Epithelial transport of Noscapine across cell monolayer and influence of absorption enhancers on in vitro permeation and bioavailability: Implications for intestinal absorption

Journal of Drug Targeting

Volumn 22, Issue 6, 2014, Pages 498-508

  Chougule, Mahavir B ^a   Patel, Apurva R ^b   Patlolla, Ram ^b   Jackson, Tanise ^b   Sachdeva, Mandip Singh ^b  

^a UNIVERSITY OF HAWAII AT HILO   (United States)

^b FLORIDA A AND M UNIVERSITY   (United States)

Author keywords

Absorption enhancer; Bioavailability; Captisol; Cell monolayer; Chitosan; Noscapine

Indexed keywords

BETA CYCLODEXTRIN SULFOBUTYL ETHER; CHITOSAN; NOSCAPINE; ANTITUSSIVE AGENT;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CACO 2 CELL LINE; CELL MEMBRANE TRANSPORT; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG EFFECT; DRUG FORMULATION; DRUG PENETRATION; DRUG TRANSPORT; EPITHELIUM; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; INTESTINE ABSORPTION; NONHUMAN; PH; PLASMA CONCENTRATION-TIME CURVE; PRIORITY JOURNAL; RAT; ANIMAL; BIOAVAILABILITY; CELL CULTURE; DOG; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLUBILITY; SPRAGUE DAWLEY RAT;

ANIMALS; ANTITUSSIVE AGENTS; BIOLOGICAL AVAILABILITY; CACO-2 CELLS; CELLS, CULTURED; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOGS; HUMANS; HYDROGEN-ION CONCENTRATION; INTESTINAL ABSORPTION; NOSCAPINE; RATS; RATS, SPRAGUE-DAWLEY; SOLUBILITY;

EID: 84902298182     PISSN: 1061186X     EISSN: 10292330     Source Type: Journal    
DOI: 10.3109/1061186X.2014.894046     Document Type: Article

References (61)

