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Abstract:

The UV-absorption, fluorescence excitation and emission spectra of the alkaloids eudistomin N (6-bromo-nor-harmane) and eudistomin O (8-bromo-nor-harmane) were described. In order to perform a comparative analysis, we also studied other bromo-β-carbolines and the corresponding non-substituted-carboline. Thus, 6-bromo-, 8-bromo-, 6,8-dibromo-, 3,6-dibromo- and 3,6,8-tribromo-derivatives of nor-harmane, harmane and harmine were studied. These studies were performed in EtOH and in EtOH + 1% perchloric acid solutions (pa). Furthermore, fluorescence quantum yields (φf) in acetonitrile and acetonitrile + 1% perchloric acid solutions at 298 K were measured. The HOMO and LUMO energy, the positions (γmax) and oscillator strength (f) of the 1S1 ← 1S0 band for all the neutral and protonated β-carbolines studied was calculated and compared with the experimental data. The pKa values in aqueous solution for eudistomin N and O (6-bromo- and 8-bromo-nor-harmane), for 6-bromo-, 8-bromo- and 6,8-dibromo-harmane, and for 6-bromo- and 8-bromo-harmine were spectrophotometrically measured (pKa(H2O). The change of the acid-base character of these compounds on going from the ground state (pKa) to the first electronic excited singlet state (pKa* as ΔpKa = pKa* - pKa = 0.625 Δν̄/T, in ethanol solution at 298 K were calculated (ΔpKa(EtOH)). Proton affinities (PA) for all the compounds studied defined as minus the enthalpy change of the reaction M + H+ → MH+ (gas state) were calculated. Basicity relative to pyridine (ΔHrPy) defined as the enthalpy change of the isodesmic reaction MH+ + Py → M + PyH+ (gas state) was also calculated. The effect of bromine as substituent on the properties of the β-carboline moiety in nor-harmane, harmane and harmine is discussed. © 2005 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Photochemistry of the alkaloids eudistomin N (6-bromo-nor-harmane) and eudistomin O (8-bromo-nor-harmane) and other bromo-β-carbolines
Autor:Tarzi, O.I.; Erra-Balsells, R.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón II 3rd, 1428-Buenos Aires, Argentina
Palabras clave:Bromo-β-carbolines; Bromo-harmane; Bromo-harmine; Bromo-nor-harmane; Eudistomin N; Eudistomin O; acetonitrile; alcohol; alkaloid; antivirus agent; beta carboline; beta carboline derivative; eudistomin derivative; eudistomin N; eudistomin O; harman; harmine; perchloric acid; pyridine; unclassified drug; acid base balance; aqueous solution; article; calculation; chemical reaction; controlled study; drug solution; drug structure; enthalpy; Eudistoma; fluorescence spectroscopy; gas; herbal medicine; medicinal plant; oscillation; photochemistry; priority journal; proton transport; quantum yield; ultraviolet spectroscopy; Carbolines; Molecular Structure; Photochemistry; Spectrometry, Fluorescence; Spectrophotometry; Structure-Activity Relationship; Ultraviolet Rays
Año:2005
Volumen:80
Número:1
Página de inicio:29
Página de fin:45
DOI: http://dx.doi.org/10.1016/j.jphotobiol.2005.02.004
Título revista:Journal of Photochemistry and Photobiology B: Biology
Título revista abreviado:J. Photochem. Photobiol. B Biol.
ISSN:10111344
CODEN:JPPBE
CAS:acetonitrile, 75-05-8; alcohol, 64-17-5; beta carboline, 244-63-3; harman, 486-84-0; harmine, 343-27-1, 442-51-3; perchloric acid, 7601-90-3; pyridine, 110-86-1; Carbolines; eudistomin N, 59444-69-8; eudistomin O, 88704-40-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10111344_v80_n1_p29_Tarzi

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Citas:

---------- APA ----------
Tarzi, O.I. & Erra-Balsells, R. (2005) . Photochemistry of the alkaloids eudistomin N (6-bromo-nor-harmane) and eudistomin O (8-bromo-nor-harmane) and other bromo-β-carbolines. Journal of Photochemistry and Photobiology B: Biology, 80(1), 29-45.
http://dx.doi.org/10.1016/j.jphotobiol.2005.02.004
---------- CHICAGO ----------
Tarzi, O.I., Erra-Balsells, R. "Photochemistry of the alkaloids eudistomin N (6-bromo-nor-harmane) and eudistomin O (8-bromo-nor-harmane) and other bromo-β-carbolines" . Journal of Photochemistry and Photobiology B: Biology 80, no. 1 (2005) : 29-45.
http://dx.doi.org/10.1016/j.jphotobiol.2005.02.004
---------- MLA ----------
Tarzi, O.I., Erra-Balsells, R. "Photochemistry of the alkaloids eudistomin N (6-bromo-nor-harmane) and eudistomin O (8-bromo-nor-harmane) and other bromo-β-carbolines" . Journal of Photochemistry and Photobiology B: Biology, vol. 80, no. 1, 2005, pp. 29-45.
http://dx.doi.org/10.1016/j.jphotobiol.2005.02.004
---------- VANCOUVER ----------
Tarzi, O.I., Erra-Balsells, R. Photochemistry of the alkaloids eudistomin N (6-bromo-nor-harmane) and eudistomin O (8-bromo-nor-harmane) and other bromo-β-carbolines. J. Photochem. Photobiol. B Biol. 2005;80(1):29-45.
http://dx.doi.org/10.1016/j.jphotobiol.2005.02.004