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Volumn 88, Issue 2, 2014, Pages 351-360

Carboxymethylcellulose-tetrahydrocurcumin conjugates for colon-specific delivery of a novel anti-cancer agent, 4-amino tetrahydrocurcumin

Author keywords

Carboxymethylcellulose; Colon specific drug delivery; Colonic cancer; Cytotoxic ability; Polymer conjugates; Tetrahydrocurcumin

Indexed keywords

4 AMINO TETRAHYDROCURCUMIN; 4 AMINOBENZOIC ACID; 4 AMINOHIPPURIC ACID; ANTINEOPLASTIC AGENT; AZO REDUCTASE; CARBOXYMETHYLCELLULOSE; CURCUMIN; POLYCYCLIC AROMATIC HYDROCARBON; POLYMER; PRODRUG; UNCLASSIFIED DRUG; WATER; TETRAHYDROCURCUMIN;

EID: 84908368867     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2014.05.011     Document Type: Article
Times cited : (39)

References (46)
  • 4
    • 33847264434 scopus 로고    scopus 로고
    • Telomerase targeted anticancer bioactive prodrug by antisense-based approach
    • N. Kapoor, A.J. Sharma, V. Dwivedi, A. Kumar, U. Pati, and K. Misra Telomerase targeted anticancer bioactive prodrug by antisense-based approach Cancer Lett. 248 2007 245 250
    • (2007) Cancer Lett. , vol.248 , pp. 245-250
    • Kapoor, N.1    Sharma, A.J.2    Dwivedi, V.3    Kumar, A.4    Pati, U.5    Misra, K.6
  • 6
    • 27144456477 scopus 로고    scopus 로고
    • Curcumin therapy in inflammatory bowel disease: A pilot study
    • P.R. Holt, S. Katz, and R. Kirshoff Curcumin therapy in inflammatory bowel disease: a pilot study Dig. Dis. Sci. 50 2005 2191 2193
    • (2005) Dig. Dis. Sci. , vol.50 , pp. 2191-2193
    • Holt, P.R.1    Katz, S.2    Kirshoff, R.3
  • 8
    • 0030839940 scopus 로고    scopus 로고
    • Stability of curcumin in buffer solutions and characterization of its degradation products
    • Y.J. Wang, M.H. Pan, A.L. Cheng, L.I. Lin, Y.S. Ho, and C.Y. Hsieh Stability of curcumin in buffer solutions and characterization of its degradation products J. Pharm. Biomed. Anal. 15 1997 1867 1876
    • (1997) J. Pharm. Biomed. Anal. , vol.15 , pp. 1867-1876
    • Wang, Y.J.1    Pan, M.H.2    Cheng, A.L.3    Lin, L.I.4    Ho, Y.S.5    Hsieh, C.Y.6
  • 9
    • 0001394917 scopus 로고
    • Studies of curcumin and curcuminoids: V. Alkaline degradation of curcumin
    • H.H. Tonnesen, and J. Karlsen Studies of curcumin and curcuminoids: V. Alkaline degradation of curcumin Z. Lebensm.-Unters. Forsch. 180 1985 132 134
    • (1985) Z. Lebensm.-Unters. Forsch. , vol.180 , pp. 132-134
    • Tonnesen, H.H.1    Karlsen, J.2
  • 10
    • 0022066944 scopus 로고
    • Studies of curcumin and curcuminoids: VI. Kinetics of curcumin degradation in aqueous solution
    • H.H. Tonnesen, and J. Karlsen Studies of curcumin and curcuminoids: VI. Kinetics of curcumin degradation in aqueous solution Z. Lebensm.-Unters. Forsch. 180 1985 402 404
    • (1985) Z. Lebensm.-Unters. Forsch. , vol.180 , pp. 402-404
    • Tonnesen, H.H.1    Karlsen, J.2
  • 11
    • 0032926620 scopus 로고    scopus 로고
    • Biotransformation of curcumin through reduction and glucuronidation in mice
    • M.H. Pan, T.M. Huang, and J.K. Lin Biotransformation of curcumin through reduction and glucuronidation in mice Drug Metab. Dispos. 27 1999 486 494
