(Pentamethylcyclopentadienato)rhodium complexes for delivery of the curcumin anticancer drug [Rhodium pentamethylcyclopentadienato complexes for delivery of the curcumin anti-cancer drug]

Markham, Jack; Liang, Jun; Levina, Aviva; Mak, Rachel; Johannessen, Bernt; Kappen, Peter; Glover, Chris J.; Lai, Barry; Vogt, Stefan; Lay, Peter A.

doi:10.1002/ejic.201601331

Title: (Pentamethylcyclopentadienato)rhodium complexes for delivery of the curcumin anticancer drug [Rhodium pentamethylcyclopentadienato complexes for delivery of the curcumin anti-cancer drug]

Journal Article · Mon Jan 23 00:00:00 EST 2017 · European Journal of Inorganic Chemistry

DOI:https://doi.org/10.1002/ejic.201601331· OSTI ID:1371909

Markham, Jack ^[1]; Liang, Jun ^[1];

^[1];

^[2];

^[3];

^[1]

The Univ. of Sydney, NSW (Australia)
Australian Synchrotron, Clayton, VIC (Australia)
Argonne National Lab. (ANL), Lemont, IL (United States)

[Rh ^III (*Cp)Cl(X,Y)] ^{n +} complexes {X, Y = Cl, PTA, n = 0 ( 2 ); X, Y = en, n = 1 ( 3 , Cl ^– salt; 4 , PF ₆ ^– salt); X, Y = acac, n = 0 ( 5 ); X, Y = cur, n = 0 ( 6 ), where *Cp = pentamethylcyclopentadienato, curH = curcumin; PTA = 1,3,5‐triaza‐7‐phosphatricyclo[3.3.1.1]decane; en = 1,2‐ethanediamine; acac = acetylacetonato = 2,4‐pentanedionato(1–)} were synthesized from [Rh(*Cp)(µ‐Cl)Cl] ₂ ( 1 ). While 2 – 5 were inactive against human epithelial A549 lung‐cancer cells in assays of cytotoxicity, and antimetastatic and proapoptotic behaviors, 6 had a cytotoxic activity similar to that of curH over 72 h, but at 24 h in real‐time cell migration assays, it was less active, showing slow release of curH. All complexes underwent ligand‐exchange reactions with biomolecules and cells within the timeframes of the assays (X‐ray absorption spectroscopy). Intracellular elemental distributions (X‐ray fluorescence microscopy) showed that 6 effectively delivered curH to cells, where it was released. Other elemental distributions and caspase activities were consistent with preapoptotic activities. As such, 6 is a promising delivery agent for bioactive ligands, such as curH. However, pure curcumin itself showed a previously unrecognized ability to promote migration of A549 cells at subtoxic concentrations in the presence of endothelial growth factor, which may be a concern for its widespread use as a nutritional supplement and as a potential drug. This aspect warrants further research.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-06CH11357; DE‐AC02‐06CH11357

OSTI ID:: 1371909

Alternate ID(s):: OSTI ID: 1401271

Journal Information:: European Journal of Inorganic Chemistry, Vol. 2017, Issue 12; ISSN 1434-1948

Publisher:: ChemPubSoc EuropeCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 18 works

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References (78)

