A selenopyrylium photosensitizer for photodynamic therapy related in structure to the antitumor agent AA1 with potent in vivo activity and no long-term skin photosensitization

Journal of Medicinal Chemistry

Volumn 43, Issue 23, 2000, Pages 4488-4498

  Leonard, K A ^a   Hall, J P ^a   Nelen, M I ^a   Davies, S R ^c   Gollnick, S O ^c   Camacho, S ^c   Oseroff, A R ^c   Gibson, S L ^b   Hilf, R ^b   Detty, M R ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b UNIVERSITY OF ROCHESTER MEDICAL CENTER   (United States)

^c ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 AMINOPHENYLACETYLENE; ANTINEOPLASTIC AGENT; CHALCOGEN; CYTOCHROME C OXIDASE; DYE; METHANOL; OXYGEN; PHOTOSENSITIZING AGENT; SELENOPYRYLIUM DERIVATIVE; SUPEROXIDE DISMUTASE; TUNGSTEN; UNCLASSIFIED DRUG;

ABSORPTION; ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG POTENCY; MITOCHONDRION; NONHUMAN; PHOTODYNAMICS; PHOTOSENSITIZATION; PHOTOTOXICITY; QUANTUM MECHANICS; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TARGET CELL;

ACUTE TOXICITY TESTS; ADENOCARCINOMA; ANILINE COMPOUNDS; ANIMALS; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; ELECTRON TRANSPORT COMPLEX IV; ENZYME INHIBITORS; FEMALE; MAMMARY NEOPLASMS, ANIMAL; MICE; MICE, INBRED BALB C; OCTANOLS; ORGANOMETALLIC COMPOUNDS; ORGANOSELENIUM COMPOUNDS; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; RATS; RATS, INBRED F344; SELENIUM; SKIN; SOLUBILITY; SPECTROPHOTOMETRY; THIOPHENES; TUMOR CELLS, CULTURED; WATER; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 0034676329     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000154p     Document Type: Article

References (41)

1. Photodynamic Therapy
2. Uptake, localization, and photodynamic effect of meso-tetra(hydroxyphenyl)porphine and its corresponding chlorin in normal tumor tissues of mice bearing mammary carcinoma
3. How Does Photodynamic Therapy Work?
4. Photodynamic Therapeutics: Basic principles and clinical applications
5. Mitochondrial toxicity of cationic photosensitizers for photochemotherapy
6. GRP78 Induction by calcium ionophore potentiates photodynamic therapy using the mitochondrial targeting dye victoria blue BO
7. Apoptosis induction by different pathways with methylene blue derivative and light from mitochondrial sites in V79 cells
8. Phototoxicity, redox behavior, and pharmacokinetics of benzophenoxazine analogues in EMT-6 murine sarcoma cells
9. Photodynamic destruction of lysosomes mediated by nile blue photosensitizers
10. Lysosomal localization and mechanism of uptake of nile blue photosensitizers in tumor cells
11. Novel Photodynamic effects of a benzophenothiazine on two different murine sarcomas
12. Intramitechondrial dyes allow selective in vitro photolysis of carcinoma
13. Mechanisms of mitachondrial photosensitization by the cationic dye N,N′-bis(2-ethyl-1,3-dioxylene)kryptocyanine (EDKC): Preferential inactivation of complex I in the Electron transport chain
14. Photosensitization by 3,3′-dicyclohexyloxacarbocyanine iodide: Specific disruption of microtubules inactivation of organelle motility
15. Photoactivation enhances the mitochondrial toxicity of the cationic rhodacyanine MKT-077
16. Selective damage to carcinoma mitochondria by the rhodacyanine MKT-077
17. Chalcogenapyrylium dyes as photochemotherapeutic agents. 2. Tumor uptake, mitochondrial targeting singlet-oxygen-induced inhibition of cytochrome c oxidase
18. Intracellular localization of a chalcogenapyrylium dye probed by spectroscopy and sites of photodamage
19. Photosensitization of human glioma cells by chalcogenapyrylium dye
20. 2,4,6-Triarylchalcogenopyrylium dyes related in structure to the antitumor agent AA1 as in vitro sensitizers for the photodynamic therapy of cancer
21. Synthesis and evaluation of chaleogenopyrylium dyes as potential sensitizers for the photodynamic therapy of cancer
22. Mitochondrial and plasma membrane potentials cause unusual accumulation and retention of rhodamine 123 by breast adenocarcinoma-derived MCF-7 cells
23. Selective toxicity of rhodamine-123 in carcinoma cells in vitro
24. Anticarcinoma activity in vivo of rhodamine 123, a mitochondrial-specific dye
25. Basis for the selective cytotoxicity of Rh123
26. Increased rhodamine 123 uptake by carcinoma cells
27. Recent advances in the study of mitochondria in living cells
28. AA1, a newly synthesized monovalent lipophilic cation, expresses potent in vivo antitumor activity
29. A simple economical synthetic route to p-ethynylaniline and ethynyl-terminated substrates
30. Silicon in synthesis: Stabase adducts - A new primary amine protecting group: Alkylation of ethyl glycinate
31. Telluropyrylium dyes. 1. 2,6-diphenyltelluropyrylium dyes
32. Chalcogenopyranones from disodium chalcogenide additions to 1,4-pentadiyn-3-ones. The role of enol ethers as intermediates
33. Can cellular photetoxicity be accurately predicted on the basis of sensitizer photophysics?
34. Photodynamic therapy with chalcogenopyrylium dyes
35. Photobleaching of photofrin II as a means of eliminating skin photosensitivity
36. Photosensitization of mitochondrial cytochrome c oxidase by hemateporphyrin derivative and related porphyrins in vitro and in vivo
37. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxlcity assays
38. Biochemical and morphological properties of a new lactating tumor line in the rat
39. Effects of insulin in vivo and in vitro on amino acid transport into cells from R3230AC mammary adenocarcinoma and their relationship to tumor growth
40. Interdependence of energy density, drug dose, and oxygen on hematoporphyrin induced photosensitization of tumor mitochondria