Design and Biological Evaluation of Manganese- and Ruthenium-Based Hybrid CO-RMs (HYCOs).
Animals
Carbon Monoxide
/ chemistry
Cell Line
Crystallography, X-Ray
Dose-Response Relationship, Drug
Drug Design
Fumarates
/ chemistry
Manganese
/ chemistry
Mice
Models, Molecular
Molecular Structure
NF-E2-Related Factor 2
/ metabolism
Organometallic Compounds
/ chemical synthesis
Ruthenium
/ chemistry
Structure-Activity Relationship
biological activity
drug design
manganese
medicinal chemistry
ruthenium
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
18 09 2019
18 09 2019
Historique:
received:
16
07
2019
pubmed:
19
7
2019
medline:
23
9
2020
entrez:
19
7
2019
Statut:
ppublish
Résumé
Interest in the therapeutic effects of carbon monoxide (CO), a product of heme degradation catalyzed by the enzyme heme oxygenase-1 (HO-1), has led to the development of CO-releasing molecules (CO-RMs) for the controlled delivery of this gas in vivo. We recently proposed conjugating a cobalt-based CO-RM with various activators of nuclear factor erythroid 2-related factor 2 (Nrf2), the transcription factor that regulates HO-1 expression, in order to exploit the beneficial effects of exogenous and endogenous CO. In this study, we describe the preparation of hybrid molecules (termed HYCOs) conjugating a fumaric acid derivative as an Nrf2 activator to a Mn- or a Ru-based CO-RM known to be pharmacologically active. With the exception of an acyl-manganese complex, these hybrids were obtained by associating the two bioactive entities by means of a linker of variable structure. X-ray diffraction analyses and preliminary biological investigations are also presented.
Identifiants
pubmed: 31319021
doi: 10.1002/cmdc.201900426
doi:
Substances chimiques
Fumarates
0
NF-E2-Related Factor 2
0
Nfe2l2 protein, mouse
0
Organometallic Compounds
0
Manganese
42Z2K6ZL8P
Carbon Monoxide
7U1EE4V452
Ruthenium
7UI0TKC3U5
fumaric acid
88XHZ13131
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1684-1691Subventions
Organisme : Institut de Chimie et des Matériaux de Paris Est (ICMPE)
ID : projet transverse
Pays : International
Organisme : Agence Nationale de la Recherche
ID : ANR-12-ISV5-0001-01
Pays : International
Organisme : SATT Erganeo (fmr. Idf Innov)
ID : HYCO
Pays : International
Organisme : Université Paris-Est
ID : CHROM
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
R. Foresti, M. G. Bani-Hani, R. Motterlini, Intensive Care Med. 2008, 34, 649-658;
R. Motterlini, L. E. Otterbein, Nat. Rev. Drug Discovery 2010, 9, 728-743.
R. Motterlini, P. Sawle, S. Bains, J. Hammad, R. Alberto, R. Foresti, C. J. Green, FASEB J. 2005, 19, 284-286;
N. Abeyrathna, K. Washington, C. Bashur, Y. Liao, Org. Biomol. Chem. 2017, 15, 8692-8699;
T. Slanina, P. Sebej, Photochem. Photobiol. Sci. 2018, 17, 692-710;
Y. Zheng, X. Ji, B. Yu, K. Ji, D. Gallo, E. Csizmadia, M. Zhu, M. R. Choudhury, L. K. C. De La Cruz, V. Chittavong, Z. Pan, Z. Yuan, L. E. Otterbein, B. Wang, Nat. Chem. 2018, 10, 787-794.
