In vivo fate of lipid-silybin conjugate nanoparticles: Implications on enhanced oral bioavailability

Nanomedicine: Nanotechnology, Biology, and Medicine

Volumn 13, Issue 8, 2017, Pages 2643-2654

  Ma, Yuhua ^a,b   He, Haisheng ^a   Xia, Fei ^a   Li, Yingxia ^a   Lu, Yan ^a   Chen, Daofeng ^a   Qi, Jianping ^a   Lu, Yi ^a   Zhang, Wei ^a   Wu, Wei ^a  

^a FUDAN UNIVERSITY   (China)

^b QINGHAI NATIONALITIES UNIVERSITY   (China)

Author keywords

Drug delivery; Lipid drug conjugate; Oral; Silybin; Solid lipid nanoparticles

Indexed keywords

BIOCHEMISTRY; CELL CULTURE; CHAIN LENGTH; CHAINS; DRUG DELIVERY; FLAVONOIDS; NANOPARTICLES; SYNTHESIS (CHEMICAL); TARGETED DRUG DELIVERY;

ABSORPTION ENHANCEMENT; DRUG-CONJUGATES; LIPID CHAINS; ORAL; ORAL BIOAVAILABILITIES; SILYBIN; SOLID LIPID NANOPARTICLE (SLN); SOLID LIPID NANOPARTICLES;

CONTROLLED DRUG DELIVERY;

LIPID; NANOPARTICLE; SILIBININ; SOLID LIPID NANOPARTICLE; ANTIOXIDANT; SILYMARIN;

ARTICLE; CACO-2 CELL LINE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPARATIVE STUDY; CONFOCAL LASER SCANNING MICROSCOPY; COVALENT BOND; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG PENETRATION; DRUG RELEASE; ELECTROSPRAY MASS SPECTROMETRY; HT-29-MTX CELL LINE; IN VIVO STUDY; PARTICLE SIZE; PH; PROTON NUCLEAR MAGNETIC RESONANCE; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL; ANIMAL; BIOAVAILABILITY; CELL LINE; CHEMISTRY; HUMAN; HYDROLYSIS; LIPID METABOLISM; METABOLISM; ORAL DRUG ADMINISTRATION; RAT;

ADMINISTRATION, ORAL; ANIMALS; ANTIOXIDANTS; BIOLOGICAL AVAILABILITY; CACO-2 CELLS; CELL LINE; HUMANS; HYDROLYSIS; LIPID METABOLISM; LIPIDS; NANOPARTICLES; RATS; SILYMARIN;

EID: 85028309906     PISSN: 15499634     EISSN: 15499642     Source Type: Journal    
DOI: 10.1016/j.nano.2017.07.014     Document Type: Article

References (50)

