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Spectroscopy
Volume 22, Issue 2-3, Pages 187-198
http://dx.doi.org/10.3233/SPE-2008-0335

Role of H-bond formation in the photoreactivity of curcumin

Luca Nardo,1,2 Roberta Paderno,1 Alessandra Andreoni,1 Már Másson,2 Tone Haukvik,3 and Hanne Hjorth TØnnesen3

1CNISM–INFM–CNR and Department of Physics and Mathematics, University of Insubria at Como, Como, Italy
2Faculty of Pharmacy, University of Iceland, Hagi, Reykjavik, Iceland
3School of Pharmacy, University of Oslo, Oslo, Norway
4CNISM–INFM–CNR and Department of Physics and Mathematics, University of Insubria at Como, Via Valleggio, 11-22100 Como, Italy

Copyright © 2008 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Citations to this Article [64 citations]

The following is the list of published articles that have cited the current article.

  • K. Indira Priyadarsini, “Photophysics, photochemistry and photobiology of curcumin: Studies from organic solutions, bio-mimetics and living cells,” Journal Of Photochemistry And Photobiology C-Photochemistry Reviews, vol. 10, no. 2, pp. 81–95, 2009. View at Publisher · View at Google Scholar
  • Ramkrishna Adhikary, Prasun Mukherjee, Tak W. Kee, and Jacob W. Petrich, “Excited-State Intramolecular Hydrogen Atom Transfer and Solvation Dynamics of the Medicinal Pigment Curcumin,” Journal Of Physical Chemistry B, vol. 113, no. 15, pp. 5255–5261, 2009. View at Publisher · View at Google Scholar
  • Luca Nardo, Alessandra Andreoni, Maria Bondani, Mar Masson, and Hanne Hjorth Tonnesen, “Studies on curcumin and curcuminoids. XXXIV. Photophysical properties of a symmetrical, non-substituted curcumin analogue,” Journal Of Photochemistry And Photobiology B-Biology, vol. 97, no. 2, pp. 77–86, 2009. View at Publisher · View at Google Scholar
  • T. Haukvik, E. Bruzell, S. Kristensen, and H. H. Tonnesen, “Photokilling of bacteria by curcumin in different aqueous preparations. Studies on curcumin and curcuminoids XXXVII,” Pharmazie, vol. 64, no. 10, pp. 666–673, 2009. View at Publisher · View at Google Scholar
  • Luca Nardo, Maria Bondani, and Alessandra Andreoni, “Discrimination of the binding mode of DNA ligands by single-photon timing,” Spectroscopy-An International Journal, vol. 23, no. 1, pp. 11–28, 2009. View at Publisher · View at Google Scholar
  • Rajib Ghosh, Jahur A. Mondal, and Dipak K. Palit, “Ultrafast Dynamics of the Excited States of Curcumin in Solution,” Journal of Physical Chemistry B, vol. 114, no. 37, pp. 12129–12143, 2010. View at Publisher · View at Google Scholar
  • T. Haukvik, E. Bruzell, S. Kristensen, and H. H. Tonnesen, “Photokilling of bacteria by curcumin in selected polyethylene glycol 400 (PEG 400) preparations Studies on curcumin and curcuminoids, XLI,” Pharmazie, vol. 65, no. 8, pp. 600–606, 2010. View at Publisher · View at Google Scholar
  • Anne Bee Hegge, T. Andersen, J.E. Melvik, S. Kristensen, and H.H. Tønnesen, “Evaluation of novel alginate foams as drug delivery systems in antimicrobial photodynamic therapy (aPDT) of infected wounds-An in vitro study: Studies on curcumin and curcuminoides XL,” Journal of Pharmaceutical Sciences, vol. 99, no. 8, pp. 3499–3513, 2010. View at Publisher · View at Google Scholar
  • Ramkrishna Adhikary, Philip J. Carlson, Tak W. Kee, and Jacob W. Petrich, “Excited-State Intramolecular Hydrogen Atom Transfer of Curcumin in Surfactant Micelles,” Journal Of Physical Chemistry B, vol. 114, no. 8, pp. 2997–3004, 2010. View at Publisher · View at Google Scholar
