Cyclodextrin modulates the cytotoxic effects of chlorhexidine on microrganisms and cells in vitro

References

• Abdelwahed W, Degobert G, Dubes A, et al. (2008). Sulfated and non-sulfated amphiphilic-β-cyclodextrins: impact of their structural properties on the physicochemical properties of nanoparticles. Int J Pharm 351:289–95
   PubMedGoogle Scholar
• Adriaanse AH, Muytjens HL, Heessen FWA, et al. (1996). In vitro activity of chlorhexidine, hexetidine and bacitracin against perinatal pathogens. J Antimicrob Chemother 37:192–4
   PubMed Web of Science ®Google Scholar
• Ahmed SM, Casu B, Cedro A, et al. (1994). Disruption of micellar aggregates of glangioside GM-1 by complexation with α-cyclodextrin. Int J Pharm 109:99–106
   Google Scholar
• Alleyn CD, O’Neal RB, Strong SL, et al. (1991). The effect of chlorhexidine treatment of root surfaces on the attachment of human gingival fibroblast in vitro. J Periodontol 62:434–8
   PubMed Web of Science ®Google Scholar
• Arthington-Skaggs BA, Jradi H, Desai T, et al. (1999). Quantitation of ergosterol content: novel method for determination of fluconazole susceptibility of Candida albicans. J Clin Microbiol 37:3332–7
   PubMed Web of Science ®Google Scholar
• Atger VM, Moya ML, Stoudt GW, et al. (1997). Cyclodextrins as catalysts for the removal of cholesterol from macrophage foam cells. J Clin Invest 99:773–80
   PubMed Web of Science ®Google Scholar
• Babich H, Wurzburger BJ, Rubin YL, et al. (1995). An in vitro study on the cytotoxicity of chlorhexidine digluconate to human gingival cells. Cell Biol Toxicol 11:79–88
   PubMed Web of Science ®Google Scholar
• Badi N, Guégan P. (2007). Per-O-(3-hydroxy)propyl-β-cyclodextrin: a cyclodextrin derivative bearing only primary hydroxyl groups. Carbohydrate Res 342:1989–91
   PubMed Web of Science ®Google Scholar
• Barman H, Walch ML, Latinovic-Golic S, et al. (2006). Cholesterol in negatively charged lipid bilayers modulates the effect of the antimicrobial protein granulysin. J Membrane Biol 212:29–39
   PubMed Web of Science ®Google Scholar
• Beseničar MP, Bavdek A, Kladnik A, et al. (2008). Kinetics of cholesterol extraction lipid membranes by methyl-β-cyclodextrin – A surface plasmon resonance approach. Biochem Biophys Acta 1778:175–84
   PubMed Web of Science ®Google Scholar
• Best AJ, Nixon MF, Taylor GJS. (2007). Brief exposure of 0.05% chlorhexidine does not impair non-osteoarthritic human cartilage metabolism. J Hospital Infect 67:67–71
   PubMed Web of Science ®Google Scholar
• Cabral CT, Fernandes MH. (2007). In vitro comparison of chlorhexidine and povidone–iodine on the long-term proliferation and functional activity of human alveolar bone cells. Clin Oral Invest 11:155–64
   PubMed Web of Science ®Google Scholar
• Cal K, Centkowska K. (2008). Use of cyclodextrins in topical formulations: practical aspects. Eur J Pharm Biopharm 68:467–78
   PubMed Web of Science ®Google Scholar
• Clejan S, Bittman R. (1984). Kinetics of cholesterol and phospholipid exchange between Mycoplasma gallisepticum cells and lipid vesicles. Alterations in membrane cholesterol and protein content. J Biol Chem 259:441–8
   PubMed Web of Science ®Google Scholar
• CLSI (Clinical and Laboratory Standards Institute/NCCLS). (2005a). Performance Standards for Antimicrobial Susceptibility Testing; Fifteenth Informational Supplement. CLSI/NCCLS document M100-S15 [ISBN 1-56238-556-9]. Wayne, Pennsylvania USA, 19087-98
   Google Scholar
• CLSI (Clinical and Laboratory Standard Institute). (2005b). Reference method for broth dilution Antifungal susceptibility testing of yeast: approved standards. Document CLSI M27-A2, CLSI, Wayne, Pennsylvania USA
   Google Scholar
• Cortés ME, Sinisterra RD, Ávila-Campos MJ, et al. (2001). The chlorhexidine:beta-ciclodextrin inclusion complex: preparation, characterization and microbiological evaluation. J Inclusion Phen Macrocyclic Chem 40:297–302
