Systemic delivery of curcumin: 21st century solutions for an ancient conundrum

Current Drug Discovery Technologies

Volumn 6, Issue 3, 2009, Pages 192-199

  Bisht, Savita ^a,b   Maitra, Anirban ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b Cancer Research Building II ^*  (United States)

Author keywords

Bioavailability; Cancer; Curcumin; Nanocurcumin; Polymeric nanoparticle

Indexed keywords

1 VINYL 2 PYRROLIDINONE; CURCUMIN; DOXORUBICIN; HUMAN SERUM ALBUMIN; LIPOSOME; MACROGOL; N MALEOYL GLYCINE CURCUMIN; N MALEOYL VALINE CURCUMIN; NANOPARTICLE; PACLITAXEL; PACLITAXEL POLIGLUMEX; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; PHOSPHOLIPID DERIVATIVE; PIPERINE; POLY(N ISOPROPYLACRYLAMIDE); UNCLASSIFIED DRUG; WATER;

ADENOMATOUS POLYP; ADVANCED CANCER; AMENORRHEA; ANTIANGIOGENIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; CHEMOPROPHYLAXIS; CLINICAL TRIAL; COLORECTAL CANCER; DIARRHEA; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG DOSE ESCALATION; DRUG ELIMINATION; DRUG EXCRETION; DRUG FORMULATION; DRUG HALF LIFE; DRUG METABOLISM; DRUG POTENTIATION; DRUG SAFETY; DRUG SOLUBILITY; DRUG TISSUE LEVEL; FEVER; GASTROINTESTINAL DISEASE; HEAD AND NECK CARCINOMA; HUMAN; INFLAMMATORY DISEASE; LEUKODERMA; LIVER CANCER; METASTASIS; MICELLE; NAUSEA; NONHUMAN; PRIORITY JOURNAL; REVIEW; RHEUMATIC DISEASE; RHEUMATOID ARTHRITIS; SKIN DISEASE; SQUAMOUS CELL CARCINOMA; UNSPECIFIED SIDE EFFECT; URINARY DYSFUNCTION;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; BIOLOGICAL AVAILABILITY; CURCUMIN; HUMANS; MODELS, BIOLOGICAL; PHARMACEUTICAL PREPARATIONS;

EID: 69249093874     PISSN: 15701638     EISSN: None     Source Type: Journal    
DOI: 10.2174/157016309789054933     Document Type: Review

References (90)