Rhodium(III) and iridium(III) complexes as anticancer agents Geldmacher, Yvonne; Oleszak, Melanie; Sheldrick, William S. Inorganica Chimica Acta, Vol. 393 https://doi.org/10.1016/j.ica.2012.06.046	journal	December 2012
Characterization of a Ruthenium(III)/NAMI-A Adduct with Bovine Serum Albumin that Exhibits a High Anti-Metastatic Activity Liu, Mimi; Lim, Zhi Jun; Gwee, Yee Yen Angewandte Chemie International Edition, Vol. 49, Issue 9 https://doi.org/10.1002/anie.200906079	journal	February 2010
ATHENA , ARTEMIS , HEPHAESTUS : data analysis for X-ray absorption spectroscopy using IFEFFIT Ravel, B.; Newville, M. Journal of Synchrotron Radiation, Vol. 12, Issue 4 https://doi.org/10.1107/S0909049505012719	journal	June 2005
X-ray-induced photo-chemistry and X-ray absorption spectroscopy of biological samples George, Graham N.; Pickering, Ingrid J.; Pushie, M. Jake Journal of Synchrotron Radiation, Vol. 19, Issue 6 https://doi.org/10.1107/S090904951203943X	journal	October 2012
Organometallic rhodium( iii ) and iridium( iii ) cyclopentadienyl complexes with curcumin and bisdemethoxycurcumin co-ligands Pettinari, Riccardo; Marchetti, Fabio; Pettinari, Claudio Dalton Transactions, Vol. 44, Issue 47 https://doi.org/10.1039/C5DT03037D	journal	January 2015
Phase I/II study with ruthenium compound NAMI-A and gemcitabine in patients with non-small cell lung cancer after first line therapy Leijen, Suzanne; Burgers, Sjaak A.; Baas, Paul Investigational New Drugs, Vol. 33, Issue 1 https://doi.org/10.1007/s10637-014-0179-1	journal	October 2014
In Vitro Evaluation of Rhodium and Osmium RAPTA Analogues: The Case for Organometallic Anticancer Drugs Not Based on Ruthenium Dorcier, Antoine; Ang, Wee Han; Bolaño, Sandra Organometallics, Vol. 25, Issue 17 https://doi.org/10.1021/om060394o	journal	August 2006
Curcumin inhibits the migration and invasion of human A549 lung cancer cells through the inhibition of matrix metalloproteinase-2 and -9 and Vascular Endothelial Growth Factor (VEGF) Lin, Song-Shei; Lai, Kuang-Chi; Hsu, Shu-Chun Cancer Letters, Vol. 285, Issue 2 https://doi.org/10.1016/j.canlet.2009.04.037	journal	November 2009
Anti-cancer effects of curcumin on lung cancer through the inhibition of EZH2 and NOTCH1 Wu, Guo-Qing; Chai, Ke-Qun; Zhu, Xiu-Ming Oncotarget, Vol. 7, Issue 18 https://doi.org/10.18632/oncotarget.8532	journal	April 2016
Coordination compounds in cancer: Past, present and perspectives Trudu, Federica; Amato, Filippo; Vaňhara, Petr Journal of Applied Biomedicine, Vol. 13, Issue 2 https://doi.org/10.1016/j.jab.2015.03.003	journal	May 2015
Arene-Ru ^II Complexes of Curcumin Exert Antitumor Activity via Proteasome Inhibition and Apoptosis Induction Bonfili, Laura; Pettinari, Riccardo; Cuccioloni, Massimiliano ChemMedChem, Vol. 7, Issue 11 https://doi.org/10.1002/cmdc.201200341	journal	September 2012
A potential role for protein tyrosine phosphatase inhibition by a RuIII–edta complex (edta = ethylenediaminetetraacetate) in its biological activity Chatterjee, Debabrata; Mitra, Anannya; Levina, Aviva Chemical Communications, Issue 25 https://doi.org/10.1039/b803261k	journal	January 2008
Biotransformations of Antidiabetic Vanadium Prodrugs in Mammalian Cells and Cell Culture Media: A XANES Spectroscopic Study Levina, Aviva; McLeod, Andrew I.; Pulte, Anna Inorganic Chemistry, Vol. 54, Issue 14 https://doi.org/10.1021/ic5028948	journal	April 2015
