Photophysical Properties of Tin Ethyl Etiopurpurin I (SnET2) and Tin Octaethylbenzochlorin (SnOEBC) in Solution and Bound to Albumin

Abstract— The photophysical characteristics of two second‐generation PDT photosensitizers, tin ethyl etiopurpurin I (SnET2) and tin octaethylbenzochlorin (SnOEBC), have been measured in homogeneous solution and when bound to bovine serum albumin (BSA). The ground state and triplet state absorption spectra have been characterized, as have triplet lifetimes and quantum yields for intersys‐tem crossing, singlet oxygen formation and photobleaching. In total, these parameters provide a complete set of data that can be used to quantitatively compare the photosensitizing efficiencies of these molecules. The photo‐bleaching quantum yield of SnET2 is increased dramatically when it is bound to BSA, thus limiting the production of singlet oxygen at incident fluences above 1 J/cm2. In contrast, the quantum yield of photobleaching of SnOEBC is at least an order of magnitude lower than that of SnET2 under these conditions and does not significantly limit the photosensitization process for typical in vivo or in vitro fluences. This difference is expected to play a significant role in determining the relative photosensitizing ability of these compounds in vivo.

[1]  R. Keck,et al.  PHOTODYNAMIC THERAPY: EFFECT ON THE ENDOTHELIAL CELL OF THE RAT AORTA , 1991, Photochemistry and photobiology.

[2]  Brian W. Pogue,et al.  Dosimetry for pulsed laser photodynamic therapy , 1996, Photonics West.

[3]  B W Henderson,et al.  OXYGEN LIMITATION OF DIRECT TUMOR CELL KILL DURING PHOTODYNAMIC TREATMENT OF A MURINE TUMOR MODEL , 1989, Photochemistry and photobiology.

[4]  M. Cork,et al.  Comparative genetic association of human leukocyte antigen class II and tumor necrosis factor-alpha with dermatitis herpetiformis. , 1995, The Journal of investigative dermatology.

[5]  D. Kessel,et al.  DIRECT DETECTION OF SINGLET OXYGEN SENSITIZED BY HAEMATOPORPHYRIN AND RELATED COMPOUNDS , 1986, Photochemistry and photobiology.

[6]  E. Land,et al.  PHOTOPHYSICAL PROPERTIES OF meso‐TETRAPHENYLPORPHYRIN and SOME meso‐TETRA(HYDROXYPHENYL)PORPHYRINS , 1988, Photochemistry and photobiology.

[7]  T. Dougherty Photodynamic therapy. , 1993, Photochemistry and photobiology.

[8]  D. Kessel,et al.  A photophysical study of some purpurins , 1990 .

[9]  T. Hasan,et al.  PHOTOPHYSICAL AND PHOTOSENSITIZING PROPERTIES OF BENZOPORPHYRIN DERIVATIVE MONOACID RING A (BPD‐MA) * , 1994, Photochemistry and photobiology.

[10]  G. Garbo Purpurins and benzochlorins as sensitizers for photodynamic therapy. , 1996, Journal of photochemistry and photobiology. B, Biology.

[11]  Greta M. Garbo,et al.  Use of liposomes, emulsions, or inclusion complexes may potentiate in-vivo effects of SnET2 , 1990, Photonics West - Lasers and Applications in Science and Engineering.

[12]  P. Sekher,et al.  Spectroscopic studies of tin ethyl etiopurpurin in homogeneous and heterogeneous systems. , 1993, Journal of photochemistry and photobiology. B, Biology.

[13]  R. Redmond,et al.  PHOTOPHYSICAL PROPERTIES OF 3,3′‐DIALKYLTHIACARBOCYANINE DYES IN HOMOGENEOUS SOLUTION , 1993, Photochemistry and photobiology.

[14]  G. Garbo,et al.  TIN ETIOPURPURIN DICHLORIDE‐SENSITIZED LIPID PHOTOOXIDATION OF ERYTHROCYTE MEMBRANES , 1990, Photochemistry and photobiology.

[15]  John Aurie Dean,et al.  Lange's Handbook of Chemistry , 1978 .

[16]  R. Redmond,et al.  Environmental Effects on Cellular Photosensitization: Correlation of Phototoxicity Mechanism with Transient Absorption Spectroscopy Measurements , 1998, Photochemistry and photobiology.

[17]  I. Kochevar,et al.  Influence of dye and protein location on photosensitization of the plasma membrane. , 1994, Biochimica et biophysica acta.

[18]  Determination of rate constants of 1O2 consumption by 1O2 acceptors in weakly deactivating solvents , 1989 .

[19]  D. Kessel,et al.  THE ROLE OF LIPOPROTEINS IN THE DISTRIBUTION OF TIN ETIOPURPURIN (SnET2) IN THE TUMOR‐BEARING RAT , 1993, Photochemistry and photobiology.

[20]  R. Schmidt,et al.  Phenalenone, a universal reference compound for the determination of quantum yields of singlet oxygen O2(1Δg) sensitization , 1994 .

[21]  Daniel R. Doiron,et al.  Uptake of the photosensitizer tin ethyl etiopupurin by the canine prostate and its tissue effects when combined with red light , 1995, Photonics West.

[22]  A Smith,et al.  The interaction of human serum albumin and hemopexin with porphyrins. , 1980, Biochimica et biophysica acta.