Synthesis, characterization, and DNA-binding properties of (1,2-diaminoethane)platinum(II) complexes linked to the DNA intercalator acridine orange by trimethylene and hexamethylene chains

Bowler, Bruce E.; Ahmed, Kazi J.; Sundquist, Wesley I.; Hollis, L. Steven; Whang, Edward E.; Lippard, Stephen J.

doi:10.1021/ja00186a022

Cited by 100 publications

(69 citation statements)

References 2 publications

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“…Analogous interaction modes were also reported for proflavine, [41] acridine orange [21,42] and acridine orange derivatives. [26,43] This study has shown that the bifunctional molecule D and its Zn II complex ([ZnD]) interact with double-stranded DNA, to form stable complexes.…”

Section: Discussionsupporting

confidence: 73%

“…[21,[23][24][25][26][27][28] Because the aggregation process can interfere with all other equilibria, the ability of D and its Zn II complex to form aggregates was investigated first.…”

Section: Resultsmentioning

confidence: 99%

“…[10,19,20] The intercalative binding of these complexes to nucleic acids constitute a prerequisite for the consequent slow attack of Pt II on the base nitrogen atom. [21,22] On the basis of the above-mentioned arguments, we found it interesting to synthesise a new fluorescent metallointercalator and to investigate its interaction with double-stranded calf thymus DNA. This molecule, 3,6-di-A C H T U N G T R E N N U N G amine-9-[6,6-bis(2-aminoethyl)-1,6-diaminohexyl]acridine, from now on denoted as D (dye) is characterised by a proflavine unit with a diethylenetriamine moiety that is able to chelate metal ions.…”

Section: Introductionmentioning

confidence: 99%

“…A novel structural aspect of D is that the metal-binding site is linked to the C9 position of the acridine group instead of the N10 position, as is the case in similar metallointercalators. [21] Because the N10 atom of D is expected to be protonated at physiological pH in both the metal-free ligand and its metal complexes, we found it interesting to analyse the effect of a positively charged N10 ammonium group on the DNA-binding process. Actually, this ammonium group might be able to influence the interaction with DNA through the formation of electrostatic and hydrogen-bond interactions with oxygen atoms of the polyanion.…”

Section: Introductionmentioning

confidence: 99%

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DNA Binding by a New Metallointercalator that Contains a Proflavine Group Bearing a Hanging Chelating Unit

Bazzicalupi

Bencini

Bianchi

et al. 2007

Chemistry A European J

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The new bifunctional molecule 3,6‐diamine‐9‐[6,6‐bis(2‐aminoethyl)‐1,6‐diaminohexyl]acridine (D), which is characterised by both an aromatic moiety and a separate metal‐complexing polyamine centre, has been synthesised. The characteristics of D and its ZnII complex ([ZnD]) (protonation and metal‐complexing constants, optical properties and self‐aggregation phenomena) have been analysed by means of NMR spectroscopy, potentiometric, spectrophotometric and spectrofluorimetric techniques. The equilibria and kinetics of the binding process of D and [ZnD] to calf thymus DNA have been investigated at I=0.11 M (NaCl) and 298.1 K by using spectroscopic methods and the stopped‐flow technique. Static measurements show biphasic behaviour for both D–DNA and [ZnD]–DNA systems; this reveals the occurrence of two different binding processes depending on the polymer‐to‐dye molar ratio (P/D). The binding mode that occurs at low P/D values is interpreted in terms of external binding with a notable contribution from the polyamine residue. The binding mode at high P/D values corresponds to intercalation of the proflavine residue. Stopped‐flow, circular dichroism and supercoiled‐DNA unwinding experiments corroborate the proposed mechanism. Molecular‐modelling studies support the intercalative process and evidence the influence of NH+⋅⋅⋅O interactions between the protonated acridine nitrogen atom and the oxygen atoms of the polyanion; these interactions play a key role in determining the conformation of DNA adducts.

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Section: Discussionsupporting

confidence: 73%

“…[21,[23][24][25][26][27][28] Because the aggregation process can interfere with all other equilibria, the ability of D and its Zn II complex to form aggregates was investigated first.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

DNA Binding by a New Metallointercalator that Contains a Proflavine Group Bearing a Hanging Chelating Unit

Bazzicalupi

Bencini

Bianchi

et al. 2007

Chemistry A European J

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“…This red shift (Dl = 10 nm) is in agreement with the results reported by other authors for acridine orange (AO) and for a Pt(II) complex bearing a pendant AO fragment, and is consistent with an intercalative binding of the compounds. [17][18][19] As the DNA concentration increases, the shoulder at 470 nm diminishes in intensity. Such a shoulder can be assigned to the presence of dimeric species, resulting from the self-association of AO rings, their formation being less probable when the compounds bind to DNA.…”

Section: Uv-visible Spectroscopymentioning

confidence: 99%

Tricarbonyl M(I) (M = Re, 99mTc) complexes bearing acridine fluorophores: synthesis, characterization, DNA interaction studies and nuclear targeting

Esteves¹,

Xavier²,

Gama³

et al. 2010

Org. Biomol. Chem.

