Impact Of Penetratin Stereochemistry On The Oral Bioavailability Of Insulin-Loaded Solid Lipid Nanoparticles

References

• Gedawy A, Martinez J, Al-Salami H, Dass CR. Oral insulin delivery: existing barriers and current counter-strategies. J Pharm Pharmacol. 2018;70(2):197–213. doi:10.1111/jphp.1285229193053
   PubMed Web of Science ®Google Scholar
• Wong CY, Martinez J, Dass CR. Oral delivery of insulin for treatment of diabetes: status quo, challenges and opportunities. J Pharm Pharmacol. 2016;68(9):1093–1108. doi:10.1111/jphp.1260727364922
   PubMed Web of Science ®Google Scholar
• Khan Ghilzai NM. New developments in insulin delivery. Drug Dev Ind Pharm. 2003;29(3):253–265. doi:10.1081/DDC-12001819912741607
   PubMed Web of Science ®Google Scholar
• Smart AL, Gaisford S, Basit AW. Oral peptide and protein delivery: intestinal obstacles and commercial prospects. Expert Opin Drug Deliv. 2014;11(8):1323–1335. doi:10.1517/17425247.2014.91707724816134
   PubMed Web of Science ®Google Scholar
• Lundquist P, Artursson P. Oral absorption of peptides and nanoparticles across the human intestine: opportunities, limitations and studies in human tissues. Adv Drug Deliv Rev. 2016;106(Pt B):256–276. doi:10.1016/j.addr.2016.07.00727496705
   PubMed Web of Science ®Google Scholar
• Kamei N, Morishita M, Eda Y, Ida N, Nishio R, Takayama K. Usefulness of cell-penetrating peptides to improve intestinal insulin absorption. J Control Release. 2008;132(1):21–25. doi:10.1016/j.jconrel.2008.08.00118727945
   PubMed Web of Science ®Google Scholar
• Khafagy E-S, Iwamae R, Kamei N, Takeda-Morishita M. Region-dependent role of cell-penetrating peptides in insulin absorption across the rat small intestinal membrane. AAPS J. 2015;17(6):1427–1437. doi:10.1208/s12248-015-9804-y26216471
   PubMedGoogle Scholar
• Nielsen EJ, Yoshida S, Kamei N, et al. In vivo proof of concept of oral insulin delivery based on a co-administration strategy with the cell-penetrating peptide penetratin. J Control Release. 2014;189:19–24. doi:10.1016/j.jconrel.2014.06.02224973720
   PubMed Web of Science ®Google Scholar
• Gamboa JM, Leong KW. In vitro and in vivo models for the study of oral delivery of nanoparticles. Adv Drug Deliv Rev. 2013;65(6):800–810. doi:10.1016/j.addr.2013.01.00323415952
   PubMed Web of Science ®Google Scholar
• Fan W, Xia D, Zhu Q, Hu L, Gan Y. Intracellular transport of nanocarriers across the intestinal epithelium. Drug Discov Today. 2016;21(5):856–863. doi:10.1016/j.drudis.2016.04.00727094490
   PubMed Web of Science ®Google Scholar
• Beloqui A, des Rieux A, Préat V. Mechanisms of transport of polymeric and lipidic nanoparticles across the intestinal barrier. Adv Drug Deliv Rev. 2016;106(PtB):242–255. doi:10.1016/j.addr.2016.04.01427117710
   PubMedGoogle Scholar
• Silva S, Almeida AJ, Vale N. Combination of cell-penetrating peptides with nanoparticles for therapeutic application: a review. Biomolecules. 2019;9(1):pii: E22. doi:10.3390/biom9010022
   Web of Science ®Google Scholar
• Farkhani SM, Valizadeh A, Karami H, Mohammadi S, Sohrabi N, Badrzadeh F. Cell penetrating peptides: efficient vectors for delivery of nanoparticles, nanocarriers, therapeutic and diagnostic molecules. Peptides. 2014;57:78–94. doi:10.1016/j.peptides.2014.04.01524795041
   PubMed Web of Science ®Google Scholar
• Guo F, Zhang M, Gao Y, et al. Modified nanoparticles with cell-penetrating peptide and amphipathic chitosan derivative for enhanced oral colon absorption of insulin: preparation and evaluation. Drug Deliv. 2016;23:2003–2014. doi:10.3109/10717544.2015.104848926181840
