BIOMAT Database Logo BIOMAT Database Logo

Singlet oxygen generation of porphyrins, chlorins, and phthalocyanines. 1989

S Kimel, and B J Tromberg, and W G Roberts, and M W Berns

The production of singlet oxygen was measured indirectly for three classes of photosensitizers: porphyrins (Photofrin II, TPPS4), chlorins (MACE, DACE), and a phthalocyanine (CASPc). Buffered solutions of sensitizers and singlet oxygen acceptors were irradiated with a CW dye laser and the oxygen depletion was monitored electrochemically with a Clark-type microelectrode. A comparison of oxygen-depletion rate constants and quantum efficiencies yields the order of efficiency of the sensitizers: TPPS4 greater than MACE greater than PII greater than DACE greater than CASPc. For singlet oxygen acceptors the order was: furfuryl alcohol greater than imidazole greater than tryptophan. CHO cell suspensions were also used as acceptors. Here the order of efficiency (per absorbed photon) was PII greater than MACE approximately CASPc. Expressed in terms of oxygen depletion per cell the order was CASPc approximately PII greater than MACE. When performing cell clonogenicity studies the order of efficiencies, expressed as percentage cell kill per unit weight of sensitizer, was CASPc greater than PII greater than MACE approximately DACE. The discrepancy between the efficiencies of sensitizers to generate singlet oxygen and their cytotoxicity was explained in terms of photodegradation (for the chlorins), intracellular localization (for PII), and contributions from a Type I mechanism (for CASPc).

UI MeSH Term Description Entries
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D010053 Ovary The reproductive organ (GONADS) in female animals. In vertebrates, the ovary contains two functional parts: the OVARIAN FOLLICLE for the production of female germ cells (OOGENESIS); and the endocrine cells (GRANULOSA CELLS; THECA CELLS; and LUTEAL CELLS) for the production of ESTROGENS and PROGESTERONE. Ovaries
D010100 Oxygen An element with atomic symbol O, atomic number 8, and atomic weight [15.99903; 15.99977]. It is the most abundant element on earth and essential for respiration. Dioxygen,Oxygen-16,Oxygen 16
D010860 Pigments, Biological Any normal or abnormal coloring matter in PLANTS; ANIMALS or micro-organisms. Biological Pigments
D011166 Porphyrins A group of compounds containing the porphin structure, four pyrrole rings connected by methine bridges in a cyclic configuration to which a variety of side chains are attached. The nature of the side chain is indicated by a prefix, as uroporphyrin, hematoporphyrin, etc. The porphyrins, in combination with iron, form the heme component in biologically significant compounds such as hemoglobin and myoglobin. Porphyrin
D002460 Cell Line Established cell cultures that have the potential to propagate indefinitely. Cell Lines,Line, Cell,Lines, Cell
D002470 Cell Survival The span of viability of a cell characterized by the capacity to perform certain functions such as metabolism, growth, reproduction, some form of responsiveness, and adaptability. Cell Viability,Cell Viabilities,Survival, Cell,Viabilities, Cell,Viability, Cell
D003412 Cricetulus A genus of the family Muridae consisting of eleven species. C. migratorius, the grey or Armenian hamster, and C. griseus, the Chinese hamster, are the two species used in biomedical research. Hamsters, Armenian,Hamsters, Chinese,Hamsters, Grey,Armenian Hamster,Armenian Hamsters,Chinese Hamster,Chinese Hamsters,Grey Hamster,Grey Hamsters,Hamster, Armenian,Hamster, Chinese,Hamster, Grey
D004563 Electrochemistry The study of chemical changes resulting from electrical action and electrical activity resulting from chemical changes. Electrochemistries
D005260 Female Females

Related Publications

S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
Modified porphyrins, chlorins, phthalocyanines, and purpurins: second-generation photosensitizers for photodynamic therapy.
April 1989, Seminars in hematology,
S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
Quenching of singlet molecular oxygen by phthalocyanines and naphthalocyanines.
May 1992, Photochemistry and photobiology,
S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
Singlet oxygen generation by porphyrins and the kinetics of 9,10-dimethylanthracene photosensitization in liposomes.
May 1993, Photochemistry and photobiology,
S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
[Quenching of singlet oxygen with chlorophylls and porphyrins].
January 1982, Biofizika,
S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
Comparing Singlet Oxygen Generation of Schiff Base Substituted Novel Silicon Phthalocyanines by Sonophotochemical and Photochemical Applications.
January 2023, Photochemistry and photobiology,
S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
Dendrimer porphyrins and phthalocyanines.
November 2009, Chemical reviews,
S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
[Suppression of singlet oxygen luminescence by porphyrins and metalloporphyrins].
January 1978, Biofizika,
S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
β-Pyrrole Functionalized Push or Pull Porphyrins: Excited Charge Transfer Promoted Singlet Oxygen Generation.
September 2023, The journal of physical chemistry. A,
S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
On the singlet states of porphyrins, chlorins and bacteriochlorins and their ability to harvest red/infrared light.
July 2012, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology,
S Kimel, and B J Tromberg, and W G Roberts, and M W Berns
Mechanochemical generation of singlet oxygen.
March 2020, RSC advances,
Copied contents to your clipboard!