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Cooperative Binding And Stabilization Of The Medicinal Pigment Curcumin By Diamide Linked γ-cyclodextrin Dimers: A Spectroscopic Characterization.

T. Harada, Duc-Truc Pham, Mandy H M Leung, H. T. Ngo, S. Lincoln, C. Easton, T. Kee
Published 2011 · Chemistry, Medicine

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Diamide linked γ-cyclodextrin (γ-CD) dimers are used to capture curcumin and suppress its decomposition in water. In this study, succinamide and urea linked γ-CD dimers joined through the C6(A) carbon on each γ-CD are used. The γ-CD dimers, 66γCD(2)su and 66γCD(2)ur, show a remarkable ability to suppress the decomposition of curcumin and extend its half-life from less than 30 min to greater than 16 h. The 1:1 association of curcumin with 66γCD(2)su and 66γCD(2)ur has high stability constants of 8.7 × 10(6) M(-1) and 2.0 × 10(6) M(-1), respectively. In addition, 2D (1)H NOESY NMR results show specific hydrogen interactions in the association of curcumin with 66γCD(2)su and 66γCD(2)ur, consistent with the cooperative binding of curcumin by both γ-CD annuli of 66γCD(2)su and 66γCD(2)ur. The interactions between curcumin in the linked γ-CD dimers and surfactant micelles were studied using fluorescence spectroscopy. While linked γ-CD dimer-bound curcumin has a negligible fluorescence quantum yield, a significant increase in fluorescence intensity (Φ(fl) > 2%) in the presence of micelles suggests that curcumin is delivered to the micelle. The overall results indicate that the diamide linked γ-CD dimers are highly promising systems for curcumin delivery in vivo due to effective curcumin stabilization.
This paper references
10.1111/j.1751-1097.1999.tb08277.x
Solvent Dependence of the Fluorescence Lifetimes of Xanthene Dyes
D. Magde (1999)
10.1021/JA00829A034
The mechanism of the aminolysis of acetate esters.
A. Satterthwait (1974)
10.1021/AR0502275
Cooperative binding and multiple recognition by bridged bis(beta-cyclodextrin)s with functional linkers.
Y. Liu (2006)
10.1097/01.PRS.0000148372.75342.D9
Curcumin Treatment Enhances the Repair and Regeneration of Wounds in Mice Exposed to Hemibody &ggr;-Irradiation
G. Jagetia (2005)
10.1126/SCIENCE.1093941
Curcumin, a Major Constituent of Turmeric, Corrects Cystic Fibrosis Defects
M. Egan (2004)
10.1016/j.ejps.2009.02.019
Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer.
J. Shaikh (2009)
10.1002/ANIE.200604757
Efficient fluorescence enhancement and cooperative binding of an organic dye in a supra-biomolecular host-protein assembly.
A. C. Bhasikuttan (2007)
10.1071/C96168
A Versatile Synthesis of Linked Cyclodextrins
C. Easton (1997)
10.2217/nnm.10.9
Curcumin-encapsulated MePEG/PCL diblock copolymeric micelles: a novel controlled delivery vehicle for cancer therapy.
C. Mohanty (2010)
10.1021/jp901234z
Excited-state intramolecular hydrogen atom transfer and solvation dynamics of the medicinal pigment curcumin.
R. Adhikary (2009)
10.1016/J.BCP.2007.08.016
Curcumin as "Curecumin": from kitchen to clinic.
A. Goel (2008)
10.1016/J.CPLETT.2007.01.006
Interaction of curcumin with human serum albumin: Thermodynamic properties, fluorescence energy transfer and denaturation effects
A. Barik (2007)
10.1002/CHIN.197940061
Symmetries of hydrogen-bonded enol forms of diketones as determined by x-ray photoelectron spectroscopy
R. S. Brown (1979)
10.1021/ED100292R
Kinetic and Mechanistic Studies of the Deuterium Exchange in Classical Keto-Enol Tautomeric Equilibrium Reactions.
M. Nichols (2010)
10.1016/J.MOLLIQ.2003.12.013
Binding and distribution characteristics of curcumin solubilized in CTAB micelle
M. Iwunze (2004)
10.1007/BF01042637
Studies on curcumin and curcuminoids
H. Tønnesen (1985)
10.1002/1521-3765(20001103)6:21<4034::AID-CHEM4034>3.0.CO;2-3
Cyclodextrin dimers as receptor molecules for steroid sensors.
M. R. de Jong (2000)
10.1562/0031-8655(2000)072<0625:EOSOTE>2.0.CO;2
Effect of Solvent on the Excited-state Photophysical Properties of Curcumin¶
S. M. Khopde (2000)
10.1248/CPB.41.1640
Nematocidal activity of turmeric: synergistic action of curcuminoids.
