Diacetylcurcumin: a new photosensitizer for antimicrobial photodynamic therapy in Streptococcus mutans biofilms

References

• Araújo NC, de Menezes RF, Carneiro VSM, Dos Santos-Neto AP, Fontana CR, Bagnato VS, Harvey CM, Gerbi MEM. 2017. Photodynamic inactivation of cariogenic pathogens using curcumin as photosensitizer. Photomed Laser Surg 35: 259–263. doi: 10.1089/pho.2016.4156
   PubMed Web of Science ®Google Scholar
• Araújo NC, Fontana CR, Bagnato VS, Gerbi ME. 2012. Photodynamic effects of curcumin against cariogenic pathogens. Photomed Laser Surg. 30: 393–399. doi: 10.1089/pho.2011.3195
   PubMed Web of Science ®Google Scholar
• Araújo NC, Fontana CR, Bagnato VS, Gerbu ME. 2014. Photodynamic antimicrobial therapy of curcumin in biofilms and carious dentine. Lasers Med Sci. 29: 629–635. doi: 10.1007/s10103-013-1369-3
   PubMed Web of Science ®Google Scholar
• Arrow P, Raheb J, Miller M. 2013. Brief oral health promotion intervention among parentes of young children to reduce early childhood dental decay. BMC Public Health. 13: 245. doi: 10.1186/1471-2458-13-245
   PubMed Web of Science ®Google Scholar
• Asai A, Miyazawa T. 2000. Occurrence of orally administered curcuminoid as glucuronide and glucuronide/sulfate conjugates in rat plasma. Life Sciences. 67: 2785–2793. doi: 10.1016/S0024-3205(00)00868-7
   PubMed Web of Science ®Google Scholar
• Beaumont K, Webster R, Gardner I, Dack K. 2003. Design of ester prodrugs to enhance oral absortion of poorly permeable compounds: challenges to the discovery scientist. Curr Drog Metab. 4: 461–485. doi: 10.2174/1389200033489253
   PubMed Web of Science ®Google Scholar
• Blanco KC, Inada NM, Carbinato FM, Bagnato VS. 2017. Antimicrobial efficacy of curcumin formulations by therapy. Journal of Pharmacy and Pharmacology. 5: 506–511.
   Google Scholar
• Cheng AL, Hsu CH, Lin JK, Hsu MM, Ho YF, Shen TS, Ko JY, Lin JT, Lin BR, Ming-Shiang W, et al. 2001. Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or pre-malignant lesions. Anticancer Res. 21: 2895–2900.
   PubMed Web of Science ®Google Scholar
• Chibebe Júnior J, Sabino CP, Tan X, Junqueira JC, Wang Y, Fuchs BB, Jorge AO, Tegos GP, Hamblin MR, Mylonakis E. 2013. Selective photoinactivation of Candida albicans in the non-vertebrate host infection model Galleria mellonella. BMC Microbiol. 13: 217. doi: 10.1186/1471-2180-13-217
   PubMed Web of Science ®Google Scholar
• Chignell CF, Bilski P, Reszka KJ, Motten AG, Sik RH, Dahl TA. 1994. Spectral and photochemical properties of curcumin. Photochem Photobiol. 59: 295–302. doi: 10.1111/j.1751-1097.1994.tb05037.x
   PubMed Web of Science ®Google Scholar
• Dahl TA, McGowan WM, Shand MA, Srinivasan VS. 1989. Photokilling of bacteria by the natural dye curcumin. Arch Microbiol. 151: 183–185. doi: 10.1007/BF00414437
   PubMed Web of Science ®Google Scholar
• Deodhar SD, Sethi R, Srimal RC. 1980. Preliminary study on antirheumatic activity of curcumin (diferuloyl methane). Indian J Med Res. 138: 632–634.
