Cyclodextrin complexes of reduced bromonoscapine in guar gum microspheres enhance colonic drug delivery

Molecular Pharmaceutics

Volumn 11, Issue 12, 2014, Pages 4339-4349

  Madan, Jitender ^a   Gundala, Sushma R ^a   Baruah, Bharat ^b   Nagaraju, Mulpuri ^a   Yates, Clayton ^c   Turner, Timothy ^c   Rangari, Vijay ^c   Hamelberg, Donald ^a   Reid, Michelle D ^d   Aneja, Ritu ^a  

^a GEORGIA STATE UNIVERSITY   (United States)

^b KENNESAW STATE UNIVERSITY   (United States)

^c TUSKEGEE UNIVERSITY   (United States)

^d EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

colon cancer; cytotoxicity; guar gum microspheres (GGMs); methyl cyclodextrin (methyl CD); Red Br Nos; cyclodextrin ( CD)

Indexed keywords

BETA CYCLODEXTRIN; CYCLODEXTRIN; GUAR GUM; METHYL BETA CYCLODEXTRIN; MICROSPHERE; NOSCAPINE; PHOSPHATE BUFFERED SALINE; PROTON; UNCLASSIFIED DRUG; [9 BROMO 5 (4,5 DIMETHOXY 1,3 DIHYDROISOBENZOFURAN 1 YL) 4 METHOXY 6 METHYL 5,6,7,8 TETRAHYDRO 1,3 DIOXOLO[4,5 G]ISOQUINOLINE]; BETA CYCLODEXTRIN DERIVATIVE; GALACTAN; MANNAN; METHYL-BETA-CYCLODEXTRIN; PLANT GUM;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL PROLIFERATION ASSAY; COMPLEX FORMATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG RELEASE; DRUG SOLUBILITY; DRUG STABILITY; ENCAPSULATION; HT 29 CELL LINE; HUMAN; HUMAN CELL; IC50; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; SOLID STATE; STOICHIOMETRY; CHEMISTRY; DIFFERENTIAL SCANNING CALORIMETRY;

BETA-CYCLODEXTRINS; CALORIMETRY, DIFFERENTIAL SCANNING; CYCLODEXTRINS; GALACTANS; HT29 CELLS; HUMANS; MANNANS; MICROSPHERES; NOSCAPINE; PLANT GUMS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84914174024     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500408n     Document Type: Article

References (44)

