Critical determinant of intestinal permeability and oral bioavailability of pegylated all trans-retinoic acid prodrug-based nanomicelles: Chain length of poly (ethylene glycol) corona

Colloids and Surfaces B: Biointerfaces

Volumn 130, Issue , 2015, Pages 133-140

  Li, Zhenbao ^a   Han, Xiaopeng ^a   Zhai, Yinglei ^a   Lian, He ^a   Zhang, Dong ^a   Zhang, Wenjuan ^a   Wang, Yongjun ^a   He, Zhonggui ^a   Liu, Zheng ^a   Sun, Jin ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

All trans retinoic acid; Membrane permeability; Oral bioavailability; PEG chain length; Prodrug based nanomicelles

Indexed keywords

BIOCHEMISTRY; CARDIOVASCULAR SYSTEM; CHAIN LENGTH; CHAINS; CHEMICAL STABILITY; DRUG PRODUCTS; EMULSIFICATION; ESTERIFICATION; NANOPARTICLES; PLASMA STABILITY; POLYETHYLENE GLYCOLS; POLYOLS;

ALL-TRANS RETINOIC ACIDS; EMULSION-SOLVENT EVAPORATION METHOD; ESTERIFICATION REACTIONS; INTESTINAL PERMEABILITIES; INTRAVENOUS ADMINISTRATION; MEMBRANE PERMEABILITY; NANOMICELLES; ORAL BIOAVAILABILITIES;

LOADING;

MACROGOL; PEGYLATED ALL TRANS RETINOIC ACID PRODRUG BASED NANOMICELLE; RETINOIC ACID; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; MACROGOL DERIVATIVE; NANOPARTICLE; PRODRUG;

ANIMAL EXPERIMENT; AQUEOUS SOLUTION; AREA UNDER THE CURVE; ARTICLE; CELL INTERACTION; COLON; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BLOOD LEVEL; DRUG CONJUGATION; DRUG FORMULATION; DRUG HALF LIFE; DRUG STABILITY; DRUG SYNTHESIS; DUODENUM; EVAPORATION; HYDROLYSIS; ILEUM; INTESTINE MUCOSA PERMEABILITY; JEJUNUM; MALE; MAXIMUM PLASMA CONCENTRATION; MICELLE; NANOEMULSION; NONHUMAN; PRIORITY JOURNAL; RAT; SOLVENT EFFECT; TISSUE HOMOGENATE; ANIMAL; BIOAVAILABILITY; CHEMICAL STRUCTURE; CHEMISTRY; ENDOCYTOSIS; INTESTINE; KINETICS; METABOLIC CLEARANCE RATE; METABOLISM; MOLECULAR WEIGHT; ORAL DRUG ADMINISTRATION; PERMEABILITY; SPRAGUE DAWLEY RAT; TISSUE DISTRIBUTION; TRANSMISSION ELECTRON MICROSCOPY; ULTRASTRUCTURE;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; AREA UNDER CURVE; BIOLOGICAL AVAILABILITY; ENDOCYTOSIS; INTESTINES; KINETICS; MALE; METABOLIC CLEARANCE RATE; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; NANOPARTICLES; PERMEABILITY; POLYETHYLENE GLYCOLS; PRODRUGS; RATS, SPRAGUE-DAWLEY; TISSUE DISTRIBUTION; TRETINOIN;

EID: 84930180009     PISSN: 09277765     EISSN: 18734367     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2015.03.036     Document Type: Article

References (41)