  • Monica Caselli, Erika Ferrari, Carol Imbriano, Francesca Pignedoli, Monica Saladini, and Glauco Ponterini, “Probing solute-solvent hydrogen bonding with fluorescent water-soluble curcuminoids,” Journal Of Photochemistry And Photobiology A-Chemistry, vol. 210, no. 2-3, pp. 115–124, 2010. View at Publisher · View at Google Scholar
  • Luca Nardo, Alessandra Andreoni, and Hanne Hjorth Tønnesen, “Intramolecular H-Bond Formation Mediated De-Excitation of Curcuminoids: A Time-Resolved Fluorescence Study,” Hydrogen Bonding and Transfer in the Excited State, pp. 353–375, 2010. View at Publisher · View at Google Scholar
  • Ramkrishna Adhikary, Charles A. Barnes, Rachel L. Trampel, Samuel J. Wallace, Tak W. Kee, and Jacob W. Petrich, “Photoinduced trans-to-cis Isomerization of Cyclocurcumin,” Journal of Physical Chemistry B, vol. 115, no. 36, pp. 10707–10714, 2011. View at Publisher · View at Google Scholar
  • Ilseung Yang, Seung Min Jin, Junhee Kang, Venkatnarayan Ramanathan, Hyung Min Kim, Yung Doug Suh, and Seong Keun Kim, “Excited State Dynamics of Curcumin and Solvent Hydrogen Bonding,” Bulletin of The Korean Chemical Society, vol. 32, no. 8, pp. 3090–3093, 2011. View at Publisher · View at Google Scholar
  • Luca Nardo, Alessandra Andreoni, Mar Masson, Tone Haukvik, and Hanne Hjorth Tonnesen, “Studies on Curcumin and Curcuminoids. XXXIX. Photophysical Properties of Bisdemethoxycurcumin,” Journal Of Fluorescence, vol. 21, no. 2, pp. 627–635, 2011. View at Publisher · View at Google Scholar
  • Anne Bee Hegge, T. Andersen, J. E. Melvik, E. Bruzell, S. Kristensen, and H. H. Tonnesen, “Formulation and Bacterial Phototoxicity of Curcumin Loaded Alginate Foams for Wound Treatment Applications: Studies on Curcumin and Curcuminoides XLII,” Journal Of Pharmaceutical Sciences, vol. 100, no. 1, pp. 174–185, 2011. View at Publisher · View at Google Scholar
  • Tak W. Kee, Ramkrishna Adhikary, Philip J. Carlson, Prasun Mukherjee, and Jacob W. Petrich, “Femtosecond Fluorescence Upconversion Investigations on the Excited-State Photophysics of Curcumin,” Australian Journal Of Chemistry, vol. 64, no. 1, pp. 23–30, 2011. View at Publisher · View at Google Scholar
  • T. Haukvik, E. Bruzell, S. Kristensen, and H. H. Tonnesen, “A screening of curcumin derivatives for antibacterial phototoxic effects Studies on curcumin and curcuminoids. XLIII,” Pharmazie, vol. 66, no. 1, pp. 69–74, 2011. View at Publisher · View at Google Scholar
  • Luca Nardo, Angelo Maspero, Marco Selva, Maria Bondani, Giovanni Palmisano, Erika Ferrari, and Monica Saladini, “Excited-state dynamics of bis-dehydroxycurcumin carboxylic acid, a water-soluble derivative of the photosensitizer curcumin,” Journal of Physical Chemistry A, vol. 116, no. 37, pp. 9321–9330, 2012. View at Publisher · View at Google Scholar
  • R.K. Saini, and K. Das, “Picosecond spectral relaxation of curcumin excited state in a binary solvent mixture of toluene and methanol,” Journal of Physical Chemistry B, vol. 116, no. 34, pp. 10357–10363, 2012. View at Publisher · View at Google Scholar
  • Chiranjib Ghatak, Vishal Govind Rao, Sarthak Mandal, Surajit Ghosh, and Nilmoni Sarkar, “An Understanding of the Modulation of Photophysical Properties of Curcumin inside a Micelle Formed by an Ionic Liquid: A New Possibility of Tunable Drug Delivery System,” Journal Of Physical Chemistry B, vol. 116, no. 10, pp. 3369–3379, 2012. View at Publisher · View at Google Scholar
