118854-71-0Relevant articles and documents
Synthesis and Biological Evaluation of Organometallic Complexes Bearing Bis-1,8-naphthalimide Ligands
Streciwilk, Wojciech,Terenzi, Alessio,Lo Nardo, Federico,Prochnow, Pascal,Bandow, Julia Elisabeth,Keppler, Bernhard K.,Ott, Ingo
, p. 3104 - 3112 (2018)
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.
Metal NHC Complexes with Naphthalimide Ligands as DNA-Interacting Antiproliferative Agents
Streciwilk, Wojciech,Terenzi, Alessio,Misgeld, Rainer,Frias, Corazon,Jones, Peter G.,Prokop, Aram,Keppler, Bernhard K.,Ott, Ingo
, p. 214 - 225 (2017)
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.
Preparation method of luminous adjustable composite ionic liquid
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Paragraph 0027; 0071-0072, (2019/10/01)
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.
