Transporting Antitumor Drug Tamoxifen and Its Metabolites, 4-Hydroxytamoxifen and Endoxifen by Chitosan Nanoparticles

PLoS ONE

Volumn 8, Issue 3, 2013, Pages

  Agudelo, Daniel ^a   Sanyakamdhorn, Sriwanna ^a   Nafisi, Shoherh ^b   Tajmir Riahi, Heidar Ali ^a  

^a UNIVERSITÉ DU QUÉBEC À TROIS RIVIÈRES   (Canada)

^b SAN JOSE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AFIMOXIFENE; CHITOSAN; ENDOXIFEN; NANOPARTICLE; TAMOXIFEN;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; DRUG BINDING SITE; DRUG STRUCTURE; ENCAPSULATION; FLUORESCENCE SPECTROSCOPY; HYDROPHILICITY; HYDROPHOBICITY; INFRARED SPECTROSCOPY; MOLECULAR DOCKING; MOLECULAR MODEL; STRUCTURE ANALYSIS;

CHITOSAN; DRUG DELIVERY SYSTEMS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NANOPARTICLES; SPECTROMETRY, FLUORESCENCE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TAMOXIFEN;

EID: 84875123875     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0060250     Document Type: Article

References (40)

1. Jordan V C, (2006) Tamoxifen (ICI46,474) as a targeted therapy to treat and prevent breast cancer. Br J Pharmacol 147 (Suppl):: S269-S276.
2. Spears M, Bartlett J, (2009) The potential role of estrogen receptors and the SRC family as targets for the treatment of breast cancer. Expert Opin Ther Targets 13: 665-674.
3. Brauch J, Jordan VC, (2009) Targeting of tamoxifen to enhance antitumour action for the treatment and prevention of breast cancer. Eur J Cancer 45: 2274-2283.
4. Hayes T G, (2009) Pharmacologic treatment of male breast cancer. Expert Opin Pharmacother 10: 2499-510.
5. Nabholtz J M, Gligorov J, (2006) The emerging role of aromatase inhibitors in the adjuvant management of breast cancer. Rev Recent Clin Trials 1: 237-249.
6. Jordan V C, (2008) Tamoxifen: catalyst for the change to targeted therapy. Eur J Cancer 44: 30-38.
7. Jordan V C, (2007) New insights into the metabolism of tamoxifen and its role in the treatment and prevention of breast cancer. Steroids 72: 829-842.
8. Lien E A, Solheim E, Ueland P M, (1991) Distribution of tamoxifen and its metabolites in rat and human tissues during steady-state treatment. Cancer Res 51: 4837-4844.
9. Furlanut M, Franceschi L, Pasqual E, Bacchetti S, Poz D, et al. (2007) Tamoxifen and its main metabolites serum and tissue concentrations in breast cancer women. Ther Drug Monit 29: 349-352.
10. Hoskins J M, Carey L A, McLeod H L, (2009) CYP2D6 and tamoxifen: DNA matters in breast cancer. Nat Rev Cancer 9: 576-586.
11. Schroth W, Goetz MP, Hamann U, Fasching P A, Schmidt M, et al. (2009) Association between CYP2D6 polymorphisms and outcomes among women with early stage breast cancer treated with tamoxifen. JAMA 302: 1429-1436.
12. Bijl M J, van Schaik R H, Lammers L A, Hofman A, Vulto AG, et al. (2009) The CYP2D6*4 polymorphism affects breast cancer survival in tamoxifen users. Breast Cancer Res Treat 118: 125-130.
13. Pacheco N, Gamica-Gonzalez M, Gimeno M, Barzana E, Trombotto S, et al. (2011) Structural characterization of chitin and chitosan obtained by biological and chemical methods. Biomacromolecules 12: 3285-3290.
14. Rabea EI, Badawy MET, Stevens CV, Smagghe G, Steurbaut W, (2003) Chitosan as antimicrobial agent: application and mode of action. Biomacromolecules 4: 1457-1465.
15. Dang JM, Leong KW, (2006) Natural polymers for gene delivery and tissue Engineering. Adv Drug Deliv Rev 58: 487-499.
16. Gan Q, Wang T, (2007) Chitosan nanaoparticles as protein delivery carrier- systematic examination of fabrication conditions for efficient loading and release. Colloids Surfaces B. Biointerfaces 59: 24-34.
17. Mao S, Shuai X, Unger F, Simon M, (2004) The depolymerization of chitosan: effects on physicochemical and biological properties. Int J Pharm 281: 45-54.
18. Saranya N, Moorthi A, Saravanan S, Pandima Devi M, Selvamurugan N, (2001) Chitosan and its derivatives for gene delivery. Intl J Biol Macromol 48: 234-238.