F. Kiuchi (1993)
10.1016/j.cellbi.2005.10.024
Antiproliferation and apoptosis induced by curcumin in human ovarian cancer cells
Mingxin Shi (2006)
Enzyme structure and mechanism
A. Fersht (1977)
Anticancer potential of curcumin: preclinical and clinical studies.
B. Aggarwal (2003)
10.1016/S0731-7085(96)02024-9
Stability of curcumin in buffer solutions and characterization of its degradation products.
Y. Wang (1997)
10.1562/0031-8655(2003)077<0597:PSOBOC>2.0.CO;2
Photophysical Studies on Binding of Curcumin to Bovine Serum Albumin¶
A. Barik (2003)
10.1016/0039-9140(96)01958-3
Investigation of equilibria in solution. Determination of equilibrium constants with the HYPERQUAD suite of programs.
P. Gans (1996)
10.1021/la903772e
The role of charge in the surfactant-assisted stabilization of the natural product curcumin.
Zifan Wang (2010)
10.1126/SCIENCE.3413482
Induction of an antibody that catalyzes the hydrolysis of an amide bond.
K. Janda (1988)
10.1021/JP960701B
Cooperative Binding of 6-(p-Toluidinyl)naphthalene-2-sulfonate by β-Cyclodextrin Dimers
A. C. A. Haskard (1996)
10.1295/polymj.12.29
Cooperative Binding by Cyclodextrin Dimers
Akira Harada (1980)
Catalysis in chemistry and enzymology
W. Jencks (1969)
10.1021/NP060263S
NMR study of the solution structure of curcumin.
Florastina L Payton (2007)
10.1021/la804215v
Effective stabilization of curcumin by association to plasma proteins: human serum albumin and fibrinogen.
Mandy H M Leung (2009)
10.1016/J.PHYMED.2003.12.011
The effect of turmeric extracts on inflammatory mediator production.
R. Lantz (2005)
10.1016/S0142-9612(03)00625-2
Dermal wound healing processes with curcumin incorporated collagen films.
D. Gopinath (2004)
10.1186/1477-3155-5-3
Polymeric nanoparticle-encapsulated curcumin ("nanocurcumin"): a novel strategy for human cancer therapy
S. Bisht (2007)
10.1021/OL015820A
Unique fluorescence behavior of rhodamine B upon inclusion complexation with novel bis(beta-cyclodextrin-6-yl) 2,2'-bipyridine-4,4'-dicarboxylate.
Y. Liu (2001)
10.1016/J.TET.2010.02.005
Synthesis of C6A-to-C6A and C3A-to-C3A diamide linked γ-cyclodextrin dimers
Duc-Truc Pham (2010)
10.1111/j.1751-1097.1994.tb05037.x
SPECTRAL AND PHOTOCHEMICAL PROPERTIES OF CURCUMIN
Colin F. Chignell (1994)
10.1074/JBC.M404751200
Curcumin Inhibits Formation of Amyloid β Oligomers and Fibrils, Binds Plaques, and Reduces Amyloid in Vivo*
F. Yang (2005)
10.1016/S0378-5173(02)00323-X
Studies of curcumin and curcuminoids. XXVII. Cyclodextrin complexation: solubility, chemical and photochemical stability.
H. Tønnesen (2002)
10.1002/POC.610060609
Simultaneous determination of primary and secondary thermodynamic isotope effects in tautomeric equilibria
B. Zhang (1993)
10.1021/la800780w
Encapsulation of curcumin in cationic micelles suppresses alkaline hydrolysis.
Mandy H M Leung (2008)
10.1021/JP073510P
New insights in cyclodextrin: surfactant mixed systems from the use of neutral and anionic cyclodextrin derivatives.
L. García-Río (2007)



This paper is referenced by
10.1016/J.COLSURFB.2019.04.038
Effect of casein on pure lecithin liposome: Mixed biomacromolecular system for providing superior stabilization to hydrophobic molecules.
S. Panja (2019)
Spectroscopic investigations on the molecular motions and solution chemistry of the medicinal pigment curcumin.
Mandy H M Leung (2015)
10.1016/J.VIBSPEC.2012.06.008
Encapsulation and isomerization of curcumin with cyclodextrins characterized by electronic and vibrational spectroscopy
Eduardo López-Tobar (2012)
AMERICAN UNIVERSITY OF BEIRUT INTERACTION OF CURCUMIN WITH RHAMNOLIPIDS , DSPC LIPOSOMES AND CYCLODEXTRAN MOF ; CURCUMIN AS A MOLECULAR PROBE TO INVESTIGATE HETEROGENEOUS SYSTEMS by
Zeinab Hassan Moussa (2016)
10.1080/01932691.2019.1592687
Solubility and stability enhancement of curcumin in Soluplus® polymeric micelles: a spectroscopic study
S. Rani (2020)
10.1021/jp507272f
Femtosecond transient absorption spectroscopy of the medicinal agent curcumin in diamide linked γ-cyclodextrin dimers.
