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Supercritical Fluid Technology for Development of Solid Lipid Particles Entrapping Curcumin

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Supercritical Fluid Technology for Development of Solid Lipid Particles Entrapping Curcumin DOUTORADO EM ENGENHARIA INDUSTRIAL ANDRÉ LUIZ SANTOS SÃO PEDRO Supercritical fluid technology for development of solid lipid particles entrapping curcumin SALVADOR 2016 UNIVERSIDADE FEDERAL DA BAHIA ESCOLA POLITÉCNICA PROGRAMA DE PÓS-GRADUAÇÃO EM ENGENHARIA INDUSTRIAL Supercritical fluid technology for development of solid lipid particles entrapping curcumin by André Luiz Santos São Pedro Salvador, 2016 André Luiz Santos São Pedro Supercritical fluid technology for development of solid lipid particles entrapping curcumin Thesis presented to the Industrial Engineering Post- Graduation Program in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Industrial Engineering, under supervision of Prof. Dr. Elaine C. de M. Cabral Albuquerque, Prof. Dr. Silvio A. B. Vieira de Melo, with co-supervision of Prof. Dr. Alberto Bertucco during sandwich PhD period and contribution of Prof. Dr. Rosana Lopes Fialho and Prof Dr. Cristiane Flora Villareal. Salvador, 2016 II I dedicate this work to my beloved and one of a kind mum Rute Maria Santos São Pedro (in memoriam) III "Just because someone stumbles and loses their path, doesn't mean they're lost forever." (Prof Charles Francis Xavier) “The glory of friendship is not the outstretched hand, not the kindly smile, nor the joy of companionship; it is the spiritual inspiration that comes to one when you discover that someone else believes in you and is willing to trust you with a friendship.” (Ralph Waldo Emerson) IV Acknowledgments During the course of this work there were so many changes and ups and downs on its own conception, as well as on its execution. To walk through a path like this without taking shortcuts or being favored in any sense demands a lot of faith, effort and mainly a bunch of help. So, gratitude is the fairest way to follow. Firstly I dedicate all moments of resilience, all strength to stand, every little push, every single insight on the construction of this thesis to the All-love Almighty God. Certainly I could not get at this point without the wisdom, amity and endless love of my sisters and brothers lent by God Laisse Evangelista, Suzana Moura, Lusiane Bahia, Danilo dos Anjos, Caroline Moura, Lucas Ramos, Silvia Cruvinel, Viviane Guimarães, Viviane Arrais and Berthier Alves. I cannot thank enough to Islane Espírito Santo, Cinara Vasconcelos, Cassia Detoni, Tamara Angelo, Alice Kiperstok, Ludmila Chaves, Milena Lima, Maiana Pitombo, Paula Becerra, Shana Menezes and Fernanda Magalhães. You not only lighted up my scientific path, but also, made me a greater man. I could never forget my beloved "awesome" worldwide fellows Maria Grazia Tremo, Jacopo Sacquegno, Gianluca Tornese, Mattia Marini, Alice Schirone, Moritz Pfletschinger, Merili Luuk, Enric Luzán, Hannah Bridle, Amaia Goienetxea, Kaisu Halonen, Belen del Rio, Asia Firek and Fabian Selamadam who made me get confidence to believe in myself to face the unknown and not fear the struggle, and the art of partying hard. The old continent was very generous to me. To keep myself together, Federica Catena, Giovanni Rigon, Alberto Bortolami, Alessandro Simonato and Laura Decqual became true soulmates and confidants. Thanks to Sebastian Willmitzer and Metin Karaylan for support and friendship. This thesis definitely only could come to an end thanks to dedication, patience and effort of outstand co-workers-turned good friends. I am in great debit with my hardworker intern Stefania dalla Villa, the always dedicated, gifted and patient technician Lucio Gelmi and my lab colleagues and great savers Renato Cipriani, Elia Tercero, Micol della Zassa, Alberto Biasin, Nicola Michelon and Nicola Gemo from University of Padova. In the Federal Univesity of Bahia, Tatiane Woytysiak V and Robinson Carvalho were truly angels. Not only saved my life several times as also taught me essential lessons of being a good professional. Further, my deep gratitude to Cassio Santana from Fiocruz. To those who received the most challenging task of guiding I owe all my gratitude. Prof Elaine Cabral has been more than a supervisor, but a scientific mother. A role model of professional, scientist and person to be followed. Thank you for investing in me and believing in me. Prof. Silvio Melo, Profa. Rosana Fialho, Profa. Gloria Meyberg and Prof. Alberto Bertucco, I dedicate to you a great thank for introducing me into the tricky world of Engineering. Profa Cristiane Villareal, thanks for the wise advises. Also a great thank to Prof. Paolo Caliceti and Stefano Salmaso for co- supervising me and teach me so many things. Finally, I would like to thank the Coordination for the Improvement of Higher Education Personnel (CAPES) for all the support in Brazil, as well as in Italy by means of Sandwich Doctoral Institutional Program Overseas (PDSE, grant number: BEX0155/12-8). VI SÃO PEDRO, André Luiz Santos. Supercritical fluid technology for development of solid lipid particles entrapping curcumin. 