A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications
Abstract
The synthesis and characterization of a family of [60]fullerocurcuminoids obtained via Bingel reactions is reported. The new C60 derivatives include curcumin and curcuminoids with a variety of end groups. Preliminary biological experiments show the potential activity of the compound containing a curcumin addend, which exhibits moderate anti-HIV-1 and radical scavenger properties, but no anti-cancer activity. In addition, the new fullerocurcuminoids exhibit HOMO/LUMO energy levels that are reasonably matched with those of perovskites and when they were tested in perovskite solar cells (PSCs) as the electron transporting material (ETM), photoconversion efficiencies ranging from 14.04–14.95% were obtained, whereas a value of 16.23% was obtained for [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) based devices.
- Authors:
-
more »
- Univ. of Texas at El Paso, TX (United States). Dept. of Chemistry
- Univ. of Texas at El Paso, TX (United States). Dept. of Chemistry; Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States). Physical and Life Sciences
- Univ. de Chile, Santiago (Chile). Facultad de Ciencias Fisicas Y Matematicas, Dept. de Ingenieria Quimica, Biotechnolgia y Materiales
- Univ. Autónoma de Barcelona, Bellaterra (Spain). Inst. de Ciencia de Materials de Barcelona (ICMAP-CSIC)
- Univ. of Texas at El Paso, TX (United States). Dept. of Biological Sciences, Border Biomedical Research Center
- Univ. Autónoma de Barcelona, Bellaterra (Spain). Inst. de Ciencia de Materials de Barcelona (ICMAP-CSIC); Inst. Catalana de Recerca i Estudis Avançats (ICREA), Barcelona (Spain)
- Publication Date:
- Research Org.:
- Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States); Univ. of Texas at El Paso, TX (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC); National Science Foundation (NSF); Robert A. Welch Foundation; National Fund for Scientific and Technological Development (FONDECYT); Comisión Nacional de Investigación Científica y Tecnológica (Conicyt); Spanish Government; Centres of Excellence in R&D; Generalitat de Catalunya; Fundacio Montcelimar; Consejo Superior de Investigaciones Científicas (CSIC); National Institute of General Medical Sciences (NIGMS); National Institutes of Health (NIH); National Institute on Minority Health and Health Disparities (NIMHD)
- OSTI Identifier:
- 1624960
- Grant/Contract Number:
- AC52-07NA27344; AH-0033; 1161775, 3170509; 5 SC1 AI098238-02; 5G12MD007592
- Resource Type:
- Accepted Manuscript
- Journal Name:
- RSC Advances
- Additional Journal Information:
- Journal Volume: 8; Journal Issue: 73; Journal ID: ISSN 2046-2069
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Chemistry
Citation Formats
Castro, Edison, Cerón, Maira R., Garcia, Andrea Hernandez, Kim, Quentin, Etcheverry-Berríos, Alvaro, Morel, Mauricio J., Díaz-Torres, Raúl, Qian, Wenjie, Martinez, Zachary, Mendez, Lois, Perez, Frank, Santoyo, Christy A., Gimeno-Muñoz, Raquel, Esper, Ronda, Gutierrez, Denisse A., Varela-Ramirez, Armando, Aguilera, Renato J., Llano, Manuel, Soler, Monica, Aliaga-Alcalde, Núria, and Echegoyen, Luis. A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications. United States: N. p., 2018.
Web. doi:10.1039/c8ra08334g.
Castro, Edison, Cerón, Maira R., Garcia, Andrea Hernandez, Kim, Quentin, Etcheverry-Berríos, Alvaro, Morel, Mauricio J., Díaz-Torres, Raúl, Qian, Wenjie, Martinez, Zachary, Mendez, Lois, Perez, Frank, Santoyo, Christy A., Gimeno-Muñoz, Raquel, Esper, Ronda, Gutierrez, Denisse A., Varela-Ramirez, Armando, Aguilera, Renato J., Llano, Manuel, Soler, Monica, Aliaga-Alcalde, Núria, & Echegoyen, Luis. A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications. United States. https://doi.org/10.1039/c8ra08334g
Castro, Edison, Cerón, Maira R., Garcia, Andrea Hernandez, Kim, Quentin, Etcheverry-Berríos, Alvaro, Morel, Mauricio J., Díaz-Torres, Raúl, Qian, Wenjie, Martinez, Zachary, Mendez, Lois, Perez, Frank, Santoyo, Christy A., Gimeno-Muñoz, Raquel, Esper, Ronda, Gutierrez, Denisse A., Varela-Ramirez, Armando, Aguilera, Renato J., Llano, Manuel, Soler, Monica, Aliaga-Alcalde, Núria, and Echegoyen, Luis. Thu .
