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Extract of curcuminoids loaded on polycaprolactone and pluronic nanoparticles: chemical and structural properties

  • Lizandra Viana Maurat da RochaEmail author
  • Laura Coelho Merat
  • Livia Rodrigues de Menezes
  • Priscilla Vanessa Finotelli
  • Paulo Sergio Rangel Cruz da Silva
  • Maria Inês Bruno Tavares
Original Article
  • 4 Downloads

Abstract

The purpose of this work was to obtain and characterize curcuminoids loaded nanoparticles based on polycaprolactone and poloxamer whose pharmaceutical applicability justifies its relevance since polyphenolic compounds carriers have anti-inflammatory, antioxidant, antitumor and anti-amyloid potential. The curcuminoids’ extracts (CUR) were obtained from Turmeric (Curcuma longa Linn.) using acetone as organic solvent. Its chemical characterization was done by Fourier transform infrared spectroscopy (FTIR), high-performance liquid chromatography (HPLC) and chiefly by nuclear magnetic resonance (NMR). The polymeric nanoparticles (NPs) were prepared by nanoprecipitation, maintaining all reaction parameters, except for the amount of CUR incorporated in the polycaprolactone (PCL) matrix, which was, respectively, 0%, 5%, 10%, 15% and 20% (percentage in relation to PCL mass) in samples here called 0, 5, 10, 15 and 20. The obtained NPs were analyzed in suspension for size study (by dynamic light scattering—DLS), zeta potential (ZP) and color change, and in powder form, after freeze-drying, for structural study of molecular mobility (by TD-NMR), Scanning electron microscopy (SEM), encapsulation efficiency, and elucidation of composition and incorporation of the extract (by NMR and FTIR). It was possible to obtain very stable spherical CUR-NPs, of size within the nanometric scale, even after 3 months of storage. The desirable surface charge and size for biomedical applications were not effectively hampered by lyophilization as well. After nanoprecipitation there was no degradation of the CUR or chemical interaction with the polymers, which is fundamental for the maintenance, enhancement and viability of its properties. Evaluating the structural NPs’ properties, cost–benefit and possible system saturation, samples 15 and 20 demonstrated excess CUR. The methods used for both extraction and encapsulation proved to be efficient, reproducible, practical and inexpensive, which is very advantageous for a potential scaling and use of CUR-NPs in the pharmaceutical industry.

Keywords

Polycaprolactone Polymeric nanoparticles Characterization Curcuminoids Nanoprecipitation 

Notes

Acknowledgements

We acknowledge IMA/UFRJ, FF/UFRJ. We would like to thank CNPq, FAPERJ and CAPES for funding. This study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior-Brasil (CAPES)-Finance Code 001.