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 486-494
    • Pan, M.H.1    Huang, T.M.2    Lin, J.K.3
  • 12
    • 0034492793 scopus 로고    scopus 로고
    • Recent studies on the biofunctions and biotransformations of curcumin
    • J.K. Lin, M.H. Pan, and S.Y.L. Shiau Recent studies on the biofunctions and biotransformations of curcumin BioFactors 13 2000 153 158
    • (2000) BioFactors , vol.13 , pp. 153-158
    • Lin, J.K.1    Pan, M.H.2    Shiau, S.Y.L.3
  • 13
    • 33846066817 scopus 로고    scopus 로고
    • Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives
    • P. Somporn, C. Phisalaphong, S. Nakornchai, S. Unchern, and N.P. Morales Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives Bio. Pharm. Bull. 30 2007 74 78
    • (2007) Bio. Pharm. Bull. , vol.30 , pp. 74-78
    • Somporn, P.1    Phisalaphong, C.2    Nakornchai, S.3    Unchern, S.4    Morales, N.P.5
  • 14
    • 0029979805 scopus 로고    scopus 로고
    • Involvement of the β-diketone moiety in the antioxidative mechanism of tetrahydrocurcumin
    • Y. Sugiyama, S. Kawakishi, and T. Osawa Involvement of the β-diketone moiety in the antioxidative mechanism of tetrahydrocurcumin Biochem. Pharmacol. 52 1996 519 525
    • (1996) Biochem. Pharmacol. , vol.52 , pp. 519-525
    • Sugiyama, Y.1    Kawakishi, S.2    Osawa, T.3
  • 15
    • 44849122833 scopus 로고    scopus 로고
    • Anti-cancer and anti-angiogenic effects of curcumin and tetrahydrocurcumin on implanted hepatocellular carcinoma in nude mice
    • P. Yoysungnoen, P. Wirachwong, C. Changtam, A. Suksamrarn, and S. Patumraj Anti-cancer and anti-angiogenic effects of curcumin and tetrahydrocurcumin on implanted hepatocellular carcinoma in nude mice World J. Gastroenterol. 14 2008 2003 2009
    • (2008) World J. Gastroenterol. , vol.14 , pp. 2003-2009
    • Yoysungnoen, P.1    Wirachwong, P.2    Changtam, C.3    Suksamrarn, A.4    Patumraj, S.5
  • 16
    • 8844286917 scopus 로고    scopus 로고
    • New oral delivery systems for treatment of inflammatory bowel disease
    • D.R. Friend New oral delivery systems for treatment of inflammatory bowel disease Adv. Drug Delivery Rev. 57 2005 247 265
    • (2005) Adv. Drug Delivery Rev. , vol.57 , pp. 247-265
    • Friend, D.R.1
  • 17
    • 36749064579 scopus 로고    scopus 로고
    • Colon-specific drug delivery for mebeverine hydrochloride
    • S. Omar, B. Aldosari, and H. Refai Colon-specific drug delivery for mebeverine hydrochloride J. Drug Targeting 15 2007 691 700
    • (2007) J. Drug Targeting , vol.15 , pp. 691-700
    • Omar, S.1    Aldosari, B.2    Refai, H.3
  • 18
    • 79952173525 scopus 로고    scopus 로고
    • Curcumin nanoparticles: Preparation, characterization, and antimicrobial study
    • R.K. Basniwal, H.S. Buttar, V.K. Jain, and N. Jain Curcumin nanoparticles: preparation, characterization, and antimicrobial study J. Agric. Food Chem. 59 2011 2056 2061
    • (2011) J. Agric. Food Chem. , vol.59 , pp. 2056-2061
    • Basniwal, R.K.1    Buttar, H.S.2    Jain, V.K.3    Jain, N.4
  • 19
    • 84862812367 scopus 로고    scopus 로고
    • Preparation of nanoparticles of poorly water-soluble antioxidant curcumin by antisolvent precipitation methods