1. Han X, Shen T, Lou H. Dietary polyphenols and their biological significance. Int J Mol Sci 2007; 8: 950-988 (Pubitemid 47523244)
2. Yang CS, Landau JM, Huang MT, Newmark HL. Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu Rev Nutr 2001; 21: 381-406. (Pubitemid 32695277)
3. Chen D, Dou QP. Tea Polyphenols and their role in cancer prevention and chemotherapy. Int J Mol Sci 2008; 9: 1196-1206
4. Shishodia S, Sethi G, Aggarwal BB. Curcumin: getting back to the roots. Ann NY Acad Sci 2005; 1056: 206-217
5. Milobedzka J, Kostanceki V, Lampe V. Structure of curcumin. Chem Ber ;10(43): 2163.
6. Heath DD, Khwaja F, Rock CL. Curcumin content of turmeric and curry powders. FASEB J 2004(18): A125.
7. Sharma RA, Gescher AJ, Steward WP. Curcumin: the story so far. Eur J Cancer 2005; 41(13): 1955-1968
8. Maheshwari RK, Singh AK, Gaddipati J, Srimal RC. Multiple biological activities of curcumin: a short review. Life Sci 2006; 78(18): 2081-2087
9. Duvoix A, Blasius R, Delhalle S, et al. Chemopreventive and therapeutic effects of curcumin. Cancer Lett 2005; 223(2): 181-190
10. Aggarwal BB, Kumar A, Bharti AC. Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res 2003; 23(1A): 363-398 (Pubitemid 36361976)
11. Wang Z, Zhang Y, Banerjee S, Li Y, Sarkar FH. Notch-1 downregulation by curcumin is associated with the inhibition of cell growth and the induction of apoptosis in pancreatic cancer cells. Cancer 2006; 106(11): 2503-2513 (Pubitemid 43787677)
12. Lev-Ari S, Zinger H, Kazanov D, et al. Curcumin synergistically potentiates the growth inhibitory and pro-apoptotic effects of celecoxib in pancreatic adenocarcinoma cells. Biomed Pharmacother 2005; 59(Suppl 2): S276-80. (Pubitemid 43303888)
13. Aggarwal BB, Shishodia S, Takada Y, et al. Curcumin suppresses the paclitaxel-induced nuclear factor-kappaB pathway in breast cancer cells and inhibits lung metastasis of human breast cancer in nude mice. Clin Cancer Res 2005; 11(20): 7490-7498 (Pubitemid 41507710)
14. Khor TO, Keum YS, Lin W, et al. Combined inhibitory effects of curcumin and phenethyl isothiocyanate on the growth of human PC-3 prostate xenografts in immunodeficient mice. Cancer Res 2006; 66(2): 613-621 (Pubitemid 43165919)
15. Deeb D, Jiang H, Gao X, et al. Curcumin sensitizes prostate cancer cells to tumor necrosis factor-related apoptosis-inducing ligand/Apo2L by inhibiting nuclear factor-kappaB through suppression of IkappaBalpha phosphorylation. Mol Cancer Ther 2004; 3(7): 803-812 (Pubitemid 39193762)
16. Lev-Ari S, Strier L, Kazanov D, et al. Celecoxib and curcumin synergistically inhibit the growth of colorectal cancer cells. Clin Cancer Res 2005; 11(18): 6738-6744 (Pubitemid 41339017)
17. Inano H, Onoda M, Inafuku N, et al. Chemoprevention by curcumin during the promotion stage of tumorigenesis of mammary gland in rats irradiated with gamma-rays. Carcinogenesis 1999; 20(6): 1011-1018 (Pubitemid 29263744)
18. Chuang SE, Kuo ML, Hsu CH, et al. Curcumin-containing diet inhibits diethylnitrosamine-induced murine hepatocarcinogenesis. Carcinogenesis 2000; 21(2): 331-335
19. Singh SV, Hu X, Srivastava SK, et al. Mechanism of inhibition of benzo[a]pyrene-induced forestomach cancer in mice by dietary curcumin. Carcinogenesis 1998; 19(8): 1357-1360 (Pubitemid 28409831)
20. Li N, Chen X, Liao J, et al. Inhibition of 7,12-dimethylbenz[a]- anthracene (DMBA)-induced oral carcinogenesis in hamsters by tea and curcumin. Carcinogenesis 2002; 23(8): 1307-1313 (Pubitemid 34905839)
21. Kawamori T, Lubet R, Steele VE, et al. Chemopreventive effect of curcumin, a naturally occurring anti-inflammatory agent, during the promotion/progression stages of colon cancer. Cancer Res 1999; 59(3): 597-601. (Pubitemid 29076056)
22. Cruz-Correa M, Shoskes DA, Sanchez P, et al. Combination treatment with curcumin and quercetin of adenomas in familial adenomatous polyposis. Clin Gastroenterol Hepatol 2006; 4(8): 1035-1038 (Pubitemid 44118839)
23. NCI D. Clinical development plan: Curcumin. J Cell Biochem Suppl 1996; 26: 72-85.