1. Segal MS, Goldstein MM, Attinger EO. The use of noscapine (narcotine) as an antitussive agent. Dis Chest 1957;30: 305-9.
2. Aneja R, Vangapandu SN, Lopus M, et al. Development of a novel nitro-derivative of noscapine for the potential treatment of drugresistant ovarian cancer and T-cell lymphoma. Mol Pharmacol 2006;69: 1801-9.
3. Aneja R, Zhou J, Zhou B, et al. Treatment of hormone-refractory breast cancer: apoptosis and regression of human tumors implanted in mice. Mol Cancer Ther 2006;5: 2366-77.
4. Barken I, Geller J, Rogosnitzky M. Prophylactic noscapine therapy inhibits human prostate cancer progression and metastasis in a mouse model. Anticancer Res 2010;30: 399-401.
5. Jhaveri N, Cho H, Torres S, et al. Noscapine inhibits tumor growth in TMZ-resistant gliomas. Cancer Lett 2011;312: 245-52.
6. Li S, He J, Cao G, et al. Noscapine induced apoptosis via downregulation of survivin in human neuroblastoma cells having wild type or null p53. PLoS One 2012;7:e40076.
7. Liu M, Luo XJ, Liao F, et al. Noscapine induces mitochondriamediated apoptosis in gastric cancer cells in vitro and in vivo. Cancer Chemother Pharmacol 2011;67: 605-12.
8. Naik PK, Santoshi S, Joshi HC. Noscapinoids with anti-cancer activity against human acute lymphoblastic leukemia cells (CEM): a three dimensional chemical space pharmacophore modeling and electronic feature analysis. J Mol Model 2012;18: 307-18.
9. Su W, Huang L, Ao Q, et al. Noscapine sensitizes chemoresistant ovarian cancer cells to cisplatin through inhibition of HIF-1alpha. Cancer Lett 2011;305: 94-9.
10. Yang ZR, Liu M, Peng XL, et al. Noscapine induces mitochondriamediated apoptosis in human colon cancer cells in vivo and in vitro. Biochem Biophys Res Commun 2012;421: 627-33.
11. Chougule M, Patel AR, Sachdeva P, et al. Anticancer activity of Noscapine, an opioid alkaloid in combination with cisplatin in human non-small cell lung cancer. Lung Cancer 2011;71: 271-82.
12. Chougule MB, Patel A, Sachdeva P, et al. Enhanced anticancer activity of gemcitabine in combination with noscapine via antiangiogenic and apoptotic pathway against non-small cell lung cancer. PLoS One 2011;6:e27394.
13. Chougule MB, Patel AR, Jackson T, Singh M. Antitumor activity of Noscapine in combination with Doxorubicin in triple negative breast cancer. PLoS One 2011;6:e17733.
14. Jackson T, Chougule MB, Ichite N, et al. Antitumor activity of noscapine in human non-small cell lung cancer xenograft model. Cancer Chemother Pharmacol 2008;63: 117-26.
15. Aneja R, Zhou J, Vangapandu SN. Drug-resistant T-lymphoid tumors undergo apoptosis selectively in response to an antimicrotubule agent, EM011. Blood 2006;107: 2486-92.
16. Anderson JT, Ting AE, Boozer S, et al. Identification of novel and improved antimitotic agents derived from noscapine. J Med Chem 2005;48: 7096-8.
17. Jordan MA. Mechanism of action of antitumor drugs that interact with microtubules and tubulin. Curr Med Chem Anticancer Agents 2002;2: 1-17.
18. Markman M. Managing taxane toxicities. Support Care Cancer 2003;11: 144-7.
19. Van Zuylen L, Verweij J, Sparreboom A. Role of formulation vehicles in taxane pharmacology. Invest New Drugs 2001;19: 125-41. (Pubitemid 32423718)
20. Stanton RA, Gernert KM, Nettles JH, Aneja R. Drugs that target dynamic microtubules: a new molecular perspective. Med Res Rev 2011;31: 443-81.
21. Debono AJ, Xie JH, Ventura S, et al. Synthesis and biological evaluation of N-substituted noscapine analogues. Chem Med Chem 2012;7: 2122-33.
22. Madan J, Baruah B, Nagaraju M, et al. Molecular cycloencapsulation augments solubility and improves therapeutic index of brominated noscapine in prostate cancer cells. Mol Pharm 2012; 9: 1470-80.
23. Naik PK, Chatterji BP, Vangapandu SN, et al. Rational design, synthesis and biological evaluations of amino-noscapine: a high affinity tubulin-binding noscapinoid. J Comput Aided Mol Des 2011;25: 443-54.
24. Naik PK, Lopus M, Aneja R, et al. In silico inspired design and synthesis of a novel tubulin-binding anti-cancer drug: folate conjugated noscapine (Targetin). J Comput Aided Mol Des 2012; 26: 233-47.
25. Mishra RC, Karna P, Gundala SR, et al. Second generation benzofuranone ring substituted noscapine analogs: synthesis and biological evaluation. Biochem Pharmacol 2011;82: 110-21.
26. Madan J, Pandey RS, Jain UK, et al. Sterically stabilized gelatin microassemblies of noscapine enhance cytotoxicity, apoptosis and drug delivery in lung cancer cells. Colloids Surf B Biointerfaces 2013;107: 235-44.
27. Madan J, Pandey RS, Jain V, et al. Poly (ethylene)-glycol conjugated solid lipid nanoparticles of noscapine improve biological half-life, brain delivery and efficacy in glioblastoma cells. Nanomedicine 2013;9: 492-503.
28. Madan J, Dhiman N, Sardana S, et al. Long-circulating poly(ethylene glycol)-grafted gelatin nanoparticles customized for intracellular delivery of noscapine: preparation, in-vitro characterization, structure elucidation, pharmacokinetics, and cytotoxicity analyses. Anticancer Drugs 2011;22: 543-55.
29. Chandra R, Madan J, Singh P, et al. Implications of nanoscale based drug delivery systems in delivery and targeting tubulin binding agent, noscapine in cancer cells. Curr Drug Metab 2012;13: 1476-83.
30. Sebak S, Mirzaei M, Malhotra M, et al. Human serum albumin nanoparticles as an efficient noscapine drug delivery system for potential use in breast cancer: preparation and in vitro analysis. Int J Nanomed 2010;5: 525-32.
31. Karlsson MO, Dahlstrom B, Eckernas SA, et al. Pharmacokinetics of oral noscapine. Eur J Clin Pharmacol 1990;39: 275-9.