    • M. Kakran, N.G. Sahoo, I.L. Tan, and L. Li Preparation of nanoparticles of poorly water-soluble antioxidant curcumin by antisolvent precipitation methods J. Nanopart. Res. 14 2012 1 11
    • (2012) J. Nanopart. Res. , vol.14 , pp. 1-11
    • Kakran, M.1    Sahoo, N.G.2    Tan, I.L.3    Li, L.4
  • 20
    • 84855856570 scopus 로고    scopus 로고
    • Gold nanoparticles generated and stabilized by water soluble curcumin polymer conjugate: Blood compatibility evaluation and targeted drug delivery onto cancer cells
    • S. Manju, and K. Sreenivasan Gold nanoparticles generated and stabilized by water soluble curcumin polymer conjugate: blood compatibility evaluation and targeted drug delivery onto cancer cells J. Colloid Interface Sci. 368 2012 144 151
    • (2012) J. Colloid Interface Sci. , vol.368 , pp. 144-151
    • Manju, S.1    Sreenivasan, K.2
  • 22
    • 0037139415 scopus 로고    scopus 로고
    • Colon-specific drug delivery: New approaches and in vitro/in vivo evaluation
    • L. Yang, J.S. Chu, and J.A. Fix Colon-specific drug delivery: new approaches and in vitro/in vivo evaluation Int. J. Pharm. 235 2002 1 15
    • (2002) Int. J. Pharm. , vol.235 , pp. 1-15
    • Yang, L.1    Chu, J.S.2    Fix, J.A.3
  • 23
  • 24
    • 65949086186 scopus 로고    scopus 로고
    • Practical method for functionalized peptide or amide bond formation in aqueous media with EDC as activator
    • Y.J. Pu, R.K. Vaid, S.K. Boini, R.W. Towsley, C.W. Doecke, and D.A. Mictchell Practical method for functionalized peptide or amide bond formation in aqueous media with EDC as activator Org. Process Res. Dev. 13 2009 310 314
    • (2009) Org. Process Res. Dev. , vol.13 , pp. 310-314
    • Pu, Y.J.1    Vaid, R.K.2    Boini, S.K.3    Towsley, R.W.4    Doecke, C.W.5    Mictchell, D.A.6
  • 25
    • 11144260746 scopus 로고
    • Reaction of ketene silyl acetals with diazonium salt: A novel α-amino acid ester synthesis
    • T. Sakakura, and M. Tanaka Reaction of ketene silyl acetals with diazonium salt: a novel α-amino acid ester synthesis J. Chem. Soc. 621 1985 1309 1310
    • (1985) J. Chem. Soc. , vol.621 , pp. 1309-1310
    • Sakakura, T.1    Tanaka, M.2
  • 28
    • 0033812181 scopus 로고    scopus 로고
    • Synthesis and in vitro/in vivo evaluation of 5-aminosalicyl-glycine as a colon-specific prodrug of 5-aminosalicylic acid
    • Y.J. Jung, J.S. Lee, and Y.M. Kim Synthesis and in vitro/in vivo evaluation of 5-aminosalicyl-glycine as a colon-specific prodrug of 5-aminosalicylic acid J. Pharm. Sci. 89 2000 594 602
    • (2000) J. Pharm. Sci. , vol.89 , pp. 594-602
    • Jung, Y.J.1    Lee, J.S.2    Kim, Y.M.3
  • 29
    • 9644302324 scopus 로고    scopus 로고
    • Synthesis and properties of polysaccharide prodrugs of 5-aminosalicylic acid as potential colon-specific delivery systems
    • M. Zou, H. Okamoto, G. Cheng, X. Hao, J. Sun, F. Cui, and K. Danjo Synthesis and properties of polysaccharide prodrugs of 5-aminosalicylic acid as potential colon-specific delivery systems Eur. J. Pharm. Biopharm. 59 2005 155 160
    • (2005) Eur. J. Pharm. Biopharm. , vol.59 , pp. 155-160