   Google Scholar
• Denizot F, Lang R. 1986. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods. 89: 271–277. doi: 10.1016/0022-1759(86)90368-6
   PubMed Web of Science ®Google Scholar
• Desbois AP, Coote PJ. 2011. Wax moth larva (Galleria mellonella): an in vivo model for assessing the efficacy of antistaphylococcal agents. J Antimicrob Chemother. 66: 1785–1790. doi: 10.1093/jac/dkr198
   PubMed Web of Science ®Google Scholar
• Diniz IMA, Horta ID, Azevedo CS, Elmadjian TR, Matos AB, Simionato MRL, Marques MM. 2015. Antimicrobial photodynamic therapy: a promise candidate for caries lesions treatment. Photodiagnosis Photodyn Ther. 12: 511–518. doi: 10.1016/j.pdpdt.2015.04.006
   PubMed Web of Science ®Google Scholar
• Dos Santos JD, de Alvarenga JA, Rossoni RD, García MT, Moraes RM, Anbinder AL, Cardoso Jorge AO, Junqueira JC. 2017. Immunomodulatory effect of photodynamic therapy in Galleria mellonella infected with Porphyromonas gingivalis. Microb Pathog. 110: 507–511. doi: 10.1016/j.micpath.2017.07.045
   PubMed Web of Science ®Google Scholar
• Dovigo LN, Pavarina AC, Ribeiro AP, Brunetti IL, Costa CA, Jacomassi D, Bagnato VS, Kurachi C. 2011. Investigation of the photodynamic effects of curcumin against Candida albicans. Photochem Photobiol. 87: 895–903. doi: 10.1111/j.1751-1097.2011.00937.x
   PubMed Web of Science ®Google Scholar
• Evans BA, Rozen DE. 2012. A Streptococcus pneumoniae infection model in larvae of the wax moth Galleria mellonella. Eur J Clin Microbiol Infect Dis. 31: 2653–2660. doi: 10.1007/s10096-012-1609-7
   PubMed Web of Science ®Google Scholar
• Fracalossi C, Nagata JY, Pellosi DS, Terada RSS, Hioka N, Baesso ML, Sato F, Rosalen PL, Caetano W, Fujimaki M. 2016. Singlet oxygen production by combining erythrosine and halogen light for photodynamic inactivation of Streptococcus mutans. Photodiagnosis Photodyn Ther. 15: 127–132. doi: 10.1016/j.pdpdt.2016.06.011
   PubMed Web of Science ®Google Scholar
• Freires IA, Sardi JC, de Castro RD, Rosalen PL. 2017. Alternative animal and non-animal models for drug discovery and development: bonus or burden? Pharm Res. 34: 681–686. doi: 10.1007/s11095-016-2069-z
   PubMed Web of Science ®Google Scholar
• Garcia VG, Longo M, Gualberto Júnior EC, Bosco AF, Nagata MJ, Ervolino E, Theodoro LH. 2014. Effect of the concentration of phenothiazine photosensitizers in antimicrobial photodynamic therapy on bone loss and the immune inflammatory response of induced periodontitis in rats. J Periodont Res. 49: 584–594. doi: 10.1111/jre.12138
   PubMed Web of Science ®Google Scholar
• Haukvik T, Bruzell E, Kristensen S, Tønnesen HH. 2010. Photokilling of bacteria by curcumin in selected polyethylene glycol 400 (PEG 400) preparations. Studies on curcumin and curcuminoids, XLI. Pharmazie. 65: 600–606.