2015. Doctoral Thesis - Escola Politécnica, Universidade Federal da Bahia, Salvador, 2015. Abstract Curcuma longa appears as one of the main sources of a phenolic compound with a multitarget bioactivity profile named as curcumin. As main drawbacks, the photosensitivity and high lipophilicity have limited the use of curcumin on pharmaceutical field. The encapsulation technology has been investigated as the approach of choice to overcome these limitations. Solid lipid nanoparticles (SLN®) and microparticles (SLM) have been pictured as a very interesting platforms on development of formulations for biomedical applications. Since traditional SLN®/SLM production methods possess a series of limitations, the processing by supercritical carbon dioxide (scCO2) has been widely investigated, since scCO2 is namely recognized by its special physicochemical features, at relatively mild operation conditions without any incremental toxicological risk to pharmaceutical manufacture chain. Concerning to this, the aim of this work was to investigate the use of scCO2-based technology for the production of curcumin-loaded SLN®/SLM formulations. SLM were obtained by PGSS, where [tristearin+soy phosphatidylcholine (PC)+dimethylsulfoxide (DMSO)+curcumin] mixtures were processed. Samples with (tristearin+PC)/(DMSO+curcumin) w/w ratios ranging from 65.6:1 to 3:1 were prepared either in the presence or absence of helium and then processed by PGSS. The SLM size ranged from 7.8 to 70.0 µm, and the drug loading yield was found to be between 30 and 87 drug/lipid w/w%. The particles obtained from lipid mixtures with low DMSO feed were homogeneous in size. The formulation prepared with the highest DMSO feed yielded a bimodal particle size distribution with significant aggregation. Interestingly, the use of helium in the preparation of the lipid mixture was found to improve drug loading and particle dimensional features. However, by far, the most interesting result was the obtainment of a homogenous population of SLN® within the 0.5% curcumin samples. With an average size of 118.5 nm, no indication of chemical incompatibility among curcumin and SLN® excipients was found on infrared studies and in vitro tests demonstrated that the carrier components reduced significantly the cytotoxicity of curcumin. In addition, the preparation process was not found to degrade curcumin, indicating that PGSS can be properly set-up for the preparation of curcumin lipid particles. VII SÃO PEDRO, André Luiz Santos. Supercritical fluid technology for development of solid lipid particles entrapping curcumin. 2015. Tesi di Dottorato - Escola Politécnica, Universidade Federal da Bahia, Salvador, 2015. Riassunto La Curcuma longa sorge come una delle principali fonti di un composto fenolico con un profilo bioattività multitarget conosciuto come curcumina. Come inconvenienti principali, la fotosensibilità e l'alta lipofilità limitanno l'uso della curcumina nel campo farmaceutico. La tecnologia di incapsulamento è stata studiata come metodo di scelta per superare queste limitazioni. Le nanoparticelle lipidiche solide (NLS) e microparticelle lipidiche solide (MLS) sono state descritte come piattaforme molto interessante per lo sviluppo di formulazioni per applicazioni biomediche. Poiché tradizionali metodi di produzione NLS/MLS possiedono una serie di limitazioni, il trattamento da biossido di carbonio supercritico (scCO2) è stato ampiamente studiato, poiché scCO2 è cioè riconosciuto dalle sue caratteristiche fisico-chimiche speciali, in condizioni operative relativamente blande senza alcun rischio tossicologico incrementale farmaceutica a catena. Riguardo a questo lo scopo di questa tesi è stato quello di esaminare l'uso della tecnologia a base di scCO2 per la produzione di formulazione di NLS/MLS caricate con curcumina. MLS sono stati ottenuti da PGSS, dalle miscele composti di tristearina, fosfatidilcolina di soia (PC), dimetilsolfossido (DMSO) e curcumina. I campioni con i rapporti p/p (tristearin + PC) / (DMSO + curcumina) che vanno da 65,6: 1 a 3: 1 sono stati preparati sia in presenza o assenza di elio e poi elaborati da PGSS. Il diametro medio delle MLS ha ocillato fra 7,8 e 70,0 µm e la resa di farmaco carico è stato compreso fra 30 e 87 farmaco / lipidi p/p%. Le particelle ottenute delle miscele lipidiche con basso contenuto di DMSO hanno presentato dimensioni omogenei. Le formulazione preparate con il massimo contenuto di DMSO hanno prodotto particelle con dimensioni di distribuzione bimodale con l'aggregazione significativa. È interessante notare che l'uso di elio nella preparazione della
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