T. R. Johnson, B. E. Mann, J. E. Clark, R. Foresti, C. J. Green, R. Motterlini, Angew. Chem. Int. Ed. 2003, 42, 3722-3729;
Angew. Chem. 2003, 115, 3850-3858;
R. Motterlini, B. E. Mann, R. Foresti, Expert Opin. Invest. Drugs 2005, 14, 1305-1318;
B. E. Mann, Organometallics 2012, 31, 5728-5735;
C. C. Romão, W. A. Blaettler, J. D. Seixas, G. J. L. Bernardes, Chem. Soc. Rev. 2012, 41, 3571-3583;
U. Schatzschneider, Br. J. Pharmacol. 2015, 172, 1638-1650.
J. E. Clark, P. Naughton, S. Shurey, C. J. Green, T. R. Johnson, B. E. Mann, R. Foresti, R. Motterlini, Circ. Res. 2003, 93, 178;
R. Motterlini, Biochem. Soc. Trans. 2007, 35, 1142-1146;
R. Motterlini, B. Haas, R. Foresti, Med. Gas Res. 2012, 2, 28;
R. N. Bhattacharjee, M. Richard-Mohamed, Q. Sun, A. Haig, G. Aboalsamh, P. Barrett, R. Mayer, I. Alhasan, K. Pineda-Solis, L. Jiang, H. Alharbi, M. Saha, E. Patterson, A. Sener, G. Cepinskas, A. M. Jevnikar, P. P. W. Luke, Transplantation 2018, 102, 1066-1074.
A. C. Kautz, P. C. Kunz, C. Janiak, Dalton Trans. 2016, 45, 18045-18063.
R. Motterlini, R. Foresti, Am. J. Physiol. Cell Physiol. 2017, 312, C302-C313;
C. Steiger, C. Hermann, L. Meinel, Eur. J. Pharm. Biopharm. 2017, 118, 3-12.
S. Romanski, E. Stamellou, J. T. Jaraba, D. Storz, B. K. Kraemer, M. Hafner, S. Amslinger, H. G. Schmalz, B. A. Yard, Free Radical Biol. Med. 2013, 65, 78-88;
E. Stamellou, D. Storz, S. Botov, E. Ntasis, J. Wedel, S. Sollazzo, B. K. Kraemer, W. van Son, M. Seelen, H. G. Schmalz, A. Schmidt, M. Hafner, B. A. Yard, Redox Biol. 2014, 2, 739-748.
M. A. Wright, J. A. Wright, Dalton Trans. 2016, 45, 6801-6811;
J. Marhenke, K. Trevino, C. Works, Coord. Chem. Rev. 2016, 306, 533-543;
E. Kottelat, F. Zobi, Inorganics 2017, 5(2), 24 10.3390/inorganics5020024 .
R. Motterlini, R. Foresti, Antioxid. Redox Signaling 2014, 20, 1810-1826.
J. L. Wilson, S. Fayad Kobeissi, S. Oudir, B. Haas, B. Michel, J.-L. Dubois Rande, A. Ollivier, T. Martens, M. Rivard, R. Motterlini, R. Foresti, Chem. Eur. J. 2014, 20, 14698-14704.
R. A. Linker, D.-H. Lee, S. Ryan, A. M. van Dam, R. Conrad, P. Bista, W. Zeng, X. Hronowsky, A. Buko, S. Chollate, G. Ellrichmann, W. Brück, K. Dawson, S. Goelz, S. Wiese, R. H. Scannevin, M. Lukashev, R. Gold, Brain 2011, 134, 678-692;
R. H. Scannevin, S. Chollate, M.-Y. Jung, M. Shackett, H. Patel, P. Bista, W. Zeng, S. Ryan, M. Yamamoto, M. Lukashev, K. J. Rhodes, J. Pharmacol. Exp. Ther. 2012, 341, 274-284;
M. S. Brennan, H. Patel, N. Allaire, A. Thai, P. Cullen, S. Ryan, M. Lukashev, P. Bista, R. Huang, K. J. Rhodes, R. H. Scannevin, Antioxid. Redox Signaling 2016, 24, 1058-1071.
B. Bauer, A.-L. Göderz, H. Braumüller, J. M. Neudörfl, M. Röcken, T. Wieder, H.-G. Schmalz, ChemMedChem 2017, 12, 1927-1930.