24. Eigner D, Scholz D. Ferula asa-foetida and Curcuma longa in traditional medical treatment and diet in Nepal. J Ethnopharmacol 1999; 67(1): 1-6. (Pubitemid 29389737)
25. Chainani-Wu N. Safety and anti-inflammatory activity of curcumin: a component of turmeric (Curcuma longa). J Altern Complement Med 2003; 9(1): 161-168 (Pubitemid 36297021)
26. Shankar TN, Shantha NV, Ramesh HP, Murthy IA, Murthy VS. Toxicity studies on turmeric (Curcuma longa): acute toxicity studies in rats, guineapigs & monkeys. Indian J Exp Biol 1980; 18(1): 73-75
27. Wahlstrom B, Blennow G. A study on the fate of curcumin in the rat. Acta Pharmacol Toxicol 1978; 43(2): 86-92.
28. Majeed M, Badmaev V, Shivakumar U, Rajendran R. Curcuminoids. Antioxidant Phytonutrients Piscataway, NJ: Nutriscience Publishers, Inc. 1995.
29. Deshpande SS, Lalitha VS, Ingle AD, Raste AS, Gadre SG, Maru GB. Subchronic oral toxicity of turmeric and ethanolic turmeric extract in female mice and rats. Toxicol Lett 1998; 95(3): 183-193
30. Gupta B, Kulshrestha VK, Srivastava RK, Prasad DN. Mechanisms of curcumin induced gastric ulcer in rats. Indian J Med Res 1980; 71: 806-814 (Pubitemid 11234309)
31. Sharma RA, Ireson CR, Verschoyle RD, et al. Effects of dietary curcumin on glutathione S-transferase and malondialdehyde-DNA adducts in rat liver and colon mucosa: relationship with drug levels. Clin Cancer Res 2001; 7(5): 1452-1458
32. Perkins S, Verschoyle RD, Hill K, et al. Chemopreventive efficacy and pharmacokinetics of curcumin in the min/+ mouse, a model of familial adenomatous polyposis. Cancer Epidemiol Biomarkers Prev 2002; 11(6): 535-540 (Pubitemid 34615160)
33. Ganiger S, Malleshappa HN, Krishnappa H, Rajashekhar G, Ramakrishna Rao V, Sullivan F. A two generation reproductive toxicity study with curcumin, turmeric yellow, in Wistar rats. Food Chem Toxicol 2007; 45(1): 64-69 (Pubitemid 44803075)
34. Cheng AL, Hsu CH, Lin JK, et al. Phase I clinical trial of curcumin, a chemopreventive agent, in patients with high-risk or premalignant lesions. Anticancer Res 2001; 21(4B): 2895-2900
35. Deodhar SD, Sethi R, Srimal RC. Preliminary study on antirheumatic activity of curcumin (diferuloyl methane). Indian J Med Res 1980; 71: 632-634 (Pubitemid 10058826)
36. James JS. Curcumin : Clinical trial finds no antiviral effect. AIDS Treatment News 1996; 242: 1-2.
37. Sharma RA, Euden SA, Platton SL, et al. Phase I clinical trial of oral curcumin: biomarkers of systemic activity and compliance. Clin Cancer Res 2004; 10(20): 6847-6854
38. Lal B, Kapoor AK, Agrawal PK, Asthana OP, Srimal RC. Role of curcumin in idiopathic inflammatory orbital pseudotumours. Phytother Res 2000; 14(6): 443-447 (Pubitemid 30694583)
39. Lal B, Kapoor AK, Asthana OP, et al. Efficacy of curcumin in the management of chronic anterior uveitis. Phytother Res 1999; 13(4): 318-322 (Pubitemid 29308449)
40. Ravindranath V, Chandrasekhara N. Absorption and tissue distribution of curcumin in rats. Toxicology1980; 16(3): 259-265
41. Ravindranath V, Chandrasekhara N. Metabolism of curcumin - studies with [3H]curcumin. Toxicology 1981; 22(4): 337-344
42. Holder GM, Plummer JL, Ryan AJ. The metabolism and excretion of curcumin (1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione) in the rat. Xenobiotica 1978; 8(12): 761-768
43. Ravindranath V, Chandrasekhara N. In vitro studies on the intestinal absorption of curcumin in rats. Toxicology 1981; 20(2-3): 251-257
44. Pan MH, Huang TM, Lin JK. Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metab Dispos 1999; 27(4): 486-494
45. Ireson C, Orr S, Jones DJ, et al. Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production. Cancer Res 2001; 61(3): 1058-1064
46. Ireson CR, Jones DJ, Orr S, et al. Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiol Biomarkers Prev 2002; 11(1): 105-111 (Pubitemid 34118319)
47. Sharma RA, McLelland HR, Hill KA, et al. Pharmacodynamic and pharmacokinetic study of oral Curcuma extract in patients with colorectal cancer. Clin Cancer Res 2001; 7(7): 1894-1900 (Pubitemid 32994823)
