Development of food grade 3D printable ink based on pectin containing cannabidiol/cyclodextrin inclusion complexes

References

• Lv P, Zhang D, Guo M, et al. Structural analysis and cytotoxicity of host-guest inclusion complexes of cannabidiol with three native cyclodextrins. J Drug Deliv Sci Technol. 2019;51:337–344.
   Web of Science ®Google Scholar
• Burstein S. Cannabidiol (CBD) and its analogs: a review of their effects on inflammation. Bioorg Med Chem. 2015;23(7):1377–1385.
   PubMed Web of Science ®Google Scholar
• Dinu AR, Rogobete AF, Bratu T, et al. Cannabis Sativa revisited—crosstalk between microRNA expression, inflammation, oxidative stress, and endocannabinoid response system in critically ill patients with Sepsis. Cells. 2020;9(2):307.
   Web of Science ®Google Scholar
• Millar SA, Stone NL, Yates AS, et al. A systematic review on the pharmacokinetics of cannabidiol in humans. Front Pharmacol. 2018;9:1365.
   PubMed Web of Science ®Google Scholar
• Sarris J, Sinclair J, Karamacoska D, et al. Medicinal cannabis for psychiatric disorders: a clinically-focused systematic review. BMC Psychiatry. 2020;20(1):24.
   PubMed Web of Science ®Google Scholar
• Wassmann CS, Højrup P, Klitgaard JK. Cannabidiol is an effective helper compound in combination with bacitracin to kill Gram-positive bacteria. Sci Rep. 2020;10(1):1–12.
   PubMed Web of Science ®Google Scholar
• Ivanov VN, Grabham PW, Wu C-C, et al. Inhibition of autophagic flux differently modulates cannabidiol-induced death in 2D and 3D glioblastoma cell cultures. Sci Rep. 2020;10(1):2687.
   Web of Science ®Google Scholar
• Tayo B, Taylor L, Sahebkar F, et al. A phase I, open-label, parallel-group, single-dose trial of the pharmacokinetics, safety, and tolerability of cannabidiol in subjects with mild to severe renal impairment. Clin Pharmacokinet. 2020;59(6):747–755.
   PubMed Web of Science ®Google Scholar
• Mannila J, Järvinen T, Järvinen K, et al. Precipitation complexation method produces cannabidiol/β-cyclodextrin inclusion complex suitable for sublingual administration of cannabidiol. J Pharm Sci. 2007;96(2):312–319.
   PubMed Web of Science ®Google Scholar
• Izgelov D, Shmoeli E, Domb AJ, et al. The effect of medium chain and long chain triglycerides incorporated in self-nano emulsifying drug delivery systems on oral absorption of cannabinoids in rats. Int J Pharm. 2020;580:119201.
   PubMed Web of Science ®Google Scholar
• Kolakovic R, Viitala T, Ihalainen P, et al. Printing technologies in fabrication of drug delivery systems. Expert Opin Drug Deliv. 2013;10(12):1711–1723.
   PubMed Web of Science ®Google Scholar
• Preis M, Breitkreutz J, Sandler N. Perspective: concepts of printing technologies for oral film formulations. Int J Pharm. 2015;494(2):578–584.
   PubMed Web of Science ®Google Scholar
• Eleftheriadis GK, Monou PK, Bouropoulos N, et al. In vitro evaluation of 2D-printed edible films for the buccal delivery of diclofenac sodium. Materials. 2018;11(5):864.
   Web of Science ®Google Scholar
• Tian Y, Orlu M, Woerdenbag HJ, et al. Oromucosal films: from patient centricity to production by printing techniques. Expert Opin Drug Deliv. 2019;16(9):981–993.
   PubMed Web of Science ®Google Scholar
• Trofimiuk M, Wasilewska K, Winnicka K. How to modify drug release in paediatric dosage forms? Novel technologies and modern approaches with regard to children’s population. IJMS. 2019;20(13):3200.
   Google Scholar
• Gioumouxouzis CI, Karavasili C, Fatouros DG. Recent advances in pharmaceutical dosage forms and devices using additive manufacturing technologies. Drug Discov Today. 2019;24(2):636–643.
