The Role of Singlet Oxygen in Photoreactivity and Phototoxicity of Curcumin.
Journal
Photochemistry and photobiology
ISSN: 1751-1097
Titre abrégé: Photochem Photobiol
Pays: United States
ID NLM: 0376425
Informations de publication
Date de publication:
Jan 2023
Jan 2023
Historique:
received:
12
04
2022
accepted:
11
06
2022
pubmed:
18
6
2022
medline:
25
1
2023
entrez:
17
6
2022
Statut:
ppublish
Résumé
Curcumin is a plant-derived yellow-orange compound widely used as a spice, dye and food additive. It is also believed to have therapeutic effects against different disorders. On the other hand, there are data showing its phototoxicity against bacteria, fungi and various mammalian cells. Since the mechanism of its phototoxic action is not fully understood, we investigated here the phototoxic potential of curcumin in liposomal model membranes and in HaCaT cells. First, detection of singlet oxygen (
Substances chimiques
Singlet Oxygen
17778-80-2
Curcumin
IT942ZTH98
Liposomes
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
57-67Informations de copyright
© 2022 American Society for Photobiology.
Références
Dujic, J., S. Kippenberger, A. Ramirez-Bosca, J. Diaz-Alperi, J. Bereiter-Hahn, R. Kaufmann, A. Bernd and M. Hofmann (2009) Curcumin in combination with visible light inhibits tumor growth in a xenograft tumor model. Int. J. Cancer 124, 1422-1428.
Shanmugam, M. K., G. Rane, M. M. Kanchi, F. Arfuso, A. Chinnathambi, M. E. Zayed, S. A. Alharbi, B. K. Tan, A. P. Kumar and G. Sethi (2015) The multifaceted role of curcumin in cancer prevention and treatment. Molecules 20, 2728-2769.
Dahl, T. A., P. Bilski, K. J. Reszka and C. F. Chignell (1994) Photocytotoxicity of curcumin. Photochem. Photobiol. 59, 290-294.
Panahi, Y., O. Fazlolahzadeh, S. L. Atkin, M. Majeed, A. E. Butler, T. P. Johnston and A. Sahebkar (2019) Evidence of curcumin and curcumin analogue effects in skin diseases: A narrative review. J. Cell. Physiol. 234, 1165-1178.
Wu, Y., P. Zhang, H. Yang, Y. Ge and Y. Xin (2017) Effects of demethoxycurcumin on the viability and apoptosis of skin cancer cells. Mol. Med. Rep. 16, 539-546.
Barbalho, S. M., H. F. de Sousa Gonzaga, G. A. de Souza, R. de Alvares Goulart, M. L. de Sousa Gonzaga and B. de Alvarez Rezende (2021) Dermatological effects of Curcuma species: a systematic review. Clin. Exp. Dermatol. 46, 825-833.
Monroy, A., G. J. Lithgow and S. Alavez (2013) Curcumin and neurodegenerative diseases. Biofactors 39, 122-132.
Nabavi, S. F., R. Thiagarajan, L. Rastrelli, M. Daglia, E. Sobarzo-Sanchez, H. Alinezhad and S. M. Nabavi (2015) Curcumin: a natural product for diabetes and its complications. Curr. Top. Med. Chem. 15, 2445-2455.
Cozzolino, M., P. Delcanale, C. Montali, M. Tognolini, C. Giorgio, M. Corrado, L. Cavanna, P. Bianchini, A. Diaspro, S. Abbruzzetti and C. Viappiani (2019) Enhanced photosensitizing properties of protein bound curcumin. Life Sci. 233, 116710.
Patel, S. S., A. Acharya, R. S. Ray, R. Agrawal, R. Raghuwanshi and P. Jain (2020) Cellular and molecular mechanisms of curcumin in prevention and treatment of disease. Crit. Rev. Food Sci. Nutr. 60, 887-939.
Lee, H. J., S. M. Kang, S. H. Jeong, K. H. Chung and B. I. Kim (2017) Antibacterial photodynamic therapy with curcumin and Curcuma xanthorrhiza extract against Streptococcus mutans. Photodiagnosis Photodyn. Ther. 20, 116-119.