A. Nikam, A. Ollivier, M. Rivard, J. L. Wilson, K. Mebarki, T. Martens, J.-L. Dubois-Rande, R. Motterlini, R. Foresti, J. Med. Chem. 2016, 59, 756-762.
R. Motterlini, A. Nikam, S. Manin, A. Ollivier, J. L. Wilson, S. Djouadi, L. Muchova, T. Martens, M. Rivard, R. Foresti, Redox Biol. 2019, 20, 334-348.
S. H. Crook, B. E. Mann, A. J. H. M. Meijer, H. Adams, P. Sawle, D. Scapens, R. Motterlini, Dalton Trans. 2011, 40, 4230-4235.
T. R. Johnson, B. E. Mann, I. P. Teasdale, H. Adams, R. Foresti, C. J. Green, R. Motterlini, Dalton Trans. 2007, 1500-1508.
Y. Kuninobu, Y. Nishina, T. Takeuchi, K. Takai, Angew. Chem. Int. Ed. 2007, 46, 6518-6520;
Angew. Chem. 2007, 119, 6638-6640.
C. M. Lukehart, G. P. Torrence, J. V. Zeile in Inorganic Synthesis: Reagents for Transition Metal Complex and Organometallic Syntheses, Vol. 28 (Ed.: R. J. Angelici), John Wiley & Sons, New York, 1990, pp. 199-202;
P. L. Motz, D. J. Sheeran, M. Orchin, J. Organomet. Chem. 1990, 383, 201-212;
A. P. Masters, T. S. Sorensen, Can. J. Chem. 1990, 68, 502-506.
H. M. Southam, T. W. Smith, R. L. Lyon, C. Liao, C. R. Trevitt, L. A. Middlemiss, F. L. Cox, J. A. Chapman, S. F. El-Khamisy, M. Hippler, M. P. Williamson, P. J. F. Henderson, R. K. Poole, Redox Biol. 2018, 18, 114-123.
B. W. Michel, A. R. Lippert, C. J. Chang, J. Am. Chem. Soc. 2012, 134, 15668-15671.
H. Kitagishi, S. Negi, A. Kiriyama, A. Honbo, Y. Sugiura, A. T. Kawaguchi, K. Kano, Angew. Chem. Int. Ed. 2010, 49, 1312-1315;
Angew. Chem. 2010, 122, 1334-1337;
S. Minegishi, A. Yumura, H. Miyoshi, S. Negi, S. Taketani, R. Motterlini, R. Foresti, K. Kano, H. Kitagishi, J. Am. Chem. Soc. 2017, 139, 5984-5991.
L. Braud, M. Pini, L. Muchova, S. Manin, H. Kitagishi, D. Sawaki, G. Czibik, J. Ternacle, G. Derumeaux, R. Foresti, R. Motterlini, JCI Insight 2018, 3, e123485.
S. E. Denmark, A. Thorarensen, D. S. Middleton, J. Am. Chem. Soc. 1996, 118, 8266-8277.
L. Palatinus, G. Chapuis, J. Appl. Crystallogr. 2007, 40, 786-790.
G. M. Sheldrick, Acta Crystallogr. Sect. C 2015, 71, 3-8.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Crystallogr. 2009, 42, 339-341.
L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.
F. L. Rodkey, T. A. Hill, L. L. Pitts, R. F. Robertson, Clin. Chem. 1979, 25, 1388-1393.
M. G. Bani-Hani, D. Greenstein, B. E. Mann, C. J. Green, R. Motterlini, J. Pharmacol. Exp. Ther. 2006, 318, 1315-1322.
S. Fayad-Kobeissi, J. Ratovonantenaina, H. Dabire, J. L. Wilson, A. M. Rodriguez, A. Berdeaux, J.-L. Dubois-Rande, B. E. Mann, R. Motterlini, R. Foresti, Biochem. Pharmacol. 2016, 102, 64-77.