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Volumn 22, Issue 2, 2012, Pages 597-608

Studies on curcumin and curcuminoids. XLVI. Photophysical properties of dimethoxycurcumin and bis-dehydroxycurcumin

Author keywords

Curcuminoid; Excited state intramolecular proton transfer; Fluorescence decay mechanisms; Intramolecular hydrogen bonding; Solute solvent interactions

Indexed keywords

CURCUMINOID; EXCITED-STATE INTRAMOLECULAR PROTON TRANSFER; FLUORESCENCE DECAYS; INTRAMOLECULAR HYDROGEN BONDING; SOLUTE-SOLVENT INTERACTION;

EID: 84862235747     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-011-0995-z     Document Type: Article
Times cited : (18)

References (48)
  • 1
    • 0020450453 scopus 로고
    • Anti-inflammatory and irritant activities of curcumin analogues in rats
    • DOI 10.1007/BF01965935
    • Mukhopadhyay A, Basu N, Ghatak N, Gujzal PK (1982) Antiinflammatory and irritant activities of curcumin analogs in rats. Agents Actions 12:508-515 (Pubitemid 13218984)
    • (1982) Agents and Actions , vol.12 , Issue.4 , pp. 508-515
    • Mukhopadhyay, A.1    Basu, N.2    Ghatak, N.3    Gujral, P.K.4
  • 2
    • 0015785965 scopus 로고
    • Pharmacology of di-ferulyl methane (curcumin), a non-steroidal anti-inflammatory agent
    • Srimal RC, Dhawan BN (1973) Pharmacology of di-ferulyl methane (curcumin), a non-steroidal anti-inflammatory agent. J Pharm Pharmacol 25:447-452
    • (1973) J Pharm Pharmacol , vol.25 , pp. 447-452
    • Srimal, R.C.1    Dhawan, B.N.2
  • 4
    • 0031927214 scopus 로고    scopus 로고
    • Quantitation of chemopreventive synergism between (-)-epigallocatechin-3- gallate and curcumin in normal, premalignant and malignant human oral epithelial cells
    • DOI 10.1093/carcin/19.3.419
    • Khafif A, Schantz SP, Chou TC, Edelstein D, Sacks PG (1998) Quantification of chemopreventive synergism between epigallocatechin-3-gallate and curcumin in normal, premalignant and malignant human oral epithelial cells. Carcinogenesis 19:419-424 (Pubitemid 28375443)
    • (1998) Carcinogenesis , vol.19 , Issue.3 , pp. 419-424
    • Khafif, A.1    Schantz, S.P.2    Chou, T.-C.3    Edelstein, D.4    Sacks, P.G.5
  • 5
    • 0036080207 scopus 로고    scopus 로고
    • The molecular mechanisms for the antitumorigenic effect of curcumin
    • Leu TH, Maa MC (2002) The molecular mechanisms for the antitumorigenic effect of curcumin. Curr Med Chem 2:357-370
    • (2002) Curr Med Chem , vol.2 , pp. 357-370
    • Leu, T.H.1    Maa, M.C.2
  • 7
    • 4544383470 scopus 로고    scopus 로고
    • Curcumin impairs tumor suppressor p53 function in colon cancer cells
    • DOI 10.1093/carcin/bgh163
    • Moos PJ, Edes K, Mullally J, Fitzpatrick J (2004) Curcumin impairs tumor suppressor p53 function in colon cancer cells. Carcinogenesis 9:1611-1617 (Pubitemid 39214303)
    • (2004) Carcinogenesis , vol.25 , Issue.9 , pp. 1611-1617
    • Moos, P.J.1    Edes, K.2    Mullally, J.E.3    Fitzpatrick, F.A.4
  • 11
    • 0030805998 scopus 로고    scopus 로고
    • Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action
    • DOI 10.1021/jm970190x
    • Mazumder A, Neamati N, Sunder S, Schulz J, Perez H, Aich E, Pommier Y (1997) Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. J Med Chem 40:3057-3063 (Pubitemid 27391536)
    • (1997) Journal of Medicinal Chemistry , vol.40 , Issue.19 , pp. 3057-3063