48. Ruffin MT, Normolle DP, Heath DD. Dose escalation of curcumin in healthy adults. Cancer Epidemiol Biomarkers Prevent 2003; 12 (Part 2 Suppl S): 1324S.
49. Lao CD, Ruffin MTT, Normolle D, et al. Dose escalation of a curcuminoid formulation. BMC Complement Altern Med 2006; 6: 10.
50. Garcea G, Jones DJ, Singh R, et al. Detection of curcumin and its metabolites in hepatic tissue and portal blood of patients following oral administration. Br J Cancer 2004; 90(5): 1011-1015 (Pubitemid 38499692)
51. Garcea G, Berry DP, Jones DJ, et al. Consumption of the putative chemopreventive agent curcumin by cancer patients: assessment of curcumin levels in the colorectum and their pharmacodynamic consequences. Cancer Epidemiol Biomarkers Prev 2005; 14(1): 120-125 (Pubitemid 40165291)
52. Shoba G, Joy D, Joseph T, Majeed M, Rajendran R, Srinivas PS. Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta Med 1998; 64(4): 353-356 (Pubitemid 28234275)
53. Ryu EK, Choe YS, Lee KH, Choi Y, Kim BT. Curcumin and dehydrozingerone derivatives: synthesis, radiolabeling, and evaluation for beta-amyloid plaque imaging. J Med Chem 2006; 49(20): 6111-6119 (Pubitemid 44484955)
54. Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB. Bioavailability of curcumin: problems and promises. Mol Pharm 2007; 4(6): 807-818
55. Li L, Braiteh FS, Kurzrock R. Liposome-encapsulated curcumin: in vitro and in vivo effects on proliferation, apoptosis, signaling, and angiogenesis. Cancer 2005; 104(6): 1322-1331
56. Li L, Ahmed B, Mehta K, Kurzrock R. Liposomal curcumin with and without oxaliplatin: effects on cell growth, apoptosis, and angiogenesis in colorectal cancer. Mol Cancer Ther 2007; 6(4): 1276-1282 (Pubitemid 46711990)
57. Chen C, Johnston TD, Jeon H, et al. An in vitro study of liposomal curcumin: stability, toxicity and biological activity in human lymphocytes and Epstein-Barr virus-transformed human B-cells. Int J Pharm 2009; 366(1-2): 133-139
58. 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 (Pubitemid 44428033)
59. Ruby AJ, Kuttan G, Babu KD, Rajasekharan KN, Kuttan R. Antitumour and antioxidant activity of natural curcuminoids. Cancer Lett 1995; 94(1): 79-83.
60. Wang D, Veena MS, Stevenson K, et al. Liposome-encapsulated curcumin suppresses growth of head and neck squamous cell carcinoma in vitro and in xenografts through the inhibition of nuclear factor kappaB by an AKT-independent pathway. Clin Cancer Res 2008; 14(19): 6228-6236
61. Takahashi M, Kitamoto D, Imura T, Oku H, Takara K, Wada K. Characterization and bioavailability of liposomes containing a ukon extract. Biosci Biotechnol Biochem 2008; 72(5): 1199-1205 (Pubitemid 351872494)
62. Tonnesen HH. Solubility, chemical and photochemical stability of curcumin in surfactant solutions. Studies of curcumin and curcuminoids, XXVIII. Pharmazie 2002; 57(12): 820-824
63. Leung MH, Colangelo H, Kee TW. Encapsulation of curcumin in cationic micelles suppresses alkaline hydrolysis. Langmuir 2008; 24(11): 5672-5675
64. Suresh D, Srinivasan K. Studies on the in vitro absorption of spice principles - curcumin, capsaicin and piperine in rat intestines. Food Chem Toxicol 2007; 45(8): 1437-1442
65. Letchford K, Liggins R, Burt H. Solubilization of hydrophobic drugs by methoxy poly(ethyleneglycol)-block-polycaprolactone di-block copolymeric micelles: Theoritical and experimental data and correlations. J Pharm Sci 2008; 97: 1179-1190
66. Ma Z, Shayeganpour A, Brocks DR, Lavasanifar A, Samuel J. High-performance liquid chromatography analysis of curcumin in rat plasma: application to pharmacokinetics of polymeric micellar formulation of curcumin. Biomed Chromatogr 2007; 21(5): 546-552 (Pubitemid 46736190)
67. 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 (Pubitemid 351969628)
68. 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
69. 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