T. Harada (2015)
10.1021/jp411778q
Exploring the photophysics of curcumin in zwitterionic micellar system: an approach to control ESIPT process in the presence of room temperature ionic liquids (RTILs) and anionic surfactant.
Chiranjib Banerjee (2014)
10.1039/C3NJ00935A
p-Sulfonatocalix[4]arene as a carrier for curcumin
Paulpandian Muthu Mareeswaran (2014)
10.3762/bjoc.10.304
Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer
Florian Hamon (2014)
10.2174/138161213805289237
Delivery of curcumin and medicinal effects of the copper(II)-curcumin complexes.
Mandy H M Leung (2013)
10.1246/CL.160509
Dissolution of Water-insoluble Curcumin by Femtosecond-laser Ablation in the Presence of Cyclodextrins and Its Cytotoxic Bioactivity against Lung Cancer Cells
D. Nakane (2016)
10.1002/SLCT.201601630
Host-guest chemistry of linked β- and γ-cyclodextrin dimers and 1- and 2-naphthyl-sulfonamide substituted poly(acrylate)s in aqueous solution
H. L. McTernan (2017)
Ultrafast spectroscopy and drug delivery of the medicinal pigment curcumin in molecular assemblies.
Takaaki Harada (2015)
10.1039/C2CP40208D
Femtosecond transient absorption spectroscopy of copper(II)-curcumin complexes.
Mandy H M Leung (2012)
10.1021/acsomega.7b00809
Optical Spectroscopic and Morphological Characterizations of Curcuminized Silk Biomaterials: A Perspective from Drug Stabilization
S. Panja (2017)
10.1016/j.jphotobiol.2016.03.004
Stability of curcumin in different solvent and solution media: UV-visible and steady-state fluorescence spectral study.
Satyajit Mondal (2016)
10.1039/C5RA04597E
Reversible photo-responsive vesicle based on the complexation between an azobenzene containing molecule and α-cyclodextrin
J. Liu (2015)
10.1021/jp5060205
The capture and stabilization of curcumin using hydrophobically modified polyacrylate aggregates and hydrogels.
T. Harada (2014)
10.1021/mp400309s
Diamide linked γ-cyclodextrin dimers as molecular-scale delivery systems for the medicinal pigment curcumin to prostate cancer cells.
T. Harada (2013)
10.1021/acs.langmuir.5b02773
Nanoprecipitation and Spectroscopic Characterization of Curcumin-Encapsulated Polyester Nanoparticles.
Mandy H M Leung (2015)
10.1039/C6CP05648B
Excited-state dynamics of the medicinal pigment curcumin in a hydrogel.
T. Harada (2016)
10.1016/j.molliq.2020.113906
Aqueous solubilization and extraction of curcumin enhanced by imidazolium, quaternary ammonium, and tropine ionic liquids, and insight of ionic liquids-curcumin interaction
Jinghang Li (2020)
10.1021/acsami.5b01786
Dual-responsive polymer coated superparamagnetic nanoparticle for targeted drug delivery and hyperthermia treatment.
S. Patra (2015)
10.1021/jp507378w
Organic additive, 5-methylsalicylic acid induces spontaneous structural transformation of aqueous pluronic triblock copolymer solution: a spectroscopic investigation of interaction of curcumin with pluronic micellar and vesicular aggregates.
S. Ghosh (2014)
10.1016/J.CPLETT.2016.10.026
Influence of trehalose on the interaction of curcumin with surface active ionic liquid micelle and its vesicular aggregate composed of a non-ionic surfactant sorbitan stearate
Arpita Roy (2016)
10.1021/acs.langmuir.6b03845
Vesicle-to-Micelle Transition in Aqueous Solutions of l-Cysteine-Derived Carboxylate Surfactants Containing Both Hydrocarbon and Poly(ethylene glycol) Tails.
R. Ghosh (2017)
10.1021/jp406125x
Molecular basis of binding and stability of curcumin in diamide-linked γ-cyclodextrin dimers.
S. Wallace (2013)
10.1016/j.saa.2017.12.037
Spectral study on conformation switchable cationic calix[4]carbazole serving as curcumin container, stabilizer and sustained-delivery carrier.
L. Zhao (2018)
10.1080/1539445X.2015.1025981
Colloidal Dispersions of Lipids and Curcumin, and the Solubility and Degradation Kinetics of the Latter in Micellar Solution
Satyajit Mondal (2015)
Polymeric templating and alignment of fullerenes
Matthew R. Kincer (2011)
10.1021/la5023533
Effect of encapsulation of curcumin in polymeric nanoparticles: how efficient to control ESIPT process?
Chiranjib Banerjee (2014)
10.1016/J.FOODRES.2014.05.054
Encapsulation of curcumin in recombinant human H-chain ferritin increases its water-solubility and stability
L. Chen (2014)
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