   PubMed Web of Science ®Google Scholar
• Guo F, Ouyang T, Peng T, et al. Enhanced oral absorption of insulin using colon-specific nanoparticles co-modified with amphiphilic chitosan derivatives and cell-penetrating peptides. Biomater Sci. 2019;7:1493–1506. doi:10.1039/c8bm01485j30672923
   PubMedGoogle Scholar
• Liu X, Liu C, Zhang W, Xie C, Wei G, Lu W. Oligoarginine-modified biodegradable nanoparticles improve the intestinal absorption of insulin. Int J Pharm. 2013;448:159–167. doi:10.1016/j.ijpharm23538098
   PubMed Web of Science ®Google Scholar
• Zhu S, Chen S, Gao Y, et al. Enhanced oral bioavailability of insulin using PLGA nanoparticles co-modified with cell-penetrating peptides and engrailed secretion peptide (Sec). Drug Deliv. 2016;23(6):1980–1991. doi:10.3109/10717544.2015.104347226181841
   PubMed Web of Science ®Google Scholar
• Sheng J, He H, Han L, et al. Enhancing insulin oral absorption by using mucoadhesive nanoparticles loaded with LMWP-linked insulin conjugates. J Control Release. 2016;233:181–190. doi:10.1016/j.jconrel.2016.05.01527178809
   PubMed Web of Science ®Google Scholar
• Yang L, Li M, Sun Y, Zhang L. A cell-penetrating peptide conjugated carboxymethyl-β-cyclodextrin to improve intestinal absorption of insulin. Int J Biol Macromol. 2018;111:685–695. doi:10.1016/j.ijbiomac.2018.01.07729343452
   PubMed Web of Science ®Google Scholar
• Barbari GR, Dorkoosh FA, Amini M, et al. A novel nanoemulsion-based method to produce ultrasmall, water-dispersible nanoparticles from chitosan, surface modified with cell-penetrating peptide for oral delivery of proteins and peptides. Int J Nanomedicine. 2017;12:3471–3483. doi:10.2147/IJN.S11606328496323
   PubMedGoogle Scholar
• Manosroi A, Tangjai T, Sutthiwanjampa C, et al. Hypoglycemic activity and stability enhancement of human insulin-tat mixture loaded in elastic anionic niosomes. Drug Deliv. 2016;23:3157–3167. doi:10.3109/10717544.2016.115784026908204
   PubMed Web of Science ®Google Scholar
• Barbari GR, Dorkoosh F, Amini M, et al. Synthesis and characterization of a novel peptide-grafted Cs and evaluation of its nanoparticles for the oral delivery of insulin, in vitro, and in vivo study. Int J Nanomedicine. 2018;13:5127–5138. doi:10.2147/IJN.S16124030233176
   PubMed Web of Science ®Google Scholar
• Müller RH, Mäder K, Gohla S. Solid lipid nanoparticles (SLN) for controlled drug delivery - a review of the state of the art. Eur J Pharm Biopharm. 2000;50:161–177. doi:10.1016/S0939-6411(00)00087-410840199
   PubMed Web of Science ®Google Scholar
• Mehnert W, Mäder K. Solid lipid nanoparticles: production, characterization and applications. Adv Drug Deliv Rev. 2001;47:165–196. doi:10.1016/S0169-409X(01)00105-311311991
   PubMed Web of Science ®Google Scholar
• Souto EB, Müller RH. Lipid nanoparticles: effect on bioavailability and pharmacokinetic changes. Handb Exp Pharmacol. 2010;197:115–141. doi:10.1007/978-3-642-00477-3_4
   PubMedGoogle Scholar
• Muchow M, Maincent P, Müller RH. Lipid nanoparticles with a solid matrix (SLN, NLC, LDC) for oral drug delivery. Drug Dev Ind Pharm. 2008;34:1394–1405. doi:10.1080/0363904080213006118665980
   PubMed Web of Science ®Google Scholar
• Niu Z, Conejos-Sánchez I, Griffin BT, O’Driscoll CM, Alonso MJ. Lipid-based nanocarriers for oral peptide delivery. Adv Drug Deliv Rev. 2016;106:337–354. doi:10.1016/j.addr.2016.04.00127080735
