Novel kojic acid-polymer-based magnetic nanocomposites for medical applications

International Journal of Nanomedicine

Volumn 9, Issue 1, 2014, Pages 351-362

  Hussein Al Ali, Samer Hasan ^a   El Zowalaty, Mohamed Ezzat ^b,e   Hussein, Mohd Zobir ^c   Ismail, Maznah ^a,d   Dorniani, Dena ^c   Webster, Thomas J ^f,g  

^a Laboratory of Molecular Biomedicine   (Malaysia)

^b Institute of Bioscience   (Malaysia)

^c Institute of Advanced Technology   (Malaysia)

^d UNIVERSITY PUTRA MALAYSIA   (Malaysia)

^e JAZAN UNIVERSITY   (Saudi Arabia)

^f Northeastern University   (United States)

^g KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

Biological activity; Chitosan; Controlled release; Kojic acid; Magnetic nanoparticle; Polyethylene glycol

Indexed keywords

CHITOSAN; IRON OXIDE; KOJIC ACID; KOJIC ACID LOADED CHITOSAN COATED MAGNETIC COMPOSITE; KOJIC ACID LOADED CHITOSAN COATED POLYETHYLENE GLYCOL; MACROGOL; MAGNETIC NANOPARTICLE; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; DRUG BINDING; DRUG COATING; HYDROGEN BOND; INFRARED SPECTROSCOPY; MAGNETOMETRY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MOLECULAR WEIGHT; NONHUMAN; SALMONELLA ENTERICA; SCANNING ELECTRON MICROSCOPY; THERMOGRAVIMETRY; X RAY DIFFRACTION;

BIOLOGICAL ACTIVITY; CHITOSAN; CONTROLLED RELEASE; KOJIC ACID; MAGNETIC NANOPARTICLE; POLYETHYLENE GLYCOL;

ANTI-BACTERIAL AGENTS; BACTERIAL PHYSIOLOGICAL PHENOMENA; CELL SURVIVAL; DIFFUSION; MAGNETITE NANOPARTICLES; MOLECULAR CONFORMATION; PARTICLE SIZE; POLYETHYLENE GLYCOLS; PYRONES;

EID: 84892148863     PISSN: 11769114     EISSN: 11782013     Source Type: Journal    
DOI: 10.2147/IJN.S53847     Document Type: Article

References (62)