   PubMed Web of Science ®Google Scholar
• Hegge AB, Nielsen TT, Larsen KL, Bruzell E, Tønnesen HH. 2012. Impact of curcumin supersaturation in antibacterial photodynamic therapy-effect of cyclodextrin type and amount: studies on curcumin and curcuminoides XLV. J Pharm Sci. 101: 1524–1537. doi: 10.1002/jps.23046
   PubMed Web of Science ®Google Scholar
• Hsieh YH, Zhang JH, Chuang WC, Yu KH, Huang XB, Lee YC, Lee CI. 2018. An in vitro study on the effect of combined treatment with photodynamic and chemical therapies on Candida albicans. Int J Mol Sci. 19: 337. doi: 10.3390/ijms19020337
   Web of Science ®Google Scholar
• Kassebaum NJ, Bernabe E, Dahiya M, Bhandari B, Murray CJ, Marcenes W. 2015. Global burden of untreated caries: a systematic review and metaregression. J Dent Res. 94: 650–658. doi: 10.1177/0022034515573272
   PubMed Web of Science ®Google Scholar
• Konopka K, Goslinski T. 2007. Photodynamic therapy in dentistry. J Dent Res. 86: 694–707. doi: 10.1177/154405910708600803
   PubMed Web of Science ®Google Scholar
• La Rosa SL, Casey PG, Hill C, Diep DB, Nes IF, Brede DA. 2013. In vivo assessment of growth and virulence gene expression during commensal and pathogenic lifestyles of luxABCDE-tagged Enterococcus faecalis strains in murine gastrointestinal and intravenous infection models. Appl Environ Microbiol. 79: 3986–3997. doi: 10.1128/AEM.00831-13
   PubMed Web of Science ®Google Scholar
• Lee HJ, Kang SM, Jeong SH, Chung KH, Kim BI. 2017. Antibacterial photodynamic therapy with curcumin and Curcuma xanthorrhiza extract against Streptococcus mutans. Photodiagnosis Photodyn Ther. 20: 116–119. doi: 10.1016/j.pdpdt.2017.09.003
   PubMed Web of Science ®Google Scholar
• Lee YH, Park HW, Lee JH, Seo HW, Lee SY. 2012. The photodynamic therapy on Streptococcus mutans biofilms using erythrosine and dental halogen curing unit. Int J Oral Sci. 4: 196–201. doi: 10.1038/ijos.2012.63
   PubMed Web of Science ®Google Scholar
• Lima FT, Seba V, Silva G, Torrezan GS, Polaquini CR, Pinhanelli VC, Baek SJ, Fachin AL, Regasini LO, Marins M. 2018. The curcumin analog CH-5 exerts anticancer effects in human osteosarcoma cells via modulation of transcription factors p53/Sp1. Int J Mol Sci. 19: 1909. doi: 10.3390/ijms19071909
   Web of Science ®Google Scholar
• Loh JM, Adenwalla N, Wiles S, Proft T. 2013. Galleria mellonella larvae as an infection model for group A Streptococcus. Virulence. 4: 419–428. doi: 10.4161/viru.24930
   PubMed Web of Science ®Google Scholar
• Long LH, Hoi A, Halliwell B. 2010. Instability of, and generation of hydrogen peroxide by, phenolic compounds in cell culture media. Arch Biochem Biophys. 501: 162–169. doi: 10.1016/j.abb.2010.06.012
   PubMed Web of Science ®Google Scholar
• Mahran RI, Hagras MM, Sun D, Brenner DE. 2017. Bringing curcumin to the clinic in cancer prevention: a review of strategies to enhance bioavailability and efficacy. AAPS J. 19: 54–81. doi: 10.1208/s12248-016-0003-2
   PubMed Web of Science ®Google Scholar
• Maisch T. 2007. Anti-microbial photodynamic therapy: useful in the future? Lasers Med Sci. 22: 83–91. doi: 10.1007/s10103-006-0409-7
   PubMed Web of Science ®Google Scholar
• Meisel P, Kocher T. 2005. Photodynamic therapy for periodontal diseases: state of the art. J Photochem Photobiol. 79: 159–170. doi: 10.1016/j.jphotobiol.2004.11.023
   Web of Science ®Google Scholar
• Morão LG, Polaquini CR, Kopacz M, Torrezan GS, Ayusso GM, Dilarri G, Cavalca LB, Zielińska A, Scheffers DJ, Regasini LO, et al. 2018. A simplified curcumin targets the membrane of Bacillus subtilis. Microbiologyopen. 26: e00683.