Vaughn, A. R., A. Branum and R. K. Sivamani (2016) Effects of Turmeric (Curcuma longa) on Skin Health: A Systematic Review of the Clinical Evidence. Phytother. Res. 30, 1243-1264.
Ganesan, P. and D. K. Choi (2016) Current application of phytocompound-based nanocosmeceuticals for beauty and skin therapy. Int. J. Nanomedicine 11, 1987-2007.
Chignell, C. F., P. Bilski, K. J. Reszka, A. G. Motten, R. H. Sik and T. A. Dahl (1994) Spectral and photochemical properties of curcumin. Photochem. Photobiol. 59, 295-302.
Bhavya, M. L. and H. Umesh Hebbar (2019) Efficacy of blue LED in microbial inactivation: Effect of photosensitization and process parameters. Int. J. Food Microbiol. 290, 296-304.
Carmello, J. C., A. C. Pavarina, R. Oliveira and B. Johansson (2015) Genotoxic effect of photodynamic therapy mediated by curcumin on Candida albicans. FEMS Yeast Res. 15, fov018.
Dujic, J., S. Kippenberger, S. Hoffmann, A. Ramirez-Bosca, J. Miquel, J. Diaz-Alperi, J. Bereiter-Hahn, R. Kaufmann and A. Bernd (2007) Low concentrations of curcumin induce growth arrest and apoptosis in skin keratinocytes only in combination with UVA or visible light. J. Invest. Dermatol. 127, 1992-2000.
Ravindranath, V. and N. Chandrasekhara (1980) Absorption and tissue distribution of curcumin in rats. Toxicology 16, 259-265.
Shoba, G., D. Joy, T. Joseph, M. Majeed, R. Rajendran and P. S. Srinivas (1998) Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta Med. 64, 353-356.
Jobin, C., C. A. Bradham, M. P. Russo, B. Juma, A. S. Narula, D. A. Brenner and R. B. Sartor (1999) Curcumin blocks cytokine-mediated NF-kappa B activation and proinflammatory gene expression by inhibiting inhibitory factor I-kappa B kinase activity. J. Immunol. 163, 3474-3483.
Golubovic-Liakopoulos, N., S. R. Simon and B. Shah (2011) Nanotechnology use with cosmeceuticals. Semin. Cutan. Med. Surg. 30, 176-180.
Lohani, A., A. Verma, H. Joshi, N. Yadav and N. Karki (2014) Nanotechnology-based cosmeceuticals. ISRN Dermatol. 2014, 843687.
Meghea, A. (2008) Pharmaceuticals and cosmeceuticals based on soft nanotechnology techniques with antioxidative, immunostimulative and other therapeutic activities. Recent Pat. Nanotechnol. 2, 137-145.
Skalniak, L., M. Smejda, A. Cierniak, A. Adamczyk, P. Konieczny, E. Madej and A. Wolnicka-Glubisz (2018) p38 but not p53 is responsible for UVA-induced MCPIP1 expression. Mech. Ageing Dev. 172, 96-106.
Britton, G. (1995) UV/Visible spectroscopy in carotenoids. In Carotenoids, Spectroscopy (Edited by G. Britton, S. Liaaen-Jensen and H. Pfander), pp. 13-62. Birkhauser Verlag, Basel, Boston, Berlin.
Wolnicka-Glubisz, A., A. Pawlak, M. Insinska-Rak and A. Zadlo (2020) Analysis of photoreactivity and phototoxicity of riboflavin's analogue 3MeTARF. J. Photochem. Photobiol. B 205, 111820.
Olchawa, M., O. Krzysztynska-Kuleta, M. Duda, A. Pawlak, P. Pabisz, B. Czuba-Pelech and T. Sarna (2019) In vitro phototoxicity of rhodopsin photobleaching products in the retinal pigment epithelium (RPE). Free Radic. Res. 53, 456-471.
