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Exploring Antimicrobial Hydroxypropyl-β-Cyclodextrin Inclusion Complexes for Cheese Preservation: A Combined Theoretical and Experimental Study

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Abstract

Cyclodextrin enhances the activity of bioactive compounds through the formation of inclusion complexes (ICs), but its effect on diverse compound structures and processing methods is poorly understood. Here, our goal is to provide a comprehensive and cohesive insight into hydroxypropyl-β-cyclodextrin (HPβCD) complexation with cinnamaldehyde (CINN), citral (CIT), or their combination (MIX), prepared via kneading (KN), or freeze-drying (FD) using analytical techniques and computational simulations. Thermodynamic analysis revealed an exothermic and spontaneous (ΔG < 0) complexation process, with CINN-ICs exhibiting greater stability constants at 25 °C than CIT-ICs. Among the methods, CIT-KN displayed the highest efficiency (90.7%) and drug loading (9%), while CINN-KN showcased higher zeta potential (−23.2 mV), controlled release (35%), and antimicrobial activity (against both gram-positive and gram-negative bacteria). Computer simulations confirmed the absence of ternary complexes (CINN+CIT in HPβCD) and revealed the coexistence of association and ICs. Thermal analyses demonstrated high thermal stability (up to 207 °C) of included compounds, enhancing the suitability of these complexes for high-temperature processes. Additionally, CINN-KN incorporation into methylcellulose creates an active film, which effectively inhibited the proliferation of L. monocytogenes and S. Choleraesuis in cheeses (up to 1.3 cm halo inhibition), even following exposure to temperatures as high as 50 °C. Through combined experiments and computations, we uncovered how processing affects ICs performance with bioactive compounds, confirming their associative interactions with HPβCD. Thus, we underscore that the active function of ICs containing bioactive compounds relies not only on compound structure but also on processing methods, involving a collaborative interplay between both factors.

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Data Availability

The data presented in this study are available at the request of the corresponding author.

Abbreviations

CINN:

Cinnamaldehyde

CIT:

Citral

CDs:

Cyclodextrins

DS:

Degree of substitution

DL:

Drug loading

EE:

Entrapment efficiency

FD:

Freeze-drying

DFT:

Functional theory of density

ICs:

Inclusion complexes

KN:

Kneading

MC:

Methylcellulose

MIC:

Minimum bactericidal concentration

MIX:

Mixture of both cinnamaldehyde and citral

MD:

Molecular dynamics

MM:

Molecular mechanics

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Acknowledgements

The authors are grateful to the Microscope Core Facility (UFV) for using the transmission electron microscope.

Funding

This work was supported by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) – Finance code 001.

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Authors and Affiliations

  1. Department of Materials Engineering (DEMa), Federal University of São Carlos (UFSCar), São Carlos-SP, 13565-905, Brazil

    Rafael Resende Assis Silva

  2. Department of Food Technology, Federal University of Viçosa, Av. PH Rolfs, s/n, Viçosa, MG, 36570-900, Brazil

    Rafael Resende Assis Silva, Clara Suprani Marques, Taíla Veloso de Oliveira & Nilda de Fátima Ferreira Soares

  3. Department of Chemistry, Federal University of Viçosa. Av. Peter Henry Rolfs, s/n, Viçosa, MG, 36570-900, Brazil

    Luiza Alves Mendes

  4. Instituto de Ingeniería de Alimentos para el Desarrollo, Universitat Politécnica de Valencia, s/n 46022, Valencia, Spain

    Pedro Augusto Vieira Freitas

  5. Department of Chemistry, Federal University of Lavras, Campus Universitário, s/n, Lavras, MG, 37200-900, Brazil

    Luciana Matos Alves Pinto

  6. Department of Chemistry, Universitat Autònoma de Barcelona, 08193, Bellaterra, Spain

    Carlos Jaime

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  1. Rafael Resende Assis Silva
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Contributions

R.R.A.S. wrote the main manuscript text, planned, proposed methodologies, performed the experiments and data collection, discussed the results, constructed all figures (with the exception of computational modeling figures). C.S.M. contributed to writing the main manuscript, collaborated in the execution of the analytical experiments and, in addition to guiding the biological experiments, contributed to the discussion of all results. L.A.M. contributed to writing the main manuscript, collaborated in the execution of the analytical experiments and the discussion of some results. P.A.V.F. contributed to writing the main manuscript, collaborated in the execution of the analytical experiments and the discussion of some results. T.V.O. contributed to writing the main manuscript, collaborated in the execution of the analytical experiments and the discussion of some results, supervised the execution of the experiments. L.M.A.P. contributed to writing the main manuscript, contributed to the interpretation of the computer simulation and correlation of thermodynamic results. C.J. contributed to writing the main manuscript, was responsible for the computer simulation, creation of figures and tables associated with these results, discussed these results and revised the English and structure of the article. N.F.F.S. contributed to writing the main manuscript text, planned, proposed methodologies, supervised the entire experimental and written part of the scientific article. Revised the English and written structure of the article. All authors reviewed the manuscript.

Corresponding authors

Correspondence to Rafael Resende Assis Silva or Nilda de Fátima Ferreira Soares.

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Silva, R.R.A., Marques, C.S., Mendes, L.A. et al. Exploring Antimicrobial Hydroxypropyl-β-Cyclodextrin Inclusion Complexes for Cheese Preservation: A Combined Theoretical and Experimental Study. Food Bioprocess Technol (2024). https://doi.org/10.1007/s11947-024-03418-9

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