"A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications". United States. https://doi.org/10.1039/c8ra08334g. https://www.osti.gov/servlets/purl/1624960.
@article{osti_1624960,
title = {A new family of fullerene derivatives: fullerene-curcumin conjugates for biological and photovoltaic applications},
author = {Castro, Edison and Cerón, Maira R. and Garcia, Andrea Hernandez and Kim, Quentin and Etcheverry-Berríos, Alvaro and Morel, Mauricio J. and Díaz-Torres, Raúl and Qian, Wenjie and Martinez, Zachary and Mendez, Lois and Perez, Frank and Santoyo, Christy A. and Gimeno-Muñoz, Raquel and Esper, Ronda and Gutierrez, Denisse A. and Varela-Ramirez, Armando and Aguilera, Renato J. and Llano, Manuel and Soler, Monica and Aliaga-Alcalde, Núria and Echegoyen, Luis},
abstractNote = {The synthesis and characterization of a family of [60]fullerocurcuminoids obtained via Bingel reactions is reported. The new C60 derivatives include curcumin and curcuminoids with a variety of end groups. Preliminary biological experiments show the potential activity of the compound containing a curcumin addend, which exhibits moderate anti-HIV-1 and radical scavenger properties, but no anti-cancer activity. In addition, the new fullerocurcuminoids exhibit HOMO/LUMO energy levels that are reasonably matched with those of perovskites and when they were tested in perovskite solar cells (PSCs) as the electron transporting material (ETM), photoconversion efficiencies ranging from 14.04–14.95% were obtained, whereas a value of 16.23% was obtained for [6,6]-phenyl-C61-butyric acid methyl ester (PC61BM) based devices.},
doi = {10.1039/c8ra08334g},
journal = {RSC Advances},
number = 73,
volume = 8,
place = {United States},
year = {Thu Dec 13 00:00:00 EST 2018},
month = {Thu Dec 13 00:00:00 EST 2018}
}
Web of Science
Works referenced in this record:
Antioxidant capacity of novel amine derivatives of buckminsterfullerene: Determination of inhibition rate constants in a model oxidation system
journal, November 2009
- Allen, Norman S.; Zeynalov, Eldar B.; Taylor, Kimberley
- Polymer Degradation and Stability, Vol. 94, Issue 11
Fullerene derivative with a branched alkyl chain exhibits enhanced charge extraction and stability in inverted planar perovskite solar cells
journal, January 2018
- Tian, Chengbo; Castro, Edison; Betancourt-Solis, German
- New Journal of Chemistry, Vol. 42, Issue 4
Progress in fullerene-based hybrid perovskite solar cells
journal, January 2018
- Castro, Edison; Murillo, Jesse; Fernandez-Delgado, Olivia
- Journal of Materials Chemistry C, Vol. 6, Issue 11
Peculiarities of the antioxidant and radioprotective effects of hydrated C60 fullerene nanostuctures in vitro and in vivo
journal, September 2009
- Andrievsky, Grigory V.; Bruskov, Vadim I.; Tykhomyrov, Artem A.
- Free Radical Biology and Medicine, Vol. 47, Issue 6
Cyclopropanierung von Fullerenen
journal, August 1993
- Bingel, Carsten
- Chemische Berichte, Vol. 126, Issue 8
A novel curcumin-like dienone induces apoptosis in triple-negative breast cancer cells
journal, February 2016
- Robles-Escajeda, Elisa; Das, Umashankar; Ortega, Nora M.