1. Wissing, S.A., Kayser, O., Müller, R.H., Solid lipid nanoparticles for parenteral drug delivery. Adv Drug Deliv Rev 56 (2004), 1257–1272.
2. Zaro, J.L., Lipid-based drug carriers for prodrugs to enhance drug delivery. AAPS J 17 (2014), 83–92.
3. Muranishi, S., Sakai, A., Yamada, K., Murakami, M., Takada, K., Kiso, Y., Lipophilic peptides: synthesis of lauroyl thyrotropin-releasing hormone and its biological activity. Pharm Res 8 (1991), 649–652.
4. Wang, J., Luo, T., Li, S., Zhao, J., The powerful applications of polyunsaturated fatty acids in improving the therapeutic efficacy of anticancer drugs. Expert Opin Drug Deliv 9 (2011), 1–7.
5. Wang, T.Y., Liu, M., Portincasa, P., Wang, Q.H., New insights into the molecular mechanism of intestinal fatty acid absorption. Eur J Clin Invest 43 (2013), 1203–1223.
6. Mura, S., Bui, D.T., Couvreur, P., Nicolas, J., Lipid prodrug nanocarriers in cancer therapy. J Control Release 208 (2015), 25–41.
7. Jain, A.K., Jain, S., Advances in oral delivery of anti-cancer prodrugs. Expert Opin Drug Deliv 13 (2016), 1759–1775.
8. Sharma, P., Dube, B., Sawant, K., Synthesis of cytarabine lipid drug conjugate for treatment of meningeal leukemia: development, characterization and in vitro cell line studies. J Biomed Nanotechnol 8 (2012), 928–937.
9. Paliwal, R., Rai, S., Vyas, S.P., Lipid drug conjugate (LDC) nanoparticles as autolymphotrophs for oral delivery of methotrexate. J Biomed Nanotechnol 7 (2011), 130–131.
10. Olbrich, C., Gessner, A., Kayser, O., Müller, R.H., Lipid-drug-conjugate (LDC) nanoparticles as novel carrier system for the hydrophilic antitrypanosomal drug diminazenediaceturate. J Drug Target 10 (2002), 387–396.
11. Olbrich, C., Gessner, A., Schröder, W., Kayser, O., Müller, R.H., Lipid–drug conjugate nanoparticles of the hydrophilic drug diminazene – cytotoxicity testing and mouse serum adsorption. J Control Release 96 (2004), 425–435.
12. Neupane, Y.R., Sabir, M.D., Ahmad, N., Ali, M., Kohli, K., Lipid drug conjugate nanoparticle as a novel lipid nanocarrier for the oral delivery of decitabine: ex vivo gut permeation studies. Nanotechnology, 24, 2013, 415102.
13. Varshosaz, J., Hassanzadeh, F., Sadeghi, H., Andalib, S., Synthesis of octadecylamine-retinoic acid conjugate for enhanced cytotoxic effects of 5-FU using LDL targeted nanostructured lipid carriers. Eur J Med Chem 54 (2012), 429–438.
14. Desmaële, D., Gref, R., Couvreur, P., Squalenoylation: a generic platform for nanoparticular drug delivery. J Control Release 161 (2012), 609–618.
15. Zhang, C., Jin, S., Xue, X., Zhang, T., Jiang, Y., Wang, P.C., et al. Tunable self-assembly of irinotecan-fatty acid prodrugs with increased cytotoxicity to cancer cells. J Mater Chem B 4 (2016), 3286–3291.
16. Biedermann, D., Vavříková E., Cvak, L., Křen, V., Chemistry of silybin. Nat Prod Rep 31 (2014), 1138–1157.
17. Loguercio, C., Festi, D., Silybin and the liver: from basic research to clinical practice. World J Gastroenterol 17 (2011), 2288–2301.
18. Wang, H.J., Jiang, Y.Y., Lu, P., Wang, Q., Ikejima, T., An updated review at molecular pharmacological level for the mechanism of anti-tumor, antioxidant and immunoregulatory action of silibinin. Acta Pharmacol Sin 45 (2010), 413–421.
19. Theodosiou, E., Purchartová K., Stamatis, H., Kolisis, F., Křen, V., Bioavailability of silymarin flavonolignans: drug formulations and biotransformation. Phytochem Rev 13 (2014), 1–18.