1. Aneja, R.; Ghaleb, A. M.; Zhou, J.; Yang, V. W.; Joshi, H. C. p53 and p21 determine the sensitivity of noscapine-induced apoptosis in colon cancer cells Cancer Res. 2007, 67, 3862-3870
2. Yang, Z. R.; Liu, M.; Peng, X. L.; Lei, X. F.; Zhang, J. X.; Dong, W. G. Noscapine induces mitochondria-mediated apoptosis in human colon cancer cells in vivo and in vitro Biochem. Biophys. Res. Commun. 2012, 421, 627-633
3. Zhou, J.; Gupta, K.; Aggarwal, S.; Aneja, R.; Chandra, R.; Panda, D.; Joshi, H. C. Brominated derivatives of noscapine are potent microtubule-interfering agents that perturb mitosis and inhibit cell proliferation Mol. Pharmacol. 2003, 63, 799-807
4. Zhou, J.; Liu, M.; Luthra, R.; Jones, J.; Aneja, R.; Chandra, R.; Tekmal, R. R.; Joshi, H. C. EM012, a microtubule-interfering agent, inhibits the progression of multidrug-resistant human ovarian cancer both in cultured cells and in athymic nude mice Cancer Chemother. Pharmacol. 2005, 55, 461-465
5. Amidon, G. L.; Lennernas, H.; Shah, V. P.; Crison, J. R. A theoretical basis for a biopharmaceutics drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability Pharm. Res. 1995, 12, 413-420
6. Chourasia, M. K.; Jain, S. K. Pharmaceutical approaches to colon targeted drug delivery systems J. Pharm. Pharm. Sci. 2003, 6, 33-66
7. Thornton, J. R. High colonic pH promotes colorectal cancer Lancet 1981, 1, 1081-1083
8. Lamprecht, A.; Yamamoto, H.; Takeuchi, H.; Kawashim, Y. Microsphere design for the colonic delivery of 5-fluorouracil J. Controlled Release 2003, 90, 313-322
9. Jain, A.; Jain, S. K.; Ganesh, N.; Barve, J.; Beg, A. M. Design and development of ligand appended polysaccharidic nanoparticles for the delivery of oxaliplatin in colorectal cancer Nanomedicine 2010, 6, 179-190
10. Nehal Siddiqui, M. D.; Garg, G.; Sharma, P. K. A short review on novel approaches in oral fast dissolving drug delivery system and their patents Adv. Biol. Res. 2011, 5, 291-303
11. Stella, V. J.; Rajewski, R. A. Cyclodextrins: Their future in drug formulation and delivery Pharm. Res. 1997, 14, 556-567
12. Hoda, A.; Sana, A. M.; Ola, A. K.; Ahmed, H. H. Characterization of ternary complexes of meloxicam-HP-β-CD and PVP or L-arginine prepared by the spray-drying technique Acta Pharm. 2008, 58, 455-466
13. Soares da Silva, L. F.; do Carmo, F. A.; de Almeida Borges, V. R.; Monteiro, L. M.; Rodrigues, C. R.; Cabral, L. M.; de Sousa, V. P. Preparation and evaluation of lidocaine hydrochloride in cyclodextrin inclusion complexes for development of stable gel in association with chlorhexidine gluconate for urogenital use Int. J. Nanomed. 2011, 6, 1143-1154
14. Celik, S. E.; Ozyurek, M.; Tufan, A. N.; Guclu, K.; Apak, R. Spectroscopic study and antioxidant properties of the inclusion complexes of rosmarinic acid with natural and derivative cyclodextrins Spectrochim Acta, Part A 2011, 78, 1615-1624
15. Chatjigakis, A. K.; Donze, C.; Coleman, A. W.; Cardot, P. Solubility behavior of beta-cyclodextrin in water/cosolvent mixtures Anal. Chem. 1992, 64, 1632-1634
16. Banchero, M.; Ronchetti, S.; Manna, L. Characterization of ketoprofen/methyl-β-cyclodextrin complexes prepared using supercritical carbon dioxide J. Chem. 2013, 583952
17. Esseku, F.; Adeyeye, M. C. Bacteria and pH-sensitive polysaccharide-polymer films for colon targeted delivery Crit. Rev. Ther. Drug Carrier Syst. 2011, 28, 395-445
18. Krishnaiah, Y. S.; Khan, M. A. Strategies of targeting oral drug delivery systems to the colon and their potential use for the treatment of colorectal cancer Pharm. Dev. Technol. 2012, 17, 521-540
19. Vaidya, A.; Jain, A.; Khare, P.; Agrawal, R. K.; Jain, S. K. Metronidazole loaded pectin microspheres for colon targeting J. Pharm. Sci. 2009, 98, 4229-4236
20. Chaurasia, M.; Chourasia, M. K.; Jain, N. K.; Jain, A.; Soni, V.; Gupta, Y.; Jain, S. K. Cross-linked guar gum microspheres: a viable approach for improved delivery of anticancer drugs for the treatment of colorectal cancer AAPS PharmSciTech 2006, 7 (3) E143-E151 10.1208/pt070374
21. Krishnaiah, Y. S. R.; Satyanarayana, V.; Dinesh Kumar, B.; Karthikeyan, R. S. In vitro drug release studies on guar gum-based colon targeted oral drug delivery systems of 5-fluorouracil Eur. J. Pharm. Sci. 2002, 16, 185-192
22. Crociani, F.; Alessandrini, A.; Mucci, M. M.; Biavati, B. Degradation of complex carbohydrates by Bifidobacterium spp Int. J. Food Microbiol. 1994, 24, 199-210