70. Liu A, Lou H, Zhao L, Fan P. Validated LC/MS/MS assay for curcumin and tetrahydrocurcumin in rat plasma and application to pharmacokinetic study of phospholipid complex of curcumin. J Pharm Biomed Anal 2006; 40(3): 720-727 (Pubitemid 43227396)
71. Maiti K, Mukherjee K, Gantait A, Saha BP, Mukherjee PK. Curcumin-phospholipid complex: Preparation, therapeutic evaluation and pharmacokinetic study in rats. Int J Pharm 2007; 330(1-2): 155-163 (Pubitemid 46097368)
72. Marczylo TH, Verschoyle RD, Cooke DN, Morazzoni P, Steward WP, Gescher AJ. Comparison of systemic availability of curcumin with that of curcumin formulated with phosphatidylcholine. Cancer Chemother Pharmacol 2007; 60(2): 171-177 (Pubitemid 46742531)
73. Sou K, Goins B, Takeoka S, Tsuchida E, Phillips WT. Selective uptake of surface-modified phospholipid vesicles by bone marrow macrophages in vivo. Biomaterials 2007; 28(16): 2655-2666 (Pubitemid 46367213)
74. 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
75. Henderson IC, Bhatia V. Nab-paclitaxel for breast cancer: a new formulation with an improved safety profile and greater efficacy. Expert Rev Anticancer Ther 2007; 7(7): 919-943 (Pubitemid 47180894)
76. Gabizon AA, Shmeeda H, Zalipsky S. Pros and cons of the liposome platform in cancer drug targeting. J Liposome Res 2006; 16(3): 175-183 (Pubitemid 44358991)
77. Lee KS, Chung HC, Im SA, et al. Multicenter phase II trial of Genexol-PM, a Cremophor-free, polymeric micelle formulation of paclitaxel, in patients with metastatic breast cancer. Breast Cancer Res Treat 2008; 108(2): 241-250
78. Matsumura Y. Poly (amino acid) micelle nanocarriers in preclinical and clinical studies. Adv Drug Deliv Rev 2008; 60(8): 899-914.
79. Boddy AV, Plummer ER, Todd R, et al. A phase I and pharmacokinetic study of paclitaxel poliglumex (XYOTAX), investigating both 3-weekly and 2-weekly schedules. Clin Cancer Res 2005; 11(21): 7834-7840 (Pubitemid 41611628)
80. Tiyaboonchai W, Tungpradit W, Plianbangchang P. Formulation and characterization of curcuminoids loaded solid lipid nanoparticles. Int J Pharm 2007; 337(1-2): 299-306. (Pubitemid 46756048)
81. Yadav V, Pandit V, Suresh S, Yadav S. Curcumin loaded palmitic acid microparticles: Formulation and optimization using factorial design. In Pharm Communique 2008; 1: 15-18
82. Bisht S, Feldmann G, Soni S, Ravi R, Karikar C, Maitra A. Polymeric nanoparticle-encapsulated curcumin ("nanocurcumin"): a novel strategy for human cancer therapy. J Nanobiotechnol 2007; 5: 3. (Pubitemid 46705986)
83. John V, Kuttan G, Krishnankutty K. Anti-tumor studies of metal chelatesof synthetic curcuinoids. J Exp Clin Cancer Res 2002; 21: 219-224 (Pubitemid 34785558)
84. Sui Z, Salto R, Li J, Craik C, Ortiz de Montellano PR. Inhibition of the HIV-1 and HIV-2 proteases by curcumin and curcumin boron complexes. Bioorg Med Chem 1993;1(6): 415-422
85. Eybl V, Kotyzova D, Leseticky L, Bludovska M, Koutensky J. The influence of curcumin and manganese complex of curcumin on cadmium-induced oxidative damage and trace elements status in tissues of mice. J Appl Toxicol 2006; 26(3): 207-212 (Pubitemid 43773881)
86. Thompson KH, Bohmerle K, Polishchuk E, et al. Complementary inhibition of synoviocyte, smooth muscle cell or mouse lymphoma cell proliferation by a vanadyl curcumin complex compared to curcumin alone. J Inorg Biochem 2004; 98(12): 2063-2070 (Pubitemid 39489898)
87. Mohammadi K, Thompson KH, Patrick BO, et al. Synthesis and characterization of dual function vanadyl, gallium and indium curcumin complexes for medicinal applications. J Inorg Biochem 2005; 99(11): 2217-2225 (Pubitemid 41562860)
88. Lu P, Tong Q, Jiang F, et al. Preparation of curcumin prodrugs and their in vitro anti-tumor activities. J Huazhong Univ Sci Technol Med Sci 2005; 25(6): 668-678
89. Safavy A, Raisch KP, Mantena S, et al. Design and development of water-soluble curcumin conjugates as potential anticancer agents. J Med Chem 2007; 50(24): 6284-6288
90. Salmaso S, Bersani S, Semenzato A, Caliceti P. New cyclodextrin bioconjugates for active tumour targeting. J Drug Target 2007; 15(6): 379-390 (Pubitemid 47073053)