    • Mazumder, A.1    Neamati, N.2    Sunder, S.3    Schulz, J.4    Pertz, H.5    Eich, E.6    Pommier, Y.7
  • 13
    • 22944488591 scopus 로고    scopus 로고
    • Studies on curcumin and curcuminoids. XXIX. Photoinduced cytotoxicity of curcumin in selected aqueous preparations
    • DOI 10.1039/b503397g
    • Bruzell E, Morisbak E, Tønnesen HH (2005) Studies on curcumin and curcuminoids. XXIX. Photoinduced cytotoxicity of curcumin in selected aqueous preparations. Photochem Photobiol Sci 4:523-530 (Pubitemid 41044582)
    • (2005) Photochemical and Photobiological Sciences , vol.4 , Issue.7 , pp. 523-530
    • Bruzell, E.M.1    Morisbak, E.2    Tonnesen, H.H.3
  • 16
    • 0023183657 scopus 로고
    • Studies on curcumin and curcuminoids IX: Investigation of the photobiological activity of curcumin using bacterial indicator systems
    • Tonnesen HH, de Vries H, Karlsen J, van Henegouwen GB (1987) Studies on curcumin and curcuminoids IX: investigation of the photobiological activity of curcumin using bacterial indicator systems. J Pharm Sci 76:371-373 (Pubitemid 17119898)
    • (1987) Journal of Pharmaceutical Sciences , vol.76 , Issue.5 , pp. 371-373
    • Tonnesen, H.H.1    De Vries, H.2    Karlsen, J.3    Van Henegouwen, G.B.4
  • 17
    • 74949087264 scopus 로고    scopus 로고
    • Photokilling of bacteria by curcumin in different aqueous preparations. Studies on curcumin and curcuminoids. XXXVII
    • Haukvik T, Bruzell E, Kristensen S, Tønnesen HH (2009) Photokilling of bacteria by curcumin in different aqueous preparations. Studies on curcumin and curcuminoids. XXXVII. Pharmazie 64:666-673
    • (2009) Pharmazie , vol.64 , pp. 666-673
    • Haukvik, T.1    Bruzell, E.2    Kristensen, S.3    Tønnesen, H.H.4
  • 18
    • 77955870855 scopus 로고    scopus 로고
    • Photokilling of bacteria by curcumin in selected polyethylene glycol 400 (PEG 400) preparations. Studies on curcumin and curcuminoids XLI
    • Haukvik T, Bruzell E, Kristensen S, Tønnesen HH (2010) Photokilling of bacteria by curcumin in selected polyethylene glycol 400 (PEG 400) preparations. Studies on curcumin and curcuminoids XLI. Pharmazie 65:600-606
    • (2010) Pharmazie , vol.65 , pp. 600-606
    • Haukvik, T.1    Bruzell, E.2    Kristensen, S.3    Tønnesen, H.H.4
  • 19
    • 79953301826 scopus 로고    scopus 로고
    • A screening for antibacterial phototoxic effects of curcumin derivatives. Studies on curcumin and curcuminoids. XLIII
    • Haukvik T, Bruzell E, Kristensen S, Tønnesen HH (2011) A screening for antibacterial phototoxic effects of curcumin derivatives. Studies on curcumin and curcuminoids. XLIII. Pharmazie 66:69-74
    • (2011) Pharmazie , vol.66 , pp. 69-74
    • Haukvik, T.1    Bruzell, E.2    Kristensen, S.3    Tønnesen, H.H.4
  • 21
    • 47849089483 scopus 로고    scopus 로고
    • Role of H-bond formation in the photoreactivity of curcumin
    • DOI 10.3233/SPE-2008-0335, XII European Conference on the Spectroscopy of Biological Molecules, Bobigny, France, 1-6 September 2007, Part 1
    • Nardo L, Paderno R, Andreoni A, Haukvik T, Màsson M, Tønnesen HH (2008) Studies on curcumin and curcuminoids XXXII. Role of H-bond formation in the photoreactivity of curcumin. Spectroscopy 22:187-198 (Pubitemid 352039935)
    • (2008) Spectroscopy , vol.22 , Issue.2-3 , pp. 187-198
    • Nardo, L.1    Paderno, R.2    Andreoni, A.3    Masson, M.4    Haukvik, T.5    Tonnesen, H.H.6
  • 22
