Online citations, reference lists, and bibliographies.
← Back to Search

Aromatic Bis-N-hydroxyguanidinium Derivatives: Synthesis, Biophysical, And Biochemical Evaluations.

Amila Kahvedžić, S. Nathwani, D. Zisterer, I. Rozas
Published 2013 · Chemistry, Medicine

Cite This
Download PDF
Analyze on Scholarcy
Share
In this paper we report the synthesis of a new family of hydroxyguanidinium aromatic derivatives (4a-g) as potential minor groove binders and cytotoxic agents. Their DNA affinity was evaluated by thermal denaturation experiments using salmon sperm DNA. The antiproliferative effects of derivatives 4a, 4d, and 4f were evaluated in human promyelocytic HL-60, breast carcinoma MCF-7, and neuroblastoma Kelly cell lines using the AlamarBlue viability assay, and IC(50) values were obtained. All three compounds were active in the HL-60 cell line. In particular, 4b exhibits antiproliferative effects in all three cell lines while 4d reduced HL-60 and Kelly viability. Both 4b and 4d produced considerable antiproliferative activity in the Kelly cell line. Derivative 4d was chosen for further cell cycle and apoptosis studies using flow cytometric analysis of cellular DNA content.
This paper references
Hydroxyguanidine--a new antitumour drug.
R. Adamson (1972)
10.1124/dmd.108.024083
Transport of Dicationic Drugs Pentamidine and Furamidine by Human Organic Cation Transporters
X. Ming (2009)
Regulation of telomerase activity in camptothecin-induced apoptosis of human leukemia HL-60 cells.
J. Jiang (2000)
10.1038/236400A0
Biological Sciences: Hydroxyguanidine—a New Antitumour Drug
R. Adamson (1972)
10.1039/c0ob01117g
Prodrug design for the potent cardiovascular agent Nω-hydroxy-L-arginine (NOHA): synthetic approaches and physicochemical characterization.
D. Schade (2011)
10.1021/JM060295C
DNA binding affinity of bisguanidine and bis(2-aminoimidazoline) derivatives with in vivo antitrypanosomal activity.
C. Dardonville (2006)
10.1002/CHIN.200243274
The Guanidinium Group in Molecular Recognition: Design and Synthetic Approaches.
B. Orner (2002)
10.1021/JO991458Q
A versatile one-Pot synthesis of 1,3-substituted guanidines from carbamoyl isothiocyanates
Linton (2000)
10.1016/S0022-1759(97)00043-4
Assessment of the Alamar Blue assay for cellular growth and viability in vitro.
G. R. Nakayama (1997)
activity of bis-amidooximes and bis-o-alkylamidooximes prodrugs
R. Anti-pneumocystis (1996)
10.1002/chin.197950208
N-CYANAMIDOPYRROLES AND N-CYANAMIDOIMINES FROM 4-AMINO-1,2,4-TRIAZOLE
Roy A. Olofson (1979)
10.1021/bi900204w
Crystal structure of a trypanocidal 4,4'-bis(imidazolinylamino)diphenylamine bound to DNA.
Lateca S Glass (2009)
10.1007/s11224-011-9861-5
On the protonated state of amidinium-like diaromatic derivatives: X-ray and UV studies
P. S. Nagle (2011)
10.1007/s11178-005-0030-4
Synthesis and chemical transformations of mono- and disubstituted cyanamides
D. Nekrasov (2004)
10.1039/C39800000101
Efficient removal of N-benzyloxycarbonyl group by a ‘push–pull’ mechanism using thioanisole–trifluoroacetic acid, exemplified by a synthesis of Met-enkephalin
Y. Kiso (1980)
10.1021/jm7013088
New bis(2-aminoimidazoline) and bisguanidine DNA minor groove binders with potent in vivo antitrypanosomal and antiplasmodial activity.
F. Rodriguez (2008)
10.1021/OL061454P
NG-hydroxyguanidines from primary amines.
N. Martin (2006)
10.1016/j.bmc.2008.07.033
Novel synthesis and pharmacological evaluation as alpha2-adrenoceptor ligands of O-phenylisouronium salts.
Aine Goonan (2008)
10.1128/AAC.34.9.1678
Metabolic N-hydroxylation of pentamidine in vitro.
B. J. Berger (1990)
10.1021/jm901017t
Asymmetrical diaromatic guanidinium/2-aminoimidazolinium derivatives: synthesis and DNA affinity.
P. S. Nagle (2009)
10.1016/J.BBRC.2004.02.163
Aromatic N-hydroxyguanidines as new reduction cosubstrates for dopamine beta-hydroxylase.
P. Slama (2004)
10.1021/jm300296f
High DNA affinity of a series of peptide linked diaromatic guanidinium-like derivatives.
P. S. Nagle (2012)
10.1016/S0968-0896(02)00155-4
Novel substrates for nitric oxide synthases.
M. Xian (2002)
10.1016/S0006-2952(01)00570-6
Guanidino-containing drugs in cancer chemotherapy: biochemical and clinical pharmacology.
S. Ekelund (2001)
Inhibition of DNA synthesis by hydroxyurea: structure-activity relationships.
C. Young (1967)
10.1016/S0960-894X(00)00698-3
Semi-synthesis of 2-deoxo- and 3-epi-paraherquamide A.
B. H. Lee (2001)
Distribution of furamidine analogues in tumor cells: targeting of the nucleus or mitochondria depending on the amidine substitution.
A. Lansiaux (2002)
High DNA affinity of a series of amide linked aromatic dications
P. S. Nagle (2012)
10.1016/S0140-6736(96)91015-6
The war on cancer
M. Sporn (1996)
10.1016/S0960-894X(02)00185-3
Electrochemical and peroxidase oxidation study of N'-hydroxyguanidine derivatives as NO donors.
T. Cai (2002)
10.1093/NASS/2.1.95
Distamycin A, a minor groove binder, changes enediyne-induced DNA cleavage sites and enhances apoptosis.
Y. Hiraku (2002)
10.1007/s11626-998-0130-x
Application and evaluation of the alamarblue assay for cell growth and survival of fibroblasts
S. Voytik-Harbin (1998)
10.1021/JM010539N
Distribution of furamidine analogues in tumor cells: influence of the number of positive charges.
A. Lansiaux (2002)
10.1021/JM00260A015
Hydroxyguanidines. A new class of antihypertensive agents.
D. M. Bailey (1973)
10.1021/JM011006H
N-Aryl N'-hydroxyguanidines, a new class of NO-donors after selective oxidation by nitric oxide synthases: structure-activity relationship.
A. Renodon-Cornière (2002)
10.1039/c0ob00428f
Understanding the DNA binding of novel non-symmetrical guanidinium/2-aminoimidazolinium derivatives.
P. S. Nagle (2010)
10.1016/S0960-894X(96)00557-4
Anti-pneumocystis activity of bis-amidoximes and bis-o-alkylamidoximes prodrugs
D. Boykin (1996)
10.1007/bf00929755
Synthesis of aromatic cyanamides
V. Pankratov (1975)
10.1016/S0960-894X(00)00028-7
Synthesis, DNA binding, topoisomerases inhibition and cytotoxic properties of 4-arylcarboxamidopyrrolo-2-carboxyanilides.
F. Dudouit (2000)
10.1002/CHIN.200028112
Synthesis, DNA Binding, Topoisomerases Inhibition, and Cytotoxic Properties of 4-Arylcarboxamidopyrrolo-2-carboxyanilides.
F. Dudouit (2000)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar