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Reconstitution as an alternative method for 5-aminosalicylic acid intercalation in layered double hydroxide for drug delivery

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Abstract

Among a great variety of applications, layered double hydroxides (LDH) can be used as drug delivery systems improving the dissolution rate of poorly water-soluble drugs. Different methods, as co-precipitation, ion exchange, reconstitution, among others, can be used in order to intercalate drugs in the LDH interlayer space, such as 5-aminosalicylic acid (5ASA), widely used in the treatment of inflammatory bowel diseases, although it presents low bioavailability and water solubility. The chosen method can determine structural and material properties of the final product, such as crystal size, particle distribution and morphology. This study presents the reconstitution method as an alternative. The samples were characterized by elemental analysis, X-ray diffraction, infrared molecular absorption spectroscopy, thermal analysis and atomic force microscopy. The characterization proved the interaction between LDH and 5ASA by changes in the interplanar distances and hydrogen interactions between drug and layer hydroxyls. This system presented a 25.5% of drug load. Also, the microscopy showed a rough surface in the system, indicating that the drug was not only present in the LDH interlayer space, but also adsorbed on its surface. This set of data indicate that the method was efficient for 5ASA intercalation in the LDH, reinforcing the proposal of LDHs as functional pharmaceutical excipients.

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References

  1. Mishra G, Dash B, Pandey S. Layered double hydroxides: a brief review from fundamentals to application as evolving biomaterials. Appl Clay Sci. 2018;153:172–86.

    CAS  Google Scholar 

  2. Zubair M, Daud M, McKay G, Shehzad F, Al-Harthi MA. Recent progress in layered double hydroxides (LDH)-containing hybrids as adsorbents for water remediation. Appl Clay Sci. 2017;143:279–92.

    CAS  Google Scholar 

  3. Chubar N, Gilmour R, Gerda V, Mičušík M, Omastova M, Heister K, Man P, Fraissard J, Zaitsev V. Layered double hydroxides as the next generation inorganic anion exchangers: Synthetic methods versus applicability. Adv Colloid Interface Sci. 2017;245:62–80.

    CAS  PubMed  Google Scholar 

  4. Mao N, Zhou CH, Tong DS, Yu WH, Cynthia Lin CX. Exfoliation of layered double hydroxide solids into functional nanosheets. Appl Clay Sci. 2017;144:60–78.

    CAS  Google Scholar 

  5. Forano C, Costantino U, Prévot V, Gueho CT. Layered double hydroxides (LDH). Handb Clay Sci. 2010;5:745–82.

    Google Scholar 

  6. Tcheumi HL, Kameni Wendji AP, Tonle IK, Ngameni E. A low-cost layered double hydroxide (LDH) based amperometric sensor for the detection of isoproturon in water using carbon paste modified electrode. J Anal Methods Chem. 2020;2020:1–10.

    Google Scholar 

  7. Dutt MA, Hanif MA, Nadeem F, Bhatti HN. A review of advances in engineered composite materials popular for wastewater treatment. J Environ Chem Eng. 2020;8:104073.

    CAS  Google Scholar 

  8. de Castro VA, Duarte VGO, Nobre DAC, Silva GH, Constantino VRL, Pinto FG, Macedo WR, Tronto J. Plant growth regulation by seed coating with films of alginate and auxin-intercalated layered double hydroxides. Beilstein J Nanotechnol. 2020;11:1082–91.

    PubMed  PubMed Central  Google Scholar 

  9. Cai H, Peng F, Wang Y, Yi J, Cai X, Liu H, Kong Q. Improving flame retardancy of epoxy resin nanocomposites by carbon nanotubes grafted CuAl-layered double hydroxide hybrid. J Nanosci Nanotechnol. 2020;20:6406–12.

    CAS  PubMed  Google Scholar 

  10. Asimakopoulou E, Zhang J, Mckee M, et al. Effect of layered double hydroxide, expanded graphite and ammonium polyphosphate additives on thermal stability and fire performance of polyisocyanurate insulation foam. Thermochim Acta. 2020;693:178724.

    CAS  Google Scholar 

  11. Nguyen TKN, Matsui Y, Shirahata N, Dumait N, Cordier S, Grasset F, Ohashi N, Uchikoshi T. Zn-Al layered double hydroxide-based nanocomposite functionalized with an octahedral molybdenum cluster exhibiting prominent photoactive and oxidation properties. Appl Clay Sci. 2020;196:105765.

    CAS  Google Scholar 

  12. Ye Q, Huang Z, Wu P, et al. Promoting the photogeneration of hydrochar reactive oxygen species based on FeAl layered double hydroxide for diethyl phthalate degradation. J Hazard Mater. 2020;388:122120.

    CAS  PubMed  Google Scholar 

  13. Nuzhdin AL, Bukhtiyarova MV, Bukhtiyarova GA. Cu-Al mixed oxide derived from layered double hydroxide as an efficient catalyst for continuous-flow reductive amination of aromatic aldehydes. J Chem Technol Biotechnol. 2020;95:3292–9.

    CAS  Google Scholar 

  14. Gu H, Shi G, Chen HC, et al. Strong catalyst-support interactions in electrochemical oxygen evolution on Ni-Fe layered double hydroxide. ACS Energy Lett. 2020;5:3185–94.

    CAS  Google Scholar 

  15. Ponlakhet K, Jarujamrus P, Amatatongchai M, Tamuang S. FeIIFeIII layered double hydroxide nanosheets (FeIIFeIII LDHNS) as an enzyme mimic for colorimetric detection of H2O2. Anal Methods. 2019;11:4785–94.

    CAS  Google Scholar 

  16. Bruna F, Mousty C, Besse-Hoggan P, Batisson I, Prevot V. Assembly of nitroreductase and layered double hydroxides toward functional biohybrid materials. J Colloid Interface Sci. 2019;533:71–81.

    CAS  PubMed  Google Scholar 

  17. Samuei S, Rezvani Z, Shomali A, Ülker E, Karadaş F. Preparation and capacitance properties of graphene quantum dot/NiFe−layered double-hydroxide nanocomposite. Eur J Inorg Chem. 2020;3:1–10.

    Google Scholar 

  18. Zhu X, Li X, Tao H, Li M. Preparation of Co2Al layered double hydroxide nanosheet/Co2Mn bimetallic hydroxide nanoneedle nanocomposites on nickel foam for supercapacitors. J Alloys Compd. 2021;851:156868.

    CAS  Google Scholar 

  19. Pšenička M, Škoda J, Pospíšil M. Structural arrangement and properties of layered double hydroxide drug nanocarrier intercalated by sulindac and mefenamic acid solved by molecular simulation methods. Appl Clay Sci. 2020;189:105560.

    Google Scholar 

  20. Monteforte F, Bruni G, Quinzeni I, Friuli V, Maggi L, Capsoni D, Bini M. Meloxicam-LDH hybrid compound: a successful strategy to improve solubility. J Inorg Organomet Polym Mater. 2020;30:637–48.

    CAS  Google Scholar 

  21. Yousefi V, Tarhriz V, Eyvazi S, Dilmaghani A. Synthesis and application of magnetic@layered double hydroxide as an anti-inflammatory drugs nanocarrier. J Nanobiotechnology. 2020;18:155.

    CAS  PubMed  PubMed Central  Google Scholar 

  22. Zhang H, Guo SH, Zou K, Duan X. High-temperature chemical and microstructural transformations of an organic-inorganic nanohybrid captopril intercalated Mg-Al layered double hydroxide. Mater Res Bull. 2009;44:1062–9.

    CAS  Google Scholar 

  23. Xia SJ, Ni ZM, Xu Q, Hu BX, Hu J. Layered double hydroxides as supports for intercalation and sustained release of antihypertensive drugs. J Solid State Chem. 2008;181:2610–9.

    CAS  Google Scholar 

  24. Al Ali SHH, Al-Qubaisi M, Hussein MZ, Ismail M, Zainal Z, Hakim MN. Controlled release and angiotensin-converting enzyme inhibition properties of an antihypertensive drug based on a perindopril erbumine-layered double hydroxide nanocomposite. Int J Nanomedicine. 2012;7:2129–41.

    PubMed Central  Google Scholar 

  25. Pontes-Neto JG, Lyra MAM, Soares MFLR, Chaves LL, Soares-Sobrinho JL. Intercalation of olanzapine into CaAl and NiAl Layered Double Hydroxides for dissolution rate improvement: Synthesis, characterization and in vitro toxicity. J Drug Deliv Sci Technol. 2019;52:986–96.

    CAS  Google Scholar 

  26. Kim HJ, Lee JY, Kim TH, Gwak GH, Park JH, Oh JM. Radioisotope and anticancer agent incorporated layered double hydroxide for tumor targeting theranostic nanomedicine. Appl Clay Sci. 2020;186:105454.

    CAS  Google Scholar 

  27. Mei X, Hu T, Wang H, Liang R, Bu W, Wei M. Highly dispersed nano-enzyme triggered intracellular catalytic reaction toward cancer specific therapy. Biomaterials. 2020;258:120257.

    CAS  PubMed  Google Scholar 

  28. Li B, Hao G, Sun B, Gu Z, Xu ZP. Engineering a therapy-induced “immunogenic cancer cell death” amplifier to boost systemic tumor elimination. Adv Funct Mater. 2020;30:1–11.

    Google Scholar 

  29. Cherif NF, Constantino VRL, Hamdaoui O, Leroux F, Taviot-Guého C. New insights into two ciprofloxacin-intercalated arrangements for layered double hydroxide carrier materials. New J Chem. 2020;44:10076–86.

    CAS  Google Scholar 

  30. Behzadi Nia S, Pooresmaeil M, Namazi H. Carboxymethylcellulose/layered double hydroxides bio-nanocomposite hydrogel: a controlled amoxicillin nanocarrier for colonic bacterial infections treatment. Int J Biol Macromol. 2020;155:1401–9.

    CAS  PubMed  Google Scholar 

  31. Gopala Kumari SV, Manikandan NA, Pakshirajan K, Pugazhenthi G. Sustained drug release and bactericidal activity of a novel, highly biocompatible and biodegradable polymer nanocomposite loaded with norfloxacin for potential use in antibacterial therapy. J Drug Deliv Sci Technol. 2020;59:101900.

    CAS  Google Scholar 

  32. Belgheisi G, Nazarpak MH, Hashjin MS. Bone tissue engineering electrospun scaffolds based on layered double hydroxides with the ability to release vitamin D3: Fabrication, characterization and in vitro study. Appl Clay Sci. 2020;185:105434.

    CAS  Google Scholar 

  33. Nath J, Ahmed A, Saikia P, Chowdhury A, Dolui SK. Acrylic acid grafted gelatin/LDH based biocompatible hydrogel with pH-controllable release of vitamin B12. Appl Clay Sci. 2020. https://doi.org/10.1016/j.clay.2020.105569.

    Article  Google Scholar 

  34. Wang YJ, Zhou YM, He M, He Q, Zhong YY. Layer-by-layer assembly and infrared emissivity of (LDH/DNA/LDH/LTO)(n) hybrid films. Chin J Inorg Chem. 2020;36:1977–87.

    CAS  Google Scholar 

  35. Shahabadi N, Razlansari M. In vitro spectroscopic investigation of groove binding interaction of Fe3O4@CaAl-LDH@L-Dopa with calf thymus DNA. Nucleosides Nucleotides Nucleic Acids. 2020;39:1020–35.

    CAS  PubMed  Google Scholar 

  36. Acharya R, Chakraborty M, Chakraborty J. An in vitro comparative study of layered-double hydroxide nanoconjugate in the delivery of small interference and short-hairpin ribonucleic acid. Bull Mater Sci. 2020;43:1–4.

    Google Scholar 

  37. Rives V, del Arco M, Martín C. Intercalation of drugs in layered double hydroxides and their controlled release: a review. Appl Clay Sci. 2014;88–89:239–69.

    Google Scholar 

  38. Saifullah B, Hussein MZB. Inorganic nanolayers: structure, preparation, and biomedical applications. Int J Nanomed. 2015;10:5609–33.

    CAS  Google Scholar 

  39. Kaitao LI, Guirong W, Dianqing LI, Yanjun LIN, Xue D. Intercalation assembly method and intercalation process control of layered intercalated functional materials*. Chin J Chem Eng. 2013;21:453–62.

    Google Scholar 

  40. Zou K, Zhang H, Duan X. Studies on the formation of 5-aminosalicylate intercalated Zn-Al layered double hydroxides as a function of Zn/Al molar ratios and synthesis routes. Chem Eng Sci. 2007;62:2022–31.