1. Choi Y., Kim S.Y., Kim S.H., Lee K.S., Kim C., Byun Y. Long-term delivery of all-trans-retinoic acid using biodegradable PLLA/PEG-PLLA blended microspheres. Int. J. Pharm. 2001, 215:67-81.
2. Garattini E., Bolis M., Garattini S.K., Fratelli M., Centritto F., Paroni G., Gianni M., Zanetti A., Pagani A., Fisher J.N., Zambelli A., Terao M. Retinoids and breast cancer: from basic studies to the clinic and back again. Cancer Treat. Rev. 2014, 40:739-749.
3. Giannini F., Maestro R., Vukosavljevic T., Pomponi F., Boiocchi M. All-trans, 13-cis and 9-cis retinoic acids induce a fully reversible growth inhibition in HNSCC cell lines: implications for in vivo retinoic acid use. Int. J. Cancer 1997, 70:194-200.
4. Kalemkerian G.P., Jasti R.K., Celano P., Nelkin B.D., Mabry M. All-trans-retinoic acid alters myc gene expression and inhibits in vitro progression in small cell lung cancer. Cell Growth Differ. 1994, 5:55-60.
5. Chen Z., Guan P., Xu Y., Qi J., Lu Y., Wu W. Enhanced oral bioavailability of all-trans-retinoic acid by 2-hydroxypropyl-β-cyclodextrin inclusion complex pellets prepared by fluid-bed coating technique. AJPS 2011, 6:202-207.
6. Lin H.S., Chan S.Y., Low K.S., Shoon M.L., Ho P.C. Kinetic study of a 2-hydroxypropyl-beta-cyclodextrin-based formulation of all-trans-retinoic acid in Sprague-Dawley rats after oral or intravenous administration. J. Pharm. Sci. 2000, 89:260-267.
7. Wu J., Shao Y., Liu J., Chen G., Ho P.C. The medicinal use of realgar (As(4)S(4)) and its recent development as an anticancer agent. J. Ethnopharmacol. 2011, 135:595-602.
8. Chinsriwongkul A., Opanasopit P., Ngawhirunpat T., Rojanarata T., Sila-On W., Ruktanonchai U. Oleic acid enhances all-trans retinoic acid loading in nano-lipid emulsions. PDA J. Pharm. Sci. Technol. 2010, 64:113-123.
9. Narvekar M., Xue H.Y., Wong H.L. A novel hybrid delivery system: polymer-oil nanostructured carrier for controlled delivery of highly lipophilic drug all-trans-retinoic acid (ATRA). Int. J. Pharm. 2012, 436:721-731.
10. Park J.S., Koh Y.S., Bang J.Y., Jeong Y.I., Lee J.J. Antitumor effect of all-trans retinoic acid-encapsulated nanoparticles of methoxy poly(ethylene glycol)-conjugated chitosan against CT-26 colon carcinoma in vitro. J. Pharm. Sci. 2008, 97:4011-4019.
11. Su J., Zhang N., Ho P.C. Evaluation of the pharmacokinetics of all-trans-retinoic acid (ATRA) in Wistar rats after intravenous administration of ATRA loaded into tributyrin submicron emulsion and its cellular activity on caco-2 and HepG2 cell lines. J. Pharm. Sci. 2008, 97:2844-2853.
12. Estey E.H., Giles F.J., Kantarjian H., O'Brien S., Cortes J., Freireich E.J., Lopez-Berestein G., Keating M. Molecular remissions induced by liposomal-encapsulated all-trans retinoic acid in newly diagnosed acute promyelocytic leukemia. Blood 1999, 94:2230-2235.
13. Lim S.J., Kim C.K. Formulation parameters determining the physicochemical characteristics of solid lipid nanoparticles loaded with all-trans retinoic acid. Int. J. Pharm. 2002, 243:135-146.
14. Luo C., Sun J., Sun B., He Z. Prodrug-based nanoparticulate drug delivery strategies for cancer therapy. Trends Pharmacol. Sci. 2014, 35:556-566.
15. Shen Y., Jin E., Zhang B., Murphy C.J., Sui M., Zhao J., Wang J., Tang J., Fan M., Van Kirk E., Murdoch W.J. Prodrugs forming high drug loading multifunctional nanocapsules for intracellular cancer drug delivery. J. Am. Chem. Soc. 2010, 132:4259-4265.
16. Kolate A., Baradia D., Patil S., Vhora I., Kore G., Misra A. PEG - a versatile conjugating ligand for drugs and drug delivery systems. J. Control. Release 2014, 192:67-81.
17. Harris J.M., Martin N.E., Modi M. Pegylation: a novel process for modifying pharmacokinetics. Clin. Pharmacokinet. 2001, 40:539-551.
18. Wang Z., Chui W.K., Ho P.C. Design of a multifunctional PLGA nanoparticulate drug delivery system: evaluation of its physicochemical properties and anticancer activity to malignant cancer cells. Pharm. Res. 2009, 26:1162-1171.
19. Filpula D., Zhao H. Releasable PEGylation of proteins with customized linkers. Adv. Drug Deliv. Rev. 2008, 60:29-49.
20. Ye T., Zhang W., Song S., Chen F., Yang X., Wang S., Bi J., Pan W. Prodrugs incorporated into nanotechnology-based drug delivery systems for possible improvement in bioavailability of ocular drugs delivery. AJPS 2013, 8:207-217.
21. Lai S.K., O'Hanlon D.E., Harrold S., Man S.T., Wang Y.Y., Cone R., Hanes J. Rapid transport of large polymeric nanoparticles in fresh undiluted human mucus. Proc. Natl. Acad. Sci. U. S. A. 2007, 104:1482-1487.