19. Shu Z Z, Zhu K J, (2009) A novel approach to prepare tripolyphosphate: chitosan complex beads for controlled release drug delivery. Int J Pharm 201: 51-58.
20. Sanyakamdhorn S, Agudelo D, Tajmir-Riahi H A, (2013) Encapsulatin of antitumor drug doxorubicin and its analogue by chitosan nanoparticles. Biomacromolecules 14: 557-563.
21. Lakowicz J R (2006) In Principles of fluorescence spectroscopy 3rd ed; Springer: New York.
22. Tayeh N, Rungassamy T, Albani JR, (2009) Fluorescence spectral resolution of tryptophan residues in bovine and human serum albumins. J Pharm Biomed Anal 50: 107-116.
23. Fauq A H, Maharvi GM, Sinha D, (2010) A convenient synthesis of (Z)-4-hydroxy- N-desmethyltamoxifen (endoxifen). Bioorg Med Chem Lett 15: 3036-3038.
24. Brugnerotto J, Lizardi J, Goycoolea F M, Arguelles-Monal W, Desbrieres J, et al. (2000) An infrared investigation in relation with chitin and chitosan characterization. Polymer 42: 3569-3580.
25. Palpandi C, Shanmugam V, Shanmugam A, (2009) Extraction of chitin and chitosan from shell and operculum of mangrove gastropod Nerita (Dostia) crepidularia lamarcck. Intl J Med Med Sci 1: 198-205.
26. Engelke M, Bojarski P, Blob R, Diehl H, (2001) Tamoxifen perturbs lipid bilayer order and permeability: comparison of DSC, fluorescence anisotropy, Laurdan generalized polarization and carboxyfluoresceine leakage studies. Biophys Chem 90: 157-173.
27. Sarzehi S, Chamani J, (2010) Investigation on the interaction between tamoxifen and human holo-tranferrin: determination of the binding mechanism by fluorescence quenching resonance light scattering and circular dichroism methods. Intl J Biol Macromol 47: 558-569.
28. Dufour C, Dangles O, (2005) Flavnoid-serum albumin complexation: determination of binding constants and binding sites by fluorescence spectroscopy. Biochim Biophys Acta 1721: 164-173.
29. He W, Li Y, Xue C, Hu Z, Chen X, et al. (2005) Effect of Chinese medicine alpinetin on the structure of human serum albumin, Bioorg Med Chem. 13: 1837-1845.
30. Iranfar H, Rajabi O, Salari R, Chamani J, (2012) Probing the interaction of human serum albumin with ciprofloxacin in the presence of silver nanoparticles of three sizes: multispectroscopic and ζ potential investigation. J Phys Chem B 116: 1951-1964.
31. Bi S, Ding L, Tian Y, Song D, Zhou X, et al. (2004) Investigation of the interaction between flavonoids and human serum albumin. J Mol Struct 703: 37-45.
32. Jiang M, Xie MX, Zheng D, LiuY, Li XY, et al. (2004) Spectroscopic studies on the interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin. J Mol Struct 692: 71-80.
33. Skovstrip S, Hansen S G, Skrydstrup T, Schiott B, (2010) Conformational flexibility of chitosan: a molecular modeling study. Biomacromolecules 11: 3196-3207.
34. Manikrao AM, Mahajan NS, Jawarkar DR, Khatale PN, Kedar KC, et al. (2012) Thombare. Docking analysis of darunnavir as HIV protease inhibitors J Comput Methods Mol Design 2012 2: 29-43.
35. Mandeville JS, Tajmir-Riahi HA, (2010) Complexes of dendrimers with bovine serum albumin. Biomacromolecules 11: 465-472.
36. Charbonneau DM, Tajmir-Riahi H A, (2010) Study on the interaction of cationic lipids with bovine serum albumin. J Phys Chem B 114: 1148-1155.
37. Bourassa P, Kanakis DC, Tarantilis P, Polissiou MG, Tajmir-Riahi H A, (2010) Resveratrol, genistein and curcumin bind bovine serum albumin, J Phys Chem B. 114: 3348-3354.
38. Froehlich E, Jennings JC, Sedaghat-Herati MR, Tajmir-Riahi HA, (2009) Dendrimers bind human serum albumin. J Phys Chem B 113: 6986-6993.
39. Zhang G, Que Q, Pan J, Guo J, (2008) Study of the interaction between icariin and human serum albumin by fluorescence spectroscopy. J Mol Struct 881: 132-138.
40. Huang DC, Piché M, Ma G, Jean-Jacques M, Mario Khayat M (2010) Early detection and treatment monitoring of human breast cancer MCF-7 using fluorescence imaging. ART Advanced Research Technologies Inc.www.art.ca/docs/publications/WMIC2010_MCF7.pdf.