. Acc. Chem. Res. 39, 395-402.
Dántola, M. L., L. O. Reid, C. Castaño, C. Lorente, E. Oliveros and A. H. Thomas (2017) Photosensitization of peptides and proteins by pterin derivatives. Pteridines 28, 105-114.
Denofrio, M. P., A. H. Thomas and C. Lorente (2010) Oxidation of 2’-deoxyadenosine 5’-monophosphate photoinduced by Lumazine. J. Phys. Chem. A 114, 10944-10950.
Denofrio, M. P., S. Hatz, C. Lorente, F. M. Cabrerizo, P. R. Ogilby and A. H. Thomas (2009) The photosensitizing activity of lumazine using 2’-deoxyguanosine 5’-monophosphate and HeLa cells as targets. Photochem. Photobiol. Sci. 8, 1539-1549.
Denofrio, M. P., C. Lorente, T. Breitenbach, S. Hatz, F. M. Cabrerizo, A. H. Thomas and P. R. Ogilby (2011) Photodynamic effects of pterin on HeLa cells. Photochem. Photobiol. 87, 862-866.
Miñán, A., C. Lorente, A. Ipiña, A. H. Thomas, M. Fernández Lorenzo de Mele and P. L. Schilardi (2015) Photodynamic inactivation induced by carboxypterin: a novel non-toxic bactericidal strategy against planktonic cells and biofilms of Staphylococcus aureus. Biofouling 31, 459-468.
Thomas, A. H., Á. Catalá and M. Vignoni (2016) Soybean phosphatidylcholine liposomes as model membranes to study lipid peroxidation photoinduced by pterin. Biochim. Biophys. Acta Biomembr. 1858, 139-145.
Vignoni, M., N. Walalawela, S. M. Bonesi, A. Greer and A. H. Thomas (2018) Lipophilic decyl chain−pterin conjugates with sensitizer properties. Mol. Pharm. 15, 798-807.
Walalawela, N., M. Vignoni, M. N. Urrutia, S. J. Belh, E. M. Greer, A. H. Thomas and A. Greer (2018) Kinetic control in the regioselective alkylation of pterin sensitizers: A synthetic, photochemical, and theoretical study. Photochem. Photobiol. 94, 834-844.
Walalawela, N., M. N. Urrutia, A. H. Thomas, A. Greer and M. Vignoni (2019) Alkane chain-extended pterin through a pendent carboxylic acid acts as triple functioning fluorophore, 1O2 sensitizer and membrane binder. Photochem. Photobiol. 95, 1160-1168.
Abdulwahaab, B. H., B. P. Burke, J. Domarkas, J. D. Silversides, T. J. Prior and S. J. Archibald (2016) Mono- and bis-alkylation of glyoxal-bridged tetraazamacrocycles using mechanochemistry. J. Org. Chem. 81, 890-898.
Vignoni, M., M. N. Urrutia, H. C. Junqueira, A. Greer, A. Reis, M. S. Baptista, R. Itri and A. H. Thomas (2018) Photooxidation of unilamellar vesicles by a lipophilic pterin: deciphering biomembrane photodamage. Langmuir 34, 15578-15586.
Bacellar, I. O. L., M. C. Oliveira, L. S. Dantas, E. B. Costa, H. C. Junqueira, W. K. Martins, A. M. Durantini, G. Cosa, P. Di Mascio, M. Wainwright, R. Miotto, R. M. Cordeiro, S. Miyamoto and M. S. Baptista (2018) Photosensitized membrane permeabilization requires contact-dependent reactions between photosensitizer and lipids. J. Am. Chem. Soc. 140, 9606-9615.
Tasso, T. T., J. C. Schlothauer, H. C. Junqueira, T. A. Matias, K. Araki, É. Liandra-Salvador, F. C. T. Antonio, P. Homem-de-Mello and M. S. Baptista (2019) Photobleaching efficiency parallels the enhancement of membrane damage for porphyrazine photosensitizers. J. Am. Chem. Soc. 141, 15547-15556.
Gaussian 16, Revision C.01, Frisch, M. J., G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Jr Montgomery, J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman and D. J. Fox Gaussian Inc, Wallingford CT. 2016.
Dennington, R., T. Keith and J. Millam (2009) GaussView 5. Semichem Inc, Shawnee Mission, KS.
Klein, R. and I. Tatischeff (1987) Tautomerims and fluorescence of lumazine. Photochem. Photobiol. 45, 55-65.
Breugst, M., T. Tokuyasu and H. Mayr (2010) Nucleophilic reactivities of imide and amide anions. J. Org. Chem. 75, 5250-5258.
Challis, B. C., Challis, J. (1970). In The Chemistry of Amides (Edited by J. Zabicky), pp. 731-858. Interscience Publisher, London, UK.
Stirling, C. J. M. (1960) 49. Intramolecular reactions of amides. Part II. Cyclisation of amides of ω-bromo-carboxylic, acids. J. Chem. Soc, 255-262.
Dopp, D. and H. Dopp. Houben-Weyl Methods of Organic Chemistry, 1952-, 4th ed.; Thieme: Stuttgart, Germany, 1985; Vol. E5, pp. 934-1135.
Koch, T. H., R. J. Sluski and R. H. Moseley (1973) Photochemical reactivity of keto imino ethers. IV. Type I and type II reactions. J. Am. Chem. Soc. 95, 3957-3963.
Anderson, D. R., J. S. Keute, T. H. Koch and R. H. Moseley (1977) Di-tert-butyl nitroxide quenching of the photoaddition of olefins to the carbon-nitrogen double bond of 3-ethoxyisoindolenone. J. Am. Chem. Soc. 99, 6332-6340.
Kornblum, N., R. A. Smiley, R. K. Blackwood and D. C. Iffland (1955) The mechanism of the reaction of silver nitrite with alkyl halides. The contrasting reactions of silver and alkali metal salts with alkyl halides. The alkylation of ambident anions. J. Am. Chem. Soc. 77, 6269-6280.
Pfleiderer, W. (1957) I. Pteridine, über 2,4-dioxotetrahydropteridine. Chem. Ber. 90, 2582-2587.
Denofrio, M. P., A. H. Thomas, A. M. Braun, E. Oliveros and C. Lorente (2008) Photochemical and photophysical properties of lumazine in aqueous solutions. J. Photochem. Photobiol. A: Chem. 200, 282-286.