Novel dipeptide nanoparticles for effective curcumin delivery

International Journal of Nanomedicine

Volumn 7, Issue , 2012, Pages 4207-4222

  Alam, Shadab ^a   Panda, Jiban J ^a   Chauhan, Virander S ^a  

^a INTERNATIONAL CENTRE FOR GENETIC ENGINEERING AND BIOTECHNOLOGY   (Italy)

Author keywords

Anticancer; Curcumin; Dipeptide; Hydrophobic; Nanoparticle; Self assembly

Indexed keywords

ALPHA BETA DEHYDROPHENYLALANINE; CURCUMIN; CYCLODEXTRIN; DIPEPTIDE NANOPARTICLE; LIPID BASED NANOPARTICLE; METHIONINE PHENYLALANINE; MICROSPHERE; NANOPARTICLE; PHENYLALANINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL DEATH; CELL MEDIATED CYTOTOXICITY; CONTROLLED STUDY; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG DOSAGE FORM COMPARISON; DRUG EFFICACY; DRUG RELEASE; DRUG SOLUBILITY; DRUG STRUCTURE; FEMALE; FIBROBLAST CULTURE; HUMAN; HUMAN CELL; HYDROGEL; IN VITRO STUDY; IN VIVO STUDY; LIGHT SCATTERING; LIPOSOMAL DELIVERY; MALE; MOUSE; NANOENCAPSULATION; NONHUMAN; PARTICLE SIZE; PHYSICAL CHEMISTRY; TRANSMISSION ELECTRON MICROSCOPY;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE; CELL PROLIFERATION; CELL SURVIVAL; CURCUMIN; DIPEPTIDES; FLOW CYTOMETRY; HELA CELLS; HUMANS; MALE; MICE; MICE, INBRED BALB C; NANOPARTICLES; NEOPLASMS, EXPERIMENTAL; PARTICLE SIZE; SOLUBILITY; TISSUE DISTRIBUTION; XENOGRAFT MODEL ANTITUMOR ASSAYS;

CURCUMA LONGA; MUS;

EID: 84870365064     PISSN: 11769114     EISSN: 11782013     Source Type: Journal    
DOI: 10.2147/IJN.S33015     Document Type: Article

References (71)

