Abstract
The photoinactivation of three different human cancer cell lines, HeLa, neuroblastoma and U87 and antimicrobial activities against Gram-positive (Bacillus subtilis) and Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa) by protoporphyrin IX and protoporphyrin–dopamine conjugate were examined. The antimicrobial activities were screened by optical density measurement at 600 nm. Also, the cytotoxicity and proliferation assays were performed with LDH measurements at 490 nm and WST-1 assays at 450 nm, respectively, with and without irradiation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ali H, van Lier JE (1999) Metal complexes as photo and radiosensitizers. Chem Rev 99:2379–2450
Banfi S, Caruso E, Buccafurni L, Battini V, Zazzaron S, Barbieri P, Orlandi V (2006) Antibacterial activity of tetraaryl-porphyrin photosensitizers: an in vitro study on Gram negative and Gram positive bacteria. J Photochem Photobiol B 85:28–38
Ben Amor T, Tronchin M, Bortolotto L, Verdiglione R, Jori G (1998) Porphyrins and related compounds as photoactivatable insecticides. I. Phototoxic activity of hematoporphyrin toward Ceratitis capitata and Bactrocera oleae. Photochem Photobiol 67:206–211
Berger Y, Greppi A, Siri O, Neier R, Juillerat-Jeanneret L (2000) Ethylene glycol and amino acid derivatives of 5-aminolevulinic acid as new photosensitizing precursors of protoporphyrin IX in cells. J Med Chem 43:4738–4746
Bronshtein I, Afri M, Weitman H, Frimer AA, Smith KM, Ehrenberg B (2004) Porphyrin depth in lipid bilayers as determined by iodide and parallax fluorescence quenching methods and its effect on photosensitizing efficiency. Biophys J 87:1155–1164
Demchick P, Koch AL (1996) The permeability of the wall fabric of Escherichia coli and Bacillus subtilis. J Bacteriol 178:768–773
Dragicevic-Curic N, Scheglmann D, Albrecht V, Fahr A (2009) Development of different temoporfin-loaded invasomes-novel nanocarriers of temoporfin: characterization, stability and in vitro skin penetration studies. Colloids Surf B Biointerfaces 70:198–206
Ehrenberg B (1992) Assessment of the partitioning of probes to membranes by spectroscopic titration. J Photochem Photobiol B 14:383–386
Fabris C, Vicente MG, Hao E, Friso E, Borsetto L, Jori G, Miotto G, Colautti P, Moro D, Esposito J, Ferretti A, Rossi CR, Nitti D, Sotti G, Soncin M (2007) Tumour-localizing and -photosensitising properties of meso-tetra(4-nido-carboranylphenyl)porphyrin (H2TCP). J Photochem Photobiol B 89:131–138
Fan X, Lin L, Dalsin JL, Messersmith PB (2005) Biomimetic anchor for surface-initiated polymerization from metal substrates. J Am Chem Soc 127:15843–15847
Ferro S, Ricchelli F, Mancini G, Tognon G, Jori G (2006) Inactivation of methicillin-resistant Staphylococcus aureus (MRSA) by liposome-delivered photosensitising agents. J Photochem Photobiol B 83:98–104
Girard D, Weagle G, Gupta A, Berube G, Chapados C (2008) Preparation and in vitro biological evaluation of tetrapyrrole ethanolamide derivatives as potential anticancer agents. Bioorg Med Chem Lett 18:360–365
Kantonis G, Trikeriotis M, Ghanotakis DF (2007) Biocompatible protoporphyrin IX-containing nanohybrids with potential applications in photodynamic therapy. J Photochem Photobiol A 185:62–66
Kemikli N, Kavas H, Kazan S, Baykal A, Ozturk R (2010) Synthesis of protoporphyrin coated superparamagnetic iron oxide nanoparticles via dopamine anchor. J Alloys Compd 502:439–444
Kim MS, Kim MK, Kim KS, Chung JH, Kim SJ, Kim JH, Kim JR, Lee J, Yu BP, Chung HY (2008) Cytotoxicity of 1,2-diacetylbenzene in human neuroblastoma SHSY5Y cells is mediated by oxidative stress. Toxicology 243:216–223
Kwitniewski M, Juzeniene A, Ma LW, Glosnicka R, Graczyk A, Moan J (2009) Diamino acid derivatives of PpIX as potential photosensitizers for photodynamic therapy of squamous cell carcinoma and prostate cancer: in vitro studies. J Photochem Photobiol B 94:214–222
Malik Z, Hanania J, Nitzan Y (1990a) Bactericidal effects of photoactivated porphyrins—an alternative approach to antimicrobial drugs. J Photochem Photobiol B 5:281–293
Malik Z, Ladan H, Nitzan Y, Ehrenberg B (1990b) The bactericidal activity of a deuteroporphyrin–hemin mixture on Gram-positive bacteria—a microbiological and spectroscopic study. J Photochem Photobiol B 6:419–430
Sabens EA, Distler AM, Mieyal JJ (2010) Levodopa deactivates enzymes that regulate thiol-disulfide homeostasis and promotes neuronal cell death: implications for therapy of Parkinson’s disease. Biochemistry 49:2715–2724
Sol V, Branland P, Granet R, Kaldapa C, Verneuil B, Krausz P (1998) Nitroglycosylated meso-arylporphyrins as photoinhibitors of Gram positive bacteria. Bioorg Med Chem Lett 8:3007–3010
Sol V, Branland P, Chaleix V, Granet R, Guilloton M, Lamarche F, Verneuil B, Krausz P (2004) Amino porphyrins as photoinhibitors of Gram-positive and -negative bacteria. Bioorg Med Chem Lett 14:4207–4211
Sternberg ED, Dolphin D, Bruckner C (1998) Porphyrin-based photosensitizers for use in photodynamic therapy. Tetrahedron 54:4151–4202
Szpakowska M, Reiss J, Graczyk A, Szmigielski S, Lasocki K, Grzybowski J (1997) Susceptibility of Pseudomonas aeruginosa to a photodynamic effect of the arginine hematoporphyrin derivative. Int J Antimicrob Agents 8:23–27
Venezio FR, Divincenzo C, Sherman R, Reichman M, Origitano TC, Thompson K, Reichman OH (1985) Bactericidal effects of photoradiation therapy with hematoporphyrin derivative. J Infect Dis 151:166–169
Wu SC, Yen GC, Wang BS, Chiu CK, Yen WJ, Chang LW, Duh PD (2007) Antimutagenic and antimicrobial activities of pu-erh tea. Lwt Food Sci Technol 40:506–512
Acknowledgments
The authors are thankful to the Fatih University Research Project Foundation (P50021004 and P50020903-1) for financial support. They also appreciate Associate Professor Isil Kurnaz for donating us HeLa and SH-SY5Y cell lines.
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Sagir, T., Gencer, S., Kemikli, N. et al. Photodynamic activities of protoporphyrin IX and its dopamine conjugate against cancer and bacterial cell viability. Med Chem Res 21, 4499–4505 (2012). https://doi.org/10.1007/s00044-011-9951-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-011-9951-3