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Article

Improvement in Solubility–Permeability Interplay of Psoralens from Brosimum gaudichaudii Plant Extract upon Complexation with Hydroxypropyl-β-cyclodextrin

by
Rúbia Darc Machado
1,
Júlio C. G. Silva
1,
Luís A. D. Silva
2,
Gerlon de A. R. Oliveira
3,
Luciano M. Lião
3,
Eliana M. Lima
2,
Mariana C. de Morais
4,
Edemilson C. da Conceição
4 and
Kênnia R. Rezende
1,*
1
Laboratório de Biofarmácia e Farmacocinética (BioPk), Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia 74605-170, GO, Brazil
2
Laboratório de Nanotecnologia Farmacêutica e Sistemas de Liberação de Fármacos (FarmaTec), Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia 74605-170, GO, Brazil
3
Laboratório de Ressonância Magnética Nuclear (LabRMN), Instituto de Química, Universidade Federal de Goiás, Goiânia 74605-170, GO, Brazil
4
Laboratório de PD&I de Bioprodutos, Faculdade de Farmácia, Universidade Federal de Goiás, Goiânia 74605-170, GO, Brazil
*
Author to whom correspondence should be addressed.
Molecules 2022, 27(14), 4580; https://doi.org/10.3390/molecules27144580
Submission received: 9 June 2022 / Revised: 12 July 2022 / Accepted: 13 July 2022 / Published: 19 July 2022
(This article belongs to the Special Issue Natural Bioactive Compounds and Human Health)
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Abstract

Psoralen (PSO) and 5-methoxypsoralen (5-MOP) are widely used drugs in oral photochemotherapy against vitiligo and major bioactive components of root bark extract of Brosimum gaudichaudii Trécul (EBGT), previously standardized by LC-MS. However, the exceptionally low water solubility of these psoralens can cause incomplete and variable bioavailability limiting their applications and patient adherence to treatment. Therefore, the purpose of this work was to investigate the effects of 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) inclusion complex on the solubility and jejunal permeability of PSO and 5-MOP from EBGT. Characterization of inclusion complexes were evaluated by current methods in nuclear magnetic resonance studies on aqueous solution, Fourier transform infrared spectroscopy, thermal analysis, and scanning electron microscopy in solid state. Ex vivo rat jejunal permeability was also investigated and compared for both pure psoralens and plant extract formulation over a wide HP-β-CD concentration range (2.5 to 70 mM). Phase solubility studies of the PSO- and 5-MOP-HP-β-CD inclusion complex showed 1:1 inclusion complex formation with small stability constants (Kc < 500 M−1). PSO and 5-MOP permeability rate decreased after adding HP-β-CD by 6- and 4-fold for pure standards and EBGT markers, respectively. Nevertheless, the complexation with HP-β-CD significantly improved solubility of PSO (until 10-fold) and 5-MOP (until 31-fold). As a result, the permeability drop could be overcome by solubility augmentation, implying that the HP-β-CD inclusion complexes with PSO, 5-MOP, or EBGT can be a valuable tool for designing and developing novel oral drug product formulation containing these psoralens for the treatment of vitiligo.
Keywords: cyclodextrin; HP-β-CD; inclusion complexes; physical–chemical characterization; host–guest interaction; solubilization; ex vivo permeability; intestinal absorption; in vitro studies; furanocoumarins cyclodextrin; HP-β-CD; inclusion complexes; physical–chemical characterization; host–guest interaction; solubilization; ex vivo permeability; intestinal absorption; in vitro studies; furanocoumarins
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MDPI and ACS Style

Machado, R.D.; Silva, J.C.G.; Silva, L.A.D.; Oliveira, G.d.A.R.; Lião, L.M.; Lima, E.M.; de Morais, M.C.; da Conceição, E.C.; Rezende, K.R. Improvement in Solubility–Permeability Interplay of Psoralens from Brosimum gaudichaudii Plant Extract upon Complexation with Hydroxypropyl-β-cyclodextrin. Molecules 2022, 27, 4580. https://doi.org/10.3390/molecules27144580

AMA Style

Machado RD, Silva JCG, Silva LAD, Oliveira GdAR, Lião LM, Lima EM, de Morais MC, da Conceição EC, Rezende KR. Improvement in Solubility–Permeability Interplay of Psoralens from Brosimum gaudichaudii Plant Extract upon Complexation with Hydroxypropyl-β-cyclodextrin. Molecules. 2022; 27(14):4580. https://doi.org/10.3390/molecules27144580

Chicago/Turabian Style

Machado, Rúbia Darc, Júlio C. G. Silva, Luís A. D. Silva, Gerlon de A. R. Oliveira, Luciano M. Lião, Eliana M. Lima, Mariana C. de Morais, Edemilson C. da Conceição, and Kênnia R. Rezende. 2022. "Improvement in Solubility–Permeability Interplay of Psoralens from Brosimum gaudichaudii Plant Extract upon Complexation with Hydroxypropyl-β-cyclodextrin" Molecules 27, no. 14: 4580. https://doi.org/10.3390/molecules27144580

APA Style

Machado, R. D., Silva, J. C. G., Silva, L. A. D., Oliveira, G. d. A. R., Lião, L. M., Lima, E. M., de Morais, M. C., da Conceição, E. C., & Rezende, K. R. (2022). Improvement in Solubility–Permeability Interplay of Psoralens from Brosimum gaudichaudii Plant Extract upon Complexation with Hydroxypropyl-β-cyclodextrin. Molecules, 27(14), 4580. https://doi.org/10.3390/molecules27144580

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