Cyclodextrin inclusion complexes improving antibacterial drug profiles: an update systematic review

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References

• 1. Osman M, Al Mir H, Rafei R et al. Epidemiology of antimicrobial resistance in Lebanese extra-hospital settings: an overview. J. Glob. Antimicrob. Resist. 17, 123–129 (2019).
  MedlineGoogle Scholar
• 2. Prescott JF. The resistance tsunami, antimicrobial stewardship, and the golden age of microbiology. Vet. Microbiol. 171(3–4), 273–278 (2014).
  MedlineGoogle Scholar
• 3. Vikesland P, Garner E, Gupta S, Kang S, Maile-Moskowitz A, Zhu N. Differential drivers of antimicrobial resistance across the world. Acc. Chem. Res. 52(4), 916–924 (2019).
  Medline CASGoogle Scholar
• 4. Murray CJ, Ikuta KS, Sharara F et al. Global burden of bacterial antimicrobial resistance in 2019: a systematic analysis. Lancet 399(10325), 629–655 (2022).
  Medline CASGoogle Scholar
• 5. Song Y, Han Z, Song K, Zhen T. Antibiotic consumption trends in China: evidence from six-year surveillance sales records in Shandong Province. Front. Pharmacol. 11, 1 (2020).
  MedlineGoogle Scholar
• 6. Qiao M, Ying GG, Singer AC, Zhu YG. Review of antibiotic resistance in China and its environment. Environ. Int. 110, 160–172 (2018).
  Medline CASGoogle Scholar
• 7. Daoud Z, Dropa M. Editorial: the global threat of carbapenem-resistant Gram-negative bacteria, volume II. Front. Cell. Infect. Microbiol. 13, 1–3 (2023).
  Google Scholar
• 8. Center of Disease Control Antibiotic Resistance Threats Report. CDC, GA, USA (2019). https://www.cdc.gov/drugresistance/biggest-threats.html
  Google Scholar
• 9. Pelgrift RY, Friedman AJ. Nanotechnology as a therapeutic tool to combat microbial resistance. Adv. Drug Deliv. Rev. 65(13–14), 1803–1815 (2013).
  Medline CASGoogle Scholar
• 10. Zarandona I, Barba C, Guerrero P, De la Caba K, Maté J. Development of chitosan films containing β-cyclodextrin inclusion complex for controlled release of bioactives. Food Hydrocoll. 104, doi: 10.1016/j.foodhyd.2020.105720 (2020) (Epub ahead of print).
  Google Scholar
• 11. Saokham P, Muankaew C, Jansook P, Loftsson T. Solubility of cyclodextrins and drug/cyclodextrin complexes. Molecules 23(5), 1–15 (2018).
  Google Scholar
• 12. Zhang D, Lv P, Zhou C, Zhao Y, Liao X, Yang B. Cyclodextrin-based delivery systems for cancer treatment. Mater. Sci. Eng. C 96, 872–886 (2019).
  Medline CASGoogle Scholar
• 13. Mahjoubin-Tehran M, Kovanen PT, Xu S, Jamialahmadi T, Sahebkar A. Cyclodextrins: potential therapeutics against atherosclerosis. Pharmacol. Ther. 214, doi: 10.1016/j.pharmthera.2020.107620 (2020) (Epub ahead of print).
  MedlineGoogle Scholar
• 14. Chen G, Zhou Y, Zhang W et al. Methyl-β-cyclodextrin suppresses the monocyte-endothelial adhesion triggered by lipopolysaccharide (LPS) or oxidized low-density lipoprotein (oxLDL). Pharm. Biol. 59(1), 1034 (2021).
  CASGoogle Scholar
• 15. Boczar D, Michalska K. Cyclodextrin inclusion complexes with antibiotics and antibacterial agents as drug-delivery systems – a pharmaceutical perspective. Pharmaceutics 14(7), 1–71 (2022).
  Google Scholar
• 16. Andrade TA, Freitas TS, Araújo FO et al. Physico-chemical characterization and antibacterial activity of inclusion complexes of Hyptis martiusii Benth essential oil in β-cyclodextrin. Biomed. Pharmacother. 89, 201–207 (2017).
  Medline CASGoogle Scholar
• 17. Menezes PDP, Andrade TA, Frank LA et al. Advances of nanosystems containing cyclodextrins and their applications in pharmaceuticals. Int. J. Pharm. 559, 312–328 (2019).
  Medline CASGoogle Scholar
• 18. Gandhi SR, Quintans JDS, Gandhi GR, Araújo AAS, Quintans Júnior LJ. The use of cyclodextrin inclusion complexes to improve anticancer drug profiles: a systematic review. Expert Opin. Drug Deliv. 17(8), 1069–1080 (2020).
  Medline CASGoogle Scholar
• 19. de Oliveira MG, Guimarães AG, Araújo AA, Quintans JS, Santos MR, Quintans-Júnior LJ. Cyclodextrins: improving the therapeutic response of analgesic drugs: a patent review. Expert Opin. Ther. Pat. 25(8), 897–907 (2015).
  Medline CASGoogle Scholar
• 20. dos Santos Lima B, Shanmugam S, de Souza Siqueira Quintans J, Quintans-Júnior LJ, de Souza Araújo AA. Inclusion complex with cyclodextrins enhances the bioavailability of flavonoid compounds: a systematic review. Phytochem. Rev. 18(5), 1337–1359 (2019). •• Antibiotics and cyclodextrin inclusion complexes.
  Google Scholar
• 21. Agrawal G, Bhargava S. Preparation & characterization of solid inclusion complex of cefpodoxime proxetil with β-cyclodextrin. Curr. Drug Deliv. 5(1), 1–6 (2008).
  MedlineGoogle Scholar
• 22. Aleem O, Kuchekar B, Pore Y, Late S. Effect of β-cyclodextrin and hydroxypropyl β-cyclodextrin complexation on physicochemical properties and antimicrobial activity of cefdinir. J. Pharm. Biomed. Anal. 47(3), 535–540 (2008).
  Medline CASGoogle Scholar
• 23. Mizera M, Szymanowska D, Stasiłowicz A et al. Computer-aided design of cefuroxime axetil/cyclodextrin system with enhanced solubility and antimicrobial activity. Biomolecules 10(1), 24 (2019).
  MedlineGoogle Scholar
• 24. Mendes C, Wiemes BP, Buttchevitz A et al. Investigation of β-cyclodextrin-norfloxacin inclusion complexes. Part 1. Preparation, physicochemical and microbiological characterization. Expert Rev. Anti. Infect. Ther. 13(1), 119–129 (2015).
  Medline CASGoogle Scholar
• 25. Amaro BR, Alves CCS, Ferreira GF et al. Multifunctionality of βcD/ofloxacin and HPβCD/ofloxacin complexes: improvement of the antimicrobial activity and apoptosis induction on lung adenocarcinoma A549 cells. J. Braz. Chem. Soc. 31(12), 2628–2637 (2020).
  CASGoogle Scholar
• 26. Li Y, Zhou J, Gu J, Shao Q, Chen Y. Enhanced antibacterial activity of levofloxacin/hydroxypropyl-β-cyclodextrin inclusion complex: in vitro and in vivo evaluation. Colloids Surf. B Biointerfaces 215, doi: 10.1016/j.colsurfb.2022.112514 (2022) (Epub ahead of print).
  Google Scholar
• 27. Paczkowska-Walendowska M, Rosiak N, Tykarska E et al. Tedizolid-cyclodextrin system as delayed-release drug delivery with antibacterial activity. Int. J. Mol. Sci. 22(1), 1–15 (2020).
  MedlineGoogle Scholar
• 28. Suárez DF, Consuegra J, Trajano VC et al. Structural and thermodynamic characterization of doxycycline/β-cyclodextrin supramolecular complex and its bacterial membrane interactions. Colloids Surf. B Biointerfaces 118, 194–201 (2014).
  Medline CASGoogle Scholar
• 29. Marian E, Tita B, Duteanu N et al. Antimicrobial activity of fusidic acid inclusion complexes. Int. J. Infect. Dis. 101, 65–73 (2020).
  Medline CASGoogle Scholar
• 30. Paczkowska M, Szymanowska-Powałowska D, Mizera M et al. Cyclodextrins as multifunctional excipients: influence of inclusion into β-cyclodextrin on physicochemical and biological properties of tebipenem pivoxil. PLOS ONE 14(1), e0210694 (2019).
  Medline CASGoogle Scholar
• 31. Teixeira MG, de Assis JV, Soares CGP et al. Theoretical and experimental study of inclusion complexes formed by isoniazid and modified β-cyclodextrins: ¹ H NMR structural determination and antibacterial activity evaluation. J. Phys. Chem. B 118(1), 81–93 (2014).
  Medline CASGoogle Scholar
• 32. Shanmuga Priya A, Sivakamavalli J, Vaseeharan B, Stalin T. Improvement on dissolution rate of inclusion complex of rifabutin drug with β-cyclodextrin. Int. J. Biol. Macromol. 62, 472–480 (2013).
  MedlineGoogle Scholar
• 33. Tan Q, He D, Wu M et al. Characterization, activity, and computer modeling of a molecular inclusion complex containing rifaldazine. Int. J. Nanomedicine 8, 477–484 (2013).
  MedlineGoogle Scholar
• 34. Dan Córdoba AV, Aiassa V, Longhi MR, Quevedo MA, Zoppi A. Improved activity of rifampicin against biofilms of Staphylococcus aureus by multicomponent complexation. AAPS PharmSciTech 21(5), 163 (2020). •• Natural products and cyclodextrin inclusion complexes.
  MedlineGoogle Scholar
• 35. Zhang G, Yuan C, Sun Y. Effect of selective encapsulation of hydroxypropyl-β-cyclodextrin on components and antibacterial properties of star anise essential oil. Molecules 23(5), 1126 (2018).
  MedlineGoogle Scholar
• 36. Guo L, Cao X, Yang S et al. Characterization, solubility and antibacterial activity of inclusion complex of questin with hydroxypropyl-β-cyclodextrin. 3 Biotech 9(4), 123 (2019).
  MedlineGoogle Scholar
• 37. Ayoub AM, Gutberlet B, Preis E et al. Parietin cyclodextrin-inclusion complex as an effective formulation for bacterial photoinactivation. Pharmaceutics 14(2), 357 (2022).
  Medline CASGoogle Scholar
• 38. Cui H, Siva S, Lin L. Ultrasound processed cuminaldehyde/2-hydroxypropyl-β-cyclodextrin inclusion complex: preparation, characterization and antibacterial activity. Ultrason. Sonochem. 56, 84–93 (2019).
  Medline CASGoogle Scholar
• 39. Nikolic IL, Savic IM, Popsavin MM et al. Preparation, characterization and antimicrobial activity of inclusion complex of biochanin A with (2-hydroxypropyl)-β-cyclodextrin. J. Pharm. Pharmacol. 70(11), 1485–1493 (2018).
  Medline CASGoogle Scholar
• 40. Oliveira FS, Freitas TS, Cruz RPD et al. Evaluation of the antibacterial and modulatory potential of α-bisabolol, β-cyclodextrin and α-bisabolol/β-cyclodextrin complex. Biomed. Pharmacother. 92, 1111–1118 (2017).
  Medline CASGoogle Scholar
• 41. Lin L, Mao X, Sun Y, Cui H. Antibacterial mechanism of artemisinin/beta-cyclodextrins against methicillin-resistant Staphylococcus aureus (MRSA). Microb. Pathog. 118, 66–73 (2018).