20. Nguyen, M.H., Hong, Y., Dong, B., Hadinoto, K., A supersaturating delivery system of silibinin exhibiting high payload achieved by amorphous nano-complexation with chitosan. Eur J Pharm Sci 89 (2016), 163–171.
21. Zhou, X., Chen, Z., Preparation and performance evaluation of emulsomes as a drug delivery system for silybin. Arch Pharm Res 38 (2015), 2193–2200.
22. Varshosaz, J., Minaiyan, M., Khaleghi, N., Eudragit nanoparticles loaded with silybin: a detailed study of preparation, freeze-drying condition and in vitro/in vivo evaluation. J Microencapsul 32 (2015), 211–223.
23. Jia, L.J., Zhang, D.R., Li, Z.Y., Feng, F.F., Wang, Y.C., Dai, W.T., et al. Preparation and characterization of silybin-loaded nanostructured lipid carriers. Drug Deliv 17 (2010), 11–18.
24. Calligaris, S., Comuzzo, P., Bot, F., Lippe, G., Zironi, R., Anese, M., et al. Nanoemulsions as delivery systems of hydrophobic silybin from silymarin extract: effect of oil type on silybin solubility, in vitro bioaccessibility and stability. LWT - Food Sci Technol 63 (2015), 77–84.
25. Rodrigues, S.F., Fiel, L.A., Shimada, A.L., Pereira, N.R., Guterres, S.S., Pohlmann, A.R., et al. Lipid-core nanocapsules act as a drug shuttle through the blood brain barrier and reduce glioblastoma after intravenous or oral administration. J Biomed Nanotechnol 12 (2016), 986–1000.
26. Eroglu, H., Yenilmez, A., An investigation of the usability of solid lipid nanoparticles radiolabelled with Tc-99m as imaging agents in liver-spleen scintigraphy. J Biomed Nanotechnol 12 (2016), 1501–1509.
27. Wei, J.P., Chen, X.L., Wang, X.Y., Li, J.C., Shi, S.G., Liu, G., et al. Polyethylene glycol phospholipids encapsulated silicon 2,3-naphthalocyanine dihydroxide nanoparticles (SiNcOH-DSPE-PEG(NH2) NPs) for single NIR laser induced cancer combination therapy. Chin Chem Lett, 2017, 10.1016/j.cclet.2017.01.007.
28. Aresh, W., Liu, Y., Sine, J., Thayer, D., Puri, A., Huang, Y., et al. The morphology of self-assembled lipid-based nanoparticles affects their uptake by cancer cells. J Biomed Nanotechnol 12 (2016), 1852–1863.
29. Chuang, C.H., Wu, P.C., Tsai, T.H., Fang, Y.P., Tsai, Y.H., Cheng, T.C., et al. Development of pH-sensitive ctionic PEGylated solid lipid nanoparticles for selective cancer-targeted therapy. J Biomed Nanotechnol 13 (2017), 92–203.
30. Pooja, D., Kulhari, H., Kuncha, M., Rachamalla, S.S., Adams, D.J., Bansal, V., et al. Improving efficacy, oral bioavailability, and delivery of paclitaxel using protein-grafted solid lipid nanoparticles. Mol Pharm 13 (2016), 3903–3912.
31. Zhang, Y., Li, Z., Zhang, K., Yang, G., Wang, Z., Zhao, J., et al. Ethyl oleate-containing nanostructured lipid carriers improve oral bioavailability of trans-ferulic acid ascompared with conventional solid lipid nanoparticles. Int J Pharm 511 (2016), 57–64.
32. Guada, M., Lasa-Saracíbar, B., Lana, H., Dios-Viéitez Mdel, C., Blanco-Prieto, M.J., Lipid nanoparticles enhance the absorption of cyclosporine a through the gastrointestinal barrier: in vitro and in vivo studies. Int J Pharm 500 (2016), 154–161.
33. Borkar, N., Holm, R., Yang, M., Müllertz, A., Mu, H., In vivo evaluation of lipid-based formulations for oral delivery of apomorphine and its diester prodrugs. Int J Pharm 513 (2016), 211–217.
34. Porter, C.J., Trevaskis, N.L., Charman, W.N., Lipids and lipid-based formulations: optimizing the oral delivery of lipophilic drugs. Nat Rev Drug Discov 6 (2007), 231–248.