Olchawa, M. M., O. I. Krzysztynska-Kuleta, K. T. Mokrzynski, P. M. Sarna and T. J. Sarna (2020) Quercetin protects ARPE-19 cells against photic stress mediated by the products of rhodopsin photobleaching. Photochem. Photobiol. Sci. 19, 1022-1034.
Olchawa, M. M., G. M. Szewczyk, A. C. Zadlo, O. I. Krzysztynska-Kuleta and T. J. Sarna (2021) The effect of aging and antioxidants on photoreactivity and phototoxicity of human melanosomes: An in vitro study. Pigment Cell Melanoma Res. 34, 670-682.
Olchawa, M. M., G. M. Szewczyk, A. C. Zadlo, M. W. Sarna, D. Wnuk and T. J. Sarna (2020) The effect of antioxidants on photoreactivity and phototoxic potential of RPE melanolipofuscin granules from human donors of different age. Antioxidants (Basel) 9.
Wisniewska, A. and W. K. Subczynski (1998) Effects of polar carotenoids on the shape of the hydrophobic barrier of phospholipid bilayers. Biochim. Biophys. Acta 1368, 235-246.
Olchawa, M. M., A. M. Herrnreiter, A. K. Pilat, C. M. Skumatz, M. Niziolek-Kierecka, J. M. Burke and T. J. Sarna (2015) Zeaxanthin and alpha-tocopherol reduce the inhibitory effects of photodynamic stress on phagocytosis by ARPE-19 cells. Free Radic. Biol. Med. 89, 873-882.
Korytowski, W., G. J. Bachowski and A. W. Girotti (1993) Analysis of cholesterol and phospholipid hydroperoxides by high-performance liquid chromatography with mercury drop electrochemical detection. Anal. Biochem. 213, 111-119.
Korytowski, W., P. G. Geiger and A. W. Girotti (1995) High-performance liquid chromatography with mercury cathode electrochemical detection: application to lipid hydroperoxide analysis. J. Chromatogr. B Biomed. Appl. 670, 189-197.
Cheeseman, K. A. (1990) Methods of measuring lipid peroxidation in biological systems: an overview. In Free Radicals, Lipoproteins and Membrane Lipids (Edited by D. -B. L. Crastes de Paulet A and R. Raoletti), pp. 143-152. Plenum Press, New York.
Wolnicka-Glubisz, A., M. Lukasik, A. Pawlak, A. Wielgus, M. Niziolek-Kierecka and T. Sarna (2009) Peroxidation of lipids in liposomal membranes of different composition photosensitized by chlorpromazine. Photochem. Photobiol. Sci. 8, 241-247.
Sarna, T., A. Duleba, W. Korytowski and H. Swartz (1980) Interaction of melanin with oxygen. Arch. Biochem. Biophys. 200, 140-148.
Wrona, M., W. Korytowski, M. Rozanowska, T. Sarna and T. G. Truscott (2003) Cooperation of antioxidants in protection against photosensitized oxidation. Free Radic. Biol. Med. 35, 1319-1329.
Halpern, H., M. Peric, T. D. Nguyen, D. P. Spencer, B. A. Teicher, Y. J. Lin and M. K. Bowman (1990) Selective isotopic labeling of a nitroxide spin label to enhance sensitivity for T2 oxymetry. J. Magn. Reson. 90, 40-51.
Khopde, S. M., K. I. Priyadarsini, D. K. Palit and T. Mukherjee (2000) Effect of solvent on the excited-state photophysical properties of curcumin. Photochem. Photobiol. 72, 625-631.
Choudhuri, T., S. Pal, M. L. Agwarwal, T. Das and G. Sa (2002) Curcumin induces apoptosis in human breast cancer cells through p53-dependent Bax induction. FEBS Lett. 512, 334-340.
Wozniak, M., M. Nowak, A. Lazebna, K. Wiecek, I. Jablonska, K. Szpadel, A. Grzeszczak, J. Gubernator and P. Ziolkowski (2021) The comparison of in vitro photosensitizing efficacy of curcumin-loaded liposomes following photodynamic therapy on melanoma MUG-Mel2, squamous cell carcinoma SCC-25, and normal keratinocyte HaCaT cells. Pharmaceuticals (Basel) 14.