    • 71849105717 scopus 로고    scopus 로고
    • Studies on curcumin and curcuminoids XXXIV. Photophysical properties of a symmetrical, non-substituted curcumin analogue
    • Nardo L, Andreoni A, Bondani M, Màsson M, Tønnesen HH (2009) Studies on curcumin and curcuminoids XXXIV. Photophysical properties of a symmetrical, non-substituted curcumin analogue. J Photochem Photobiol B: Biol 97:77-86
    • (2009) J Photochem Photobiol B: Biol , vol.97 , pp. 77-86
    • Nardo, L.1    Andreoni, A.2    Bondani, M.3    Màsson, M.4    Tønnesen, H.H.5
  • 23
    • 80053121407 scopus 로고    scopus 로고
    • Studies on curcumin and curcuminoids XXXIX. Photophysical properties of bisdemethoxycurcumin
    • Nardo L, Andreoni A, Haukvik T, Màsson M, Tønnesen HH (2011) Studies on curcumin and curcuminoids XXXIX. Photophysical properties of bisdemethoxycurcumin. J Fluorescence 21:627-635
    • (2011) J Fluorescence , vol.21 , pp. 627-635
    • Nardo, L.1    Andreoni, A.2    Haukvik, T.3    Màsson, M.4    Tønnesen, H.H.5
  • 25
    • 0022764965 scopus 로고
    • Studies on curcumin and curcuminoids. VIII. Photochemical stability of curcumin
    • Tønnesen HH, Karlsen J, van Henegouwen GB (1986) Studies on curcumin and curcuminoids. VIII. Photochemical stability of curcumin. Z Lebensm Unters Forsch 183:116-122
    • (1986) Z Lebensm Unters Forsch , vol.183 , pp. 116-122
    • Tønnesen, H.H.1    Karlsen, J.2    Van Henegouwen, G.B.3
  • 27
    • 0001593634 scopus 로고
    • Clarke MJ, Goodenough JB, Ibers JA, Jørgensen CK, Mingos DMP, Neilands JB, Reinen D, Sadler PJ, Weiss R, Williams RJP eds Verlag, Berlin Springer
    • Emsley J (1984) In: Clarke MJ, Goodenough JB, Ibers JA, Jørgensen CK, Mingos DMP, Neilands JB, Reinen D, Sadler PJ, Weiss R, Williams RJP (eds) Structure and bonding. Springer Verlag, Berlin, pp 148-191
    • (1984) Structure and Bonding , pp. 148-191
    • Emsley, J.1
  • 29
    • 0004123611 scopus 로고
    • Rappoport Z ed, Wiley, New York
    • Weedon AC (1990) In: Rappoport Z (ed) The chemistry of enols. Wiley, New York, pp 591-638
    • (1990) The Chemistry of Enols , pp. 591-638
    • Weedon, A.C.1
  • 30
  • 31
    • 0001617853 scopus 로고
    • Structural studies of curcuminoids. I. The crystal structure of curcumin
    • Tønnesen HH, Karlsen J, Mostad A (1982) Structural studies of curcuminoids. I. The crystal structure of curcumin. Acta Chem Scand B 36:475-479
    • (1982) Acta Chem Scand B , vol.36 , pp. 475-479
    • Tønnesen, H.H.1    Karlsen, J.2    Mostad, A.3
  • 32
    • 0008816540 scopus 로고
    • Structural studies of curcuminoids. II. Crystal structure of 1, 7-Bis(4-hydroxyphenyl)-1, 6-heptadiene-3, 5-dione -Methanol complex
    • Tonnesen HH, Karlsen J, Mostad A, Pedersen U, Rasmussen PB, Lawesson SO (1983) Structural studies of curcuminoids. II. Crystal structure of 1, 7-Bis(4-hydroxyphenyl)-1, 6-heptadiene-3, 5-dione -Methanol complex. Acta Chem Scand B 37:179-185
    • (1983) Acta Chem Scand B , vol.37 , pp. 179-185
    • Tonnesen, H.H.1    Karlsen, J.2    Mostad, A.3    Pedersen, U.4    Rasmussen, P.B.5    Lawesson, S.O.6
  • 33
    • 0008300568 scopus 로고
    • Structural studies of curcuminoids. IV. Crystal structure of 1, 7-Bis(4-hydroxyphenyl)-1, 6-heptadiene-3, 5-dione Hydrate
    • Tonnesen HH, Karlsen J, Mostad A, Pedersen U, Rasmussen PB, Lawesson SO (1988) Structural studies of curcuminoids. IV. Crystal structure of 1, 7-Bis(4-hydroxyphenyl)-1, 6-heptadiene-3, 5-dione Hydrate. Acta Chem Scand B 42:23-27
