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CIENCIA Fisica.Vp:Corelventura CIENCIA 16(3), 370 - 378, 2008 Maracaibo, Venezuela Correlations between theoretical calculations and experimental photochemical reactivity of hydroxyanthraquinone drugs present in Aloe vera Fernando Ruette1*, Franklin Vargas2 y Lourdes Rivas1 1Laboratorio de Química Computacional, 2 Laboratorio de Fotoquímica, Centro de Química, Instituto Venezolano de Investigaciones Científicas (Ivic), Apartado 21827, Caracas 1020-A, Venezuela. Recibido: 29-10-07 Aceptado: 13-09-08 Abstract The phototoxic drugs (S) (aloe-emodin (1), emodin (2), and rhein (3)) were studied with the parametric method CATIVIC in order to find correlations between calculated theoretical proper- ties and the experimental photodegradation rate. These correlations can be explained through the formation of free radical intermediates, singlet oxygen and stable photoproducts. A corres- pondence between calculated dipolar moment and heat of formation with photolysis rate and f quantum yield ( fl) of anthraquinones (1, 2 and 3) was found. In addition, HOMO energy correla- l - 1 tes with the wavelength of excitation ( exc). Formation of S , SH°, and O2 intermediates were eva- - luated and confirmed as feasible. The O2 anion is found to be the most probable species in the photooxidation of biological substrates. Key words: anthraquinones, Aloe vera, photolability, CATIVIC, theoretical correlations, photochemical reactivity. Correlaciones entre cálculos teóricos y la reactividad fotoquímica experimental de drogas hidroxiantraquinonas presentes en la Aloe vera Resumen Las drogas fototóxicas (S) aloe-emodina (1), emodina (2) y rhein (3) fueron estudiadas con el método paramétrico CATIVIC con la finalidad de encontrar las correlaciones entre las propie- dades calculadas teóricamente y la velocidad de fotodegradación experimental. Estas coorrela- ciones pueden explicarse a través de la formación de intermediarios de radicales libres, oxígeno singlete y fotoproductos estables. Se encontró una correspondencia entre el momento bipolar y l el calor de formación, calculados con la velocidad de fotólisis y el rendimiento cuántico ( exc)de - 1 las atraquinonas (1, 2 y 3). La formación de los intermediarios S , SH°, y O2 fue evaluada y con- firmada como factible. Se encontró que el anión es la especie más probable en la fotoionización de los sustratos biológicos. Palabras claves: antraquinonas, Aloe vera, fotolabilidad, CATIVIC, correlaciones teóricas, reactividad fotoquímica. * Autor.. para la correspondencia. E-mail: [email protected] Scientific Journal of the Experimental Faculty of Sciences, at the Universidad del Zulia Volume 16 Nº 3, July-September 2008 F. Ruette et. al. / Ciencia Vol. 16, Nº 3 (2008) 370 - 378 371 1. Introduction reactive oxygen species or nucleic acids and amino acids oxidation by the excited triplet Anthraquinones (1,8-dihydroxyanthra state specie (12), as also it photoinduces quinones, (DHA)) are present in several cleavage on DNA by aloe-emodin (13). Photo- plants mainly as glycosides. These com- toxicity due to occasional or therapeutical pounds have both therapeutic and cytotoxic contact with chemicals is attracting clinical properties related with diverse types of hu- and research interest because of its increas- man affections. For example, aloe-emodin ing relevance. Progress in this field has (1,8-dihydroxy-3-hydroxy-methylanthra probably been hindered by its intrinsic com- quinone, (1)) is a compound present in Aloe plexity; therefore, the need for an interdisci- vera leaves, which exhibits antifungal (1), plinary approach and the lack of reliable in mutagenic (2), and tumorigenic properties vitro tests for assaying the photosensitizing (3). Although in a recent report aloe-emodin capability of xenobiotics in general. was postulated as a new lead antitumor drug (4); emodin (1,3,8-trihydroxy-6-methylan In connection with these facts, the cor- thraquinone, (2)) possesses anticancer, diu- relation between experimental data of UV-A retic, antibacterial, vasorelaxant (5) and and visible irradiations on aloe-emodin, anti-inflammatory effects (6); and rhein emodin, and rhein molecules and electronic (1,8-dihydroxyanthraquinone-3-carboxilic properties of these drugs and their free radi- acid, (3)) is the active metabolite of diace- cal intermediates formed during its photo- tylrhein that can be used as a drug for the degradation may be of great importance to treatment of patients with osteoarthritis. establish the molecular bases of their photo- stability and their phototoxicity. On the other hand, some synthetic and vegetable-origin anthraquinones have Theoretical calculations with the para- shown to be able to produce free radicals metric method CATIVIC were carried out to and singlet oxygen highly cytotoxic, when understand