References

  1. Aggarwal BB, Sung B (2009) Pharmacological basis for the role of curcumin in chronic diseases: an age-old spice with modern targets. Trends Pharmacol Sci. http://linkinghub.elsevier.com/retrieve/pii/S0165614708002526
  2. Ahmed T, Gilani A-H (2014) Therapeutic potential of turmeric in Alzheimer’s disease: curcumin or curcuminoids? Phyther Res.  https://doi.org/10.1002/ptr.5030 CrossRefGoogle Scholar
  3. Alakhova DY, Kabanov AV (2014) Pluronics and MDR reversal: an update. Mol Pharm.  https://doi.org/10.1021/mp500298q CrossRefGoogle Scholar
  4. Almería B, Deng W, Fahmy TM, Gomez A (2010) Controlling the morphology of electrospray-generated PLGA microparticles fordrug delivery. J Colloid Interface Sci 343(1):125–133CrossRefGoogle Scholar
  5. Badri W, Miladi K, Nazari QA, Fessi H, Elaissari A (2017) Effect of process and formulation parameters on polycaprolactone nanoparticles prepared by solvent displacement. Colloids Surf A Physicochem Eng Aspects 516:238–244CrossRefGoogle Scholar
  6. Beck-Broichsitter M, Rytting E, Lebhardt T, Wang X, Kissel T (2010) Preparation of nanoparticles by solvent displacement for drug delivery: a shift in the “ouzo region” upon drug loading. Eur J Pharm Sci.  https://doi.org/10.1016/j.ejps.2010.06.007 CrossRefGoogle Scholar
  7. Belkacemi A, Doggui S, Dao L, Ramassamy C (2011) Challenges associated with curcumin therapy in Alzheimer disease. Expert Rev Mol Med. http://www.journals.cambridge.org/abstract_S1462399411002055
  8. Biazar E, Majdi, Zafari M, Avar M, Aminifard S, Zaeifi D (2011) Nanotoxicology and nanoparticle safety in biomedical designs. Int J Nanomed. http://www.dovepress.com/nanotoxicology-and-nanoparticle-safety-in-biomedical-designs-peer-reviewed-article-IJN
  9. Carpentier R, Lipka E, Howsam M, Betbeder D (2015) Evolution of availability of curcumin inside poly-lactic-co-glycolic acid nanoparticles: impact on antioxidant and antinitrosant properties. Int J Nanomed. http://www.dovepress.com/evolution-of-availability-of-curcumin-inside-poly-lactic-co-glycolic-a-peer-reviewed-article-IJN
  10. Champion JA, Mitragotri S (2006) Role of target geometry in phagocytosis. Proc Nat Acad Sci USA 103(13):4930–4934CrossRefGoogle Scholar
  11. Da Silva Filho CRM, de Souza AG, da Conceição MM, da Silva TG, Silva TMS, Ribeiro APL (2009) Avaliação da bioatividade dos extratos de cúrcuma (Curcuma longa L., Zingiberaceae) em Artemia salina e Biomphalaria glabrata. Rev Bras Farmacogn. http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2009000600022&lng=pt&nrm=iso&tlng=pt
  12. Dash TK, Konkimalla VB (2012) Poly-ε-caprolactone based formulations for drug delivery and tissue engineering: a review. J Control Release.  https://doi.org/10.1016/j.jconrel.2011.09.064 CrossRefGoogle Scholar
  13. Eugenio TR, Zonia GG, Robinson HE, Quirino AC, Christian V, Manuel AS (2014) Empleo de ultrasonido en la extracción de curcumina a partir de su fuente natural. Rev Cuba Plantas Med. http://scielo.sld.cu/scielo.php?script=sci_arttext&pid=S1028-47962014000100003&lng=es
  14. Fessi H, Puisieux F, Devissaguet JP, Ammoury N, Benita S (1989) Nanocapsule formation by interfacial polymer deposition following solvent displacement. Int J Pharm. http://www.jstor.org/stable/10.1086/678774
  15. Fonte P, Reis S, Sarmento B (2016) Facts and evidences on the lyophilization of polymeric nanoparticles for drug delivery. J Control Release.  https://doi.org/10.1016/j.jconrel.2016.01.034 CrossRefGoogle Scholar
  16. Gaumet M, Vargas A, Gurny R, Delie F (2008) Nanoparticles for drug delivery: the need for precision in reporting particle size parameters. Eur J Pharm Biopharm. http://linkinghub.elsevier.com/retrieve/pii/S0939641107002895
