Abstract
The triarylmethane dye Victoria blue BO (VBBO) is a known photosensitizer which has been shown to induce a cytotoxic response in vitro. Several novel Victoria blue derivatives, with varying physicochemical properties, have been compared to VBBO, with respect both to dark toxicity and phototoxicity, on a mouse mammary tumour cell line, EMT6. Photosensitizer uptake was observed using confocal fluorescence microscopy. The chemical differences, particularly in the naphthyl substitution of the derivatives were shown to alter the light:dark toxicity differential and the uptake of the photosensitizers.
Keywords: confocal microscopy, mammary tumour, photosensitizers, Victoria bleu
Full Text
The Full Text of this article is available as a PDF (131.0 KB).
References
- Barker CC, Bride MH, Hallas G and Stamp A (1961) Steric effects of di-and triarylmethanes. Part III. Electronic absorption spectra of derivatives of Malachite green containing substituents in the phenyl ring. J Chem Soc 1285-1290.
- Boyle RW, Leznof CC, van Lier JE. Biological activities of phthalocyanines-XVI. Tetrahydroxy-and tetraalkylhydroxy zinc phthalocyanines. Effect of alkyl chain length on in vitro and in vivo photodynamic activities. Br J Cancer. 1993;67:1177–1181. doi: 10.1038/bjc.1993.222. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Brown SB, Truscott G. New light on cancer therapy. Chem Brit. 1993;29:955–958. [Google Scholar]
- Browning CH. In: Experimental Chemotherapy. Schnitzer, Hawking, editors. New York: Academic Press; 1964. p. 27. [Google Scholar]
- Carmichael J, DeGraff WG, Gazdar AF, Minna JD, Mitchell JB. Evaluation of a tetrazolium-based semiautomated colourimetric assay: assessment of chemosensitivity testing. Cancer Res. 1987;47:936–942. [PubMed] [Google Scholar]
- Cincotta L, Foley JW. Novel phenothiazinium photosensitizers for photodynamic therapy. SPIE. 1988;997:145–153. [Google Scholar]
- Cincotta L, Foley JW, Maceachern T, Lampros E, Cincotta AH. Novel photodynamic effects of a benzophenoxazine on two different murine sarcomas. Cancer Res. 1994;54:1249–1258. [PubMed] [Google Scholar]
- Cox C (1993) In vitro studies on the cellular mechanisms of resistance to cytotoxic compounds with special reference to multidrug resistance and cancer chemotherapy. PhD thesis, University of Central Lancashire.
- Fiedorowicz F, Galindo JR, Julliard M, Mannoni P, Chanon M. Efficient photodynamic action of Victoria Blue BO against the human leukemic cell lines K-562 and TF-1. Photochem Photobiol. 1993;58:356–361. doi: 10.1111/j.1751-1097.1993.tb09574.x. [DOI] [PubMed] [Google Scholar]
- Goldacre RJ and Phillips JN (1949) The ionization of basic triphenylmethane dyes. J Chem Soc 1724-1732.
- Henderson B, Dougherty TJ. How does photodynamic therapy work? Photochem Photobiol. 1992;55:145–157. doi: 10.1111/j.1751-1097.1992.tb04222.x. [DOI] [PubMed] [Google Scholar]
- Guinot SGR, Hepworth JD, Wainwright M. The effects of cyclic terminal groups in di-and tri-arylmethane dyes. Part 2. Steric and electronic effects in derivatives of Victoria blue. J Chem Soc, Perkin Transactions. 1998;2:297–303. [Google Scholar]
- Iwamoto Y, Itoyama T, Yasuda K, Morita T, Shimizu T, Masuzawa T., Yanagihara Y. Photodynamic DNA strand breaking activities of acridine compounds. Biol Pharmacol Bull. 1993;16:1244–1247. doi: 10.1248/bpb.16.1244. [DOI] [PubMed] [Google Scholar]
- Melloni E, Dasdia T, Fava G, Rocca G, Zunino F, Marchesini R. In vitro photosensitizing properties of Rhodamine 123 on different human tumour cell lines. Photochem Photobiol. 1988;48:311–314. doi: 10.1111/j.1751-1097.1988.tb02826.x. [DOI] [PubMed] [Google Scholar]
- Modica-Napolitano JS, Joyal JL, Ara G, Oseroff AR, Aprille JR. Mitochondrial toxicity of cationic photosensitizers for photochemotherapy. Cancer Res. 1990;50:7876–7881. [PubMed] [Google Scholar]
- Montforts FP, Meier A, Scheurich G, Haake G, Bats J. Chlorins designed for photodynamic tumour therapy and as model systems for photosynthesis. Ang Chem Int Ed. 1992;31:1592–1594. [Google Scholar]
- Morgan J, Whitaker JE, Oseroff AR. GRP78 induction by calcium ionophore potentiates photodynamic therapy using the mitochondrial targeting dye Victoria Blue BO. Photochem Photobiol. 1998;67:155–164. [PubMed] [Google Scholar]
- Oster G. Dye binding to high polymers. J Polymer Sci. 1955;36:235–244. [Google Scholar]
- Patel J, Rideout D, Wadwa KS, Oseroff AR. Design of novel analogs of Victoria blue BO (VBBO) for photodynamic therapy. Abstracts Papers Am Chem Soc. 1992;203:37. [Google Scholar]
- Pooler JP, Valenzo DP. Physicochemical determinants of the sensitizing effectiveness for photooxidation of nerve membranes by fluorescein derivatives. Photochem Photobiol. 1970;30:491–498. doi: 10.1111/j.1751-1097.1979.tb07168.x. [DOI] [PubMed] [Google Scholar]
- Riley JF. Retardation of growth of a transplantable carcinoma in mice fed basic metachromatic dyes. Cancer Res. 1948;8:183–188. [PubMed] [Google Scholar]
- Viola A, Hadjur C, Jeunet A, Julliard M. Electron paramagnetic resonance evidence of the generation of superoxide (O2- and hydroxyl (OH) radicals by irradiation of a new photodynamic therapy photosensitizer, Victoria Blue BO. J Photochem Photobiol B: Biology. 1996;32:49–58. doi: 10.1016/1011-1344(95)07199-7. [DOI] [PubMed] [Google Scholar]
- Wadwa K, Smith S, Oseroff AR. Cationic triarylmethane photosensitisers for selective photochemotherapy: Victoria Blue-BO, Victoria Blue-R and Malachite Green. SPIE. 1988;997:154–160. [Google Scholar]
- Wainwright M. Non-porphyrin photosensitizers in biomedicine. Chem Soc Rev. 1996;25:351–359. [Google Scholar]
- Wainwright M, Phoenix DA, Rice L, Burrow S.M., Waring JJ. Increased cytotoxicity and phototoxicity in the methylene blue series via chromophore methylation. J Photochem Photobiol, B: Biology. 1997;40:233–239. doi: 10.1016/s1011-1344(97)00061-4. [DOI] [PubMed] [Google Scholar]
- Wieman TJ, Fingar VH. Photodynamic Therapy. Lasers Gen Surg. 1992;72:609–622. doi: 10.1016/s0039-6109(16)45736-1. [DOI] [PubMed] [Google Scholar]