22. Wang Y.Y., Lai S.K., Suk J.S., Pace A., Cone R., Hanes J. Addressing the PEG mucoadhesivity paradox to engineer nanoparticles that slip through the human mucus barrier. Angew. Chem. Int. Ed. Engl. 2008, 47:9726-9729.
23. Song Q., Wang X., Hu Q., Huang M., Yao L., Qi H., Qiu Y., Jiang X., Chen J., Chen H., Gao X. Cellular internalization pathway and transcellular transport of pegylated polyester nanoparticles in Caco-2 cells. Int. J. Pharm. 2013, 445:58-68.
24. Hu F.Q., Meng P., Dai Y.Q., Du Y.Z., You J., Wei X.H., Yuan H. PEGylated chitosan-based polymer micelle as an intracellular delivery carrier for anti-tumor targeting therapy. Eur. J. Pharm. Biopharm. 2008, 70:749-757.
25. Luo C., Sun J., Du Y., He Z. Emerging integrated nanohybrid drug delivery systems to facilitate the intravenous-to-oral switch in cancer chemotherapy. J. Control. Release 2014, 176:94-103.
26. Wang J., Sun J., Chen Q., Gao Y., Li L., Li H., Leng D., Wang Y., Sun Y., Jing Y., Wang S., He Z. Star-shape copolymer of lysine-linked di-tocopherol polyethylene glycol 2000 succinate for doxorubicin delivery with reversal of multidrug resistance. Biomaterials 2012, 33:6877-6888.
27. Ai X., Niu H., He Z. Thin-film hydration preparation method and stability test of DOX-loaded disulfide-linked polyethylene glycol 5000-lysine-di-tocopherol succinate nanomicelles. AJPS 2014, 9:244-250.
28. Zhang Y., Sun J., Gao Y., Jin L., Xu Y., Lian H., Sun Y., Liu J., Fan R., Zhang T., He Z. A carrier-mediated prodrug approach to improve the oral absorption of antileukemic drug decitabine. Mol. Pharm. 2013, 10:3195-3202.
29. Liu Y., Zhai Y., Han X., Liu X., Liu W., Wu C., Li L., Du Y., Lian H., Wang Y., He Z., Sun J. Bioadhesive chitosan-coated cyclodextrin-based supramolecular nanomicelles to enhance the oral bioavailability of doxorubicin. J. Nanopart. Res. 2014, 16:1-15.
30. Lian H., Zhang T., Sun J., Liu X., Ren G., Kou L., Zhang Y., Han X., Ding W., Ai X., Wu C., Li L., Wang Y., Sun Y., Wang S., He Z. Enhanced oral delivery of paclitaxel using acetylcysteine functionalized chitosan-vitamin E succinate nanomicelles based on a mucus bioadhesion and penetration mechanism. Mol. Pharm. 2013, 10:3447-3458.
31. Alexis F., Pridgen E., Molnar L.K., Farokhzad O.C. Factors affecting the clearance and biodistribution of polymeric nanoparticles. Mol. Pharm. 2008, 5:505-515.
32. Kievit F.M., Wang F.Y., Fang C., Mok H., Wang K., Silber J.R., Ellenbogen R.G., Zhang M. Doxorubicin loaded iron oxide nanoparticles overcome multidrug resistance in cancer in vitro. J. Control. Release 2011, 152:76-83.
33. Ashjari M., Khoee S., Mahdavian A.R., Rahmatolahzadeh R. Self-assembled nanomicelles using PLGA-PEG amphiphilic block copolymer for insulin delivery: a physicochemical investigation and determination of CMC values. J. Mater. Sci. Mater. Med. 2012, 23:943-953.
34. Feeney O.M., Williams H.D., Pouton C.W., Porter C.J. 'Stealth' lipid-based formulations: poly(ethylene glycol)-mediated digestion inhibition improves oral bioavailability of a model poorly water soluble drug. J. Control. Release 2014, 192:219-227.
35. Buyukozturk F., Benneyan J.C., Carrier R.L. Impact of emulsion-based drug delivery systems on intestinal permeability and drug release kinetics. J. Control. Release 2010, 142:22-30.
36. Xia W.J., Onyuksel H. Mechanistic studies on surfactant-induced membrane permeability enhancement. Pharm. Res. 2000, 17:612-618.
37. Atuma C., Strugala V., Allen A., Holm L. The adherent gastrointestinal mucus gel layer: thickness and physical state in vivo. Am. J. Physiol. Gastrointest. Liver Physiol. 2001, 280:G922-G929.
38. Lai S.K., Wang Y.Y., Hanes J. Mucus-penetrating nanoparticles for drug and gene delivery to mucosal tissues. Adv. Drug Deliv. Rev. 2009, 61:158-171.
39. Szentkuti L., Lorenz K. The thickness of the mucus layer in different segments of the rat intestine. Histochem. J. 1995, 27:466-472.
40. Masaoka Y., Tanaka Y., Kataoka M., Sakuma S., Yamashita S. Site of drug absorption after oral administration: assessment of membrane permeability and luminal concentration of drugs in each segment of gastrointestinal tract. Eur. J. Pharm. Sci. 2006, 29:240-250.
41. Zhang W., Sun J., Fang W., Ai X., Cai C., Tang Y., Su X., Feng Z., Liu Y., Tao M., Yan X., Chen G., He Z. Nanomicelles based on X-shaped four-armed peglyated distearylglycerol as long circulating system for doxorubicin delivery. Eur. J. Pharm. Sci. 2015, 66:96-106.