   Google Scholar
• Najafi S, Khayamzadeh M, Paknejad M, Poursepanj G, Kharazi Fard MJ, Bahador A. 2016. An in vitro comparison of antimicrobial effects of curcumin-based photodynamic therapy and chlorhexidine, on Aggregatibacter actinomycetemcomitans. J Lasers Med Sci. 7: 21–25. doi: 10.15171/jlms.2016.05
   PubMed Web of Science ®Google Scholar
• Nelson KM, Dahlin JL, Bisson J, Graham J, Pauli GF, Walters MA. 2017. The essential medicinal chemistry of curcumin. J Med Chem. 60: 1620–1637. doi: 10.1021/acs.jmedchem.6b00975
   PubMed Web of Science ®Google Scholar
• Oliveira ABB, de Matos RPA, Stuqui B, Torrezan GS, Polaquini CA, Regasini LO, Calmon MF, Rahal P. 2018. Cytotoxicity and antitumoral activity by apoptosis induction of AC13: a brominated curcumina analogue. Pharmacogn Mag. 14: 611–616.
   Web of Science ®Google Scholar
• Panhóca VH, Florez F, Faria Júnior NB, Rastelli ANS, Tanomaru JMG, Kurachi C, Bagnato VS. 2016. Evaluation of antimicrobial photodynamic therapy against Streptococcus mutans biofilm in situ. J Contemp Dent Pract. 17: 184–191. doi: 10.5005/jp-journals-10024-1825
   PubMedGoogle Scholar
• Paschoal MA, Tonon CC, Spolidório DMP, Bagnato VS, Giusti JSM, Santos–Pinto L. 2013. Photodynamic potential of curcumin and blue LED against Streptococcus mutans in a planktonic culture. Photodiagnosis Photodyn Ther. 10: 313–319. doi: 10.1016/j.pdpdt.2013.02.002
   PubMed Web of Science ®Google Scholar
• Pinto JG, Fontana LC, de Oliveira MA, Kurachi C, Raniero LJ, Ferreira-Strixino J. 2016. In vitro evaluation of photodynamic therapy using curcumina on Leishmania major and Leishmania braziliensis. Lasers Med Sci. 31: 883–890. doi: 10.1007/s10103-016-1928-5
   PubMed Web of Science ®Google Scholar
• Rochelle SLA, Sardi JCO, Freires IA, Galvão LCC, Lazarini JG, Alencar SM, Rosalen PL. 2016. The anti-biofilm potential of commonly discarded agro-industrial residues agains opportunistic pathogens. Ind crops prod. 87: 150–160. doi: 10.1016/j.indcrop.2016.03.044
   Web of Science ®Google Scholar
• Saitawee D, Teerakapong A, Morales NP, Jitprasertwong P, Hormdee D. 2018. Photodynamic therapy of Curcuma longa extract stimulated with blue light against Aggregatibacter actinomycetemcomitans. Photodiagnosis Photodyn Ther. 22: 101–105. doi: 10.1016/j.pdpdt.2018.03.001
   PubMed Web of Science ®Google Scholar
• Sanitá PV, Pavarina AC, Dovigo LN, Ribeiro APD, Andrade MC, Mima EGO. 2018. Curcumin-mediated anti-microbial photodynamic therapy against Candida dubliniensis biofilms. Lasers Med Sci. 33: 709–717. doi: 10.1007/s10103-017-2382-8
   PubMed Web of Science ®Google Scholar
• Santamaria L, Prino G. 1972. List of the photodynamic substances. Res Progr Org Biol Med Chem. 3: 11–35.