  • L. Nardo, A. Andreoni, M. Bondani, M. Masson, T. Haukvik, and H. H. Tonnesen, “Studies on Curcumin and Curcuminoids. XLVI. Photophysical Properties of Dimethoxycurcumin and Bis-dehydroxycurcumin,” Journal Of Fluorescence, vol. 22, no. 2, pp. 597–608, 2012. View at Publisher · View at Google Scholar
  • Andreas Noack, Gerd Hause, and Karsten Maeder, “Physicochemical characterization of curcuminoid-loaded solid lipid nanoparticles,” International Journal Of Pharmaceutics, vol. 423, no. 2, pp. 440–451, 2012. View at Publisher · View at Google Scholar
  • Mandy H. M. Leung, Duc-Truc Pham, Stephen F. Lincoln, and Tak W. Kee, “Femtosecond transient absorption spectroscopy of copper(ii)-curcumin complexes,” Physical Chemistry Chemical Physics, vol. 14, no. 39, pp. 13580–13587, 2012. View at Publisher · View at Google Scholar
  • M. Adília Lemos, and Graham Hungerford, “ The Binding of Curcuma longa Extract with Bovine Serum Albumin Monitored via Time-Resolved Fluorescence ,” Photochemistry and Photobiology, 2013. View at Publisher · View at Google Scholar
  • Edward G. Randles, and Peter R. Bergethon, “Reaction Field Analysis and Lipid Bilayer Location for Lipophilic Fluorophores,” The Journal of Physical Chemistry B, pp. 130822092813006, 2013. View at Publisher · View at Google Scholar
  • Tingting Qian, Li Kun, Bo Gao, Rongrong Zhu, Xianzheng Wu, and ShiLong Wang, “Photo-ionization and Photo-excitation of Curcumin Investigated by Laser Flash Photolysis,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2013. View at Publisher · View at Google Scholar
  • R.K. Saini, and K. Das, “Picosecond Spectral Relaxation of Curcumin Excited State in toluene-alcohol Mixtures,” Journal of Luminescence, 2013. View at Publisher · View at Google Scholar
  • Chiranjib Banerjee, Chiranjib Ghatak, Sarthak Mandal, Surajit Ghosh, Jagannath Kuchlyan, and Nilmoni Sarkar, “Curcumin in Reverse Micelle: An Example to Control Excited-State Intramolecular Proton Transfer (ESIPT) in Confined Media,” The Journal of Physical Chemistry B, vol. 117, no. 23, pp. 6906–6916, 2013. View at Publisher · View at Google Scholar
  • Sarthak Mandal, Chiranjib Banerjee, Surajit Ghosh, Jagannath Kuchlyan, and Nilmoni Sarkar, “Modulation of the Photophysical Properties of Curcumin in Non-ionic Surfactant (Tween-20) Forming Micelles and Niosomes: A Comparative Study of Different Microenvironments,” The Journal of Physical Chemistry B, pp. 130517173703006, 2013. View at Publisher · View at Google Scholar
  • R. Singh, S. Kristensen, and H.H. Tønnesen, “Influence of vehicle properties and excipients on hydrolytic and photochemical stability of curcumin in preparations containing Pluronics: Studies of curcumin and curcuminoids XLVIII,” Pharmazie, vol. 68, no. 3, pp. 160–169, 2013. View at Publisher · View at Google Scholar
  • Dóra Tátraaljai, Balázs Kirschweng, János Kovács, Eniko Földes, and Béla Pukánszky, “Processing stabilisation of PE with a natural antioxidant, curcumin,” European Polymer Journal, 2013. View at Publisher · View at Google Scholar
  • Sarthak Mandal, Surajit Ghosh, Debasis Banik, Chiranjib Banerjee, Jagannath Kuchlyan, and Nilmoni Sarkar, “An Investigation into the Effect of the Structure of Bile Salt Aggregates on the Binding Interactions and ESIHT Dynamics of Curcumin: A Photophysical Approach to Probe Bile Salt Aggregates as a Potential Drug Carrier,” The Journal of Physical Chemistry B, pp. 131008112440006, 2013. View at Publisher · View at Google Scholar
