Acridine-based Anticancer Drugs

Denny, William A.; Baguley, Bruce C.

doi:10.1007/978-1-349-13330-7_7

Cited by 21 publications

(8 citation statements)

References 152 publications

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“…Recently, 9-aminoacridine has been assayed, in comparison with other acridine derivatives such as pharmacotherapeutic for prion disease Creutzfeldt-Jacob disease (CJD) [ 6 ]. The incorporation of bulky groups into the acridine moiety does not allow the intercalation of the chromophor between the DNA base pairs and causes decreasing of the antitumor activity [ 7 ].…”

Section: Introductionmentioning

confidence: 99%

Complexes of Pd(II) and Pt(II) with 9-Aminoacridine: Reactions with DNA and Study of Their Antiproliferative Activity

Riera

Moreno

Ciudad

et al. 2007

Bioinorganic Chemistry and Applications

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Four new metal complexes {M = Pd(II) or Pt(II)} containing the ligand 9-aminoacridine (9AA) were prepared. The compounds were characterized by FT-IR and 1H, 13C, and 195Pt NMR spectroscopies. Crystal structure of the palladium complex of formulae [Pd(9AA)(μ-Cl)]2 · 2DMF was determined by X-ray diffraction. Two 9-acridine molecules in the imine form bind symmetrically to the metal ions in a bidentate fashion through the imine nitrogen atom and the C(1) atom of the aminoacridine closing a new five-membered ring. By reaction with phosphine or pyridine, the Cl bridges broke and compounds with general formulae [Pd(9AA)Cl(L)] (where L = PPh3 or py) were formed. A mononuclear complex of platinum of formulae [Pt(9AA)Cl(DMSO)] was also obtained by direct reaction of 9-aminoacridine and the complex [PtCl2(DMSO2]. The capacity of the compounds to modify the secondary and tertiary structures of DNA was evaluated by means of circular dichroism and electrophoretic mobility. Both palladium and platinum compounds proved active in the modification of both the secondary and tertiary DNA structures. AFM images showed noticeable modifications of the morphology of the plasmid pBR322 DNA by the compounds probably due to the intercalation of the complexes between base pairs of the DNA molecule. Finally, the palladium complex was tested for antiproliferative activity against three different human tumor cell lines. The results suggest that the palladium complex of formula [Pd(9AA)(μ-Cl)]2 has significant antiproliferative activity, although it is less active than cisplatin.

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Section: Introductionmentioning

confidence: 99%

Complexes of Pd(II) and Pt(II) with 9-Aminoacridine: Reactions with DNA and Study of Their Antiproliferative Activity

Riera

Moreno

Ciudad

et al. 2007

Bioinorganic Chemistry and Applications

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“…The cytotoxic mechanism of the quinone derivatives has been extensively studied, and one possible mechanism of action has been suggested as a DNA topoisomerase inhibitor via DNA-intercalation, or reducing quinone moiety by oxidoreductase [31][32][33][34][35]. According to the protocol reported previously, the DNA-intercalating molecule must have a planar tricyclic or tetracyclic ring with a length of 3-4Å and a width of 6-8Å.…”

Section: Resultsmentioning

confidence: 99%

A simple and convenient procedure for the synthesis of naphthoquinone fused cyclic α‐aminophosphoryl chloride

Wang

Miao

Chen

2007

Heteroatom Chemistry

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“…On the other hand, the acridone nucleus constitutes an interesting class of natural products that serve as chemical intermediates in the synthesis of several alkaloids [17]. Acridones were known for their pharmacological activities as antiviral [18,19], antimicrobial [20][21][22], antitumor [23,24], antimalarial [25,26], and anticancer [27,28]. Moreover, the fluorescence of acridones allows these molecules to be important chemosensors for selective recognition of metals and pollutants in biological and ecological areas [29].…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Regioselective Synthesis and 2D-NMR Studies of New 1,2,3-Triazole Compounds Derived from Acridone

Aarjane

Slassi

Tazi

et al. 2021

Journal of Chemistry

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A simple and mild protocol towards the synthesis of new 1,2,3-triazole compounds derived from acridone has been developed via regiospecific 1,3-dipolar cycloaddition reaction between 10-(prop-2-yn-1-yl)acridone derivatives and aromatic azides using CuI as a catalyst. The cycloaddition reaction has been performed using conventional as well as microwave-assisted methods. Microwave-assisted synthesis caused a significant reduction in the reaction times and improvement in the yields of all the synthesized compounds compared with the conventional method. The structure of the 1,4-disubstituted 1,2,3-triazoles has been elucidated by IR, HRMS, 1H-NMR, 13C-NMR, and 2D NMR (1H-13C HMBC, 1H-1H COSY, and 1H-1H NOESY) spectroscopies.

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Acridine-based Anticancer Drugs

Cited by 21 publications

References 152 publications

Complexes of Pd(II) and Pt(II) with 9-Aminoacridine: Reactions with DNA and Study of Their Antiproliferative Activity

Complexes of Pd(II) and Pt(II) with 9-Aminoacridine: Reactions with DNA and Study of Their Antiproliferative Activity

A simple and convenient procedure for the synthesis of naphthoquinone fused cyclic α‐aminophosphoryl chloride

Microwave-Assisted Regioselective Synthesis and 2D-NMR Studies of New 1,2,3-Triazole Compounds Derived from Acridone

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