Reactivity and Speciation of Anti-Diabetic Vanadium Complexes in Whole Blood and Its Components: The Important Role of Red Blood Cells Levina, Aviva; McLeod, Andrew I.; Gasparini, Sylvia J. Inorganic Chemistry, Vol. 54, Issue 16 https://doi.org/10.1021/acs.inorgchem.5b00665	journal	July 2015
Ruthenium-based chemotherapeutics: are they ready for prime time? Antonarakis, Emmanuel S.; Emadi, Ashkan Cancer Chemotherapy and Pharmacology, Vol. 66, Issue 1 https://doi.org/10.1007/s00280-010-1293-1	journal	March 2010
X-ray Absorption and EPR Spectroscopic Studies of the Biotransformations of Chromium(VI) in Mammalian Cells. Is Chromodulin an Artifact of Isolation Methods? Levina, Aviva; Harris, Hugh H.; Lay, Peter A. Journal of the American Chemical Society, Vol. 129, Issue 5 https://doi.org/10.1021/ja063792r	journal	February 2007
Cytotoxic half-sandwich rhodium(III) complexes: Polypyridyl ligand influence on their DNA binding properties and cellular uptake Scharwitz, Michael A.; Ott, Ingo; Geldmacher, Yvonne Journal of Organometallic Chemistry, Vol. 693, Issue 13 https://doi.org/10.1016/j.jorganchem.2008.04.002	journal	June 2008
Synthesis, reactivities and anti-cancer properties of ruthenium(II) complexes with a thiaether macrocyclic ligand O’Riley, Hannah A.; Levina, Aviva; Aitken, Jade B. Inorganica Chimica Acta, Vol. 454 https://doi.org/10.1016/j.ica.2016.07.050	journal	January 2017
Transferrin binding and transferrin-mediated cellular uptake of the ruthenium coordination compound KP1019, studied by means of AAS, ESI-MS and CD spectroscopy Pongratz, Martina; Schluga, Petra; Jakupec, Michael A. Journal of Analytical Atomic Spectrometry, Vol. 19, Issue 1 https://doi.org/10.1039/b309160k	journal	January 2004
Rhodium and its compounds as potential agents in cancer treatment Katsaros, N.; Anagnostopoulou, A. Critical Reviews in Oncology/Hematology, Vol. 42, Issue 3 https://doi.org/10.1016/S1040-8428(01)00222-0	journal	June 2002
In vitro and in vivo activity and cross resistance profiles of novel ruthenium (II) organometallic arene complexes in human ovarian cancer Aird, R. E.; Cummings, J.; Ritchie, A. A. British Journal of Cancer, Vol. 86, Issue 10 https://doi.org/10.1038/sj.bjc.6600290	journal	May 2002
Binding of Organometallic Ruthenium(II) and Osmium(II) Complexes to an Oligonucleotide: A Combined Mass Spectrometric and Theoretical Study ^† Dorcier, Antoine; Dyson, Paul J.; Gossens, Christian Organometallics, Vol. 24, Issue 9 https://doi.org/10.1021/om049022a	journal	April 2005
Antioxidation and Tyrosinase Inhibition of Polyphenolic Curcumin Analogs Du, Zhi-Yun; Jiang, Yong-Fu; Tang, Zhi-Kai Bioscience, Biotechnology, and Biochemistry, Vol. 75, Issue 12 https://doi.org/10.1271/bbb.110547	journal	December 2011
From bench to bedside – preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019 or FFC14A) Hartinger, Christian G.; Zorbas-Seifried, Stefanie; Jakupec, Michael A. Journal of Inorganic Biochemistry, Vol. 100, Issue 5-6 https://doi.org/10.1016/j.jinorgbio.2006.02.013	journal	May 2006
Organic reactions involving transition metals. Part I. Formation of pentamethylcyclopentadienylrhodium complexes by reaction of hexamethylbicyclo[2,2,0]hexa-2,5-diene with rhodium trichloride Booth, B. L.; Haszeldine, R. N.; Hill, M. Journal of the Chemical Society A: Inorganic, Physical, Theoretical https://doi.org/10.1039/j19690001299	journal	January 1969
Molecular mode of action of NKP-1339 – a clinically investigated ruthenium-based drug – involves ER- and ROS-related effects in colon carcinoma cell lines Flocke, Lea S.; Trondl, Robert; Jakupec, Michael A. Investigational New Drugs, Vol. 34, Issue 3 https://doi.org/10.1007/s10637-016-0337-8	journal	March 2016