  • Mary Bebawy, Frederick Luk, Rebecca S. Mason, Wing-Hin Lee, Ching-Yee Loo, and Ramin Rohanizadeh, “Curcumin and its Derivatives: Their Application in Neuropharmacology and Neuroscience in the 21st Century,” Current Neuropharmacology, vol. 11, no. 4, pp. 338–378, 2013. View at Publisher · View at Google Scholar
  • Ravinder Singh, Hanne Hjorth Tønnesen, Solveig Kristensen, and Kristian Berg, “The influence of Pluronics® on dark cytotoxicity, photocytotoxicity, localization and uptake of curcumin in cancer cells: studies of curcumin and curcuminoids XLIX,” Photochemical & Photobiological Sciences, vol. 12, no. 3, pp. 559, 2013. View at Publisher · View at Google Scholar
  • Marco Lamperti, Angelo Maspero, Hanne H. Tonnesen, Maria Bondani, and Luca Nardo, “Elucidation of the Relationships between H-Bonding Patterns and Excited State Dynamics in Cyclovalone,” Molecules, vol. 19, no. 9, pp. 13282–13304, 2014. View at Publisher · View at Google Scholar
  • Surajit Ghosh, Jagannath Kuchlyan, Debasis Banik, Niloy Kundu, Arpita Roy, Chiranjib Banerjee, and Nilmoni Sarkar, “Organic Additive, 5-Methyl Salicylic Acid, Induces Spontaneous Structural Transformation of Aqueous Pluronic Triblock Copolymer Solution: A Spectroscopic Investigation of Interaction of Curcumin with Pluronic Micellar and Vesicular aggregates,” The Journal of Physical Chemistry B, pp. 140905104129006, 2014. View at Publisher · View at Google Scholar
  • Shing Fung Chow, Limin Shi, Wai Wing Ng, Kari Hoi Yan Leung, Karthik Nagapudi, Changquan C. Sun, and Albert Hee-lum Chow, “Kinetic entrapment of a hidden curcumin cocrystal with phloroglucinol,” Crystal Growth & Design, pp. 140902124703005, 2014. View at Publisher · View at Google Scholar
  • Yana Manolova, Vera Deneva, and Liudmil Antonov, “The Effect of The Water on The Curcumin Tautomerism: A Quantitative Approach,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014. View at Publisher · View at Google Scholar
  • Sydney Peng, Wei-Lun Hung, Yu-Shiang Peng, and I-Ming Chu, “Oligoalanine-modified Pluronic-F127 nanocarriers for the delivery of curcumin with enhanced entrapment efficiency,” Journal of Biomaterials Science, Polymer Edition, pp. 1–15, 2014. View at Publisher · View at Google Scholar
  • Chiranjib Banerjee, Surajit Ghosh, Sarthak Mandal, Jagannath Kuchlyan, Niloy Kundu, and Nilmoni Sarkar, “Exploring the Photophysics of Curcumin in Zwitterionic Micellar System: An Approach to Control ESIPT Process in Presence of Room Temperature Ionic Liquids (RTILs) and Anionic Surfactant,” The Journal of Physical Chemistry B, pp. 140311123518002, 2014. View at Publisher · View at Google Scholar
  • Katherine Akulov, Ron Simkovitch, Yuval Erez, Rinat Gepshtein, Tal Schwartz, and Dan Huppert, “Acid Effect on Photobase Properties of Curcumin,” The Journal of Physical Chemistry A, pp. 140306112443009, 2014. View at Publisher · View at Google Scholar
  • Gyuldzhan Yakub, Antoniya Toncheva, Nevena Manolova, Iliya Rashkov, Veselin Kussovski, and Dobri Danchev, “Curcumin-loaded poly(l-lactide-co-D,l-lactide) electrospun fibers: Preparation and antioxidant, anticoagulant, and antibacterial properties,” Journal of Bioactive and Compatible Polymers, vol. 29, no. 6, pp. 607–627, 2014. View at Publisher · View at Google Scholar