    CAS  Google Scholar 

  41. Ribeiro LNM, Alcântara ACS, Darder M, Aranda P, Araújo-Moreira FM, Ruiz-Hitzky E. Pectin-coated chitosan-LDH bionanocomposite beads as potential systems for colon-targeted drug delivery. Int J Pharm. 2014;463:1–9.

    CAS  PubMed  Google Scholar 

  42. Pérez-Barrado E, Pujol MC, Aguiló M, Cesteros Y, Díaz F, Pallarès J, Marsal LF, Salagre P. Fast aging treatment for the synthesis of hydrocalumites using microwaves. Appl Clay Sci. 2013;80–81:313–9.

    Google Scholar 

  43. Ruan XX, Sun P, Ouyang XX, Qian GR. Characteristics and mechanisms of sorption of organic contaminants onto sodium dodecyl sulfate modified Ca-Al layered double hydroxides. Chin Sci Bull. 2011;56:3431–6.

    CAS  Google Scholar 

  44. Lonkar SP, Kutlu B, Leuteritz A, Heinrich G. Nanohybrids of phenolic antioxidant intercalated into MgAl-layered double hydroxide clay. Appl Clay Sci. 2013;71:8–14.

    CAS  Google Scholar 

  45. Zhang H, Zou K, Sun H, Duan X. A magnetic organic-inorganic composite: Synthesis and characterization of magnetic 5-aminosalicylic acid intercalated layered double hydroxides. J Solid State Chem. 2005;178:3485–93.

    CAS  Google Scholar 

  46. Chen H, Qian G, Ruan X, Frost RL. Removal process of nickel(II) by using dodecyl sulfate intercalated calcium aluminum layered double hydroxide. Appl Clay Sci. 2016;4:419–24.

    Google Scholar 

  47. Shafiei SS, Solati-Hashjin M, Rahim-Zadeh H, Samadikuchaksaraei A. Synthesis and characterisation of nanocrystalline Ca-Al layered double hydroxide {[Ca2Al(OH)6]NO3·nH2O}: in vitro study. Adv Appl Ceram. 2012;112:59–65.

    Google Scholar 

  48. Banić-Tomišić Z, Kojić-Prodić B, Širola I. Hydrogen bonds in the crystal packings of mesalazine and mesalazine hydrochloride. J Mol Struct. 1997;416:209–20.

    Google Scholar 

  49. Baghel S, Cathcart H, O’Reilly NJ. Polymeric amorphous solid dispersions: a review of amorphization, crystallization, stabilization, solid-state characterization, and aqueous solubilization of biopharmaceutical classification system class II drugs. J Pharm Sci. 2016;105:2527–44.

    CAS  PubMed  Google Scholar 

  50. Nassar MY, El-Shahat MF, Khalile SM, El-Desawy M, Mohamed EA. Structure investigation of mesalazine drug using thermal analyses, mass spectrometry, DFT calculations, and NBO analysis. J Therm Anal Calorim. 2014;117:463–71.

    CAS  Google Scholar 

  51. Santos NC, Castanho MARB. An overview of the biophysical applications of atomic force microscopy. Biophys Chem. 2004;107:133–49.

    CAS  PubMed  Google Scholar 

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Acknowledgements

The authors thank the Coordenação de Pessoal de Nível Superior—CAPES, the Conselho Nacional de Desenvolvimento Científico e Tecnológico—CNPq, and Fundação de Amparo à Ciência e Tecnologia do Estado de Pernambuco—FACEPE.

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Authors and Affiliations

  1. Departamento de Ciências Farmacêuticas, Núcleo de Controle de Qualidade de Medicamentos E Correlatos, Federal University of Pernambuco, Recife, Brazil

    J. G. Pontes-Neto, T. R. F. Silva, M. F. R. Soares & J. L. Soares-Sobrinho

  2. Núcleo de Pesquisa Em Biodiversidade E Biotecnologia, Federal University of Piauí, Parnaíba, PI, Brazil

    F. O. S. Ribeiro & D. A. Silva

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  1. J. G. Pontes-Neto
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Pontes-Neto, J.G., Silva, T.R.F., Ribeiro, F.O.S. et al. Reconstitution as an alternative method for 5-aminosalicylic acid intercalation in layered double hydroxide for drug delivery. J Therm Anal Calorim 147, 3141–3149 (2022). https://doi.org/10.1007/s10973-021-10684-8

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