Reactivity of [{η5-C5Me5RhCl(μ-Cl)}2] towards some potentially bidentate ligands García, Gabriel; Sánchez, Gregorio; Romero, Isabel Journal of Organometallic Chemistry, Vol. 408, Issue 2 https://doi.org/10.1016/0022-328X(91)86388-7	journal	May 1991
Formation of DNA Adducts by the Anticancer Drug Carboplatin: Different Nucleotide Sequence Preferences in Vitro and in Cells Blommaert, Frank A.; van Dijk-Knijnenburg, Helma C. M.; Dijt, Fransje J. Biochemistry, Vol. 34, Issue 26 https://doi.org/10.1021/bi00026a031	journal	July 1995
Combining Multiple Comparisons and Modeling Techniques in Dose-Response Studies Bretz, F.; Pinheiro, J. C.; Branson, M. Biometrics, Vol. 61, Issue 3 https://doi.org/10.1111/j.1541-0420.2005.00344.x	journal	April 2005
New Insights into the Mechanisms of Spontaneous and Base-Catalysed Substitution Reactions of the Inert Metal Amine Complexes Lay, Peter A. Comments on Inorganic Chemistry, Vol. 11, Issue 5-6 https://doi.org/10.1080/02603599108035828	journal	April 1991
Oxaliplatin Graham, Joanne; Muhsin, Mohamed; Kirkpatrick, Peter Nature Reviews Drug Discovery, Vol. 3, Issue 1 https://doi.org/10.1038/nrd1287	journal	January 2004
Pentamethylcyclopentadienyl-rhodium and -iridium complexes. Part 21. Neutral and cationic β-diketonato-, η ³ -allylic, and NN″-triazenido-complexes: the X-ray crystal structure of the binuclear complex [Rh ₂ (C ₅ Me ₅ ) ₂ (acac) ₂ ][BF ₄ ] ₂ Rigby, William; Lee, Hing-Biu; Bailey, Pamela M. J. Chem. Soc., Dalton Trans., Issue 2 https://doi.org/10.1039/DT9790000387	journal	January 1979
X-ray Absorption and EPR Spectroscopic Studies of the Biotransformations of Chromium(VI) in Mammalian Cells. Is Chromodulin an Artifact of Isolation Methods? [ J. Am. Chem. Soc . 2007 , 129 , 1065−1075]. Levina, Aviva; Harris, Hugh H.; Lay, Peter A. Journal of the American Chemical Society, Vol. 129, Issue 31 https://doi.org/10.1021/ja074677z	journal	August 2007
[Cp*RhCl ₂ ] ₂ : mechanosynthesis and applications in C–H bond functionalisations under ball-milling conditions Hernández, José G.; Bolm, Carsten Chemical Communications, Vol. 51, Issue 63 https://doi.org/10.1039/C5CC04423E	journal	January 2015
Recent developments in ruthenium anticancer drugs Levina, Aviva; Mitra, Anannya; Lay, Peter A. Metallomics, Vol. 1, Issue 6 https://doi.org/10.1039/b904071d	journal	January 2009
Carcinogenic Chromium(VI) Compounds Formed by Intracellular Oxidation of Chromium(III) Dietary Supplements by Adipocytes Wu, Lindsay E.; Levina, Aviva; Harris, Hugh H. Angewandte Chemie International Edition, Vol. 55, Issue 5 https://doi.org/10.1002/anie.201509065	journal	December 2015
The Role of Epidermal Growth Factor Receptor in Cancer Metastasis and Microenvironment Sasaki, Takamitsu; Hiroki, Kuniyasu; Yamashita, Yuichi BioMed Research International, Vol. 2013 https://doi.org/10.1155/2013/546318	journal	January 2013
Characterization of a Ruthenium(III)/NAMI-A Adduct with Bovine Serum Albumin that Exhibits a High Anti-Metastatic Activity Liu, Mimi; Lim, Zhi Jun; Gwee, Yee Yen Angewandte Chemie, Vol. 122, Issue 9 https://doi.org/10.1002/ange.200906079	journal	February 2010
Fresnel zone plate stacking in the intermediate field for high efficiency focusing in the hard X-ray regime Gleber, Sophie-Charlotte; Wojcik, Michael; Liu, Jie Optics Express, Vol. 22, Issue 23 https://doi.org/10.1364/OE.22.028142	journal	January 2014