32. Lemmer HJ, Hamman JH. Paracellular drug absorption enhancement through tight junction modulation. Expert Opin Drug Deliv 2013;10: 103-14.
33. Sonaje K, Chuang EY, Lin KJ, et al. Opening of epithelial tight junctions and enhancement of paracellular permeation by chitosan: microscopic, ultrastructural, and computed-tomographic observations. Mol Pharm 2012;9: 1271-9.
34. Maestrelli F, Cirri M, Mennini N, et al. Improvement of oxaprozin solubility and permeability by the combined use of cyclodextrin, chitosan, and bile components. Eur J Pharm Biopharm 2011;78: 385-93.
35. Shah P, Jogani V, Mishra P, et al. Modulation of ganciclovir intestinal absorption in presence of absorption enhancers. J Pharm Sci 2007;96: 2710-22.
36. Mahmoudian M, Rahimi-Moghaddam P. The anti-cancer activity of noscapine: a review. Recent Pat Anticancer Drug Discov 2009;4: 92-7.
37. Patel AR, Spencer SD, Chougule MB, et al. Pharmacokinetic evaluation and in vitro-in vivo correlation (IVIVC) of novel methylene-substituted 3,30-diindolylmethane (DIM). Eur J Pharm Sci 2012;46: 8-16.
38. Aneja R, Dhiman N, Idnani J, et al. Preclinical pharmacokinetics and bioavailability of noscapine, a tubulin-binding anticancer agent. Cancer Chemother Pharmacol 2007;60: 831-9.
39. Madan J, Dhiman N, Parmar VK, et al. Inclusion complexes of noscapine in beta-cyclodextrin offer better solubility and improved pharmacokinetics. Cancer Chemother Pharmacol 2010;65: 537-48.
40. Abdalla MO, Karna P, Sajja HK, et al. Enhanced noscapine delivery using uPAR-targeted optical-MR imaging trackable nanoparticles for prostate cancer therapy. J Control Release 2011; 149: 314-22.
41. Zhou R, Moench P, Heran C, et al. pH-dependent dissolution in vitro and absorption in vivo of weakly basic drugs: development of a canine model. Pharm Res 2005;22: 188-92.
42. Tomita M, Doi N, Hayashi M. Effects of acylcarnitines on efflux transporting system in Caco-2 cell monolayers. Eur J Drug Metab Pharmacokinet 2010;35: 1-7.
43. Duvvuri M, Krise JP. A novel assay reveals that weakly basic model compounds concentrate in lysosomes to an extent greater than pH-partitioning theory would predict. Mol Pharm 2005;2: 440-8.
44. Yeh TH, Hsu LW, Tseng MT, et al. Mechanism and consequence of chitosan-mediated reversible epithelial tight junction opening. Biomaterials 2011;32: 6164-73.
45. Schipper NG, Varum KM, Artursson P. Chitosans as absorption enhancers for poorly absorbable drugs. 1: influence of molecular weight and degree of acetylation on drug transport across human intestinal epithelial (Caco-2) cells. Pharm Res 1996;13: 1686-92.
46. Kale R, Tayade P, Saraf M, Juvekar A. Molecular encapsulation of thalidomide with sulfobutyl ether-7 beta-cyclodextrin for immediate release property: enhanced in vivo antitumor and antiangiogenesis efficacy in mice. Drug Dev Ind Pharm 2008;34: 149-56.
47. Holvoet C, Heyden YV, Plaizi-Vercammen J. Inclusion complexation of diazepam with different cyclodextrins in formulations for parenteral use. Pharmazie 2005;60: 598-603.
48. Kurkov SV, Madden DE, Carr D, Loftsson T. The effect of parenterally administered cyclodextrins on the pharmacokinetics of coadministered drugs. J Pharm Sci 2012;101: 4402-8.
49. Davis ME. The first targeted delivery of siRNA in humans via a self-assembling, cyclodextrin polymer-based nanoparticle: from concept to clinic. Mol Pharm 2009;6: 659-68.
50. Saremi S, Dinarvand R, Kebriaeezadeh A, et al. Enhanced oral delivery of docetaxel using thiolated chitosan nanoparticles: preparation, in vitro and in vivo studies. Biomed Res Int 2013; 2013:150478 (1-8).
51. Anderberg EK, Artursson P. Epithelial transport of drugs in cell culture. VIII: effects of sodium dodecyl sulfate on cell membrane and tight junction permeability in human intestinal epithelial (Caco-2) cells. J Pharm Sci 1993;82: 392-8.
52. Gupta V, Hwang BH, Doshi N, Mitragotri S. A permeation enhancer for increasing transport of therapeutic macromolecules across the intestine. J Control Release 2013;172: 541-9.
53. Thanou M, Henderson S, Kydonieus A, Elson C. N-Sulfonato-N, Ocarboxymethylchitosan: a novel polymeric absorption enhancer for the oral delivery of macromolecules. J Control Release 2007; 117: 171-8.
54. Wu J, Shen Q, Fang L. Sulfobutylether-beta-cyclodextrin/chitosan nanoparticles enhance the oral permeability and bioavailability of docetaxel. Drug Dev Ind Pharm 2013;39: 1010-19.
55. Artursson P, Lindmark T, Davis SS, Illum L. Effect of chitosan on the permeability of monolayers of intestinal epithelial cells (Caco-2). Pharm Res 1994;11: 1358-61.
56. Thanou M, Verhoef JC, Junginger HE. Oral drug absorption enhancement by chitosan and its derivatives. Adv Drug Deliv Rev 2001;52: 117-26.
57. Chen MC, Mi FL, Liao ZX, et al. Recent advances in chitosanbased nanoparticles for oral delivery of macromolecules. Adv Drug Deliv Rev 2013;65: 865-79.
58. Martins PS, Ochoa R, Pimenta AM, et al. Mode of action of betacyclodextrin as an absorption enhancer of the water-soluble drug meglumine antimoniate. Int J Pharm 2006;325: 39-47.
59. Cano-Cebrian MJ, Zornoza T, Granero L, Polache A. Intestinal absorption enhancement via the paracellular route by fatty acids, chitosans and others: a target for drug delivery. Curr Drug Deliv 2005;2: 9-22.
60. Joshi HC, Zhou J. Noscapine and analogues as potential chemotherapeutic agents. Drug News Perspect 2000;13: 543-6.
61. Ensign LM, Cone R, Hanes J. Oral drug delivery with polymeric nanoparticles: the gastrointestinal mucus barriers. Adv Drug Deliv Rev 2012;64: 557-70.