    • Zou, M.1    Okamoto, H.2    Cheng, G.3    Hao, X.4    Sun, J.5    Cui, F.6    Danjo, K.7
  • 30
    • 0035976049 scopus 로고    scopus 로고
    • Specific inhibition of cyclooxygenase-2 (COX-2) expression by dietary curcumin in HT-29 human colon cancer cells
    • A. Goel, C.R. Boland, and D.P. Chauhan Specific inhibition of cyclooxygenase-2 (COX-2) expression by dietary curcumin in HT-29 human colon cancer cells Cancer Lett. 172 2001 111 118
    • (2001) Cancer Lett. , vol.172 , pp. 111-118
    • Goel, A.1    Boland, C.R.2    Chauhan, D.P.3
  • 31
    • 26844576835 scopus 로고    scopus 로고
    • Amide bond formation and peptide coupling
    • C.A.G.N. Montalbetti, and V. Falque Amide bond formation and peptide coupling Tetrahedron 61 2005 10827 10852
    • (2005) Tetrahedron , vol.61 , pp. 10827-10852
    • Montalbetti, C.A.G.N.1    Falque, V.2
  • 33
    • 0038546904 scopus 로고    scopus 로고
    • The colon as a possible target for orally administered peptide and protein drugs
    • S. Haupt, and A. Rubinstein The colon as a possible target for orally administered peptide and protein drugs Ther. Drug Carrier Syst. 19 2002 499 551
    • (2002) Ther. Drug Carrier Syst. , vol.19 , pp. 499-551
    • Haupt, S.1    Rubinstein, A.2
  • 34
    • 0021160430 scopus 로고
    • Cellulose and human gut
    • J.H. Cummings Cellulose and human gut Gut 25 1984 805 810
    • (1984) Gut , vol.25 , pp. 805-810
    • Cummings, J.H.1
  • 37
    • 67349161777 scopus 로고    scopus 로고
    • Synthesis and anaerobic biodegradation of indomethacin-conjugated cellulose ethers used for colon-specific drug delivery
    • X. Cai, L. Yang, L.M. Zhang, and Q. Wu Synthesis and anaerobic biodegradation of indomethacin-conjugated cellulose ethers used for colon-specific drug delivery Bioresour. Technol. 100 2009 4164 4170
    • (2009) Bioresour. Technol. , vol.100 , pp. 4164-4170
    • Cai, X.1    Yang, L.2    Zhang, L.M.3    Wu, Q.4
  • 38
    • 37549009531 scopus 로고    scopus 로고
    • Oridonin induced autophagy in human cervical carcinoma Hela cells through Ras, JNK, and 38 regulation
    • Q. Cui, S. Tashiro, S. Onodera, M. Minami, and T. Ikejima Oridonin induced autophagy in human cervical carcinoma Hela cells through Ras, JNK, and 38 regulation J. Pharmacol. Sci. 105 2007 317 325
    • (2007) J. Pharmacol. Sci. , vol.105 , pp. 317-325
    • Cui, Q.1    Tashiro, S.2    Onodera, S.3    Minami, M.4    Ikejima, T.5
  • 40
    • 84905222856 scopus 로고    scopus 로고
    • Yerba mate (IIex Paraguariensis St. Hilaire) saponins inhibit human colon cancer cell proliferation
    • M.H. Tunick, E.G. Mejia, Oxford University Press Inc. New York
    • S. Puangpraphant, M.A. Berhow, and E. Mejia Yerba mate (IIex Paraguariensis St. Hilaire) saponins inhibit human colon cancer cell proliferation M.H. Tunick, E.G. Mejia, Hispanic Foods: Chemistry and Bioactive Compounds 2012 Oxford University Press Inc. New York 307 321
    • (2012) Hispanic Foods: Chemistry and Bioactive Compounds , pp. 307-321
    • Puangpraphant, S.1    Berhow, M.A.2    Mejia, E.3
  • 41
    • 45849140110 scopus 로고    scopus 로고
    • Curcumin induces apoptosis in HCT-116 human colon cancer cells in a p21-independent manner
