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Synthesis, characterization and antimalarial activity of new chromium arene-quinoline half sandwich complexes.

Glans, Lotta LU ; Taylor, Dale ; de Kock, Carmen ; Smith, Peter J ; Haukka, Matti ; Moss, John R and Nordlander, Ebbe LU (2011) In Journal of Inorganic Biochemistry 105(7). p.985-990
Abstract
Organometallic analogs of chloroquine (CQ) are of interest as drug candidates that may be able to overcome the widespread chloroquine resistance developed by malaria parasites. Two new chromium arene CQ-analogs: [η(6)-N-(7-chloroquinolin-4-yl)-N'-(2-dimethylamino-methylbenzyl)-ethane-1,2-diamine]tricarbonylchromium 4 and [η(6)-N-(7-chloroquinolin-4-yl)-N'-(2-dimethylaminobenzyl)-ethane-1,2-diamine]tricarbonylchromium 9 have been synthesized and characterized. In addition, X-ray crystal structures of the intermediates (η(6)-benzyldimethylamine)tricarbonylchromium 2, [η(6)-2-((dimethylamino)methyl) benzaldehyde]tricarbonylchromium 3 and p-(η(6)-dimethylaminobenzaldehyde)tricarbonyl chromium 8 are reported. Compound 4 was more active than... (More)
Organometallic analogs of chloroquine (CQ) are of interest as drug candidates that may be able to overcome the widespread chloroquine resistance developed by malaria parasites. Two new chromium arene CQ-analogs: [η(6)-N-(7-chloroquinolin-4-yl)-N'-(2-dimethylamino-methylbenzyl)-ethane-1,2-diamine]tricarbonylchromium 4 and [η(6)-N-(7-chloroquinolin-4-yl)-N'-(2-dimethylaminobenzyl)-ethane-1,2-diamine]tricarbonylchromium 9 have been synthesized and characterized. In addition, X-ray crystal structures of the intermediates (η(6)-benzyldimethylamine)tricarbonylchromium 2, [η(6)-2-((dimethylamino)methyl) benzaldehyde]tricarbonylchromium 3 and p-(η(6)-dimethylaminobenzaldehyde)tricarbonyl chromium 8 are reported. Compound 4 was more active than chloroquine against both CQ-sensitive and CQ-resistant strains of Plasmodium falciparum when antimalarial activity was tested in vitro. The activity of 4 against the CQ-resistant parasite strain was twice as high as for the organic ligand alone (IC(50) values of 33.9nM versus 63.1nM). (Less)
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Inorganic Biochemistry
volume
105
issue
7
pages
985 - 990
publisher
Elsevier
external identifiers
  • wos:000291518700008
  • pmid:21565148
  • scopus:79955721427
ISSN
1873-3344
DOI
10.1016/j.jinorgbio.2011.03.019
language
English
LU publication?
yes
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Chemical Physics (S) (011001060)
id
8f3090a4-337c-4c21-bb91-0bf0c60bad61 (old id 1972703)
date added to LUP
2016-04-01 13:53:11
date last changed
2021-09-01 05:37:56
@article{8f3090a4-337c-4c21-bb91-0bf0c60bad61,
  abstract     = {Organometallic analogs of chloroquine (CQ) are of interest as drug candidates that may be able to overcome the widespread chloroquine resistance developed by malaria parasites. Two new chromium arene CQ-analogs: [η(6)-N-(7-chloroquinolin-4-yl)-N'-(2-dimethylamino-methylbenzyl)-ethane-1,2-diamine]tricarbonylchromium 4 and [η(6)-N-(7-chloroquinolin-4-yl)-N'-(2-dimethylaminobenzyl)-ethane-1,2-diamine]tricarbonylchromium 9 have been synthesized and characterized. In addition, X-ray crystal structures of the intermediates (η(6)-benzyldimethylamine)tricarbonylchromium 2, [η(6)-2-((dimethylamino)methyl) benzaldehyde]tricarbonylchromium 3 and p-(η(6)-dimethylaminobenzaldehyde)tricarbonyl chromium 8 are reported. Compound 4 was more active than chloroquine against both CQ-sensitive and CQ-resistant strains of Plasmodium falciparum when antimalarial activity was tested in vitro. The activity of 4 against the CQ-resistant parasite strain was twice as high as for the organic ligand alone (IC(50) values of 33.9nM versus 63.1nM).},
  author       = {Glans, Lotta and Taylor, Dale and de Kock, Carmen and Smith, Peter J and Haukka, Matti and Moss, John R and Nordlander, Ebbe},
  issn         = {1873-3344},
  language     = {eng},
  number       = {7},
  pages        = {985--990},
  publisher    = {Elsevier},
  series       = {Journal of Inorganic Biochemistry},
  title        = {Synthesis, characterization and antimalarial activity of new chromium arene-quinoline half sandwich complexes.},
  url          = {http://dx.doi.org/10.1016/j.jinorgbio.2011.03.019},
  doi          = {10.1016/j.jinorgbio.2011.03.019},
  volume       = {105},
  year         = {2011},
}