  • Prasanna Neelakantan, Cheng Qing Cheng, Vinoddhine Ravichandran, Teresa Mao, Priyanka Sriraman, Swetha Sridharan, Chandana Subbarao, Subash Sharma, and Anil Kishen, “Photoactivation of curcumin and sodium hypochlorite to enhance antibiofilm efficacy in root canal dentin,” Photodiagnosis and Photodynamic Therapy, 2014. View at Publisher · View at Google Scholar
  • Marianne Lilletvedt Tovsen, Ellen Bruzell, Erika Ferrari, Monica Saladini, Vivek S. Gaware, Már Másson, Solveig Kristensen, and Hanne Hjorth Tønnesen, “Antibacterial phototoxic effects of synthetic asymmetric and glycosylated curcuminoids in aqueous formulations,” Journal of Photochemistry and Photobiology B: Biology, vol. 140, pp. 150–156, 2014. View at Publisher · View at Google Scholar
  • Takaaki Harada, Hamish L. McTernan, Duc-Truc Pham, Stephen F. Lincoln, and Tak W. Kee, “Femtosecond Transient Absorption Spectroscopy of the Medicinal Agent Curcumin in Diamide Linked γ-Cyclodextrin Dimers,” The Journal of Physical Chemistry B, pp. 141002111004005, 2014. View at Publisher · View at Google Scholar
  • Michal Heger, Rowan F. van Golen, Mans Broekgaarden, and Martin C. Michel, “The Molecular Basis for the Pharmacokinetics and Pharmacodynamics of Curcumin and Its Metabolites in Relation to Cancers,” Pharmacological Reviews, vol. 66, no. 1, pp. 222–307, 2014. View at Publisher · View at Google Scholar
  • Yuval Erez, Ron Simkovitch, Shay Shomer, Rinat Gepshtein, and Dan Huppert, “Effect of Acid on the Ultraviolet–Visible Absorption and Emission Properties of Curcumin,” The Journal of Physical Chemistry A, pp. 140123152217006, 2014. View at Publisher · View at Google Scholar
  • Kristine Opsvik Wikene, Ellen Bruzell, and Hanne Hjorth Tønnesen, “Characterization and antimicrobial phototoxicity of curcumin dissolved in natural deep eutectic solvents,” European Journal of Pharmaceutical Sciences, 2015. View at Publisher · View at Google Scholar
  • Sangwoo Park, and Sang-Yup Lee, “Significant Enhancement of Curcumin Photoluminescence by a Photosensitizing Organogel: An Optical Sensor for Pyrrole Detection,” Sensors and Actuators B: Chemical, 2015. View at Publisher · View at Google Scholar
  • M. Lemos, Katarína Sárniková, Francesca Bot, Monica Anese, and Graham Hungerford, “Use of Time-Resolved Fluorescence to Monitor Bioactive Compounds in Plant Based Foodstuffs,” Biosensors, vol. 5, no. 3, pp. 367–397, 2015. View at Publisher · View at Google Scholar
  • Milica Vukićević, and Hanne Hjorth Tønnesen, “Interaction between curcumin and human serum albumin in the presence of excipients and the effect of binding on curcumin photostability,” Pharmaceutical Development and Technology, pp. 1–9, 2015. View at Publisher · View at Google Scholar
  • Mandy H. M. Leung, Takaaki Harada, Sheng Dai, and Tak W. Kee, “Nanoprecipitation and Spectroscopic Characterization of Curcumin-Encapsulated Polyester Nanoparticles,” Langmuir, pp. 151015111932002, 2015. View at Publisher · View at Google Scholar
  • Zoran M. Markovic, Jovana R. Prekodravac, Dragana D. Tosic, Ivanka D. Holclajtner-Antunovic, Momir S. Milosavljevic, Miroslav D. Dramicanin, and Biljana M. Todorovic-Markovic, “Facile synthesis of water-soluble curcumin nanocrystals,” Journal Of The Serbian Chemical Society, vol. 80, no. 1, pp. 63–72, 2015. View at Publisher · View at Google Scholar