    • J.L. Watson, R. Hill, P.W. Lee, C.A. Giacomantonio, and D.W. Hoskin Curcumin induces apoptosis in HCT-116 human colon cancer cells in a p21-independent manner Exp. Mol. Pathol. 84 2008 230 233
    • (2008) Exp. Mol. Pathol. , vol.84 , pp. 230-233
    • Watson, J.L.1    Hill, R.2    Lee, P.W.3    Giacomantonio, C.A.4    Hoskin, D.W.5
  • 42
    • 21244498576 scopus 로고    scopus 로고
    • Curcumin selectively induces apoptosis in deregulated cyclin D1-expressed cells at G2 phase of cell cycle in a p53-dependent manner
    • T. Choudhuri, S. Pal, T. Das, and G. Sa Curcumin selectively induces apoptosis in deregulated cyclin D1-expressed cells at G2 phase of cell cycle in a p53-dependent manner J. Biol. Chem. 280 2005 20059 20068
    • (2005) J. Biol. Chem. , vol.280 , pp. 20059-20068
    • Choudhuri, T.1    Pal, S.2    Das, T.3    Sa, G.4
  • 43
    • 0037026270 scopus 로고    scopus 로고
    • Studies of curcumin and curcuminoids. XVII. Cyclodextrin complexation: Solubility, chemical and photochemical stability
    • H.H. Tonnesen, M. Masson, and T. Loftsson Studies of curcumin and curcuminoids. XVII. Cyclodextrin complexation: solubility, chemical and photochemical stability Int. J. Pharm. 244 2002 127 135
    • (2002) Int. J. Pharm. , vol.244 , pp. 127-135
    • Tonnesen, H.H.1    Masson, M.2    Loftsson, T.3
  • 44
    • 5444265248 scopus 로고    scopus 로고
    • A theoretical investigation on intramolecular hydrogen-atom transfer in curcumin
    • L. Kong, K.I. Priyadarsini, and H.Y. Zhang A theoretical investigation on intramolecular hydrogen-atom transfer in curcumin J. Mol. Struct. (Theochem) 685 2004 111 116
    • (2004) J. Mol. Struct. (Theochem) , vol.685 , pp. 111-116
    • Kong, L.1    Priyadarsini, K.I.2    Zhang, H.Y.3
  • 45
    • 34548058841 scopus 로고    scopus 로고
    • Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and termerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism
    • S.K. Sandur, M.K. Pandey, B. Sung, K.S. Ahn, A. Murakami, G. Sethi, P. Limtrakul, V. Badmaev, and B.B. Aggarwal Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and termerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism Carcinogenesis 28 2007 1765 1773
    • (2007) Carcinogenesis , vol.28 , pp. 1765-1773
    • Sandur, S.K.1    Pandey, M.K.2    Sung, B.3    Ahn, K.S.4    Murakami, A.5    Sethi, G.6    Limtrakul, P.7    Badmaev, V.8    Aggarwal, B.B.9
  • 46
    • 80155194987 scopus 로고    scopus 로고
    • Tetrahydrocurcumin, a major metabolite of curcumin, induced autophagic cell death through coordinative modulation of PI3K/Akt-mTOR and MARK signaling pathways in human leukemia HL-60 cells
    • J.C. Wu, C.S. Lai, V. Badmaev, K. Nagabhushanam, C.T. Ho, and M.H. Pan Tetrahydrocurcumin, a major metabolite of curcumin, induced autophagic cell death through coordinative modulation of PI3K/Akt-mTOR and MARK signaling pathways in human leukemia HL-60 cells Mol. Nutr. Food Res. 55 2011 1646 1654
    • (2011) Mol. Nutr. Food Res. , vol.55 , pp. 1646-1654
    • Wu, J.C.1    Lai, C.S.2    Badmaev, V.3    Nagabhushanam, K.4    Ho, C.T.5    Pan, M.H.6


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