1. Brouet I, Ohshima H. Curcumin, an anti-tumour promoter and anti-inflammatory agent, inhibits induction of nitric oxide synthase in activated macrophages. Biochem Biophys Res Commun. 1995;206(2):533-540.
2. Ammon HP, Wahl MA. Pharmacology of Curcuma longa. Planta Med. 1991;57(1):1-7.
3. Maheshwari RK, Singh AK, Gaddipati J, Srimal RC. Multiple biological activities of curcumin: a short review. Life Sci. 2006;78(18): 2081-2087.
4. Rao CV, Rivenson A, Simi B, Reddy BS. Chemoprevention of colon carcinogenesis by dietary curcumin, a naturally occurring plant phenolic compound. Cancer Res. 1995;55(2):259-266.
5. Moragoda L, Jaszewski R, Majumdar AP. Curcumin induced modulation of cell cycle and apoptosis in gastric and colon cancer cells. Anticancer Res. 2001;21(2A):873-878.
6. Mehta K, Pantazis P, McQueen T, Aggarwal BB. Antiproliferative effect of curcumin (diferuloylmethane) against human breast tumor cell lines. Anticancer Drugs. 1997;8(5):470-481.
7. Kuttan R, Bhanumathy P, Nirmala K, George MC. Potential anticancer activity of turmeric (Curcuma longa). Cancer Lett. 1985;29(2):197-202.
8. Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB. Bioavailability of curcumin: problems and promises. Mol Pharm. 2007;4(6):807-818.
9. Kunwar A, Barik A, Pandey R, Priyadarsini KI. Transport of liposomal and albumin loaded curcumin to living cells: an absorption and fluorescence spectroscopic study. Biochim Biophys Acta. 2006;1760(10):1513-1520.
10. Sou K, Inenaga S, Takeoka S, Tsuchida E. Loading of curcumin into macrophages using lipid-based nanoparticles. Int J Pharm. 2008;352(1-2):287-293.
11. Kumar V, Lewis SA, Mutalik S, Shenoy DB, Venkatesh, Udupa N. Biodegradable microspheres of curcumin for treatment of inflammation. Indian J Physiol Pharmacol. 2002;46(2):209-217.
12. Tiyaboonchai W, Tungpradit W, Plianbangchang P. Formulation and characterization of curcuminoids loaded solid lipid nanoparticles. Int J Pharm. 2007;337(1-2):299-306.
13. Dobrovolskaia MA, McNeil SE. Immunological properties of engineered nanomaterials. Nat Nanotechnol. 2007;2(8):469-478.
14. Hoet PH, Brüske-Hohlfeld I, Salata OV. NPs-known and unknown health risks. J Nanobiotechnology. 2004;2(1):12.
15. Mendel D, Ellman JA, Chang Z, Veenstra DL, Kollman PA, Schultz PG. Probing protein stability with unnatural amino acids. Science. 1992;256(5065):1798-1802.
16. English ML, Stammer CH. The enzyme stability of dehydropeptides. Biochem Biophys Res Commun. 1978;83(4):1464-1467.
17. Adessi C, Soto C. Converting a peptide into a drug: strategies to improve stability and bioavailability. Curr Med Chem. 2002;9(9):963-978.
18. Panda JJ, Kaul A, Alam S, Babbar AK, Mishra AK, Chauhan VS. Designed peptides as model self-assembling nanosystems: characterization and potential biomedical applications. Ther Deliv. 2011;2:193-204.
19. Mishra A, Panda JJ, Basu A, Chauhan VS. Nanovesicles based on self-assembly of conformationally constrained aromatic residue containing amphiphilic dipeptides. Langmuir. 2008;24(9):4571-4576.
20. Sahu A, Bora U, Kasoju N, Goswami P. Synthesis of novel biodegradable and self-assembling methoxy poly(ethylene glycol)-palmitate nanocarrier for curcumin delivery to cancer cells. Acta Biomater. 2008;4(6):1752-1761.
21. Mulik R, Mahadik K, Paradkar A. Development of curcuminoids loaded poly(butyl) cyanoacrylate nanoparticles: Physicochemical characterization and stability study. Eur J Pharm Sci. 2009;37(3-4):395-404.
22. Koria P, Yagi H, Kitagawa Y, etal. Self-assembling elastin-like peptides growth factor chimeric nanoparticles for the treatment of chronic wounds. Proc Natl Acad Sci U S A. 2011;108(3):1034-1039.
23. Chang CH, In HJ, Takahashi S, etal. Assembling nanoparticle catalysts with nanospheres for periodic carbon nanotube structure growth. Nanotechnology. 2011;22(3):035301.
24. Daniel MC, Tsvetkova IB, Quinkert ZT, etal. Role of surface charge density in nanoparticle-templated assembly of bromovirus protein cages. ACS Nano. 2010;4(7):3853-3860.