1. Barrett AP. A long-term prospective clinical study of oral complications during conventional chemotherapy for acute leukemia. Oral Surg Med Path. 1987;63(3):313-316.
2. Branda RF, Naud SJ, Brooks EM, Chen Z, Muss H. Effect of vitamin B12, folate, and dietary supplements on breast carcinoma chemotherapy-induced mucositis and neutropenia. Cancer. 2004;101(5):1058-1064.
3. Danilenko DM, Ring BD, Yanagihara D, et al. Keratinocyte growth factor is an important endogenous mediator of hair follicle growth, development, and differentiation. Normalization of the nu/nu follicular differentiation defect and amelioration of chemotherapy-induced alopecia. Am J Pathol. 1995;147(1):145-154.
4. Akbulut M, D'Addio SM, Gindy ME, Prud'homme RK. Novel methods of targeted drug delivery: the potential of multifunctional nanoparticles. Expert Rev Clin Pharmacol. 2009;2(3):265-282.
5. Chari RV. Targeted cancer therapy: conferring specificity to cytotoxic drugs. Acc Chem Res. 2007;41(1):98-107.
6. Kim S, Kim JY, Huh KM, Acharya G, Park K. Hydrotropic polymer micelles containing acrylic acid moieties for oral delivery of paclitaxel. J Controlled Release. 2008;132(3):222-229.
7. Tran N, Webster TJ. Magnetic nanoparticles: biomedical applications and challenges. J Mater Chem. 2010;20(40):8760-8767.
8. Mahmoudi M, Sant S, Wang B, Laurent S, Sen T. Superparamagnetic iron oxide nanoparticles (SPIONs): development, surface modification and applications in chemotherapy. Adv Drug Deliv Rev. 2011;63(1-2):24-46.
9. Gupta AK, Gupta M. Synthesis and surface engineering of iron oxide nanoparticles for biomedical applications. Biomaterials. 2005;26(18):3995-4021.
10. Alexiou C, Schmid RJ, Jurgons R, et al. Targeting cancer cells: magnetic nanoparticles as drug carriers. Eur Biophys J. 2006;35(5):446-450.
11. Pankhurst QA, Connolly J, Jones SK, Dobson J. Applications of magnetic nanoparticles in biomedicine. J Phys D Appl Phys. 2003; 36(13):R167.
12. Alexiou C, Arnold W, Hulin P, et al. Magnetic mitoxantrone nanoparticle detection by histology, X-ray and MRI after magnetic tumor targeting. J Magn Magn Mater. 2001;225(1-2):187-193.
13. Jain TK, Morales MA, Sahoo SK, Leslie-Pelecky DL, Labhasetwar V. Iron oxide nanoparticles for sustained delivery of anticancer agents. Mol Pharm. 2005;2(3):194-205.
14. Kaaki K, Hervé-Aubert K, Chiper M, et al. Magnetic nanocarriers of doxorubicin coated with poly(ethylene glycol) and folic acid: relation between coating structure, surface properties, colloidal stability, and cancer cell targeting. Langmuir. 2012;28(2):1496-1505.
15. Kayal S, Ramanujan RV. Doxorubicin loaded PVA coated iron oxide nanoparticles for targeted drug delivery. Mater Sci Eng C. 2010;30(3):484-490.
16. Quan Q, Xie J, Gao H, et al. HSA coated iron oxide nanoparticles as drug delivery vehicles for cancer therapy. Mol Pharm. 2011;8(5): 1669-1676.
17. Saboktakin MR, Tabatabaie R, Maharramov A, Ramazanov MA. Synthesis and characterization of superparamagnetic chitosan-dextran sulfate hydrogels as nano carriers for colon-specific drug delivery. Carbohydr Polym. 2010;81(2):372-376.
18. Finotelli PV, Da Silva D, Sola-Penna M, et al. Microcapsules of alginate/chitosan containing magnetic nanoparticles for controlled release of insulin. Colloids Surf B Biointerfaces. 2010;81(1):206-211.
19. Qu JB, Shao HH, Jing GL, Huang F. PEG-chitosan-coated iron oxide nanoparticles with high saturated magnetization as carriers of 10-hydroxycamptothecin: preparation, characterization and cytotoxicity studies. Colloids Surf B Biointerfaces. 2013;102:37-44.
20. Dorniani D, Hussein MZ, Kura AU, Fakurazi S, Shaari AH, Ahmad Z. Preparation of Fe3O4 magnetic nanoparticles coated with gallic acid for drug delivery. Int J Nanomedicine. 2012;7:5745-5756.