   PubMed Web of Science ®Google Scholar
• Goyanes A, Buanz ABM, Basit AW, et al. Fused-filament 3D printing (3DP) for fabrication of tablets. Int J Pharm. 2014;476(1–2):88–92.
   PubMed Web of Science ®Google Scholar
• Trenfield SJ, Xian Tan H, Awad A, et al. Track-and-trace: novel anti-counterfeit measures for 3D printed personalized drug products using smart material inks. Int J Pharm. 2019;567:118443.
   PubMed Web of Science ®Google Scholar
• Maroni A, Melocchi A, Parietti F, et al. 3D printed multi-compartment capsular devices for two-pulse oral drug delivery. J Control Release. 2017;268:10–18.
   PubMed Web of Science ®Google Scholar
• Pereira BC, Isreb A, Forbes RT, et al ‘Temporary plasticiser’: a novel solution to fabricate 3D printed patient-centred cardiovascular ‘Polypill’ architectures. Eur J Pharm Biopharm. 2019;135:94–103.
   PubMed Web of Science ®Google Scholar
• Goyanes A, Fina F, Martorana A, et al. Development of modified release 3D printed tablets (printlets) with pharmaceutical excipients using additive manufacturing. Int J Pharm. 2017;527(1–2):21–30.
   PubMedGoogle Scholar
• Isreb A, Baj K, Wojsz M, et al 3D printed oral theophylline doses with innovative ‘radiator-like’ design: impact of polyethylene oxide (PEO) molecular weight. Int J Pharm. 2019;564:98–105.
   PubMed Web of Science ®Google Scholar
• Eleftheriadis GK, Katsiotis CS, Bouropoulos N, et al. FDM-printed pH-responsive capsules for the oral delivery of a model macromolecular dye. Pharm Dev Technol. 2020;25(4):517–523.
   PubMed Web of Science ®Google Scholar
• Gioumouxouzis CI, Baklavaridis A, Katsamenis OL, et al. A 3D printed bilayer oral solid dosage form combining metformin for prolonged and glimepiride for immediate drug delivery. Eur J Pharm Sci. 2018;120:40–52.
   PubMed Web of Science ®Google Scholar
• Eleftheriadis GK, Monou PK, Bouropoulos N, et al. Fabrication of mucoadhesive buccal films for local administration of ketoprofen and lidocaine hydrochloride by combining fused deposition modeling and inkjet printing. J Pharm Sci. 2020;S0022–3549(20)30271–9.
   Google Scholar
• Eleftheriadis GK, Ritzoulis C, Bouropoulos N, et al. Unidirectional drug release from 3D printed mucoadhesive buccal films using FDM technology: in vitro and ex vivo evaluation. Eur J Pharm Biopharm. 2019;144:180–192.
   PubMed Web of Science ®Google Scholar
• Eleftheriadis GK, Kc Andreadis DA, Tzetzis D, Ritzoulis C, et al. Inkjet printing of a thermolabile model drug onto FDM-printed substrates: formulation and evaluation. Drug Dev Ind Pharm. 2020;1–12.
   PubMed Web of Science ®Google Scholar
• Jamróz W, Kurek M, Łyszczarz E, et al. 3D printed orodispersible films with Aripiprazole. Int J Pharm. 2017;533(2):413–420.
   PubMed Web of Science ®Google Scholar
• Ehtezazi T, Algellay M, Islam Y, et al. The application of 3D printing in the formulation of multilayered fast dissolving oral films. J Pharm Sci. 2018;107(4):1076–1085.
   PubMed Web of Science ®Google Scholar
• Devine DM. Polymer-based additive manufacturing: biomedical applications. Cham: Springer International Publishing; 2019
   Google Scholar
• Jiang H, Fu J, Li M, et al. 3D-printed wearable personalized orthodontic retainers for sustained release of clonidine hydrochloride. AAPS PharmSciTech. 2019;20(7):260.
