The photosensitizing activity of lumazine using 2′-deoxyguanosine 5′-monophosphate and HeLa cells as targets

Lumazines are an important family of heterocyclic compounds present in biological systems as biosynthetic precursors and/or products of metabolic degradation. Upon UV irradiation, the specific compound called lumazine (pteridine-2,4(1,3H)-dione) is able to generate singlet oxygen ( 1O2), which is on...

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Autor principal: Denofrio, M.P
Otros Autores: Hatz, S., Lorente, C., Cabrerizo, F.M, Ogilby, P.R, Thomas, A.H
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2009
Acceso en línea:Registro en Scopus
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024 7 |2 scopus  |a 2-s2.0-71049179464 
024 7 |2 cas  |a deoxyguanosine phosphate, 902-04-5; lumazine, 487-21-8; 2'-deoxyguanosine 5'-phosphate, 902-04-5; Deoxyguanine Nucleotides; Photosensitizing Agents; Pteridines; Singlet Oxygen, 17778-80-2; Solutions; Water, 7732-18-5; lumazine, 487-21-8 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a PPSHC 
100 1 |a Denofrio, M.P. 
245 1 4 |a The photosensitizing activity of lumazine using 2′-deoxyguanosine 5′-monophosphate and HeLa cells as targets 
260 |c 2009 
270 1 0 |m Cabrerizo, F. M.; CIHIDECAR, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón 2 3p, Buenos Aires, Argentina; email: athomas@inifta.unlp.edu.ar 
506 |2 openaire  |e Política editorial 
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504 |a Breitenbach, T., Kuimova, M.K., Gbur, P., Hatz, S., Schack, N.B., Pedersen, B.W., Lambert, J.D.C., Ogilby, P.R., Photosensitized production of singlet oxygen: Spatially-resolved optical studies in single cells (2009) Photochem. Photobiol. Sci., 8, pp. 442-452 
504 |a Marzano, C., Baccichetti, F., Carlassare, F., Chilin, A., Lora, S., Bordin, F., DNA damage induced by 4,6,8,9-tetramethyl-2H-furo[2,3-h]quinolin-2-one, a new furocoumarin analog: Biological consequences (2000) Photochem. Photobiol., 71, pp. 263-272 
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504 |a Knobloch, B., Sigel, H., Okruszek, A., Sigel, R.K.O., Acid-base properties of the nucleic-acid model 2′- deoxyguanylyl(5′→3′)-2′-deoxy-5′-guanylate, d(pGpG)3-, and of related guanine derivatives (2006) Org. Biomol. Chem., 4, pp. 1085-1090 
520 3 |a Lumazines are an important family of heterocyclic compounds present in biological systems as biosynthetic precursors and/or products of metabolic degradation. Upon UV irradiation, the specific compound called lumazine (pteridine-2,4(1,3H)-dione) is able to generate singlet oxygen ( 1O2), which is one of the main chemical species responsible for photodynamic effects. To further assess the photosensitizing capability of lumazine (Lum) experiments were performed using the nucleotide 2′-deoxyguanosine 5′-monophosphate (dGMP) and, independently, cervical cancer cells (HeLa cell line) as targets. In the dGMP experiments, the data revealed that dGMP indeed undergoes oxidation/oxygenation photoinduced by Lum. Moreover, dGMP disappearance proceeds through two competing pathways: (1) electron transfer between dGMP and excited-state Lum (Type I process) and (2) reaction of dGMP with 1O2 produced by Lum (Type II process). The multistep processes involved are convoluted and susceptible to changes in experimental conditions. The independent studies with HeLa cells included fluorescence analysis of cell extracts and phototoxicity experiments performed at the single-cell level. Results showed that, upon Lum uptake and irradiation, photodynamic effects occur. In particular, the mitochondria and cell membrane were perturbed, both of which reflect key stages in cell death. The data reported herein illustrate how the irradiation of an endogenous biological compound can have various effects which, depending on the system, can be manifested in different ways. © The Royal Society of Chemistry and Owner Societies 2009.  |l eng 
593 |a INIFTA, Departamento de Química, Universidad Nacional de la Plata, C.C. 16, Suc. 4 (1900), La Plata, Argentina 
593 |a Center for Oxygen Microscopy and Imaging, Department of Chemistry, Versity of Aarhus, 8000 rhus, Denmark 
593 |a CIHIDECAR, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón 2 3p, Buenos Aires, Argentina 
690 1 0 |a DEOXYGUANOSINE PHOSPHATE 
690 1 0 |a LUMAZINE 
690 1 0 |a ARTICLE 
690 1 0 |a CELL MEMBRANE 
690 1 0 |a ELECTRON TRANSPORT 
690 1 0 |a FLUORESCENCE ANALYSIS 
690 1 0 |a HELA CELL 
690 1 0 |a HUMAN 
690 1 0 |a HUMAN CELL 
690 1 0 |a OXIDATION 
690 1 0 |a OXYGENATION 
690 1 0 |a PHOTODYNAMICS 
690 1 0 |a PHOTOTOXICITY 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a UTERINE CERVIX CANCER 
690 1 0 |a BIOLOGICAL TRANSPORT 
690 1 0 |a DEOXYGUANINE NUCLEOTIDES 
690 1 0 |a ELECTRON TRANSPORT 
690 1 0 |a HELA CELLS 
690 1 0 |a HUMANS 
690 1 0 |a HYDROGEN-ION CONCENTRATION 
690 1 0 |a PHOTOSENSITIZING AGENTS 
690 1 0 |a PTERIDINES 
690 1 0 |a SINGLET OXYGEN 
690 1 0 |a SOLUTIONS 
690 1 0 |a ULTRAVIOLET RAYS 
690 1 0 |a WATER 
700 1 |a Hatz, S. 
700 1 |a Lorente, C. 
700 1 |a Cabrerizo, F.M. 
700 1 |a Ogilby, P.R. 
700 1 |a Thomas, A.H. 
773 0 |d 2009  |g v. 8  |h pp. 1539-1549  |k n. 11  |p Photochem. Photobiol. Sci.  |x 1474905X  |t Photochemical and Photobiological Sciences 
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