    • (1988) Acta Chem Scand B , vol.42 , pp. 23-27
    • Tonnesen, H.H.1    Karlsen, J.2    Mostad, A.3    Pedersen, U.4    Rasmussen, P.B.5    Lawesson, S.O.6
  • 34
    • 0008816541 scopus 로고
    • Structural studies on curcuminoids. III. Crystal structure of 1, 7-diphenyl-1, 5-heptadiene-3, 5-dione
    • Mostad A, Pedersen U, Rasmussen PB, Lawesson SO (1983) Structural studies on curcuminoids. III. Crystal structure of 1, 7-diphenyl-1, 5-heptadiene-3, 5-dione. Acta Chem Scand B 37:901-905
    • (1983) Acta Chem Scand B , vol.37 , pp. 901-905
    • Mostad, A.1    Pedersen, U.2    Rasmussen, P.B.3    Lawesson, S.O.4
  • 35
    • 0008842234 scopus 로고
    • Structural studies on curcuminoids. V. Crystal structures of 1, 7-bis 3, 4-dimethoxyphenyl)-4-benzyl-1, 6-heptadiene-3, 5-dione (DDBHDD) and 1, 7-bis(4-hydroxy-3-methoxyphenyl)-4-(2-oxo-2-ethoxyethyl)-1, 6-heptadiene-3, 5-dione (DHMEDD)
    • Gorbitz CH, Mostad A, Pedersen U, Rasmussen PB, Lawesson SO (1986) Structural studies on curcuminoids. V. Crystal structures of 1, 7-bis(3, 4-dimethoxyphenyl)-4-benzyl-1, 6-heptadiene-3, 5-dione (DDBHDD) and 1, 7-bis(4-hydroxy-3-methoxyphenyl)-4-(2-oxo-2-ethoxyethyl)-1, 6-heptadiene-3, 5-dione (DHMEDD). Acta Chem Scand B 40:420-429
    • (1986) Acta Chem Scand B , vol.40 , pp. 420-429
    • Gorbitz, C.H.1    Mostad, A.2    Pedersen, U.3    Rasmussen, P.B.4    Lawesson, S.O.5
  • 36
    • 4243664295 scopus 로고
    • A survey of Hammett substituent constants and resonance and field parameters
    • Hansch C, Leo A, Taft RW (1991) A survey of Hammett substituent constants and resonance and field parameters. Chem Rev 91:165-195
    • (1991) Chem Rev , vol.91 , pp. 165-195
    • Hansch, C.1    Leo, A.2    Taft, R.W.3
  • 37
    • 0004123611 scopus 로고
    • Rappoport Z ed, Wiley, New York
    • Toullec J (1990) In: Rappoport Z (ed) The chemistry of enols. Wiley, New York, pp 324-398
    • (1990) The Chemistry of Enols. , pp. 324-398
    • Toullec, J.1
  • 38
    • 0347354157 scopus 로고
    • Theoretical study of electron-donor and spectroscopic properties pf substituted phenols in various solvents
    • Semenov SG, Khodyreva NV (1994) Theoretical study of electron-donor and spectroscopic properties pf substituted phenols in various solvents. J Mol Struct 337:89-97
    • (1994) J Mol Struct , vol.337 , pp. 89-97
    • Semenov, S.G.1    Khodyreva, N.V.2
  • 39
    • 34248684129 scopus 로고    scopus 로고
    • Studies on curcumin and curcuminoids. XXXI. Symmetric and asymmetric curcuminoids: Stability, activity and complexation with cyclodextrin
    • DOI 10.1016/j.ijpharm.2007.01.013, PII S0378517307000488
    • Tomren MA, Màsson M, Loftsson T, Tønnesen HH (2007) Studies on curcumin and curcuminoids. XXXI. Symmetric and asymmetric curcuminoids: stability, activity and complexation with cyclodextrin. Int J Pharm 338:27-34 (Pubitemid 46777212)
    • (2007) International Journal of Pharmaceutics , vol.338 , Issue.1-2 , pp. 27-34
    • Tomren, M.A.1    Masson, M.2    Loftsson, T.3    Tonnesen, H.H.4
  • 40
    • 3042814814 scopus 로고    scopus 로고
    • Corrected fluorescence spectra and quantum yields for a series of compounds in the visible spectral region
    • Velapoldi R, Tønnesen HH (2004) Corrected fluorescence spectra and quantum yields for a series of compounds in the visible spectral region. J Fluorescence 14:465-472