electronic and structural as- they are irradiated with visible light (7). Spe- pects of 1, 2 and 3 molecules and their re- cifically, phototoxicity indications have been spective radicals; see fig. 1. Correlation be- detected in vitro in Chinese hamster V79 tween electronic structure and reactivity has cells irradiated with light UVA and UVB in been used to understand some details of the presence of emodin (8). These findings these complex systems. A simple method suggest, in general terms, that the irradia- and new theoretical tools were employed to tion of DHAs can lead to the production of try to explain the behavior of the above men- reactive oxygen species able to produce toxic tioned molecules. effects on diverse cellular systems. Also, The present work is organized in the fol- some evidences in vivo confirm the impor- lowing manner. A brief description of the ba- tance of discoveries in vitro. For example, sis of the method employed is presented in two cases of photodermatitis have been re- section 2 with the corresponding tools to ported: the first one (9), caused by an- evaluate properties of interest. Section 3 thraquinone (9,10-anthracenedione) and deals with the discussion of experimental re- the other one by a preparation coming from sults and interpretation of theoretical calcu- Aloe vera (10). lations in order to propose an explanation of Recent photochemical works have experimental facts. Finally conclusions and shown a comparative study of the photosta- comments are presented in Section 4. bility and phototoxicity (photohemolysis on human erythrocytes) (11). Other researches 2. Theoretical method have also shown that emodic acid is poten- The theoretical calculations were car- tially phototoxic through photogeneration of ried out in the program CATIVIC (14) based Scientific Journal of the Experimental Faculty of Sciences, at the Universidad del Zulia Volume 16 Nº 3, July-September 2008 372 Correlations between theoretical calculations and experimental photochemical reactivity $= &= $ # & "= ! = " # % ' ! $ & " = #= ' '= '> $= % "= Carbon Oxygen Hydrogen Figure 1. Structure of anthraquinones aloe-emodin (1), emodin (2) and rhein (3) molecules. on simulation techniques of parametric traction, electron-electron repulsion, reso- methods (15-17). For example, the binding nance, and core-core repulsion, respectively energy functional for a molecular system of (15). It is easy to see that the total energy for N atoms can be defined as, a molecular system (E) is divided in diatomic e e ( XY ) and monoatomic ( X )energy terms 12/ æ 2 ö çå I - I ÷ min DE I Î ç EEexa pa ÷ [1] pa f è ø E =+å eeå [4] ISÎ XXY X XY> I = 1({}{}{}{} Efjpa XXmmnn,,, k U X m nRes XY , The molecular and atomic parameters come from the semi-empirical method {}Rep,,,{}{} V g {}R ) [2] XY XYmmVV XY XY MINDO/SR (18) that is based on MINDO/3 (19). The bond strength was analyzed using where f is a family of functionals of bind- different tools: bond orders, diatomic ener- Y gies (DE) (20) and diatomic bonding energies ing energy. I is associated to the state I that belongs to an orthonormal set of eigenfunc- (DBE) (21). In the case of DBE, the X-Y bond {}Y strength is may be defined as, tions of Hexa that is complete in a sub- I space S of the Hilbert space (H). The E pa and I ()-=ee + () - +-()e DBE X YXY f X X Y X fXYY Y [5] E exa variables are parametric and exact en- ergy functionals for the state I, respectively. I and The term E pa depends on elementary of one-center {}{}{}jkUmmnn,, m n, two- ()-=eeå XX X fXXXYXY Y / [6] ¹ centers YX {}{}{}{}V ,,g Res , Rep para- XYmmnn XY XY m n XY m n 3. Investigations and results metric functionals, and the set of intera- There is sufficient evidence that etha- tomic distances {}R . These one-center XY nolic solutions of 1-3 compounds, shown in functionals correspond to electronic repul- fig. 1 are photolabile under aerobic condi- sion, exchange, and kinetic and attractive tions by irradiation with visible light (340- energy, respectively. On the other hand, 500 nm). The photolysis of the drugs 1-3 was two-center functionals are electron-core at- reported by Vargas et ál. (11) under these Scientific Journal of the Experimental Faculty of Sciences, at the Universidad del Zulia Volume 16 Nº 3, July-September 2008 F. Ruette et. al. / Ciencia Vol. 16, Nº 3 (2008) 370 - 378 373 conditions and was followed by monitoring ings can be explained in terms of the micro- the changes of their absorption and emis- environment effects on the spectroscopic sion bands. These authors concluded that properties of the molecules. Absorption the photolability of ethanolic solutions of spectra change dramatically with solvent aloe-emodin and emodin are higher than properties, such as polarity, polarizability, rhein under visible
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