Targeting antioxidant pathways with ferrocenylated N-heterocyclic carbene supported gold(i) complexes in A549 lung cancer cells† †Electronic supplementary information (ESI) available. CCDC 1419940 and 1419941. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc03519h
Ferrocenylated-Au( i ) carbenes were designed, synthesized, and studied for their ability to generate reactive oxygen species and target antioxidant pathways via multiple mechanisms. Ferrocene containing N-heterocyclic carbene (NHC) ligated gold( i ) complexes of the type [Au(NHC) 2 ] + were prepare...
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| Published in | Chemical science (Cambridge) Vol. 7; no. 2; pp. 1245 - 1256 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Royal Society of Chemistry
29.10.2015
|
| Subjects | |
| Online Access | Get full text |
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| Abstract | Ferrocenylated-Au(
i
) carbenes were designed, synthesized, and studied for their ability to generate reactive oxygen species and target antioxidant pathways
via
multiple mechanisms.
Ferrocene containing N-heterocyclic carbene (NHC) ligated gold(
i
) complexes of the type [Au(NHC)
2
]
+
were prepared and found to be capable of regulating the formation of reactive oxygen species (ROS)
via
multiple mechanisms. Single crystal X-ray analysis of bis(1-(ferrocenylmethyl)-3-mesitylimidazol-2-ylidene)-gold(
i
) chloride (
5
) and bis(1,3-di(ferrocenylmethyl)imidazol-2-ylidene)-gold(
i
) chloride (
6
) revealed a quasi-linear geometry around the gold(
i
) centers (
i.e.
, the C–Au–C bond angle were measured to be ∼177° and all the Au–C
carbene
bonds distances were in the range of 2.00 (7)–2.03 (1) Å). A series of cell studies indicated that cell proliferation inhibition and ROS generation were directly proportional to the amount of ferrocene contained within the [Au(NHC)
2
]
+
complexes (IC
50
of
6
<
5
< bis(1-benzyl-3-mesitylimidazol-2-ylidene)-gold(
i
) chloride (
4
)). Complexes
4–6
were also confirmed to inhibit thioredoxin reductase as inferred from lipoate reduction assays and increased chelatable intracellular zinc concentrations. RNA microarray gene expression assays revealed that
6
induces endoplasmic reticulum stress response pathways as a result of ROS increase. |
|---|---|
| AbstractList | Ferrocenylated-Au(
i
) carbenes were designed, synthesized, and studied for their ability to generate reactive oxygen species and target antioxidant pathways
via
multiple mechanisms.
Ferrocene containing N-heterocyclic carbene (NHC) ligated gold(
i
) complexes of the type [Au(NHC)
2
]
+
were prepared and found to be capable of regulating the formation of reactive oxygen species (ROS)
via
multiple mechanisms. Single crystal X-ray analysis of bis(1-(ferrocenylmethyl)-3-mesitylimidazol-2-ylidene)-gold(
i
) chloride (
5
) and bis(1,3-di(ferrocenylmethyl)imidazol-2-ylidene)-gold(
i
) chloride (
6
) revealed a quasi-linear geometry around the gold(
i
) centers (
i.e.
