Mechanism of DNA-binding of some aminoalkylamino-derivatives of anthraquinone and naphthacenequinone

Plumbridge, Terence W.; Knight, Vernon; Patel, Krunal; Brown, Jeffrey R.

doi:10.1111/j.2042-7158.1980.tb12856.x

Cited by 30 publications

(6 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chemical structures of (a–c) positively charged Pt(II) complexes, (d) catecholate‐bearing Pt(II) complexes, (e) doxorubicin and (f) mitoxantrone…”

Section: Introductionmentioning

confidence: 99%

“…Both the H 2 (BrCat) and H 2 (Aliz) ligands were chosen due to the fact that they may be prone to Pt‐O bond breaking in the intracellular medium, favouring DNA covalent binding. Finally, compared to [BrCat] 2− , the [Aliz] 2− fragment presents a more extended aromatic core combined with a chemical structure similar to those of the already tested anti‐tumour intercalating aromatic molecules doxorubicin (Chart 2e) and mitoxantrone (Chart 2f) …”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Cytotoxic performances of new anionic cyclometalated Pt(II) complexes bearing chelated O^O ligands

Ionescu

Caligiuri

Godbert

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

The in vitro biological activity towards the MDA‐MB‐231 triple‐negative breast cancer cell line of two different series of anionic Pt(II) organometallic complexes was tested. For the first time, cytotoxic activity of anionic Pt(II) complexes has been observed. The anionic compounds of general formula NBu4[(C^N)Pt(O^O)], where (C^N) represents the cyclometalated form of 2‐phenylpyridine (H(PhPy)), 2‐thienylpyridine (H(Thpy)) or 2‐benzo[h]quinoline (H(Bzq)), feature two different (O^O) chelated ligands: tetrabromocatechol [BrCat]2− (1–3) or alizarine [Aliz]2− (4–6). Complexes 1–6 displayed a significant cytotoxic effect against the studied cell line (IC50 range of 1.9–52.8 μM). For BrCat‐containing complexes 1–3, the biological activity was independent of the nature of the coordinated (C^N) ligand. In contrast, in the case of 4–6, the cytotoxicity (significantly high for 4) was concomitantly induced by the presence of either the PhPy or the [Aliz]2− ligand. Since complexes 1–6 are emissive in solution, the potential use of 4 as a theranostic agent was investigated using confocal analysis. The fluorescence signal from MDA‐MB‐231 cells incubated with 4 indicated the localization of the compound into the cytosol region.

show abstract

“…Chemical structures of (a–c) positively charged Pt(II) complexes, (d) catecholate‐bearing Pt(II) complexes, (e) doxorubicin and (f) mitoxantrone…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cytotoxic performances of new anionic cyclometalated Pt(II) complexes bearing chelated O^O ligands

Ionescu

Caligiuri

Godbert

et al. 2020

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…These organic drugs all bind by intercalation from the DNA minor groove, where binding is stabilised by electrostatic interactions between positive charges on the drug and the negatively charged phosphate backbone [35], although some, like mitoxantrone have also been shown to bind DNA by non-intercalating, electrostatic interactions [36][37][38][39][40]. Importantly, organic intercalators are also known to act by inhibiting topoisomerase (a nuclear enzyme that regulates DNA topology through single-(topoisomerase I) or doublestrand (topoisomerase II) breaks) [41][42][43][44].…”

Section: Organic Intercalatorsmentioning

confidence: 99%

DNA Intercalators in Cancer Therapy: Organic and Inorganic Drugs and Their Spectroscopic Tools of Analysis

Wheate

Brodie²,

Collins³

et al. 2007

MRMC

206

View full text Add to dashboard Cite

Since the discovery of the DNA intercalation process by Lerman in 1961 thousands of organic, inorganic octahedral (particularly ruthenium(II) and rhodium(III)) and square-planar (particularly platinum(II)) compounds have been developed as potential anticancer agents and diagnostic agents. The design and synthesis of new drugs is focused on bis-intercalators which have two intercalating groups linked via a variety of ligands, and synergistic drugs, which combine the anticancer properties of intercalation with other functionalities, such as covalent binding or boron-cages (for radiation therapy). Advances in spectroscopic techniques mean that the process of DNA intercalation can be examined in far greater detail than ever before, yielding important information on structure-activity relationships. In this review we examine the history and development of DNA intercalators as anticancer agents and advances in the analysis of DNA-drug interactions.

show abstract

“…13 It has been reported to contain anthraquinone derivatives, such as physcion, chrysophanol, aloe-emodin, emodin, rhein, [14][15][16][17][18][19][20] and anthraquinone glycosides. [16][17][18][19][20] Because emodin and aloe-emodin have been proven to have cytotoxic and DNA damage-inducing activities, 16,21 and some other natural and synthesized anthraquinone derivatives were also reported as DNA binding agents, [22][23][24][25][26][27][28][29] it can be expected that other compounds in the extract of R. palmatum (L.) may bind to DNA due to the structural similarity of the components.…”

Section: Resultsmentioning

confidence: 99%

Biological Fingerprinting Analysis by Liquid Chromatography/Mass Spectrometry for Evaluation of DNA Structural Selectivity of Multiple Compounds in Natural Products

Kong

et al. 2006

J. Comb. Chem.

View full text Add to dashboard Cite

A method by combination of centrifugal ultrafiltration (CUF) sampling with liquid chromatography-mass spectrometry (LC-MS) analysis was established to evaluate the DNA structure and sequence selectivity of the multiple compounds in a small molecule library. The developed method was applied to analyze the extracts of natural products Coptis chinensis Franch and Rheum palmatum (L.). From the obtained biological fingerprinting chromatograms, 7 compounds in C. chinensis Franch and 11 in R. palmatum (L.) were screened out as DNA binding agents. Most of these compounds were identified by standards and LC-MS analysis after the sample pretreatment with the DNA immobilized cartridge. DNA structural binding preference of the multiple active compounds in these two extracts was then evaluated simultaneously without purification.

show abstract

Mechanism of DNA-binding of some aminoalkylamino-derivatives of anthraquinone and naphthacenequinone

Cited by 30 publications

References 12 publications

Cytotoxic performances of new anionic cyclometalated Pt(II) complexes bearing chelated O^O ligands

Cytotoxic performances of new anionic cyclometalated Pt(II) complexes bearing chelated O^O ligands

DNA Intercalators in Cancer Therapy: Organic and Inorganic Drugs and Their Spectroscopic Tools of Analysis

Biological Fingerprinting Analysis by Liquid Chromatography/Mass Spectrometry for Evaluation of DNA Structural Selectivity of Multiple Compounds in Natural Products

Contact Info

Product

Resources

About