   Web of Science ®Google Scholar
• Davis ME, Brewster ME. (2004). Cyclodextrin-based pharmaceutics: past, present and future. Nature Rev 3:1023–35
   Web of Science ®Google Scholar
• Del Valle EMM. (2004). Cyclodextrins and their uses: a review. Process Biochem 39:1033–46
   Web of Science ®Google Scholar
• Denadai AML, Teixeira KIR, Santoro MM, et al. (2007). Supramolecular self-assembly of β-cyclodextrin: an effective Carrier of the antimicrobial agent chlorhexidine. Carbohydr Res 342:2286–96
   PubMed Web of Science ®Google Scholar
• Denyer SP. (1995). Mechanisms of action of antibacterial biocides. Int Biodeterior Biodegrad 36:227–45
   Web of Science ®Google Scholar
• Drisko CH. (2001). Non-surgical periodontal therapy. Periodontology 2000 25:77–88
   PubMed Web of Science ®Google Scholar
• Faria G, Cardoso CRB, Larson RE, et al. (2009). Chlorhexidine-induced apoptosis or necrosis in L929 fibroblasts: a role for endoplasmic reticulum stress. Toxicol Appl Pharm 234:256–65
   PubMed Web of Science ®Google Scholar
• Flemingson EP, Ambalavanan N, Ramakrishnan T, Vijayalakshmi R. (2008). Effect of three commercial mouth rinses on cultured human gingival fibroblast:Na in vitro study. Indian J Dent Res 19:29–35
   PubMedGoogle Scholar
• Frank DW, Gray JE, Weaver RN. (1976). Cyclodextrin nephrosis in the rat. Am J Pathol 83:367–82
   PubMed Web of Science ®Google Scholar
• Gianelli M, Chellini F, Margheri M, et al. (2008). Effect of chlorhexidine digluconate on different cell types: a molecular and ultra structural investigation. Toxicol in vitro 22:308–17
   PubMed Web of Science ®Google Scholar
• Harada A, Takashima Y, Yamaguchi H. (2009). Cyclodextrin-based supramolecular polymers. Chem Soc Rev 38:875–82
   PubMed Web of Science ®Google Scholar
• Haeberlin B, Gengenbacher T, Meinzer A. (1996). Cyclodextrin: useful excipients for oral peptide administration? Int J Pharm 137:103–10
   Web of Science ®Google Scholar
• Haynes MP, Phillips MC, Rothblat GH. (2000). Efflux of cholesterol from different cellular pools. Biochem 39:4508–17
   PubMed Web of Science ®Google Scholar
• Hidalgo E, Dominguez C. (2001). Mechanism’s underlying chlorhexidine-induced cytotoxicity. Toxicol in vitro 15:271–6
   PubMed Web of Science ®Google Scholar
• Hugo W, Longworth A. (1964). Some aspects of the mode of action of chlorhexidine. J Pharm Pharmacol 16:655–62
   PubMed Web of Science ®Google Scholar
• Irie T, Fukunaga K, Pitha J. (1992). Hydroxypropylcyclodextrins in parenteral use. I: lipid dissolution and effects on lipid transfers in vivo. J Pharm Sci 81:521–3
   PubMed Web of Science ®Google Scholar
• Jeffcoat MK, Bray KS, Ciancio SG, et al. (1998). Adjunctive use of a subgingival controlled-release chlorhexidine chip reduces probing depth and improves attachment level compared with scaling and root planing alone. J Periodontol 69:989–97
   PubMed Web of Science ®Google Scholar
• Karpanen TJ, Casey AL, Conway BR, et al. (2011). Antimicrobial activity of a chlorhexidine intravascular catheter site gel dressing. J Antimicrob Chemother 66:1777–84
   PubMed Web of Science ®Google Scholar
• Karpanen TJ, Worthington T, Hendry ER, et al. (2008). Antimicrobial efficacy of chlorhexidine digluconate alone and in combination with eucalyptus oil, tea tree oil and thymol against planktonic and biofilm cultures of Staphylococcus epidermidis. J Antimicrob Chemother 62:1031–6
   PubMed Web of Science ®Google Scholar
• Kasper JC, Friess W. (2011). The freezing step in lyophilization: physico-chemical fundamentals, freezing methods and consequences on process performance and quality attributes of biopharmaceuticals. Eur J Pharm Biopharm 78:248–63
   PubMed Web of Science ®Google Scholar