   PubMed Web of Science ®Google Scholar
• Goyanes A, Det-Amornrat U, Wang J, et al. 3D scanning and 3D printing as innovative technologies for fabricating personalized topical drug delivery systems. J Controlled Release. 2016;234:41–48.
   PubMed Web of Science ®Google Scholar
• Water JJ, Bohr A, Boetker J, et al. Three-dimensional printing of drug-eluting implants: preparation of an antimicrobial polylactide feedstock material. J Pharm Sci. 2015;104(3):1099–1107.
   PubMed Web of Science ®Google Scholar
• Eleftheriadis GK, Katsiotis CS, Genina N, et al. Manufacturing of hybrid drug delivery systems by utilizing the fused filament fabrication (FFF) technology. Expert Opin Drug Deliv. 2020;0:1–5.
   Google Scholar
• Li Q, Guan X, Cui M, et al. Preparation and investigation of novel gastro-floating tablets with 3D extrusion-based printing. Int J Pharm. 2018;535(1–2):325–332.
   PubMed Web of Science ®Google Scholar
• Haring AP, Tong Y, Halper J, et al. Programming of multicomponent temporal release profiles in 3D printed polypills via core–shell, multilayer, and gradient concentration profiles. Adv Healthcare Mater. 2018;7(16):1800213.
   Web of Science ®Google Scholar
• Khaled SA, Burley JC, Alexander MR, et al. 3D printing of five-in-one dose combination polypill with defined immediate and sustained release profiles. J Control Release. 2015;217:308–314.
   PubMed Web of Science ®Google Scholar
• Dankar I, Haddarah A, Omar FEL, et al. 3D printing technology: the new era for food customization and elaboration. Trends Food Sci Technol. 2018;75:231–242.
   Web of Science ®Google Scholar
• Andriotis EG, Eleftheriadis GK, Karavasili C, et al. Development of bio-active patches based on pectin for the treatment of ulcers and wounds using 3D-bioprinting technology. Pharmaceutics. 2020;12(1):56.
   Web of Science ®Google Scholar
• Thakur BR, Singh RK, Handa AK. Chemistry and uses of pectin-a review. Crit Rev Food Sci Nutr. 1997;37(1):47–73.
   PubMed Web of Science ®Google Scholar
• Liu L, Fishman ML, Kost J, et al. Pectin-based systems for colon-specific drug delivery via oral route. Biomaterials. 2003;24(19):3333–3343.
   PubMed Web of Science ®Google Scholar
• Rubinstein A. Microbially controlled drug delivery to the colon. Biopharm Drug Dispos. 1990;11(6):465–475.
   PubMed Web of Science ®Google Scholar
• Gambaro V, Dell’Acqua L, Farè F, et al. Determination of primary active constituents in Cannabis preparations by high-resolution gas chromatography/flame ionization detection and high-performance liquid chromatography/UV detection. Anal Chim Acta. 2002;468(2):245–254.
   Web of Science ®Google Scholar
• Marques MRC, Loebenberg R, Almukainzi M. Simulated biological fluids with possible application in dissolution testing. Dissolution Technol. 2011;18(3):15–28.
   Web of Science ®Google Scholar
• Günter EA, Markov PA, Melekhin AK, et al. Preparation and release characteristics of mesalazine loaded calcium pectin-silica gel beads based on callus cultures pectins for colon-targeted drug delivery. Int J Biol Macromol. 2018;120(Pt B):2225–2233.
   PubMedGoogle Scholar
• Challa R, Ahuja A, Ali J, et al. Cyclodextrins in drug delivery: an updated review. AAPS PharmSciTech. 2005;6(2):E329–E357.
   PubMed Web of Science ®Google Scholar
• Higuchi T, Connors A. Phase solubility techniques. Adv Anal Chem Instrum. 1965;4:117–212.
   Google Scholar
• Cannabis Oil Analysis using FTIR | Spectroscopy Solutions - Specac [Internet]. [cited 2020 Feb 21]. Available from: https://www.specac.com/en/news/calendar/2018/08/cannabis-oil-ftir-analysis
   Google Scholar
• Barman BK, Rajbanshi B, Yasmin A, et al. Exploring inclusion complexes of ionic liquids with α- and β- cyclodextrin by NMR, IR, mass, density, viscosity, surface tension and conductance study. J Mol Struct. 2018;1159:205–215.