  17. George KM, Balakrishnan CV, Chandran OG, Narayana P (1981) On the extraction of oleoresin from turmeric. Indian Spices 18:7–9Google Scholar
  18. Krishnamurthy N, Mathew AG, Nambudiri ES, Shivashankar S, Lewis YS, Natarajan CP (1976) Oil and oleoresin of turmeric. Trop Sci 18(1):37–45Google Scholar
  19. Kumar A, Sawant K (2013) Encapsulation of exemestane in polycaprolactone nanoparticles: optimization, characterization, and release kinetics. Cancer Nanotechnol. http://www.cancer-nano.com/content/4/4/
  20. Kundu S, Nithiyanantham U (2013) In situ formation of curcumin stabilized shape-selective Ag nanostructures in aqueous solution and their pronounced SERS activity. RSC Adv. http://xlink.rsc.org/?DOI=c3ra44471f
  21. Lee JS, Hwang SJ, Lee DS, Kim SC, Kim DJ (2009) Formation of poly(ethylene glycol)-poly(ε-caprolactone) nanoparticles via nanoprecipitation. Macromol Res.  https://doi.org/10.1007/BF03218657 CrossRefGoogle Scholar
  22. Leung MHM, Harada T, Dai S, Kee TW (2015) Nanoprecipitation and spectroscopic characterization of curcumin-encapsulated polyester nanoparticles. Langmuir.  https://doi.org/10.1021/acs.langmuir.5b02773 CrossRefGoogle Scholar
  23. Li Q, Xiong W, Peng L, Chen H (2015) Surface modification of MPEG-b-PCL-based nanoparticles via oxidative self-polymerization of dopamine for malignant melanoma therapy. Int J Nanomed. http://www.dovepress.com/surface-modification-of-mpeg-b-pcl-based-nanoparticles-via-oxidative-s-peer-reviewed-article-IJN
  24. Liechty WB, Kryscio DR, Slaughter BV, Peppas NA (2010) Polymers for drug delivery systems. Annu Rev Chem Biomol Eng.  https://doi.org/10.1146/annurev-chembioeng-073009-100847 CrossRefGoogle Scholar
  25. Liu Z-J, Li Z, Liu L, Tang W, Wang Y, Dong M (2016) Curcumin attenuates beta-amyloid-induced neuroinflammation via activation of peroxisome proliferator-activated receptor-gamma function in a rat model of Alzheimer’s disease. Front Pharmacol. http://journal.frontiersin.org/Article/10.3389/fphar.2016.00261/abstract
  26. Maiti P, Hall TC, Paladugu L, Kolli N, Learman C, Rossignol J (2016) A comparative study of dietary curcumin, nanocurcumin, and other classical amyloid-binding dyes for labeling and imaging of amyloid plaques in brain tissue of 5×-familial Alzheimer’s disease mice. Histochem Cell Biol.  https://doi.org/10.1007/s00418-016-1464-1 CrossRefGoogle Scholar
  27. Mali AD, Bathe RS (2015) A review on sustained release drug delivery system. GCC J Sci Technol 1(4):107–123Google Scholar
  28. Mohan PRK, Sreelakshmi G, Muraleedharan CV, Joseph R (2012) Water soluble complexes of curcumin with cyclodextrins: characterization by FT-raman spectroscopy. Vib Spectrosc.  https://doi.org/10.1016/j.vibspec.2012.05.002 CrossRefGoogle Scholar
  29. Mondal D, Griffith M, Venkatraman SS (2016) Polycaprolactone-based biomaterials for tissue engineering and drug delivery: current scenario and challenges. Int J Polym Mater Polym Biomater.  https://doi.org/10.1080/00914037.2015.1103241 CrossRefGoogle Scholar
  30. Mora-Huertas CE, Fessi H, Elaissari A (2010) Polymer-based nanocapsules for drug delivery. Int J Pharm. http://linkinghub.elsevier.com/retrieve/pii/S0378517309007273
  31. Nagahama K, Sano Y, Kumano T (2015) Anticancer drug-based multifunctional nanogels through self-assembly of dextran–curcumin conjugates toward cancer theranostics. Bioorg Med Chem Lett.  https://doi.org/10.1016/j.bmcl.2015.04.062 CrossRefGoogle Scholar
