- Synthesis and Biological Evaluation of Organometallic Complexes Bearing Bis-1,8-naphthalimide Ligands
-
Organometallic N-heterocyclic carbene (NHC) complexes with intercalating bis-naphthalimide ligands were prepared and evaluated biologically. Cytotoxic effects against tumor cells or bacteria were strongly ligand dependent with minor influence of the metal (Ag, Ru, Rh, Au) centers. Complex 8b with a rhodium(I) NHC moiety was studied in more detail for its DNA interacting properties in comparison to the metal free ligand. These studies showed a good DNA binding pattern with some preference for the telomeric quadruplex structure hTelo. Complex 8b was also shown to trigger additional coordinative binding to the DNA and therefore represents an useful tool compound with a mixed intercalative/coordinative DNA binding mode.
- Streciwilk, Wojciech,Terenzi, Alessio,Lo Nardo, Federico,Prochnow, Pascal,Bandow, Julia Elisabeth,Keppler, Bernhard K.,Ott, Ingo
-
-
Read Online
- Synthesis and investigation of anticancer potential of radiolabeled naphthalene monoimide bearing imidazolium salt
-
Imidazolium salts and derivatives have antitumor efficacy and toxic effects in different micro-organisms. In this study, an imidazolium bromide salt (NMI) was synthesized, and its antitumor potential was investigated by in vitro studies. Radiolabeling of
- Yurt Lambrecht, Fatma,Ocakoglu, Kasim,Gokhan Colak, Suleyman,Alp Ersoz, Onur,Er, Ozge
-
-
Read Online
- Metal NHC Complexes with Naphthalimide Ligands as DNA-Interacting Antiproliferative Agents
-
Naphthalimide-based N-heterocyclic carbene (NHC) complexes of the type [(1,5-cyclooctadiene)(NHC)RhCl)] (4 a–c), [(p-cymene)(NHC)RuCl2)] (5 a–c), and [(NHC)CuBr] (6 a–c) were synthesized and investigated as antiproliferative agents that target DNA. The cytotoxic effects were largely driven by the naphthalimide structure, which is a DNA-intercalating moiety. Regarding the metal center, the highest activities were observed with the rhodium complexes, and cytotoxic activity was significantly lower for the ruthenium derivatives. The stable coordination of the NHC ligands of selected complexes 4 b and 5 b in solution was confirmed, and their DNA binding properties were studied by UV/Vis spectroscopy, mass spectrometry, and circular dichroism. Stable intercalative binding into the DNA for all selected naphthalimide-based complexes is indicated by high DNA binding constants. Particularly efficient binding was observed in the case of the rhodium complex 4 b. More detailed biological studies on 4 b showed promising activities against multidrug-resistant Nalm-6 cells and confirmed an important role for mitochondrial pathways in 4 b-induced apoptosis.
- Streciwilk, Wojciech,Terenzi, Alessio,Misgeld, Rainer,Frias, Corazon,Jones, Peter G.,Prokop, Aram,Keppler, Bernhard K.,Ott, Ingo
-
-
Read Online
- The synthesis of 1,8-naphthalimide groups containing imidazolium salts/ionic liquids using I-, PF6-, TFSI- anions and their photophysical, electrochemical and thermal properties
-
1,8-Naphthalimide groups containing imidazolium iodide salts of different alkyl chain length on the imidazole group were synthesized. Hexafluorophosphate and bis(trifluoromethanesulfonyl)imide salts were obtained by ion exchange reactions. The synthesized salts were characterized using a variety of spectroscopic techniques. Fluorescence emission quenching of iodide and bis(trifluoromethanesulfonyl)imide salts were studied using a ruthenium dye, whilst that of hexafluorophosphate salts were performed using tris(8-hydroxyquinoline)aluminum. Calculated fluorescence quenching rate constants were as high as 1014 M-1 s-1 and values of the Gibbs free energy of electron transfer were [-32.04/-33.68], [-17.52/-20.74] and [-26.50/-30.89] kcal mol-1 for the iodide, hexafluorophosphate and bis(trifluoromethanesulfonyl)imide salts, respectively. The thermal stability of the synthesized salts was high especially in the case of bis(trifluoromethanesulfonyl)imide salts for which values of 470-498 °C were achieved. Photostability studies of hexafluorophosphate and bis(trifluoromethanesulfonyl)imide salts were also performed; calculated photodegradation half-life values ranged from 19.25 to 48.12 h.