, the C–Au–C bond angle were measured to be ∼177° and all the Au–C
carbene
bonds distances were in the range of 2.00 (7)–2.03 (1) Å). A series of cell studies indicated that cell proliferation inhibition and ROS generation were directly proportional to the amount of ferrocene contained within the [Au(NHC)
2
]
+
complexes (IC
50
of
6
<
5
< bis(1-benzyl-3-mesitylimidazol-2-ylidene)-gold(
i
) chloride (
4
)). Complexes
4–6
were also confirmed to inhibit thioredoxin reductase as inferred from lipoate reduction assays and increased chelatable intracellular zinc concentrations. RNA microarray gene expression assays revealed that
6
induces endoplasmic reticulum stress response pathways as a result of ROS increase. |
| Author | Arumugam, K. Sidoran, K. J. Magda, D. Mitchell, N. A. Sessler, J. L. Lynch, V. M. Arambula, J. F. Bielawski, C. W. McCall, R. |
| AuthorAffiliation | d Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA b Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA c Lumiphore, Inc. , Berkeley , California 94710 , USA e Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea a Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: jarambula@georgiasouthern.edu ; Tel: +1-912-478-2346 f Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea h Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email: kuppuswamy.arumugam@wright.edu g Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA |
| AuthorAffiliation_xml | – name: c Lumiphore, Inc. , Berkeley , California 94710 , USA – name: b Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA – name: f Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea – name: h Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email: kuppuswamy.arumugam@wright.edu – name: a Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: jarambula@georgiasouthern.edu ; Tel: +1-912-478-2346 – name: d Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA – name: g Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA – name: e Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea |
| Author_xml | – sequence: 1 givenname: J. F. surname: Arambula fullname: Arambula, J. F. organization: Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: ; Tel: +1-912-478-2346 Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA Lumiphore, Inc. , Berkeley , California 94710 , USA Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email – sequence: 2 givenname: R. surname: McCall fullname: McCall, R. organization: Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: ; Tel: +1-912-478-2346 Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA Lumiphore, Inc. , Berkeley , California 94710 , USA Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email – sequence: 3 givenname: K. J. surname: Sidoran fullname: Sidoran, K. J. organization: Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: ; Tel: +1-912-478-2346 Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA Lumiphore, Inc. , Berkeley , California 94710 , USA Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email – sequence: 4 givenname: D. surname: Magda fullname: Magda, D. organization: Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: ; Tel: +1-912-478-2346 Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA Lumiphore, Inc. , Berkeley , California 94710 , USA Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email – sequence: 5 givenname: N. A. surname: Mitchell fullname: Mitchell, N. A. organization: Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: ; Tel: +1-912-478-2346 Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA Lumiphore, Inc. , Berkeley , California 94710 , USA Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email – sequence: 6 givenname: C. W. surname: Bielawski fullname: Bielawski, C. W. organization: Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: ; Tel: +1-912-478-2346 Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA Lumiphore, Inc. , Berkeley , California 94710 , USA Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email – sequence: 7 givenname: V. M. surname: Lynch fullname: Lynch, V. M. organization: Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: ; Tel: +1-912-478-2346 Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA Lumiphore, Inc. , Berkeley , California 94710 , USA Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email – sequence: 8 givenname: J. L. surname: Sessler fullname: Sessler, J. L. organization: Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: ; Tel: +1-912-478-2346 Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA Lumiphore, Inc. , Berkeley , California 94710 , USA Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email – sequence: 9 givenname: K. surname: Arumugam fullname: Arumugam, K. organization: Department of Chemistry , Georgia Southern University , Statesboro , Georgia 30460 , USA . Email: ; Tel: +1-912-478-2346 Department of Chemistry , St. Bonaventure University , 3261 West State Road , New York , 14778 , USA Lumiphore, Inc. , Berkeley , California 94710 , USA Department of Health Sciences , Gettysburg College , Gettysburg , PA 17325-1400 , USA Center for Multidimensional Carbon Materials (CMCM) , Institute for Basic Science (IBS) , Ulsan 689-798 , Republic of Korea Department of Chemistry and Department of Energy Engineering , Ulsan National Institute of Science and Technology (UNIST) , Ulsan 689-798 , Republic of Korea Department of Chemistry , University of Texas at Austin , Austin , Texas 78712 , USA Department of Chemistry , Wright State University , 3640 Colonel Glenn Hwy , Dayton , Ohio 45435 , USA . Email |
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| Title | Targeting antioxidant pathways with ferrocenylated N-heterocyclic carbene supported gold(i) complexes in A549 lung cancer cells† †Electronic supplementary information (ESI) available. CCDC 1419940 and 1419941. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc03519h |
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