   Web of Science ®Google Scholar
• Stinchcomb AL, Valiveti S, Hammell DC, et al Human skin permeation of Delta8-tetrahydrocannabinol, cannabidiol and cannabinol. J Pharm Pharmacol. 2004;56(3):291–297.
   PubMed Web of Science ®Google Scholar
• Figueiras A, Carvalho RA, Ribeiro L, et al Solid-state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified beta-cyclodextrin. Eur J Pharm Biopharm. 2007;67(2):531–539.
   PubMed Web of Science ®Google Scholar
• Li N, Zhang Y-H, Wu Y-N, et al Inclusion complex of trimethoprim with beta-cyclodextrin. J Pharm Biomed Anal. 2005;39(3–4):824–829.
   PubMed Web of Science ®Google Scholar
• De Paula D, Oliveira DCR, Tedesco AC, et al. Enhancing effect of modified beta-cyclodextrins on in vitro skin permeation of estradiol. Rev Bras Cienc Farm. 2007;43(1):111–120.
   Google Scholar
• Sambasevam K, Mohamad S, Sarih N, et al. Synthesis and characterization of the inclusion complex of β-cyclodextrin and Azomethine. Int J Mol Sci. 2013;14(2):3671–3682.
   PubMed Web of Science ®Google Scholar
• Sideris EE, Georgiou CA, Koupparis MA, et al. Automated flow-injection serial dynamic dialysis technique in the study of drug binding with cyclodextrins. Anal Chim Acta. 1994;289(1):87–95.
   Web of Science ®Google Scholar
• Bueno MS, Chierentin L, Bongioanni A, et al. β-cyclodextrin complexation as an approach to enhance the biopharmaceutical properties of Norfloxacin B Hydrate. Carbohydr Res. 2019;485:107818
   PubMed Web of Science ®Google Scholar
• Stella VJ, Rao VM, Zannou EA, et al. Mechanisms of drug release from cyclodextrin complexes. Adv Drug Deliv Rev. 1999;36(1):3–16.
   PubMed Web of Science ®Google Scholar
• Vancauwenberghe V, Katalagarianakis L, Wang Z, et al. Pectin based food-ink formulations for 3-D printing of customizable porous food simulants. Innov Food Sci Emerg Technol. 2017;42:138–150.
   Web of Science ®Google Scholar
• Giusto G, Vercelli C, Comino F, et al. A new, easy-to-make pectin-honey hydrogel enhances wound healing in rats. BMC Complement Altern Med. 2017;17(1):266.
   PubMedGoogle Scholar
• Jug M, Maestrelli F, Mura P. Native and polymeric β-cyclodextrins in performance improvement of chitosan films aimed for buccal delivery of poorly soluble drugs. J Incl Phenom Macrocycl Chem. 2012;74(1–4):87–97.
   Web of Science ®Google Scholar
• Gadalla HH, Mohammed FA, El-Sayed AM, et al. Colon-targeting of progesterone using hybrid polymeric microspheres improves its bioavailability and in vivo biological efficacy. Int J Pharm. 2020;577:119070.
   PubMedGoogle Scholar
• Abbasi M, Sohail M, Minhas MU, et al. Novel biodegradable pH-sensitive hydrogels: An efficient controlled release system to manage ulcerative colitis. Int J Biol Macromol. 2019;136:83–96.
   PubMed Web of Science ®Google Scholar
• Shahdadi Sardou H, Akhgari A, Afrasiabi Garekani H, et al. Screening of different polysaccharides in a composite film based on Eudragit RS for subsequent use as a coating for delivery of 5-ASA to colon. Int J Pharm. 2019;568:118527.
   PubMedGoogle Scholar
• Costa P, Sousa Lobo JM. Modeling and comparison of dissolution profiles. Eur J Pharm Sci. 2001;13(2):123–133.
   PubMed Web of Science ®Google Scholar