21. Sun C, Sze R, Zhang M. Folic acid-PEG conjugated superparamagnetic nanoparticles for targeted cellular uptake and detection by MRI. J Biomed Mater Res A. 2006;78(3):550-557.
22. Arias JL, López-Viota M, López-Viota J, Delgado AV. Development of iron/ethylcellulose (core/shell) nanoparticles loaded with diclofenac sodium for arthritis treatment. Int J Pharm. 2009;382(1-2):270-276.
23. Butoescu N, Jordan O, Burdet P, et al. Dexamethasone-containing biodegradable superparamagnetic microparticles for intra-articular administration: physicochemical and magnetic properties, in vitro and in vivo drug release. Eur J Pharm Biopharm. 2009;72(3):529-538.
24. Beélik A. Kojic acid. Adv Carbohydr Chem. 1956;48(11):145-183.
25. Morton HE, Kocholaty W, Junowicz-Kocholaty R, Kelner A. Toxicity and antibiotic activity of kojic acid produced by Aspergillus luteo-virescens. J Bacteriol. 1945;50(5):579-584.
26. Prescott SC, Dunn CG. Industrial Microbiology. New York, NY: McGraw-Hill; 1940.
27. Yaduta T. Kojic acid, a new organic acid formed by Aspergillus oryzae. J. Chem Soc. Japan, 1916;37:1185-1233.
28. Aytemir MD, Karakaya G, Ekinci D. Kojic acid derivatives. In: Deniz Ekinci, editor. Medicinal Chemistry and Drug Design. 2012:1-26. Available from: http://www.intechopen.com/books/medicinal-chemistry-and-drug-design/kojic-acid-derivatives.
29. Brtko J, Rondahl L, Ficková M, Hudecová D, Eybl V, Uher M. Kojic acid and its derivatives: history and present state of art. Cent Eur J Public Health. 2004;12 Suppl:S16-S18.
30. Mohamad R, Mohamed MS, Suhaili N, Salleh MM, Ariff AB. Kojic acid: applications and development of fermentation process for production. Biotechnol Mol Biol Rev. 2010;5(2):24-37.
31. Aytemir MD, Septioǧlu E, Caliş U. Synthesis and anticonvulsant activity of new kojic acid derivatives. Arzneimittelforschung. 2010;60(1):22-29.
32. Iyengar R, McEvily AJ. Anti-browning agents: alternatives to the use of sulfites in foods. Trends Food Sci Technol. 1992;3:60-64.
33. Uchino K, Nagawa M, Tonosaki Y, Oda M, Fukuchi A. Kojic acid as an anti-speck agent (foof and nutrition). Agric Biol Chem. 1988;52(10): 2609-2610.
34. Bentley R. From miso, saké and shoyu to cosmetics: a century of science for kojic acid. Nat Prod Rep. 2006;23(6):1046-1062.
35. Mishima Y, Hatta S, Ohyama Y, Inazu M. Induction of melanogenesis suppression: cellular pharmacology and mode of differential action. Pigment Cell Res. 1988;1(6):367-374.
36. Choi CM, Berson DS. Cosmeceuticals. Seminars in Cutaneous Medicine and Surgery. 2006;25(3):163-168.
37. Cabanes J, Chazarra S, Garcia-Carmona F. Kojic acid, a cosmetic skin whitening agent, is a slow-binding inhibitor of catecholase activity of tyrosinase. J Pharm Pharmacol. 1994;46(12):982-985.
38. Beard RL, Walton GS. Kojic acid as an insecticidal mycotoxin. J Invertebr Pathol. 1969;14(1):53-59.
39. Veverka M. Synthesis of some biologically active derivatives of 2-hydroxymethyl-5-hydroxy-4H-pyran-4-one. 2. Synthesis and biological properties of S-substituted 2-thiomethyl-5-O-acyl derivatives. Chem Pap. 1992;46(3):206-210.
40. Alverson J, Cohen AC. Effect of antifungal agents on biological fitness of Lygus hesperus (Heteroptera: Miridae). J Econ Entomol. 2002;95(2):256-260.
41. Higa Y, Kawabe M, Nabae K, et al. Kojic acid-absence of tumor-initiating activity in rat liver, and of carcinogenic and photo-genotoxic potential in mouse skin. J Toxicol Sci. 2007;32(2):143-159.
42. Xiong X, Pirrung MC. Modular synthesis of candidate indole-based insulin mimics by Claisen rearrangement. Org Lett. 2008;10(6):1151-1154.
43. Yamato M, Hashigaki K, Yasumoto Y, et al. Synthesis and antitumor activity of tropolone derivatives. 6. Structure-activity relationships of antitumor-active tropolone and 8-hydroxyquinoline derivatives. J Med Chem. 1987;30(10):1897-1900.