Remodelling of Ca ²⁺ transport in cancer: how it contributes to cancer hallmarks? Prevarskaya, Natalia; Ouadid-Ahidouch, Halima; Skryma, Roman Philosophical Transactions of the Royal Society B: Biological Sciences, Vol. 369, Issue 1638 https://doi.org/10.1098/rstb.2013.0097	journal	March 2014
In Vitro Cultivation of Human Tumors: Establishment of Cell Lines Derived From a Series of Solid Tumors2 Giard, Donald J.; Aaronson, Stuart A.; Todaro, George J. JNCI: Journal of the National Cancer Institute, Vol. 51, Issue 5 https://doi.org/10.1093/jnci/51.5.1417	journal	November 1973
Development of Organometallic Ruthenium−Arene Anticancer Drugs That Resist Hydrolysis Ang, Wee Han; Daldini, Elisa; Scolaro, Claudine Inorganic Chemistry, Vol. 45, Issue 22 https://doi.org/10.1021/ic061008y	journal	October 2006
Inhibition of Cancer Cell Growth by Ruthenium(II) Arene Complexes Morris, Robert E.; Aird, Rhona E.; del Socorro Murdoch, Piedad Journal of Medicinal Chemistry, Vol. 44, Issue 22 https://doi.org/10.1021/jm010051m	journal	October 2001
Silicon nitride as a versatile growth substrate for microspectroscopic imaging and mapping of individual cells Carter, Elizabeth A.; Rayner, Benjamin S.; McLeod, Andrew I. Molecular BioSystems, Vol. 6, Issue 7 https://doi.org/10.1039/c001499k	journal	January 2010
Flux of intracellular labile zinc during apoptosis (gene-directed cell death) revealed by a specific chemical probe, Zinquin Zalewski, P. D.; Forbes, I. J.; Seamark, R. F. Chemistry & Biology, Vol. 1, Issue 3 https://doi.org/10.1016/1074-5521(94)90005-1	journal	November 1994
Curcumin induces the apoptosis of non-small cell lung cancer cells through a calcium signaling pathway Xu, Xudong; Chen, Da; Ye, Bo International Journal of Molecular Medicine, Vol. 35, Issue 6 https://doi.org/10.3892/ijmm.2015.2167	journal	April 2015
Biotransformations of Anticancer Ruthenium(III) Complexes: An X-Ray Absorption Spectroscopic Study Levina, Aviva; Aitken, Jade B.; Gwee, Yee Yen Chemistry - A European Journal, Vol. 19, Issue 11 https://doi.org/10.1002/chem.201203127	journal	January 2013
Revealing the effect of 6-gingerol, 6-shogaol and curcumin on mPGES-1, GSK-3β and β-catenin pathway in A549 cell line Eren, Demirpolat; Betul, Yerer Mukerrem Chemico-Biological Interactions, Vol. 258 https://doi.org/10.1016/j.cbi.2016.09.012	journal	October 2016
Studies on the Biotransformations and Biodistributions of Metal-Containing Drugs Using X-Ray Absorption Spectroscopy B. Aitken, Jade; Levina, Aviva; A. Lay, Peter Current Topics in Medicinal Chemistry, Vol. 11, Issue 5 https://doi.org/10.2174/156802611794785217	journal	March 2011
Reactivity of Chromium(III) Nutritional Supplements in Biological Media: An X-Ray Absorption Spectroscopic Study Nguyen, Annie; Mulyani, Irma; Levina, Aviva Inorganic Chemistry, Vol. 47, Issue 10 https://doi.org/10.1021/ic7024389	journal	May 2008
Status of the X-Ray Absorption Spectroscopy (XAS) Beamline at the Australian Synchrotron Glover, C.; McKinlay, J.; Clift, M. X-RAY ABSORPTION FINE STRUCTURE - XAFS13: 13th International Conference, AIP Conference Proceedings https://doi.org/10.1063/1.2644692	conference	January 2007
Carcinogenic Chromium(VI) Compounds Formed by Intracellular Oxidation of Chromium(III) Dietary Supplements by Adipocytes Wu, Lindsay E.; Levina, Aviva; Harris, Hugh H. Angewandte Chemie, Vol. 128, Issue 5 https://doi.org/10.1002/ange.201509065	journal	December 2015