  32. Naksuriya O, Okonogi S, Schiffelers RM, Hennink WE (2014) Curcumin nanoformulations: a review of pharmaceutical properties and preclinical studies and clinical data related to cancer treatment. Biomaterials 35(10):3365–3383CrossRefGoogle Scholar
  33. Nascimento CB, Moura CJ de, Cruvinel FWO, Paula YO (2006) Extração com solventes e quantificação dos curcuminóides a partir do pó de rizomas do açafrão (Curcuma longa L.) DE MARA ROSA – GO. In: Anais da 58a Reunião Anual da SBPC, p 1–2Google Scholar
  34. Nokhodchi A, Raja S, Patel P, Asare-Addo K (2012) The role of oral controlled release matrix tablets in drug delivery systems. BioImpacts 2(4):175–187Google Scholar
  35. Panyam J, Labhasetwar V (2004) Sustained cytoplasmic delivery of drugs with intracellular receptors using biodegradable nanoparticles. Mol Pharm.  https://doi.org/10.1021/mp034002c CrossRefGoogle Scholar
  36. Pitto-Barry A, Barry NPE (2014) Pluronic® block-copolymers in medicine: from chemical and biological versatility to rationalisation and clinical advances. Polym Chem. http://xlink.rsc.org/?DOI=C4PY00039K
  37. Quaglia F, Ostacolo L, Mazzaglia A, Villari V, Zaccaria D, Sciortino MT (2009) The intracellular effects of non-ionic amphiphilic cyclodextrin nanoparticles in the delivery of anticancer drugs. Biomaterials.  https://doi.org/10.1016/j.biomaterials.2008.09.035 CrossRefGoogle Scholar
  38. Rohman A, Sudjadi Devi, Ramadhani D, Nugroho A (2015) Analysis of curcumin in Curcuma longa and Curcuma xanthorriza using FTIR spectroscopy and chemometrics. Res J Med Plant.  https://doi.org/10.3923/rjmp.2015.179.186 CrossRefGoogle Scholar
  39. Rouhani S, Alizadeh N, Salimi S, Haji-Ghasemi T (2009) Ultrasonic assisted extraction of natural pigments from rhizomes of Curcuma longa L. Prog Color Color Coat. http://www.sid.ir/EN/VEWSSID/J_pdf/1033120090206.pdf
  40. Salmaso S, Caliceti P (2013) Stealth properties to improve therapeutic efficacy of drug nanocarriers. J Drug Deliv. http://www.hindawi.com/journals/jdd/2013/374252/
  41. Shubhra QTH, Tóth J, Gyenis J, Feczkó T (2014) Poloxamers for surface modification of hydrophobic drug carriers and their effects on drug delivery. Polym Rev.  https://doi.org/10.1080/15583724.2013.862544 CrossRefGoogle Scholar
  42. Sun M, Su X, Ding B, He X, Liu X, Yu A, Lou H, Zhai G (2012) Advances in nanotechnology-based delivery systems for curcumin. Nanomedicine 7(7)CrossRefGoogle Scholar
  43. Tavares MR, De Menezes LR, Dutra Filho JC, Cabral LM, Tavares MIB (2017) Surface-coated polycaprolactone nanoparticles with pharmaceutical application: structural and molecular mobility evaluation by TD-NMR. Polym Test.  https://doi.org/10.1016/j.polymertesting.2017.01.032 CrossRefGoogle Scholar
  44. Ulery BD, Nair LS, Laurencin CT (2011) Biomedical applications of biodegradable polymers. J Polym Sci Part B Polym Phys. http://doi.wiley.com/10.1002/polb.22259
  45. Villanova JCO, Oréfice RL, Cunha AS (2010) Aplicações farmacêuticas de polímeros. Polímeros. http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0104-14282010000100012&lng=pt&tlng=pt
  46. Xu B, Watkins R, Wu L, Zhang C, Davis R (2015) Natural product-based nanomedicine: recent advances and issues. Int J Nanomed. https://www.dovepress.com/natural-product-based-nanomedicine-recent-advances-and-issues-peer-reviewed-article-IJN

Copyright information

© King Abdulaziz City for Science and Technology 2019

Authors and Affiliations

  1. 1.Instituto de Macromoléculas Professora Eloisa Mano (IMA)-Universidade Federal do Rio de JaneiroRio de JaneiroBrazil
  2. 2.Faculdade de Farmácia-Universidade Federal do Rio de JaneiroRio de JaneiroBrazil

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