44. Fickova M, Pravdova E, Rondhal L, Uher M, Brtko J. In vitro antiproliferative and cytotoxic activities of novel kojic acid derivatives: 5-benzyloxy-2-selenocyanatomethyl- and 5-methoxy-2-selenocyanatomethyl-4-pyranone. J Appl Toxicol. 2008;28(4): 554-559.
45. Hudecová D, Uher M, Brtko J. Halogen derivatives of kojic acid with antifungal effects. Biologia. 1992;47:483-488.
46. Nohynek GJ, Kirkland D, Marzin D, Toutain H, Leclerc-Ribaud C, Jinnai H. An assessment of the genotoxicity and human health risk of topical use of kojic acid [5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one]. Food Chem Toxicol. 2004;42(1):93-105.
47. Kim JH, Chang PK, Chan KL, et al. Enhancement of commercial antifungal agents by kojic Acid. Int J Mol Sci. 2012;13(11):13867-13880.
48. Chee HY, Lee EH. Fungistatic activity of kojic acid against human pathogenic fungi and inhibition of melanin-production in Cryptococcus neoformans. Mycobiology. 2003;31(4):248-250.
49. Rodrigues AP, Carvalho AS, Santos AS, Alves CN, do Nascimento JL,Silva EO. Kojic acid, a secondary metabolite from Aspergillus sp, acts as an inducer of macrophage activation. Cell Biol Int. 2011;35(4): 335-343.
50. National Committee for Clinical Laboratory Standards. Methods for Dilution of Antimicrobial Susceptibility Test for Bacteria that Grow Aerobically. 4th ed. Approved Standard NCCLS Document M7-A4, Vol 17, No 2. Wayne, PA: NCCLS; 1997.
51. Unsoy G, Yalcin S, Khodadust R, Gunduz G, Gunduz U. Synthesis optimization and characterization of chitosan-coated iron oxide nanoparticles produced for biomedical applications. J Nanopart Res. 2012;14(11):1-13.
52. Marchessault RH, Ravenelle Fo, Zhu XX, editors. Polysaccharides for Drug Delivery and Pharmaceutical Applications. Vol 934. Washington, DC: American Chemical Society; 2006.
53. Jayanthi SA, Sukanya D, Pragasam AJA, Sagayaraj P. The influence of PEG 20,000 concentration on the size control and magnetic properties of functionalized bio-compatible magnetic nanoparticles. Der Pharma Chemica. 2013;5(1):90-102.
54. Kumar R, Inbaraj BS, Chen BH. Surface modification of superparamagnetic iron nanoparticles with calcium salt of poly(γ-glutamic acid) as coating material. Mater Res Bull. 2010;45(11):1603-1607.
55. Shan Z, Yang WS, Zhang X, Huang QM, Ye H. Preparation and characterization of carboxyl-group functionalized superparamagnetic nanoparticles and the potential for bio-applications. J Brazil Chem Soc. 2007;18(7):1329-1335.
56. Yu S, Chow GM. Carboxyl group (-CO2H) functionalized ferrimagnetic iron oxide nanoparticles for potential bio-applications. J Mater Chem. 2004;14(18):2781-2786.
57. Dung TT, Danh TM, Duc NH, Chien DM. Preparation and characterization of magnetic nanoparticles coated with polyethylene glycol. J Phys Conf Ser. 2009;187(1):012048.
58. Yue-Jian C, Juan T, Fei X, et al. Synthesis, self-assembly, and characterization of PEG-coated iron oxide nanoparticles as potential MRI contrast agent. Drug Dev Ind Pharm. 2010;36(10):1235-1244.
59. Dong L, Yan L, Hou WG, Liu SJ. Synthesis and release behavior of composites of camptothecin and layered double hydroxide. J Solid State Chem. 2010;183(8):1811-1816.
60. Sakore S, Chakraborty B. Formulation and evaluation of enalapril maleate sustained release matrix tablets. Int J Pharm Biomed Res. 2013;4(1):21-26.
61. Baláz S, Uher M, Brtko J, et al. Relationship between antifungal activity and hydrophobicity of kojic acid derivatives. Folia Microbiol (Praha). 1993;38(5):387-391.
62. Aytemir MD, Özçelik B. Synthesis and biological activities of new Mannich bases of chlorokojic acid derivatives. Med Chem Res. 2011;20(4):443-452.