   Google Scholar
• Santezi C, Tanomaru JM, Bagnato VS, Júnior OB, Dovigo LN. 2016. Potential of curcumin-mediated photodynamic inactivation to reduce oral colonization. Photodiagnosis Photodyn Ther. 15: 46–52. doi: 10.1016/j.pdpdt.2016.04.006
   PubMed Web of Science ®Google Scholar
• Sardi JCO, Polaquini CR, Freires I, Galvão LCC, Lazarini JG, Torrezan GS, Regasini LO, Rosalen PL. 2017. Antibacterial activity of diacetylcurcumin against Staphylococcus aureus results in decreased biofilm and cellular adhesion. Journal of medical microbiology. 66: 816–824.
   PubMed Web of Science ®Google Scholar
• Savietto A, Polaquini CR, Kopacz M, Scheffers DJ, Marques BC, Regasini LO, Ferreira H. 2018. Antibacterial activity of monoacetylated alkyl gallates against Xanthomonas citri subsp. citri. Arch Microbiol. 200: 929–937. doi: 10.1007/s00203-018-1502-6
   PubMed Web of Science ®Google Scholar
• Schneider C, Gordon ON, Edwards RL, Luis PB. 2015. Degradation of curcumin: from mechanism to biological implications. J Agric Food Chem. 63: 7606–7614. doi: 10.1021/acs.jafc.5b00244
   PubMed Web of Science ®Google Scholar
• Silva G, Lima FT, Seba V, Mendes ALL, Lucas TG, de Andrade BV, Torrezan GS, Polaquini CR, Garcia ME, Couto LB, et al. 2018. Curcumin analog CH-5 suppresses the proliferation, migration, and invasion of the human gastric cancer cell line HGC-27. Molecules. 23: E279.
   PubMed Web of Science ®Google Scholar
• Soukos NS, Goodson JM. 2011. Photodynamic therapy in the control of oral biofilms. Periodontol 2000. 55: 143–166. doi: 10.1111/j.1600-0757.2010.00346.x
   PubMed Web of Science ®Google Scholar
• Sreedhar A, Sarkar I, Rajan P, Pai J, Malagi S, Kamath V, Bermappa R. 2015. Comparative evaluation of the efficacy of curcumin gel with and without photo activation as an adjunct to scaling and root planing in the treatment of chronic periodontitis: a split mouth clinical and microbiological study. J Nat Sc Biol Med. 6: S102–109.
   PubMedGoogle Scholar
• Theodoro LH, Ferro-Alves ML, Longo M, Nuernberg MAA, Ferreira RP, Andreati A, Ervolino E, Duque C, Garcia, V. G. 2017. Curcumin photodynamic effect in the treatment of the induced periodontitis in rats. Lasers Med Sci. 32: 1783–1791. doi: 10.1007/s10103-017-2261-3
   PubMed Web of Science ®Google Scholar
• Tikhonova S, Booij L, D´Souza V, Crosara KTB, Siqueira WL, Emami E. 2018. Investigating the association between stress, saliva and dental caries: a scoping review. BMC Oral Health. 18: 41. doi: 10.1186/s12903-018-0500-z
   PubMed Web of Science ®Google Scholar
• Tokubo LM, Rosalen PL, Sardi JCO, Freires IA, Fujimaki MU; Umeda JE, Barbosa PM, Tecchio GO, Hioka N, de Freitas CF, et al. 2018. Antimicrobial effect of photodynamic therapy using erythrosine/methylene blue combination on Streptococcus mutans biofilm. Photodiagnosis Photodyn Ther. 23: 94–98. doi: 10.1016/j.pdpdt.2018.05.004
   PubMed Web of Science ®Google Scholar
• Tonon CC, Paschoal MA, Correia M, Spolidório DM, Bagnato VS, Giusti JS, Santos-Pinto L. 2015. Comparative effects of photodynamic therapy mediated by curcumin on standard and clinical isolate of Streptococcus mutans. J Contemp Dent Pract. 16: 1–6. doi: 10.5005/jp-journals-10024-1626
   PubMedGoogle Scholar
• Wang K, Qiu F. 2013. Curcuminoid metabolism and its contribution to the pharmacological effects. Curr Drug Metab. 14: 791–806.
   PubMed Web of Science ®Google Scholar