Reactivity of potential anti-diabetic molybdenum(VI) complexes in biological media: A XANES spectroscopic study Levina, Aviva; McLeod, Andrew I.; Seuring, Jan Journal of Inorganic Biochemistry, Vol. 101, Issue 11-12 https://doi.org/10.1016/j.jinorgbio.2007.07.016	journal	November 2007
Calcium and apoptosis: facts and hypotheses Rizzuto, Rosario; Pinton, Paolo; Ferrari, Davide Oncogene, Vol. 22, Issue 53 https://doi.org/10.1038/sj.onc.1207105	journal	November 2003
Bisdemethoxycurcumin suppresses migration and invasion of highly metastatic 95D lung cancer cells by regulating E-cadherin and vimentin expression, and inducing autophagy Xu, Jinhong; Yang, Heping; Zhou, Xiangdong Molecular Medicine Reports, Vol. 12, Issue 5 https://doi.org/10.3892/mmr.2015.4356	journal	September 2015
Calcium wave signaling in cancer cells Parkash, Jai; Asotra, Kamlesh Life Sciences, Vol. 87, Issue 19-22 https://doi.org/10.1016/j.lfs.2010.09.013	journal	November 2010
Curcumin, demethoxycurcumin and bisdemethoxycurcumin differentially inhibit cancer cell invasion through the down-regulation of MMPs and uPA Yodkeeree, Supachai; Chaiwangyen, Wittaya; Garbisa, Spiridione The Journal of Nutritional Biochemistry, Vol. 20, Issue 2 https://doi.org/10.1016/j.jnutbio.2007.12.003	journal	February 2009
Low-Dose Curcumin Stimulates Proliferation, Migration and Phagocytic Activity of Olfactory Ensheathing Cells Tello Velasquez, Johana; Watts, Michelle E.; Todorovic, Michael PLoS ONE, Vol. 9, Issue 10 https://doi.org/10.1371/journal.pone.0111787	journal	October 2014
A hard x-ray scanning microprobe for fluorescence imaging and microdiffraction at the advanced photon source Cai, Z. Sixth international conference on x-ray microscopy (XRM99), AIP Conference Proceedings https://doi.org/10.1063/1.1291193	conference	January 2000
Emerging Protein Targets for Anticancer Metallodrugs: Inhibition of Thioredoxin Reductase and Cathepsin B by Antitumor Ruthenium(II)−Arene Compounds Casini, Angela; Gabbiani, Chiara; Sorrentino, Francesca Journal of Medicinal Chemistry, Vol. 51, Issue 21 https://doi.org/10.1021/jm8006678	journal	November 2008
.pi.-Arene Aqua Complexes of Cobalt, Rhodium, Iridium, and Ruthenium: Preparation, Structure, and Kinetics of Water Exchange and Water Substitution Dadci, Lynda; Elias, Horst; Frey, Urban Inorganic Chemistry, Vol. 34, Issue 1 https://doi.org/10.1021/ic00105a048	journal	January 1995
The important role of the apoptotic effects of zinc in the development of cancers Franklin, Renty B.; Costello, Leslie C. Journal of Cellular Biochemistry, Vol. 106, Issue 5 https://doi.org/10.1002/jcb.22049	journal	April 2009
Antioxidant and Anti-Inflammatory Properties of Curcumin Menon, Venugopal P.; Sudheer, Adluri Ram The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease https://doi.org/10.1007/978-0-387-46401-5_3	book	January 2007
Curcumin, demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin and turmerones differentially regulate anti-inflammatory and anti-proliferative responses through a ROS-independent mechanism Sandur, Santosh K.; Pandey, Manoj K.; Sung, Bokyung Carcinogenesis, Vol. 28, Issue 8 https://doi.org/10.1093/carcin/bgm123	journal	May 2007
Transition metal complexes with bioactive ligands: mechanisms for selective ligand release and applications for drug delivery Renfrew, Anna K. Metallomics, Vol. 6, Issue 8 https://doi.org/10.1039/C4MT00069B	journal	January 2014
Caspase Functions in Cell Death and Disease McIlwain, D. R.; Berger, T.; Mak, T. W. Cold Spring Harbor Perspectives in Biology, Vol. 5, Issue 4 https://doi.org/10.1101/cshperspect.a008656	journal	April 2013