  Medline CASGoogle Scholar
• 42. Zhang T, Zhu L, Li M et al. Inhalable andrographolide-β-cyclodextrin inclusion complexes for treatment of Staphylococcus aureus pneumonia by regulating immune responses. Mol. Pharm. 14(5), 1718–1725 (2017).
  Medline CASGoogle Scholar
• 43. Li M, Zhu L, Zhang T, Liu B, Du L, Jin Y. Pulmonary delivery of tea tree oil-β-cyclodextrin inclusion complexes for the treatment of fungal and bacterial pneumonia. J. Pharm. Pharmacol. 69(11), 1458–1467 (2017).
  Medline CASGoogle Scholar
• 44. Siva S, Li C, Cui H, Meenatchi V, Lin L. Encapsulation of essential oil components with methyl-β-cyclodextrin using ultrasonication: solubility, characterization, DPPH and antibacterial assay. Ultrason. Sonochem. 64, doi: 10.1016/j.ultsonch.2020.104997 (2020) (Epub ahead of print).
  MedlineGoogle Scholar
• 45. de Almeida Magalhães TSS, de Oliveira Macedo PC, Kawashima Pacheco SY et al. Development and evaluation of antimicrobial and modulatory activity of inclusion complex of Euterpe oleracea Mart oil and β-cyclodextrin or HP-β-cyclodextrin. Int. J. Mol. Sci. 21(3), 942 (2020). •• Synthetic molecules and cyclodextrin inclusion complexes.
  MedlineGoogle Scholar
• 46. Briñez-Ortega E, De Almeida VL, Lopes JCD, Burgos AE. Partial inclusion of bis(1,10-phenanthroline) silver(I) salicylate in β-cyclodextrin: spectroscopic characterization, in vitro and in silico antimicrobial evaluation. An. Acad. Bras. Cienc. 92(3), e20181323 (2020).
  MedlineGoogle Scholar
• 47. Brancaccio D, Pizzo E, Cafaro V et al. Antimicrobial peptide temporin-L complexed with anionic cyclodextrins results in a potent and safe agent against sessile bacteria. Int. J. Pharm. 584, 1–37 (2020).
  Google Scholar
• 48. Del Valle EMM. Cyclodextrins and their uses: a review. Process Biochem. 39(9), 1033–1046 (2004).
  Google Scholar
• 49. Otero-Espinar FJ, Luzardo-Alvarez A, Blanco-Mendez J. Cyclodextrins: more than pharmaceutical excipients. Mini-Rev. Med. Chem. 10(8), 715–725 (2010).
  Medline CASGoogle Scholar
• 50. Jansook P, Ogawa N, Loftsson T. Cyclodextrins: structure, physicochemical properties and pharmaceutical applications. Int. J. Pharm. 535(1–2), 272–284 (2018).
  Medline CASGoogle Scholar
• 51. Tian B, Hua S, Liu J. Cyclodextrin-based delivery systems for chemotherapeutic anticancer drugs: a review. Carbohydr. Polym. 232, doi: 0.1016/j.carbpol.2019.115805 (2020) (Epub ahead of print).
  MedlineGoogle Scholar
• 52. Santos AC, Costa D, Ferreira L et al. Cyclodextrin-based delivery systems for in vivo-tested anticancer therapies. Drug Deliv. Transl. Res. 11(1), 49–71 (2021).
  Medline CASGoogle Scholar
• 53. Carneiro SB, Duarte FÍC, Heimfarth L et al. Cyclodextrin^-drug inclusion complexes: in vivo and in vitro approaches. Int. J. Mol. Sci. 20(3), 1–27 (2019).
  Google Scholar
• 54. Brewster ME, Loftsson T. Cyclodextrins as pharmaceutical solubilizers. Adv. Drug Deliv. Rev. 59(7), 645–666 (2007).
  Medline CASGoogle Scholar
• 55. Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98(5), 1743–1753 (1998).