23. Madan, J.; Dhiman, N.; Parmar, V. K.; Sardana, S.; Bharatam, P. V.; Aneja, R.; Chandra, R.; Katyal, A. Inclusion complexes of noscapine in beta-cyclodextrin offer better solubility and improved pharmacokinetics Cancer Chemother. Pharmacol. 2010, 65, 537-548
24. Madan, J.; Baruah, B.; Nagaraju, M.; Abdalla, M. O.; Yates, C.; Turner, T.; Rangari, V.; Hamelberg, D.; Aneja, R. Molecular cycloencapsulation augments solubility and improves therapeutic index of brominated noscapine in prostate cancer cells Mol. Pharmaceutics 2012, 9, 1470-1480
25. Niv, Y.; Schwartz, B.; Amsalem, Y.; Lamprecht, S. A. Human HT-29 colon carcinoma cells: mucin production and tumorigenicity in relation to growth phases Anticancer Res. 1995, 15, 2023-2027
26. de Melo, N. F.; Grillo, R.; Rosa, A. H.; Fraceto, L. F. Interaction between nitroheterocyclic compounds with beta-cyclodextrins: phase solubility and HPLC studies J. Pharm. Biomed. Anal. 2008, 47, 865-869
27. Banerjee, A.; Mikhailova, E.; Cheley, S.; Gu, L. Q.; Montoya, M.; Nagaoka, Y.; Gouaux, E.; Bayley, H. Molecular bases of cyclodextrin adapter interactions with engineered protein nanopores Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 8165-8170
28. Dennington, R., II; Keith, T.; Millam, J. Gaussview, Version 3.09; Semichem, Inc.: Shawnee Mission, KS, 2003.
29. Trott, O.; Olson, A. J. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading J. Comput. Chem. 2010, 30, 455-461
30. Case, D. A.; Darden, T. A.; Cheatham, T. E.; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Crowley, M.; Walker, R. C.; Zhang, W.; Merz, K. M.; Wang, B.; Hayik, S.; Roitberg, A.; Seabra, G.; Kolossváry, I.; Wong, K. F.; Paesani, F.; Vanicek, J.; Wu, X.; Brozell, S. R.; Steinbrecher, T.; Gohlke, H.; Yang, L.; Tan, C.; Mongan, J.; Hornak, V.; Cui, G.; Mathews, D. H.; Seetin, M. G.; Sagui, C.; Babin, V.; Kollman, P. A. AMBER 10; University of California: San Francisco, 2008.
31. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J. D.; Impey, R. W.; Klein, M. L. Comparison of simple potential functions for simulating liquid water J. Chem. Phys. 1983, 79, 926-935
32. Kirschner, K. N.; Yongye, A. B.; Tschampel, S. M.; Daniels, C. R.; Foley, B. L.; Woods, R. J. GLYCAM06: a generalizable biomolecular force field. Carbohydrates J. Comput. Chem. 2008, 29, 622-655
33. Wang, J.; Wolf, R. M.; Caldwell, J. W.; Kollman, P. A.; Case, D. A. Development and testing of a general amber force field J. Comput. Chem. 2004, 25, 1157-1174
34. Darden, T.; York, D.; Pedersen, L. Particle Mesh Ewald-an N.Log (N) method for Ewald sums in large systems J. Chem. Phys. 1993, 98, 10089-10092
35. Ryckaert, J. P.; Ciccotti, G.; Berendsen, H. J. C. Numerical integration of the Cartesian equations of motion of a system with constraints: molecular dynamics of n -alkanes J. Comput. Phys. 1977, 23, 327-341
36. Kollman, P. A.; Massova, I.; Reyes, C.; Kuhn, B.; Huo, S.; Chong, L.; Lee, M.; Lee, T.; Duan, Y.; Wang, W.; Donini, O.; Cieplak, P.; Srinivasan, J.; Case, D. A.; Cheatham, T. E. Calculating structures and free energies of complex molecules: combining molecular mechanics and continuum models Acc. Chem. Res. 2000, 33, 889-897
37. Anand, O.; Yu, L. X.; Conner, D. P.; Davit, B. M. Dissolution testing for generic drugs: an FDA perspective AAPS 2013, 13, 328-335
38. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 1983, 65, 55-63
39. 1H NMR spectroscopy, molecular modeling studies, preparation and stability study of nebulizable solutions J. Pharm. Sci. 2005, 8, 164-175
40. Forgo, P.; Gondos, G. A study of β-cyclodextrin inclusion complexes with progesterone and hydrocortisone using rotating frame overhauser spectroscopy Monatsh. Chem. 2002, 133, 101-106
41. Madan, J.; Dhiman, N.; Sardana, S.; Aneja, R.; Chandra, R.; Katyal, A. Long circulating poly (ethylene glycol)-grafted gelatin nanoparticles customized for intracellular delivery of noscapine: preparation, in-vitro characterization, structure elucidation, pharmacokinetic and cytotoxicity analysis Anticancer Drugs 2011, 22, 543-555
42. Olsson, B.; Bolme, P.; Dahlstrom, B.; Marcus, C. Excretion of noscapine in human breast milk Eur. J. Clin. Pharmacol. 1986, 30, 213-215
43. Fan, L. F.; He, W.; Chang, Y. Z.; Xiang, B.; Du, Q.; Wang, F.; Qin, M.; Cao, D. Y. Studies on chitosan/Kollicoat SR30D film coated tablets for colonic drug delivery Int. J. Pharm. 2009, 375, 8-15
44. Ungell, A. L.; Nylander, S.; Bergstrand, S.; Sjoberg, A.; Lennernas, H. Membrane transport of drugs in different regions of the intestinal tract of the rat J. Pharm. Sci. 1998, 87, 360-366