- Cellular Oncology, Vol. 39, Issue 3
Interface energetics in organo-metal halide perovskite-based photovoltaic cells
journal, January 2014
- Schulz, Philip; Edri, Eran; Kirmayer, Saar
- Energy & Environmental Science, Vol. 7, Issue 4
pH-responsive, self-assembling nanoparticle from a fullerene-tagged poly(l-glutamic acid) and its superoxide dismutase mimetic property
journal, June 2006
- Higashi, Nobuyuki; Shosu, Takeshi; Koga, Tomoyuki
- Journal of Colloid and Interface Science, Vol. 298, Issue 1
Synthesis and electroluminescence of novel copolymers containing crown ether spacers
journal, February 2003
- Sun, Qingjiang; Wang, Haiqiao; Yang, Chunhe
- Journal of Materials Chemistry, Vol. 13, Issue 4
Synthesis of Bioinspired Curcuminoid Small Molecules for Solution-Processed Organic Solar Cells with High Open-Circuit Voltage
journal, May 2017
- Archet, Florence; Yao, Dandan; Chambon, Sylvain
- ACS Energy Letters, Vol. 2, Issue 6
Determination of acidity constants of curcumin in aqueous solution and apparent rate constant of its decomposition
journal, April 2004
- Bernabé-Pineda, Margarita; Ramı́rez-Silva, Marı́a Teresa; Romero-Romo, Mario
- Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 60, Issue 5
Biological activities of curcuminoids, other biomolecules from turmeric and their derivatives – A review
journal, April 2017
- Amalraj, Augustine; Pius, Anitha; Gopi, Sreerag
- Journal of Traditional and Complementary Medicine, Vol. 7, Issue 2
C60: Buckminsterfullerene
journal, November 1985
- Kroto, H. W.; Heath, J. R.; O'Brien, S. C.
- Nature, Vol. 318, Issue 6042
Characterization of CurcuEmulsomes: nanoformulation for enhanced solubility and delivery of curcumin
journal, January 2013
- Ucisik, Mehmet H.; Küpcü, Seta; Schuster, Bernhard
- Journal of Nanobiotechnology, Vol. 11, Issue 1
Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases
journal, January 2009
- Aggarwal, Bharat B.; Harikumar, Kuzhuvelil B.
- The International Journal of Biochemistry & Cell Biology, Vol. 41, Issue 1
Performance and stability analysis of curcumin dye as a photo sensitizer used in nanostructured ZnO based DSSC
journal, March 2018
- Sinha, D.; De, D.; Ayaz, A.
- Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 193
Fullerenes in biology and medicine
journal, January 2017
- Castro, Edison; Garcia, Andrea Hernandez; Zavala, Gerardo
- Journal of Materials Chemistry B, Vol. 5, Issue 32
Multifunctional organic dyes: anion-sensing and light-harvesting properties of curcumin boron complexes
journal, January 2017
- Tsuchikawa, Masahiro; Takao, Aya; Funaki, Takashi
- RSC Advances, Vol. 7, Issue 58
Antioxidant and Free Radical Scavenging Activities of Curcumin
journal, January 2013
- Asouri, Mohsen; Ataee, Ramin; Ahmadi, Ali Asghar
- Asian Journal of Chemistry, Vol. 25, Issue 13
Synthesis and properties of bis(pyrrolidino)fullerenes bridged by a flexible alkyl-tether
journal, July 2015
- Kop, Tatjana; Bjelaković, Mira; Milić, Dragana
- Tetrahedron, Vol. 71, Issue 29
Characterization of Photovoltaic Performance of the Dye-Sensitized Solar Cell with a Novel Ruthenium Complex Having a Bisdemethoxycurcumin as a Ligand
journal, March 2012
- Ozawa, Hironobu; Kawaguchi, Hiroki; Okuyama, Yu
- AMBIO, Vol. 41, Issue S2
Fullerene C 60 conjugated with phenols as new hybrid antioxidants to improve the oxidative stability of polymers at elevated temperatures
journal, January 2017
- Czochara, R.; Kusio, J.; Litwinienko, G.
- RSC Advances, Vol. 7, Issue 70
Anti-inflammatory and anti-oxidative effect of curcumin in connective tissue type mast cell
journal, April 2013
- Nishikawa, Hirofumi; Tsutsumi, Jinsyo; Kitani, Seiichi
- Journal of Functional Foods, Vol. 5, Issue 2
Synthesis and Optical Properties of Double Antenna Pyrene-OPV- Fullerene C 60
journal, April 2012
- Domínguez-Chávez, Jorge G.; Cruz-Chávez, Enrique; Moggio, Ivana
- Fullerenes, Nanotubes and Carbon Nanostructures, Vol. 20, Issue 3
The Essential Medicinal Chemistry of Curcumin
text, January 2021
- Nelson, Km; Dahlin, Jl; Bisson, J.
- University of Illinois at Chicago
Protease Inhibitors: Current Status and Future Prospects
journal, February 2000
- Leung, Donmienne; Abbenante, Giovanni; Fairlie, David P.