35. Hu, X., Zhang, J., Yu, Z., Xie, Y., He, H., Qi, J., et al. Environment-responsive aza-BODIPY dyes quenching in water as potential probes to visualize the in vivo fate of lipid-based nanocarriers. Nanomedicine 11 (2015), 1939–1948.
36. Hu, X., Fan, W., Yu, Z., Lu, Y., Qi, J., Zhang, J., et al. Evidence does not support absorption of intact solid lipid nanoparticles via oral delivery. Nanoscale 8 (2015), 7024–7035.
37. Gazak, R., Purchartova, K., Marhol, P., Zivna, L., Sedmera, P., Valentova, K., et al. Antioxidant and antiviral activities of silybin fatty acid conjugates. Eur J Med Chem 45 (2010), 1059–1067.
38. Gupta, B., Poudel, B.K., Pathak, S., Tak, J.W., Lee, H.H., Jeong, J., et al. Effects of formulation variables on the particle size and drug encapsulation of imatinib-loaded solid lipid nanoparticles. AAPS PharmSciTech 17 (2016), 652–662.
39. Shangguan, M., Lu, Y., Qi, J., Han, J., Tian, Z., Xie, Y., et al. Binary lipids-based nanostructured lipid carriers for improved oral bioavailability of silymarin. J Biomater Appl 28 (2014), 887–896.
40. Zhao, W.L., Carreira, E.M., Conformationally restricted aza-BODIPY: a highly fluorescent, stable, near-infrared-absorbing dye. Angew Chem Int Ed Engl 44 (2005), 1677–1679.
41. Zhao, W.L., Carreira, E.M., Conformationally restricted aza-BODIPY: highly fluorescent, stable near-infrared absorbing dyes. Chemistry 12 (2006), 7254–7263.
42. Devraj, R., Williams, H.D., Warren, D.B., Mullertz, A., Porter, C.J., Pouton, C.W., In vitro digestion testing of lipid-based delivery systems: calcium ions combine with fatty acids liberated from triglyceride rich lipid solutions to form soaps and reduce the solubilization capacity of colloidal digestion products. Int J Pharm 441 (2013), 323–333.
43. Devraj, R., Williams, H.D., Warren, D.B., Mohsin, K., Porter, C.J., Pouton, C.W., In vitro assessment of drug-free and fenofibrate-containing lipid formulations using dispersion and digestion testing gives detailed insights into the likely fate of formulations in the intestine. Eur J Pharm Sci 49 (2013), 748–760.
44. Beloqui, A., Brayden, D.J., Artursson, P., Préat, V., des Rieux, A., A human intestinal M-cell-like model for investigating particle, antigen and microorganism translocation. Nat Protoc 12 (2017), 1387–1399.
45. Lopes, M.A., Abrahim, B.A., Cabral, L.M., Rodrigues, C.R., Seiça, R.M., de Baptista Veiga, F.J., et al. Intestinal absorption of insulin nanoparticles: contribution of M cells. Nanomedicine 10 (2014), 1139–1151.
46. Sun, N., Wei, X., Wu, B., Chen, J., Lu, Y., Wu, W., Enhanced dissolution of silymarin/polyvinylpyrrolidone solid dispersion pellets prepared by a one-step fluid-bed coating technique. Powder Technol 182 (2008), 72–80.
47. Dahan, A., Hoffman, A., Evaluation of a chylomicron flow blocking approach to investigate the intestinal lymphatic transport of lipophilic drugs. Eur J Pharm Sci 24 (2005), 381–388.
48. Xie, Y., Jiang, S., Xia, F., Hu, X., He, H., Yin, Z., et al. Glucan microparticles thickened with thermosensitive gels as potential carriers for oral delivery of insulin. J Mater Chem B 4 (2016), 4040–4048.
49. Xu, P., Yin, Q., Shen, J., Chen, L., Yu, H., Zhang, Z., et al. Synergistic inhibition of breast cancer metastasis by silibinin-loaded lipid nanoparticles containing TPGS. Int J Pharm 454 (2013), 21–30.
50. Zhang, J.Q., Liu, J., Li, X.L., Jasti, B.R., Preparation and characterization of solid lipid nanoparticles containing silibinin. Drug Deliv 14 (2007), 381–387.