Moustapha, A., P. A. Peretout, N. E. Rainey, F. Sureau, M. Geze, J. M. Petit, E. Dewailly, C. Slomianny and P. X. Petit (2015) Curcumin induces crosstalk between autophagy and apoptosis mediated by calcium release from the endoplasmic reticulum, lysosomal destabilization and mitochondrial events. Cell Death Discov. 1, 15017.
Song, W., Y. J. Ren, L. L. Liu, Y. Y. Zhao, Q. F. Li and H. B. Yang (2021) Curcumin induced the cell death of immortalized human keratinocytes (HaCaT) through caspase-independent and caspase-dependent pathways. Food Funct. 12, 8669-8680.
Wang, J. B., L. L. Qi, S. D. Zheng and T. X. Wu (2009) Curcumin induces apoptosis through the mitochondria-mediated apoptotic pathway in HT-29 cells. J. Zhejiang Univ. Sci. B 10, 93-102.
Rashmi, R., T. R. Santhosh Kumar and D. Karunagaran (2003) Human colon cancer cells differ in their sensitivity to curcumin-induced apoptosis and heat shock protects them by inhibiting the release of apoptosis-inducing factor and caspases. FEBS Lett. 538, 19-24.
Michalski, R., J. Zielonka, E. Gapys, A. Marcinek, J. Joseph and B. Kalyanaraman (2014) Real-time measurements of amino acid and protein hydroperoxides using coumarin boronic acid. J. Biol. Chem. 289, 22536-22553.
Rozanowska, M. B., B. Czuba-Pelech, J. T. Landrum and B. Rozanowski (2021) Comparison of antioxidant properties of dehydrolutein with lutein and zeaxanthin, and their effects on cultured retinal pigment epithelial cells. Antioxidants (Basel) 10.
Wright, A., C. L. Hawkins and M. J. Davies (2003) Photo-oxidation of cells generates long-lived intracellular protein peroxides. Free Radic. Biol. Med. 34, 637-647.
Duda, M., K. Cygan and A. Wisniewska-Becker (2020) Effects of curcumin on lipid membranes: an EPR spin-label study. Cell Biochem. Biophys. 78, 139-147.
Karewicz, A., D. Bielska, B. Gzyl-Malcher, M. Kepczynski, R. Lach and M. Nowakowska (2011) Interaction of curcumin with lipid monolayers and liposomal bilayers. Colloids Surf. B Biointerfaces 88, 231-239.
Kotenkov, S. A., G. O. I. Khaliullina, A. V. Antzutkin, O. N. Gimatdinov, R. S. Gimatdinov and A. V. Filippov (2019) Effect of cholesterol and curcumin on ordering of DMPC bilayers. Appl. Magn. Reson. 50, 511-520.
Wilkinson, F., W. P. Helman and A. B. Ross (1995) Rate constants for the decay and reactions of the lowest electronicall y excited singlet state of molecular oxygen in solutions - an expanded and revised compilation. J. Phys. Chem. Ref. Data Monogr. 24, 663-1021.
Krasnovsky, A. A., Jr. (1998) Singlet molecular oxygen in photobiochemical systems: IR phosphorescence studies. Membr. Cell Biol. 12, 665-690.
Szewczyk, G., A. Zadlo, M. Sarna, S. Ito, K. Wakamatsu and T. Sarna (2016) Aerobic photoreactivity of synthetic eumelanins and pheomelanins: generation of singlet oxygen and superoxide anion. Pigment Cell Melanoma Res. 29, 669-678.
Zbyradowski, M., M. Duda, A. Wisniewska-Becker, W. Heriyanto, J. Rajwa, D. Fiedor, M. P. Cvetkovic and L. Fiedor (2022) Triplet-driven chemical reactivity of beta-carotene and its biological implications. Nat. Commun. 13, 2474.