25. Chhabra R, Sharma J, Liu Y, Rinker S, Yan H. DNA self-assembly for nanomedicine. Adv Drug Deliv Rev. 2010;62(6):617-625.
26. Ko YT, Kale A, Hartner WC, Papahadjopoulos-Sternberg B, Torchilin VP. Self-assembling micelle-like nanoparticles based on phospholipid-polyethyleneimine conjugates for systemic gene delivery. J Control Release. 2009;133(2):132-138.
27. Zharov VP, Kim JW, Curiel DT, Everts M. Self-assembling nanoclusters in living systems: application for integrated photothermal nanodiagnostics and nanotherapy. Nanomedicine. 2005;1(4):326-345.
28. Reches M, Gazit E. Casting metal nanowires within discrete self-assembled peptide nanotubes. Science. 2003;300(5619):625-627.
29. Gupta M, Bagaria A, Mishra A, etal. Self-assembly of a dipeptide-containing conformationally restricted dehydrophenylalanine residue to form ordered nanotubes. Adv Mater. 2007;19:858-861.
30. Mahler A, Reches M, Rechter M, Cohen S, Gazit E. Rigid, self-assembled hydrogel composed of a modified aromatic dipeptide. Adv Mater. 2006;18:1365-1370.
31. Capone R, Quiroz FG, Prangkio P, etal. Amyloid-beta-induced ion flux in artificial lipid bilayers and neuronal cells: resolving a controversy. Neurotox Res. 2009;16(1):1-13.
32. Pandaey A, Gupta RK, Shrivastava R. Curcumin-the yellow magic. Asian J. Applied Sci. 2011;4:343-354.
33. Mahindu SN. Food additives: characteristics, detection and estimation, APH Publishing Corporation, New Delhi-India; 2008.
34. Das S, Suresh PK. Nanosuspension: a new vehicle for the improvement of the delivery of drugs to the ocular surface. Application to amphotericin B. Nanomedicine. 2011;7(2):242-247.
35. Chen Y, Liu J, Yang X, Zhao X, Xu H. Oleanolic acid nanosuspensions: preparation, in-vitro characterization and enhanced hepatoprotective effect. J Pharm Pharmacol. 2005;57(2):259-264.
36. Takamuku T, Wada H, Kawatoko C, Shimomura T, Kanzaki R, Takeuchi M. Amide-induced phase separation of hexafluoroisopropanol-water mixtures depending on the hydrophobicity of amides. Phys Chem Chem Phys. 2012;14(23):8335-8347.
37. Krysmann MJ, Castelletto V, McKendrick JE, etal. Self-assembly of peptide nanotubes in an organic solvent. Langmuir. 2008;24(15): 8158-8162.
38. Li H, Zhang F, Zhang Y, He J, Hu J. Organic solvents mediate self-assembly of GAV-9 peptide on mica surface. Acta Biochim Biophys Sin (Shanghai). 2007;39(4):285-289.
39. Anand P, Nair HB, Sung B, etal. Design of curcumin-loaded PLGA nanoparticles formulation with enhanced cellular uptake, and increased bioactivity in vitro and superior bioavailability in vivo. Biochem Pharmacol. 2010;79(3):330-338.
40. Cartiera MS, Ferreira EC, Caputo C, Egan ME, Caplan MJ, Saltzman WM. Partial correction of cystic fibrosis defects with PLGA nanoparticles encapsulating curcumin. Mol Pharm. 2010;7(1):86-93.
41. Gupta V, Aseh A, Rios CN, Aggarwal BB, Mathur AB. Fabrication and characterization of silk fibroin-derived curcumin nanoparticles for cancer therapy. Int J Nanomedicine. 2009;4:115-122.
42. Das RK, Kasoju N, Bora U. Encapsulation of curcumin in alginate-chitosan-pluronic composite nanoparticles for delivery to cancer cells. Nanomedicine. 2010;6(1):153-160.
43. Regev O, Gohy J, Lohmeijer BGG, etal. Dynamic light scattering and cryogenic transmission electron microscopy investigations on metallo-supramolecular aqueous micelles: evidence of secondary aggregation. Colloid Polym Sci. 2004;282(4):407-411.
44. Chaleawlert-umpon S, Pimpha N. Morphology study of superparamagnetic iron oxide-chitosan nanoparticles. Journal of Microscopy Society of Thailand. 2009;23(1):62-65.
45. Prato M, Kostarelos K, Bianco A. Functionalized carbon nanotubes in drug design and discovery. Acc Chem Res. 2008;41:60-68.
46. Liu Z, Chen K, Davis C, etal. Drug delivery with carbon nanotubes for in vivo cancer treatment. Cancer Res. 2008;68(16):6652-6660.
47. Bagalkot V, Farokhzad OC, Langer R, Jon S. An aptamer-doxorubicin physical conjugate as a novel targeted drug-delivery platform. Angew Chem Int Ed Engl. 2006;45(48):8149-8152.