  Medline CASGoogle Scholar
• 56. Zhang D, Lv P, Zhou C, Zhao Y, Liao X, Yang B. Cyclodextrin-based delivery systems for cancer treatment. Mater. Sci. Eng. C 96, 872–886 (2019).
  Medline CASGoogle Scholar
• 57. Davis ME, Brewster ME. Cyclodextrin-based pharmaceutics: past, present and future. Nat. Rev. Drug Discov. 3(12), 1023–1035 (2004).
  Medline CASGoogle Scholar
• 58. Di L, Kerns EH. Formulation. In: Drug-Like Properties. Elsevier, CA, USA, 497–510 (2016).
  Google Scholar
• 59. Wang L, Yan J, Li Y et al. The influence of hydroxypropyl-β-cyclodextrin on the solubility, dissolution, cytotoxicity, and binding of riluzole with human serum albumin. J. Pharm. Biomed. Anal. 117, 453–463 (2016).
  Medline CASGoogle Scholar
• 60. Szente L, Singhal A, Domokos A, Song B. Cyclodextrins: assessing the impact of cavity size, occupancy, and substitutions on cytotoxicity and cholesterol homeostasis. Molecules 23(5), 1228 (2018).
  MedlineGoogle Scholar
• 61. Cid-Samamed A, Rakmai J, Mejuto JC, Simal-Gandara J, Astray G. Cyclodextrins inclusion complex: preparation methods, analytical techniques and food industry applications. Food Chem. 384, 1–14 (2022).
  Google Scholar
• 62. da Silva Júnior WF, de Oliveira Pinheiro JG, Moreira CDLFA, de Souza FJJ, de Lima ÁAN. Chapter 15 – Alternative technologies to improve solubility and stability of poorly water-soluble drugs. In: Multifunctional Systems for Combined Delivery, Biosensing and Diagnostics. Grumezescu AM (Ed.). Elsevier, 281–305 (2017).
  Google Scholar
• 63. Mura P. Analytical techniques for characterization of cyclodextrin complexes in the solid state: a review. J. Pharm. Biomed. Anal. 113, 226–238 (2015).
  Medline CASGoogle Scholar
• 64. Szente L, Szemán J, Sohajda T. Analytical characterization of cyclodextrins: history, official methods and recommended new techniques. J. Pharm. Biomed. Anal. 130, 347–365 (2016).
  Medline CASGoogle Scholar
• 65. Tiwari G, Tiwari R, Rai AK. Cyclodextrins in delivery systems: applications. J. Pharm. Bioallied Sci. 2(2), 72 (2010).
  Medline CASGoogle Scholar
• 66. Goluszko P, Nowicki B. Membrane cholesterol: a crucial molecule affecting interactions of microbial pathogens with mammalian cells. Infect. Immun. 73(12), 7791 (2005).
  Medline CASGoogle Scholar
• 67. Cheung GYC, Bae JS, Otto M. Pathogenicity and virulence of Staphylococcus aureus. Virulence 12(1), 547–569 (2021).
  Medline CASGoogle Scholar
• 68. Turner NA, Sharma-Kuinkel BK, Maskarinec SA et al. Methicillin-resistant Staphylococcus aureus: an overview of basic and clinical research. Nat. Rev. Microbiol. 17(4), 203–218 (2019).
  Medline CASGoogle Scholar
• 69. Schlievert PM, Strandberg KL, Lin Y-C, Peterson ML, Leung DYM. Secreted virulence factor comparison between methicillin-resistant and methicillin-sensitive Staphylococcus aureus, and its relevance to atopic dermatitis. J. Allergy. Clinical Immunology. 125(1), 39–49 (2010).
  Medline CASGoogle Scholar
• 70. Nikolic P, Mudgil P, Harman DG, Whitehall J. Untargeted lipidomic differences between clinical strains of methicillin-sensitive and methicillin-resistant Staphylococcus aureus. Infect. Dis. (Lond.) 54(7), 497–507 (2022).