- Ozdemir, Saliha,Varlikli, Canan,Oner, Ilker,Ocakoglu, Kasim,Icli, Siddik
-
-
Read Online
- Preparation method of luminous adjustable composite ionic liquid
-
The invention relates to a novel method for preparing a fluorescence-adjustable composite ionic liquid. Firstly, 1,8-naphthalimide and aminopropyl imidazole are used for reacting to generate naphthalimide imidazole (1), a compound 1 and 1-bromo-iso-octane are used for imidazole quaternization to obtain alkylated naphthalimide imidazole bromide (2), and a compound 2 and bis(trifluoromethylsulfonyl)imide silver are used for ion exchange in methyl alcohol to obtain a target compound 3, wherein the target compound 3 is an ionic liquid and can produce bright cyan fluorescence under ultraviolet excitation. The luminous ionic liquid is taken as a donor, a fluorescent dye of which an absorption spectrum (emission spectrum) and an ionic liquid emission spectrum have an overlap is introduced as a receptor, and an FRET (fluorescence resonance energy transfer) effect can occur between the donor and the receptor. Through single ultraviolet excitation, the composite ionic liquid containing double luminescence of both the ionic liquid and the dye can be obtained, and the composite ionic liquid can be used for white light ink and a luminophor of an ultraviolet LED chip to prepare a white light LED.
- -
-
Paragraph 0027; 0071-0072
(2019/10/01)
-
- Palladium(II)/N-Heterocyclic Carbene-Catalyzed Regioselective Heteroannulation of Tertiary Propargyl Alcohols and o-Haloanilines to form 2-Alkenylindoles
-
Monometallic and bimetallic palladium(II)/N-heterocyclic carbene complexes appended with naphthalimide or bisnaphthalimide moieties were designed, synthesized, and characterized. Employment of these catalysts brings about the step-economic and regioselective heteroannulation of tertiary propargyl alcohols with o-haloanilines resulting in biologically and pharmaceutically relevant 2-alkenylindoles. Basis for the regioselective heteroannulation is unraveled by coordination of the propargylic hydroxy moiety to palladium during insertion. Embracing this methodology, a single regioisomer of unsymmetrical 2,3-disubstituted indoles could be achieved through late-stage modification. The role of the naphthalimide or bisnaphthalimide appended to the NHC on the catalytic efficiency has been studied. (Figure presented.).
- Panyam, Pradeep Kumar Reddy,Gandhi, Thirumanavelan
-
supporting information
p. 1144 - 1151
(2017/04/13)
-
- Gold(I) N-heterocyclic carbene complexes with naphthalimide ligands as combined thioredoxin reductase inhibitors and DNA intercalators
-
Organometallic conjugates consisting of a gold(I) N-heterocyclic carbene (NHC) moiety and a naphthalimide were prepared and investigated as cytotoxic agents that interact with both DNA and the disulfide reductase enzyme thioredoxin reductase (TrxR). The c
- Meyer, Andreas,Oehninger, Luciano,Geldmacher, Yvonne,Alborzinia, Hamed,W?lfl, Stefan,Sheldrick, William S.,Ott, Ingo
-
p. 1794 - 1800
(2014/08/18)
-
- Naphthalimide-tagged ruthenium-arene anticancer complexes: Combining coordination with intercalation
-
Ruthenium(II) arene compounds have been modified with the naphthalimide group, tethered via the arene ligand, i.e. {dichloro[η6-N- (phenylalkyl)(4-dimethylamino)-1,8-naphthalimide](pta)ruthenium(II)} (alkyl = methyl, ethyl, propyl, pta = 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane), or via an imidazole group, i.e. {dichloro(η6-arene)(N-[3-(imidazol- 1-yl)propyl]-1,8-naphthalimide)ruthenium(II)} (arene = p-cymene, toluene). All the compounds are reasonably cytotoxic (ca. 2-49 μM) toward cancer cells, and the arene-linked compounds also display selectivity in that they are less cytotoxic toward model healthy cells. Mechanistic studies show that the ruthenium center does not readily react with DNA but preferentially binds to proteins. In contrast, the naphthalimide group is a strong DNA intercalator, and combined, the complexes might be expected to simultaneously cross-link DNA and proteins.
- Kilpin, Kelly J.,Clavel, Catherine M.,Edafe, Fabio,Dyson, Paul J.
-
p. 7031 - 7039,9
(2020/09/02)
-