• Kiss T, Fenyvesia F, Bácskaya I, et al. (2010). Evaluation of the cytotoxicity of β-cyclodextrin derivatives: evidence for the role of cholesterol extraction. Eur J Pharm Sci 40:376–80
   PubMed Web of Science ®Google Scholar
• Kong N, Jiang T, Zhou Z, et al. (2009). Cytotoxicity of polymerized resin cements on human dental pulp cells in vitro. Dental Mater 25:1371–5
   PubMed Web of Science ®Google Scholar
• Liu L, Guo QX. (2002). The driving forces in the inclusion complexation of cyclodextrins. J Incl Phenom Macro 42:1–14
   Web of Science ®Google Scholar
• Loftsson T, Vogensen SB, Brewster ME, et al. (2007). Effects of cyclodextrins on drug delivery through biological membranes. J Pharm Sci 96:2532–46
   PubMed Web of Science ®Google Scholar
• Loftsson T, Masson M, Brewster ME. (2004). Self-association of cyclodextrins and cyclodextrin complexes. J Pharm Sci 93:1091–9
   PubMed Web of Science ®Google Scholar
• Loftsson T, Brewster ME. (1996). Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 85:1017–25
   PubMed Web of Science ®Google Scholar
• Maggi L, Conte U, Bettinetti GP. (1998). Technological properties of crystalline and amorphous α-cyclodextrin hydrates. Int J Pharm 172:211–17
   Google Scholar
• Mariotti AJ, Rumpf D. (1999). Chlorhexidine-induced changes to human gingival fibroblasts collagen and non-collagen protein production. J Periodontol 70:1443–8
   PubMed Web of Science ®Google Scholar
• McDonnell G, Russell AD. (1999). Antiseptics and disinfectants: activity, action and resistance. Clin Microbiol Rev 12:147–79
   PubMed Web of Science ®Google Scholar
• Mesmin B, Maxfield FR. (2009). Intracellular sterol dynamics. Biochim Biophys Acta 1791:636–45
   PubMed Web of Science ®Google Scholar
• Mura P, Liguori A, Bramanti G, et al. (1992). Improvement of dissolution properties and microbiological activity of miconazole and econazole by cyclodextrin complexation. Eur J Pharm Biopharm 38:119–23
   Web of Science ®Google Scholar
• Ohvo-Rekila H, Bjorn A, Kerlund J, et al. (2000). Cyclodextrin-catalyzed extraction of fluorescent sterols from monolayer membranes and small unilamellar vesicles. Chem Phys Lipids 105:167–78
   PubMed Web of Science ®Google Scholar
• Ohvo-Rekila H, Olsio C, Slotte JP. (1997). Effects of sphingomyelin and phosphatidylcholine degradation on cyclodextrin-mediated cholesterol efflux from cultured fibroblasts. Biochim Biophys Acta 1349:131–41
   PubMed Web of Science ®Google Scholar
• Pankov R, Markovska T, Antonov P, et al. (2006). The plasma membrane lipid composition affects fusion between cells and model membranes. Chem Biol Interact 164:167–73
   PubMed Web of Science ®Google Scholar
• Pfaller MA, Burmeister L, Bartlett MS, et al. (1988). Multicenter evaluation of four methods of yeast inoculum preparation. J Clin Microbiol 26:1437–41
   PubMed Web of Science ®Google Scholar
• Pucadyil TJ, Chattopadhyay A. (2007). Cholesterol depletion induces dynamic confinement of the G-protein coupled serotonin1A receptor in the plasma membrane of living cells. Biochim Biophys Acta 1768:655–68
   PubMed Web of Science ®Google Scholar
• Raso EMG, Cortes ME, Teixeira KIR, et al. (2010). A new controlled release system of chlorhexidine and chlorhexidine:β-cd inclusion complexes based on porous silica. J Inclusion Phen Macrocyclic Chem 67:159–68
   Web of Science ®Google Scholar
• Rhoads LS, Silkworth WT, Roppolo ML, et al. (2010). Cytotoxicity of nanostructured vanadium oxide on human cells in vitro. Toxicol in vitro 24:292–6
   PubMed Web of Science ®Google Scholar
• Salim N, Moore C, Silikas N, et al. (2013). Candidacidal effect of fluconazole and chlorhexidine released from acrylic polymer. J Antimicrob Chemother 68:587–92
   PubMed Web of Science ®Google Scholar
• Shaw JE, Epand RF, Hsu JCY, et al. (2008). Cationic peptide-induced remodeling of model membranes: direct visualization by in situ atomic force microscopy. J Struct Biol 162:121–38