  CASGoogle Scholar
• 71. Loftus RW, Dexter F, Robinson ADM. Methicillin-resistant Staphylococcus aureus has greater risk of transmission in the operating room than methicillin-sensitive S aureus. Am. J. Infect. Control 46(5), 520–525 (2018).
  MedlineGoogle Scholar
• 72. Asokan G, Ramadhan T, Ahmed E, Sanad H. WHO global priority pathogens list: a bibliometric analysis of Medline-PubMed for knowledge mobilization to infection prevention and control practices in Bahrain. Oman Med. J. 34(3), 184–193 (2019).
  Medline CASGoogle Scholar
• 73. Karginov VA. Cyclodextrin derivatives as anti-infectives. Curr. Opin. Pharmacol. 13(5), 717–725 (2013).
  Medline CASGoogle Scholar
• 74. Santos AM, Santos MM, Nascimento Júnior JAC et al. Mapping of new pharmacological alternatives in the face of the emergence of antibiotic resistance in COVID-19 patents treated for opportunistic respiratory bacterial pathogens. Recent Adv. Antiinfect. Drug Discov. 17(1), 34–53 (2022).
  Medline CASGoogle Scholar
• 75. Soleymani F, Taheri F, Haerizadeh M, Haerizadeh M, Karimi A. Evaluation of medicine prescription pattern using World Health Organization prescribing indicators in Iran: a cross-sectional study. J. Res. Pharm. Pract. 3(2), 39 (2014).
  MedlineGoogle Scholar
• 76. Imperiale JC, Sosnik AD. Cyclodextrin complexes for treatment improvement in infectious diseases. Nanomedicine 10(10), 1621–1641 (2015).
  CASGoogle Scholar
• 77. Popielec A, Loftsson T. Effects of cyclodextrins on the chemical stability of drugs. Int. J. Pharm. 531(2), 532–542 (2017).
  Medline CASGoogle Scholar
• 78. Onufrak NJ, Forrest A, Gonzalez D. Pharmacokinetic and pharmacodynamic principles of anti-infective dosing. Clin. Ther. 38(9), 1930–1947 (2016).
  Medline CASGoogle Scholar
• 79. Zhu C, Jiang L, Chen TM, Hwang KK. A comparative study of artificial membrane permeability assay for high throughput profiling of drug absorption potential. Eur. J. Med. Chem. 37(5), 399–407 (2002).
  Medline CASGoogle Scholar
• 80. Breda SA, Jimenez-Kairuz AF, Manzo RH, Olivera ME. Solubility behavior and biopharmaceutical classification of novel high-solubility ciprofloxacin and norfloxacin pharmaceutical derivatives. Int. J. Pharm. 371(1–2), 106–113 (2009).
  Medline CASGoogle Scholar
• 81. Yu X, Zipp GL, Davidson GW. The effect of temperature and pH on the solubility of quinolone compounds: estimation of heat of fusion. Pharm. Res. 11(4), 522–527 (1994).
  Medline CASGoogle Scholar
• 82. Wong CE, Dolzhenko AV, Lee SM, Young DJ. Cyclodextrins: a weapon in the fight against antimicrobial resistance. J. Mol. Eng. Mater. 5(1), (2017) (Epub ahead of print).
  Google Scholar
• 83. Zhang G, Yuan C, Sun Y. Effect of selective encapsulation of hydroxypropyl-β-cyclodextrin on components and antibacterial properties of star anise essential oil. Molecules 23(5), 1–15 (2018).
  CASGoogle Scholar
• 84. Qiu N, Cheng X, Wang G et al. Inclusion complex of barbigerone with hydroxypropyl-β-cyclodextrin: preparation and in vitro evaluation. Carbohydr. Polym. 101(1), 623–630 (2014).
  Medline CASGoogle Scholar
• 85. Fair RJ, Tor Y. Antibiotics and bacterial resistance in the 21st century. Perspect. Medicin. Chem. 6(6), 25 (2014).
  MedlineGoogle Scholar