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New pyrazolyl-diamine ligands with acridine derivatives at the 4-position of the pyrazolyl ring were synthesized and characterized (L1 and L2). Coordination towards the fac- [M(CO) ). The interaction of the novel pyrazolyl-diamine ligands (L1 and L2) and rhenium(I) complexes (Re1 and Re2) with calf thymus DNA (CT-DNA) was investigated by a variety of techniques, namely UV-visible, fluorescence spectroscopy and circular and linear dichroism. Compounds L1 and Re1 have moderate affinity to CT-DNA and bind to DNA by intercalation, while L2 and Re2 have a poor affinity for CT-DNA. Moreover, LD measurements showed that L1 and Re1 act as perfect intercalators. By confocal fluorescence microscopy we found that L1 and Re1 internalize and localize in the nucleus of B16F1 murine melanoma cells. The congener Tc1 complex also targets the cell nucleus exhibiting a time-dependent cellular uptake and a fast and high nuclear internalization (67.2% of activity after 30 min). Plasmid DNA studies have shown that Tc1 converts supercoiled (sc) puc19 DNA to the open circular (oc) form.

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[RuO(dppz)(tpy)]²⁺: ein DNA‐Spaltungsreagens mit hoher DNA‐Affinität

Gupta¹,

Grover²,

Neyhart³

et al. 1992

Angewandte Chemie

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Teilgitters hat nur geringfiigige Versetzungen und Verzerrungender Phosphatgruppen zur Folge (Tabelle 1 und Abb. 1 c). Beim Vergleich der Bindungslangen in MnPO, . H,O und LiMnXO,(OH) (X = P, As) (Tabelle 2) fallt eine uberra-Tabelle 2. Mn-0-Abstinde [A] in MnPO, . H,O [7] und LiMnXO,(OH) (X = P, AS [4]) MnPO, . H,O LiMnXO,(OH) X = P As 2.142(5) 1.908(8) 2.292(5) 1.821(9) 1.944(5) 2.104(9) 1.938(6) 2.168(9) Mn-O(1) 3.886(3) ~~~~~~~~$ Mn-O(2) 1.909(3) ~~~~~~~ Mn(a)-0(3) 1.985(6) 1.966(11) ~n -0 ( 3 ) 2.284(3) Mn(b)-0(3) 1.978(6) 2.026(10) schende Anderung der Jahn-Teller-Verzerrungen der Mn0,-Oktaeder auf, die bekanntermaljen von der t , ,3e,'-Elektronenkonfiguration eines High-spin-Mn"'-Ions herruhren: In MnPO, . H,O ist die oktaedische Koordinationssphare des Mn-Atoms wie erwartet tetragonal verzerrt, das Zentralatom also [4 + 21-koordiniert, rnit vier kurzen Bindungen zu Phosphat-Sauerstoffatomen und zwei langen Bindungen zu den Sauerstoffatomen der gemeinsainen Wassermolekule. Die Mn-Atome in LiMnAsO,(OH) sind [2 + 2 + 21-koordiniert, rnit zwei kurzen und zwei langen Mn-OAs-Bindungen plus zwei weiteren Mn-OH-Bindungen, deren Langen etwa zwischen den vorigen Werten liegen (Tabelle 2), was auf die bereits diskutierte AnderungL4] in der Jahn-Teller-Aufspaltung zuriickzufuhren ist. In LiMnPO,(OH) liegen die Verzerrungen der Mn0,-Oktaeder zwischen einem [4 + 21-und einem [2 + 2 + 21-Typ. Die Koordinationsgeometrien der beiden Lithium-Derivate sind recht ahnlich, wenn man bedenkt, dalj unterschiedliche Mn-Lagen besetzt werden. In beiden Fallen sind die Mn-OH-Bindungen drastisch verkurzt, von ca. 2.30 8, in den p-Aqualiganden auf 1.98 8, fur die p-Hydroxoliganden in den beiden inaquivalenten Mn(a)O,-und Mn(b)O,-Oktaedern. Diese Anderung verringert den Mn-Mn-Abstand innerhalb der Oktaederketten von 3.976 und 4.048 8, in MnXO, . H,O (X = P, As) zu 3.561 und 3.636 8, in LiMnXO,(OH) (X = P, As). Die Li+-Ionen in LiMnPO,(OH) sind in den Kanalen parallel zur [loll-Richtung in unregelmaIJiger Weise koordiniert und haben Kontakte zu funf Arsenat-und einem Hydroxy-Sauerstoffatom; der Li-Li-Abstand betragt 3.14(3) A.

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Synthesis, characterization, and DNA-binding properties of (1,2-diaminoethane)platinum(II) complexes linked to the DNA intercalator acridine orange by trimethylene and hexamethylene chains

Cited by 100 publications

References 2 publications

DNA Binding by a New Metallointercalator that Contains a Proflavine Group Bearing a Hanging Chelating Unit

DNA Binding by a New Metallointercalator that Contains a Proflavine Group Bearing a Hanging Chelating Unit

Tricarbonyl M(I) (M = Re, 99mTc) complexes bearing acridine fluorophores: synthesis, characterization, DNA interaction studies and nuclear targeting

[RuO(dppz)(tpy)]²⁺: ein DNA‐Spaltungsreagens mit hoher DNA‐Affinität

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Synthesis, characterization, and DNA-binding properties of (1,2-diaminoethane)platinum(II) complexes linked to the DNA intercalator acridine orange by trimethylene and hexamethylene chains

Cited by 100 publications

References 2 publications

DNA Binding by a New Metallointercalator that Contains a Proflavine Group Bearing a Hanging Chelating Unit

DNA Binding by a New Metallointercalator that Contains a Proflavine Group Bearing a Hanging Chelating Unit

Tricarbonyl M(I) (M = Re, 99mTc) complexes bearing acridine fluorophores: synthesis, characterization, DNA interaction studies and nuclear targeting

[RuO(dppz)(tpy)]2+: ein DNA‐Spaltungsreagens mit hoher DNA‐Affinität

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[RuO(dppz)(tpy)]²⁺: ein DNA‐Spaltungsreagens mit hoher DNA‐Affinität