   PubMed Web of Science ®Google Scholar
• Sheppard FC, Mason DJ, Bloomfield SF, et al. (1997). Flow cytometric analysis of chlorhexidine action. FEMS Microbiol Lett 154:283–8
   PubMed Web of Science ®Google Scholar
• Slots J, Ting M. (1999). Actinobacillus actinomycetemcomitas and Porphyromonas gingivalis in human periodontal disease: occurrence and treatment. Periodontol 2000 20:82–121
   PubMed Web of Science ®Google Scholar
• Stella VJ, He Q. (2008). Cyclodextrins. Toxicol Pathol 36:30–42
   PubMed Web of Science ®Google Scholar
• Taneri F, Ozcan I, Guneri T. (2010). In vitro and in vivo evaluation of oral tablet formulations prepared with ketoconazole and hydroxypropyl-β-cyclodextrin. Drug Delivery 17:152–7
   PubMed Web of Science ®Google Scholar
• Teixeira KIR, Araújo PV, Neves BRA, et al. (2013). Ultrastructural changes in bacterial membranes induced by nano-assemblies beta-cyclodextrin chlorhexidine: SEM, AFM, and TEM evaluation. Pharm Develop Tech 18:600–8
   PubMed Web of Science ®Google Scholar
• Teixeira KIR, Araújo PV, Sinisterra RD, et al. (2012). Chlorhexidine:beta-cyclodextrin blocks yeast growth by extraction of ergosterol. Braz J Microbiol 43:810–18
   PubMed Web of Science ®Google Scholar
• Uekama K, Hirayama F, Irie T. (1998). Cyclodextrin drug carrier systems. Chem Rev 98:2045–76
   PubMed Web of Science ®Google Scholar
• Uekama K, Kondo K, Nakamura K, et al. (1995). Modification of rectal absorption of morphine from hollow-type suppositories with a combination of α-cyclodextrin and viscosity-enhancing polysaccharide. J Pharm Sci 84:15–20
   PubMed Web of Science ®Google Scholar
• Uekama K, Hirayama F, Wakuda T, et al. (1981). Effect of cyclodextrins on the hydrolysis of prostacyclin and its methyl ester in aqueous solution. Chem Pharm Bull 29:213–19
   Web of Science ®Google Scholar
• Vieira FT, Menezes DC, De Lima GM, et al. (2008). Effect of diorganotin(IV) carboxylate complexes, [N-(2-carboxyphenyl)salicylideneiminato]dimethyltin(IV), bis(µ3-oxo)bis(µ-O-aminobenzoato-O,O′)bis(O-minobenzoato)tetrakis[dimethyltin(IV)] and bis(O-aminobenzoato-O,O′) di-n-butyltin(IV), on the membrane of Candida albicans cells – a mechanistic investigation of the antifungal activity of organotin complexes. App Organometal Chem 22:433–9
   Web of Science ®Google Scholar
• Zhang W, Swearingen EB, Jun J, et al. (2010). Porphyromonas gingivalis invades osteoblasts and inhibits bone formation. Microbes Infect 12:838–45
   PubMed Web of Science ®Google Scholar
• Zhao M, Wang H, Yang B, et al. (2010). Identification of cyclodextrin inclusion complex of chlorogenic acid and its antimicrobial activity. Food Chem 120:1138–142
   Web of Science ®Google Scholar
• Zheng XM, Lu WM, Sun DZ. (2001). Enthalpy and entropy criterion for the molecular recognize of some organic complexes with beta cyclodextrin. Acta Phys Chim Sin 17:343–7
   Web of Science ®Google Scholar
• Wong GL, Cohn DV. (1975). Target cells in bone for parathormone and calcitonin are different: enrichment for each cell type by sequential digestion of mouse calvaria and selective adhesion to polymeric surfaces. Proc Natl Acad Sci USA 72:3167–71
   PubMed Web of Science ®Google Scholar
• Yang C, Li H, Goh SH, et al. (2007). Cationic star polymers consisting of alphacyclodextrin core and oligoethylenimine arms as non-viral gene delivery vectors. Biomaterials 28:3245–54
   PubMed Web of Science ®Google Scholar
• Yue IC, Poff J, Cortés ME, et al. (2004). A novel polymeric chlorhexidine delivery device for the treatment of periodontal disease. Biomaterials 25:3743–50
   PubMed Web of Science ®Google Scholar
• Yunomae K, Arima H, Hirayama F, et al. (2003). Involvement of cholesterol in the inhibitory effect of dimethyl-β-cyclodextrin on P-glycoprotein and MRP2 function in Caco-2 cells. FEBS Lett 536:3225–31
   Google Scholar