48. Farokhzad OC, Cheng J, Teply BA, etal. Targeted nanoparticle-aptamer bioconjugates for cancer chemotherapy in vivo. Proc Natl Acad Sci U S A. 2006;103(16):6315-6320.
49. Mohanty C, Sahoo SK. The in vitro stability and in vivo pharmacokinetics of curcumin prepared as an aqueous nanoparticulate formulation. Biomaterials. 2010;31(25):6597-6611.
50. Bisht S, Feldmann G, Soni S, etal. Polymeric nanoparticle-encapsulated curcumin ("nanocurcumin"): a novel strategy for human cancer therapy. J Nanobiotechnology. 2007;5:3.
51. Whitesides GM, Grzybowski B. Self-assembly at all scales. Science. 2002;295(5564):2418-2421.
52. de Groot NS, Parella T, Aviles FX, Vendrell J, Ventura S. Ile-phe dipeptide self-assembly: clues to amyloid formation. Biophys J. 2007;92(5):1732-1741.
53. Scanlon S, Aggeli A. Self-assembling peptide nanotubes. Nano Today. 2008;3:22-30.
54. Torchilin V. Tumor delivery of macromolecular drugs based on the EPR effect. Adv Drug Deliv Rev. 2011;63(3):131-135.
55. Duan J, Zhang Y, Han S, etal. Synthesis and in vitro/in vivo anti-cancer evaluation of curcumin-loaded chitosan/poly(butyl cyanoacrylate) nanoparticles. Int J Pharm. 2010;400(1-2):211-220.
56. Sahu A, Kasoju N, Bora U. Fluorescence study of the curcumin-casein micelle complexation and its application as a drug nanocarrier to cancer cells. Biomacromolecules. 2008;9(10):2905-2912.
57. Missirlis D, Kawamura R, Tirelli N, Hubbell JA. Doxorubicin encapsulation and diffusional release from stable, polymeric, hydrogel nanoparticles. Eur J Pharm Sci. 2006;29(2):120-129.
58. Nayak AP, Tiyaboonchai W, Patankar S, Madhusudhan B, Souto EB. Curcuminoids-loaded lipid nanoparticles: novel approach towards malaria treatment. Colloids Surf B Biointerfaces. 2010;81(1): 263-273.
59. Reddy RC, Vatsala PG, Keshamouni VG, Padmanaban G, Rangarajan PN. Curcumin for malaria therapy. Biochem Biophys Res Commun. 2005;326(2):472-474.
60. Dhillon N, Aggarwal BB, Newman RA, etal. Phase II trial of curcumin in patients with advanced pancreatic cancer. Clin Cancer Res. 2008;14(14):4491-4499.
61. Sharma RA, Euden SA, Platton SL, etal. Phase I clinical trial of oral curcumin: biomarkers of systemic activity and compliance. Clin Cancer Res. 2004;10(20):6847-6854.
62. Hsu YC, Weng HC, Lin S, Chien YW. Curcuminoids-cellular uptake by human primary colon cancer cells as quantitated by a sensitive HPLC assay and its relation with the inhibition of proliferation and apoptosis. J Agric Food Chem. 2007;55(20):8213-8222.
63. Ma Z, Haddadi A, Molavi O, Lavasanifar A, Lai R, Samuel J. Micelles of poly(ethylene oxide)-b-poly(epsilon-caprolactone) as vehicles for the solubilization, stabilization, and controlled delivery of curcumin. J Biomed Mater Res A. 2008;86(2):300-310.
64. Wyllie AH, Kerr JF, Currie AR. Cell death: the significance of apoptosis. Int Rev Cytol. 1980;68:251-306.
65. Fryer RA, Galustian C, Dalgleish AG. Recent advances and developments in treatment strategies against pancreatic cancer. Curr Clin Pharmacol. 2009;4(2):102-112.
66. Roy M, Chakraborty S, Siddiqi M, Bhattacharya RK. Induction of apoptosis in tumor cells by natural phenolic compounds. Asian Pac J Cancer Prev. 2002;3(1):61-67.
67. Karunagaran D, Rashmi R, Kumar TR. Induction of apoptosis by curcumin and its implications for cancer therapy. Curr Cancer Drug Targets. 2005;5(2):117-129.
68. Acharya S, Dilnawaz F, Sahoo SK. Targeted epidermal growth factor receptor nanoparticle bioconjugates for breast cancer therapy. Biomaterials. 2009;30(29):5737-5750.
69. van Engeland M, Nieland LJ, Ramaekers FC, Schutte B, Reutelingsperger CP. Annexin V-affinity assay: a review on an apoptosis detection system based on phosphatidylserine exposure. Cytometry. 1998;31(1):1-9.
70. Kluza E, Yeo SY, Schmid S, etal. Anti-tumor activity of liposomal glucocorticoids: The relevance of liposome-mediated drug delivery, intratumoral localization and systemic activity. J Control Release. 2011;151(1):10-17.
71. Rudra JS, Sun T, Bird KC, etal. Modulating adaptive immune responses to peptide self-assemblies. ACS Nano. 2012;6(2):1557-1564.