   PubMed Web of Science ®Google Scholar
• McClements DJ. Encapsulation, protection, and delivery of bioactive proteins and peptides using nanoparticle and microparticle systems: a review. Adv Colloid Interface Sci. 2018;253:1–22. doi:10.1016/j.cis.2018.02.00229478671
   PubMed Web of Science ®Google Scholar
• du Plessis LH, Marais EB, Mohammed F, Kotzé AF. Applications of lipid based formulation technologies in the delivery of biotechnology-based therapeutics. Curr Pharm Biotechnol. 2014;15(7):659–672. doi:10.2174/138920101566614080416314325091118
   PubMedGoogle Scholar
• Zhang Z, Lv H, Zhou J. Novel solid lipid nanoparticles as carriers for oral administration of insulin. Pharmazie. 2009;64:574–578. doi:10.1691/ph.2009.905119827297
   PubMed Web of Science ®Google Scholar
• Zhang ZH, Zhang YL, Zhou JP, Lv HX. Solid lipid nanoparticles modified with stearic acid-octaarginine for oral administration of insulin. Int J Nanomedicine. 2012;7:3333–3339. doi:10.2147/IJN.S3171122848162
   PubMed Web of Science ®Google Scholar
• Yassin AE, Anwer MK, Mowafy HA, El-Bagory IM, Bayomi MA, Alsarra IA. Optimization of 5-flurouracil solid-lipid nanoparticles: a preliminary study to treat colon cancer. Int J Med Sci. 2010;7(6):398–408. doi:10.7150/ijms.7.39821103076
   PubMed Web of Science ®Google Scholar
• Ansari MJ, Anwer MK, Jamil S, et al. Enhanced oral bioavailability of insulin-loaded solid lipid nanoparticles: pharmacokinetic bioavailability of insulin-loaded solid lipid nanoparticles in diabetic rats. Drug Deliv. 2016;23(6):1972–1979. doi:10.3109/10717544.2015.103966626017100
   PubMed Web of Science ®Google Scholar
• Asada H, Douen T, Mizokoshi Y, et al. Stability of acyl derivatives of insulin in the small intestine: relative importance of insulin association characteristics in aqueous solution. Pharm Res. 1994;11:1115–1120. doi:10.1023/A:10189286138377971711
   PubMed Web of Science ®Google Scholar
• Chen C, Fan T, Jin Y, et al. Orally delivered salmon calcitonin-loaded solid lipid nanoparticles prepared by micelle-double emulsion method via the combined use of different solid lipids. Nanomedicine (Lond). 2013;8(7):1085–1100. doi:10.2217/nnm.12.14123075315
   PubMed Web of Science ®Google Scholar
• Aditya NP, Aditya S, Yang H, Kim HW, Park SO, Ko S. Co-delivery of hydrophobic curcumin and hydrophilic catechin by a water-in-oil-in-water double emulsion. Food Chem. 2015;173:7–13. doi:10.1016/j.foodchem.2014.09.13125465989
   PubMed Web of Science ®Google Scholar
• Khafagy E-S, Morishita M, Takayama K. The role of intermolecular interactions with penetratin and its analogue on the enhancement of absorption of nasal therapeutic peptides. Int J Pharm. 2010;388(1–2):209–212. doi:10.1016/j.ijpharm.2009.12.06020060451
   PubMedGoogle Scholar
• Budhian A, Siegel SJ, Winey KI. Haloperidol-loaded PLGA nanoparticles: systematic study of particle size and drug content. Int J Pharm. 2007;336(2):367–375. doi:10.1016/j.ijpharm.2006.11.06117207944
   PubMed Web of Science ®Google Scholar
• Kassem M, Ali A, El-Assal M, El-badrawy A. Formulation, characterization and in vivo application of oral insulin nanotechnology using different biodegradable polymers: advanced drug delivery system. Int J Pharm Sci Res. 2018;9(9):3664–3677. doi:10.13040/IJPSR.0975-8232.9(9).3664-77
   Web of Science ®Google Scholar