Mechanisms of tumour invasion and metastasis: emerging targets for therapy Thompson, Erik W.; Price, John T. Expert Opinion on Therapeutic Targets, Vol. 6, Issue 2 https://doi.org/10.1517/14728222.6.2.217	journal	April 2002
Matrigel: Basement membrane matrix with biological activity Kleinman, Hynda K.; Martin, George R. Seminars in Cancer Biology, Vol. 15, Issue 5 https://doi.org/10.1016/j.semcancer.2005.05.004	journal	October 2005
Ruthenium(II)–Arene RAPTA Type Complexes Containing Curcumin and Bisdemethoxycurcumin Display Potent and Selective Anticancer Activity Pettinari, Riccardo; Marchetti, Fabio; Condello, Francesca Organometallics, Vol. 33, Issue 14 https://doi.org/10.1021/om500317b	journal	July 2014
High resolution x‐ray absorption spectroscopy with absolute energy calibration for the determination of absorption edge energies Kraft, S.; Stümpel, J.; Becker, P. Review of Scientific Instruments, Vol. 67, Issue 3 https://doi.org/10.1063/1.1146657	journal	March 1996
Acceleration of apoptotic cell death after the cleavage of Bcl-XL protein by caspase-3-like proteases Fujita, Naoya; Nagahashi, Ayumi; Nagashima, Kimie Oncogene, Vol. 17, Issue 10 https://doi.org/10.1038/sj.onc.1202065	journal	September 1998
Recent developments on the mechanisms of substitution reactions of octahedral coordination complexes Lay, Peter A. Coordination Chemistry Reviews, Vol. 110, Issue 2 https://doi.org/10.1016/0010-8545(91)80006-Y	journal	October 1991
Comparison of KP1019 and NAMI-A in tumour-mimetic environments Gransbury, Gemma K.; Kappen, Peter; Glover, Chris J. Metallomics, Vol. 8, Issue 8 https://doi.org/10.1039/C6MT00145A	journal	January 2016
Influence of ascorbic acid on the activity of the investigational anticancer drug KP1019 Bartel, Caroline; Egger, Alexander E.; Jakupec, Michael A. JBIC Journal of Biological Inorganic Chemistry, Vol. 16, Issue 8 https://doi.org/10.1007/s00775-011-0809-4	journal	June 2011
The versatility of mitochondrial calcium signals: From stimulation of cell metabolism to induction of cell death Rimessi, Alessandro; Giorgi, Carlotta; Pinton, Paolo Biochimica et Biophysica Acta (BBA) - Bioenergetics, Vol. 1777, Issue 7-8 https://doi.org/10.1016/j.bbabio.2008.05.449	journal	July 2008
Synthetic, structural, spectroscopic, and electrochemical studies of mixed sandwich Rh(III) and Ir(III) complexes involving Cp* and tridentate macrocycles Grant, Gregory J.; Lee, John P.; Helm, Monte L. Journal of Organometallic Chemistry, Vol. 690, Issue 3 https://doi.org/10.1016/j.jorganchem.2004.10.010	journal	January 2005
Curcumin and its analogues: Potential anticancer agents Agrawal, Dinesh Kumar; Mishra, Pushpesh Kumar Medicinal Research Reviews https://doi.org/10.1002/med.20188	journal	January 2009
MAPS : A set of software tools for analysis and visualization of 3D X-ray fluorescence data sets Vogt, S. Journal de Physique IV (Proceedings), Vol. 104 https://doi.org/10.1051/jp4:20030160	journal	March 2003

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60 APPLIED LIFE SCIENCES
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
X-ray absorption spectroscopy
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curcumin
cytotoxicity
rhodium pentamethylcyclopentadienyl complexes

Title: (Pentamethylcyclopentadienato)rhodium complexes for delivery of the curcumin anticancer drug [Rhodium pentamethylcyclopentadienato complexes for delivery of the curcumin anti-cancer drug]

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