    • (2004) J Fluorescence , vol.14 , pp. 465-472
    • Velapoldi, R.1    Tønnesen, H.H.2
  • 41
    • 37249043238 scopus 로고    scopus 로고
    • DNA-ligand binding mode discrimination by characterizing fluorescence resonance energy transfer through lifetime measurements with picosecond resolution
    • DOI 10.1111/j.1751-1097.2007.00204.x
    • Nardo L, Bondani M, Andreoni A (2008) DNA-ligand binding mode discrimination by characterizing fluorescence resonance energy transfer through lifetime measurements with picosecond resolution. Photochem Photobiol 84:101-110 (Pubitemid 350265080)
    • (2008) Photochemistry and Photobiology , vol.84 , Issue.1 , pp. 101-110
    • Nardo, L.1    Bondani, M.2    Andreoni, A.3
  • 43
    • 0041573625 scopus 로고
    • Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π*, α, and β, and some methods for simplifying the generalized solvatochromic equation
    • Kamlet MJ, Abboud JLM, Abraham MH, Taft RW (1983) Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π *, α, and β, and some methods for simplifying the generalized solvatochromic equation. J Org Chem 48:2877-2887
    • (1983) J Org Chem , vol.48 , pp. 2877-2887
    • Kamlet, M.J.1    Abboud, J.L.M.2    Abraham, M.H.3    Taft, R.W.4
  • 44
    • 33744918267 scopus 로고    scopus 로고
    • Molecular orbital basis for yellow curry spice curcumin's prevention of Alzheimer's disease
    • DOI 10.1021/jf0603533
    • Balasubramanian K (2006) Molecular orbital basis for yellow curry spice curcumin's prevention of Alzheimer's disease. J Agric Food Chem 54:3512-3520 (Pubitemid 43844175)
    • (2006) Journal of Agricultural and Food Chemistry , vol.54 , Issue.10 , pp. 3512-3520
    • Balasubramanian, K.1
  • 45
    • 84983223195 scopus 로고
    • Synthesis of naturally occurring curcuminoids and related compounds
    • Pedersen U, Rasmussen PB, Lawesson SO (1985) Synthesis of naturally occurring curcuminoids and related compounds. Liebigs Ann Chem 8:1557-1569
    • (1985) Liebigs Ann Chem , vol.8 , pp. 1557-1569
    • Pedersen, U.1    Rasmussen, P.B.2    Lawesson, S.O.3
  • 46
    • 0035790069 scopus 로고    scopus 로고
    • A laser flash photolysis study of curcumin in dioxane-water mixtures
    • Ortica F, Rodgers MAJ (2001) A laser flash photolysis study of curcumin in dioxane-water mixtures. Photochem Photobiol 74:745-751
    • (2001) Photochem Photobiol , vol.74 , pp. 745-751
    • Ortica, F.1    Rodgers, M.A.J.2
  • 47
    • 41649101305 scopus 로고    scopus 로고
    • Spectroscopic and theoretical study of the electronic structure of curcumin and related fragment molecules
    • Galasso V, Kovac B, Modelli A, Ottaviani MF, Pichierri F (2008) Spectroscopic and theoretical study of the electronic structure of curcumin and related fragment molecules. J Phys Chem A 112:2331-2338
    • (2008) J Phys Chem A , vol.112 , pp. 2331-2338
    • Galasso, V.1    Kovac, B.2    Modelli, A.3    Ottaviani, M.F.4    Pichierri, F.5
  • 48
    • 0037200362 scopus 로고    scopus 로고
    • Predicting the antioxidant activity of curcumin and curcuminoids
    • Wright JS (2002) Predicting the antioxidant activity of curcumin and curcuminoids. J Mol Struct (THEOCHEM) 591:207-217
    • (2002) J Mol Struct (THEOCHEM) , vol.591 , pp. 207-217
    • Wright, J.S.1


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