- Journal of Medicinal Chemistry, Vol. 43, Issue 3
Curcumin: A Review of Its’ Effects on Human Health
journal, October 2017
- Hewlings, Susan; Kalman, Douglas
- Foods, Vol. 6, Issue 10
Inhibition of the HIV-1 protease by fullerene derivatives: model building studies and experimental verification
journal, July 1993
- Friedman, Simon H.; DeCamp, Dianne L.; Sijbesma, Rint P.
- Journal of the American Chemical Society, Vol. 115, Issue 15
Synthesis of a fullerene derivative for the inhibition of HIV enzymes
journal, July 1993
- Sijbesma, R.; Srdanov, G.; Wudl, F.
- Journal of the American Chemical Society, Vol. 115, Issue 15
An 11-mer Amyloid Beta Peptide Fragment Provokes Chemical Mutations and Parkinsonian Biomarker Aggregation in Dopaminergic Cells: A Novel Road Map for “Transfected” Parkinson’s
journal, October 2016
- Kabiraj, Parijat; Marin, Jose Eduardo; Varela-Ramirez, Armando
- ACS Chemical Neuroscience, Vol. 7, Issue 11
The prolongation of the lifespan of rats by repeated oral administration of [60]fullerene
journal, June 2012
- Baati, Tarek; Bourasset, Fanchon; Gharbi, Najla
- Biomaterials, Vol. 33, Issue 19
Recent advances in the investigation of curcuminoids
journal, January 2008
- Itokawa, Hideji; Shi, Qian; Akiyama, Toshiyuki
- Chinese Medicine, Vol. 3, Issue 1
An Essential Role for LEDGF/p75 in HIV Integration
journal, October 2006
- Llano, M.; Saenz, D. T.; Meehan, A.
- Science, Vol. 314, Issue 5798
Fullerene C 60 with cytoprotective and cytotoxic potential: prospects as a novel treatment agent in Dermatology?
journal, February 2017
- Rondags, Angelique; Yuen, Wing Yan; Jonkman, Marcel F.
- Experimental Dermatology, Vol. 26, Issue 3
Characterization of New Cationic N , N -Dimethyl[70]fulleropyrrolidinium Iodide Derivatives as Potent HIV-1 Maturation Inhibitors
journal, November 2016
- Castro, Edison; Martinez, Zachary S.; Seong, Chang-Soo
- Journal of Medicinal Chemistry, Vol. 59, Issue 24
[60]Fullerene is a Powerful Antioxidant in Vivo with No Acute or Subacute Toxicity
journal, December 2005
- Gharbi, Najla; Pressac, Monique; Hadchouel, Michelle
- Nano Letters, Vol. 5, Issue 12
The antioxidants curcumin and quercetin inhibit inflammatory processes associated with arthritis
journal, April 2006
- Jackson, J. K.; Higo, T.; Hunter, W. L.
- Inflammation Research, Vol. 55, Issue 4
Curcumin as “Curecumin”: From kitchen to clinic
journal, February 2008
- Goel, Ajay; Kunnumakkara, Ajaikumar B.; Aggarwal, Bharat B.
- Biochemical Pharmacology, Vol. 75, Issue 4
The Essential Medicinal Chemistry of Curcumin: Miniperspective
journal, January 2017
- Nelson, Kathryn M.; Dahlin, Jayme L.; Bisson, Jonathan
- Journal of Medicinal Chemistry, Vol. 60, Issue 5
Steady-state and time-resolved direct detection EPR spectra of fullerene triplets in liquid solution and glassy matrixes: evidence for a dynamic Jahn-Teller effect in triplet C60
journal, June 1992
- Closs, Gerhard L.; Gautam, Pennathur; Zhang, Daisy
- The Journal of Physical Chemistry, Vol. 96, Issue 13
Recent advances in the investigation of curcuminoids
text, January 2008
- Toshiyuki, Akiyama,; Kuo-Hsiung, Lee,; Qian, Shi,
- BioMed Central Ltd
Human immunodeficiency virus type 1 viral protein R (Vpr) arrests cells in the G2 phase of the cell cycle by inhibiting p34cdc2 activity
journal, November 1995
- He, J.; Choe, S.; Walker, R.
- Journal of Virology, Vol. 69, Issue 11
The Essential Medicinal Chemistry of Curcumin
text, January 2021
- Nelson, Km; Dahlin, Jl; Bisson, J.
- University of Illinois at Chicago