  • Damayanti Bagchi, Siddhi Chaudhuri, Samim Sardar, Susobhan Choudhury, Nabarun Polley, Peter Lemmens, and Samir Kumar Pal, “Modulation of stability and functionality of a phyto-antioxidant by weakly interacting metal ions: curcumin in aqueous solution,” RSC Adv., vol. 5, no. 124, pp. 102516–102524, 2015. View at Publisher · View at Google Scholar
  • Jaroslav Ilnytskyi, Taras Patsahan, and Orest Pizio, “On the properties of the curcumin molecule in water. Exploration of the OPLS - united atom model by molecular dynamics computer simulation.,” Journal of Molecular Liquids, 2016. View at Publisher · View at Google Scholar
  • Arianna Maria Giani, Marco Lamperti, Angelo Maspero, Alessandro Cimino, Roberto Negri, Giovanni Battista Giovenzana, Giovanni Palmisano, and Luca Nardo, “Fluorescencestudies on 2-(het)arylperimidine derivatives,” Journal of Luminescence, 2016. View at Publisher · View at Google Scholar
  • Alvaro Etcheverry-Berríos, Ignacio Olavarría, Mickael L. Perrin, Raúl Díaz-Torres, Domingo Jullian, Ingrid Ponce, José H. Zagal, Jorge Pavez, Sergio O. Vásquez, Herre S. J. van der Zant, Diana Dulić, Núria Aliaga-Alcalde, and Monica Soler, “Multiscale Approach to the Study of the Electronic Properties of Two Thiophene Curcuminoid Molecules,” Chemistry - A European Journal, 2016. View at Publisher · View at Google Scholar
  • Gourab Karmakar, Prasant Nahak, Pritam Guha, Biplab Roy, Priyam Chettri, Manish Sapkota, Suraj Koirala, Takeshi Misono, Kanjiro Torigoe, Shilpi Ghosh, and Amiya Kumar Panda, “Effects of Fatty Acids on the Interfacial and Solution Behavior of Mixed Lipidic Aggregates Called Solid Lipid Nanoparticles,” Journal Of Oleo Science, vol. 65, no. 5, pp. 419–430, 2016. View at Publisher · View at Google Scholar
  • In-Hyeok Park, Caroline Evania Mulijanto, Hyeong-Hwan Lee, Yunji Kang, Eunji Lee, Anjana Chanthapally, Shim Sung Lee, and Jagadese J. Vittal, “Influence of Interpenetration in Diamondoid Metal–Organic Frameworks on the Photoreactivity and Sensing Properties,” Crystal Growth & Design, 2016. View at Publisher · View at Google Scholar
  • Elisa Lavigna, Nertil Xhaferaj, Aurel Tabacaru, Marco Lamperti, Luca Nardo, Massimo Mella, Claudio Pettinari, and Simona Galli, “Investigating the Structural Features and Spectroscopic Properties of Bis(tetrazolato)-Based Coordination Polymers,” Crystal Growth & Design, 2016. View at Publisher · View at Google Scholar
  • Takaaki Harada, Stephen F. Lincoln, and Tak W. Kee, “Excited-state dynamics of the medicinal pigment curcumin in a hydrogel,” Phys. Chem. Chem. Phys., 2016. View at Publisher · View at Google Scholar
  • Nidhi K. Bhatia, Shyam Kishor, Nidhi Katyal, Pankaj Gogoi, Payal Narang, and Shashank Deep, “Effect of pH and temperature on conformational equilibria and aggregation behaviour of curcumin in aqueous binary mixtures of ethanol,” RSC Adv., vol. 6, no. 105, pp. 103275–103288, 2016. View at Publisher · View at Google Scholar
  • Ágnes Alberti, Eszter Riethmüller, and Szabolcs Béni, “Characterization of diarylheptanoids: an emerging class of bioactive natural products,” Journal of Pharmaceutical and Biomedical Analysis, 2017. View at Publisher · View at Google Scholar
  • Luca Nardo, Angelo Maspero, Andrea Penoni, Giovanni Palmisano, Erika Ferrari, and Monica Saladini, “Excited state dynamics of bis-dehydroxycurcumin tert-butyl ester, a diketo-shifted derivative of the photosensitizer curcumin,” Plos One, vol. 12, no. 4, pp. e0175225, 2017. View at Publisher · View at Google Scholar