• Azevedo JR, Sizilio RH, Brito MB, et al. Physical and chemical characterization insulin loaded chitosan-TPP nanoparticles. J Therm Anal Calorim. 2011;106(3):685–689. doi:10.1007/s10973-011-1429-5
   Web of Science ®Google Scholar
• Torchilin VP. Tat peptide-mediated intracellular delivery of pharmaceutical nanocarriers. Adv Drug Deliv Rev. 2008;60(4–5):548–558. doi:10.1016/j.addr.2007.10.00818053612
   PubMed Web of Science ®Google Scholar
• Gupta B, Torchilin VP. Transactivating transcriptional activator-mediated drug delivery. Expert Opin Drug Deliv. 2006;3(2):177–190. doi:10.1517/17425247.3.2.17716506946
   PubMedGoogle Scholar
• Zorko M, Langel U. Cell-penetrating peptides: mechanism and kinetics of cargo delivery. Adv Drug Deliv Rev. 2005;57(4):529–545. doi:10.1016/j.addr.2004.10.01015722162
   PubMed Web of Science ®Google Scholar
• Chung SK, Maiti KK, Lee WS. Recent advances in cell-penetrating, non-peptide molecular carriers. Int J Pharm. 2008;354(1–2):16–22. doi:10.1016/j.ijpharm.2007.08.01617890027
   PubMedGoogle Scholar
• Wender PA, Mitchell DJ, Pattabiraman K, Pelkey ET, Steinman L, Rothbard JB. The design, synthesis and evaluation of molecules that enable or enhance cellular uptake: peptoid molecular transporters. Proc Natl Acad Sci USA. 2000;97(24):13003–13008. doi:10.1073/pnas.97.24.1300311087855
   PubMed Web of Science ®Google Scholar
• Kosuge M, Takeuchi T, Nakase I, Jones AT, Futaki S. Cellular internalization and distribution of arginine-rich peptides as a function of extracellular peptide concentration, serum, and plasma membrane associated proteoglycans. Bioconjug Chem. 2008;19(3):656–664. doi:10.1021/bc700289w18269225
   PubMedGoogle Scholar
• Meade BR, Dowdy SF. Exogenous siRNA delivery using peptide transduction domains/cell penetrating peptides. Adv Drug Deliv Rev. 2007;59(2–3):134–140. doi:10.1016/j.addr.2007.03.00417451840
   PubMedGoogle Scholar
• Pappenheimer JR, Dahl CE, Karnovsky ML, Maggio JE. Intestinal absorption and excretion of octapeptides composed of D amino acids. Proc Natl Acad Sci U S A. 1994;91(5):1942–1945. doi:10.1073/pnas.91.5.19428127911
   PubMedGoogle Scholar
• Khafagy E-S, Morishita M, Kamei N, Eda Y, Ikeno Y, Takayama K. Efficiency of cell-penetrating peptides on the nasal and intestinal absorption of therapeutic peptides and proteins. Int J Pharm. 2009;381(1):49–55. doi:10.1016/j.ijpharm.2009.07.02219646515
   PubMedGoogle Scholar
• Kamei N, Aoyama Y, Khafagy E-S, Henmi M, Takeda-Morishita M. Effect of different intestinal conditions on the intermolecular interaction between insulin and cell-penetrating peptide penetratin and on its contribution to stimulation of permeation through intestinal epithelium. Eur J Pharm Biopharm. 2015;94:42–51. doi:10.1016/j.ejpb.2015.04.03025960330
   PubMed Web of Science ®Google Scholar
• Khafagy E-S, Morishita M, Isowa K, Imai J, Takayama K. Effect of cell-penetrating peptides on the nasal absorption of insulin. J Control Release. 2009;133(2):103–108. doi:10.1016/j.jconrel.2008.09.07618930084
   PubMedGoogle Scholar
• Niu Z, Samaridou E, Jaumain E, et al. PEG-PGA enveloped octaarginine-peptide nanocomplexes: an oral peptide delivery strategy. J Control Release. 2018;276:125–139. doi:10.1016/j.jconrel.2018.03.00429518466
   PubMed Web of Science ®Google Scholar
• Khafagy E-S, Morishita M, Ida N, Nishio R, Isowa K, Takayama K. Structural requirements of penetratin absorption enhancement efficiency for insulin delivery. J Control Release. 2010;143(3):302–310. doi:10.1016/j.jconrel.2010.01.01920096319
   PubMedGoogle Scholar