A new phenanthroline–oxazine ligand: Synthesis, coordination chemistry and atypical DNA binding interaction

Malachy Mc Cann; John Mc Ginley; Kaijie Ni; Mark O’connor; Kevin Kavanagh; Vickie Mc Kee; John Colleran; Michael Devereux; Nicholas Gathergood; Niall Barron; Andreea Prisecaru; Andrew Kellett

doi:10.1039/c3cc38710k

A new phenanthroline–oxazine ligand: Synthesis, coordination chemistry and atypical DNA binding interaction

Malachy Mc Cann
, John Mc Ginley
, Kaijie Ni
, Mark O’connor
, Kevin Kavanagh
, Vickie Mc Kee
, John Colleran
, Michael Devereux
, Nicholas Gathergood
, Niall Barron
, Andreea Prisecaru
, Andrew Kellett

Technological University Dublin

Research output: Contribution to journal › Article › peer-review

Abstract

1,10-Phenanthroline-5,6-dione and l-tyrosine methyl ester react to form phenanthroline–oxazine (PDT) from which [Cu(PDT)₂](ClO₄)₂ and [Ag(PDT)₂]ClO₄·2MeOH are obtained. Binding to calf-thymus DNA by Ag(i) and Cu(ii) PDT complexes exceed bis-1,10-phenanthroline analogues and the minor groove binding drugs, pentamidine and netropsin. Furthermore, unlike the artificial metallonuclease, [Cu(phen)₂]²⁺, the [Cu(PDT)₂]²⁺ complex does not cleave DNA in the presence of added reductant indicating unique interaction with DNA.

Original language	English
Pages (from-to)	2341-2343
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	23
DOIs	https://doi.org/10.1039/c3cc38710k
Publication status	Published - 21 Feb 2013

Access to Document

10.1039/c3cc38710k

Cite this

@article{321c377222ba48de91211272d656e739,

title = "A new phenanthroline–oxazine ligand: Synthesis, coordination chemistry and atypical DNA binding interaction",

abstract = "1,10-Phenanthroline-5,6-dione and l-tyrosine methyl ester react to form phenanthroline–oxazine (PDT) from which [Cu(PDT)2](ClO4)2 and [Ag(PDT)2]ClO4·2MeOH are obtained. Binding to calf-thymus DNA by Ag(i) and Cu(ii) PDT complexes exceed bis-1,10-phenanthroline analogues and the minor groove binding drugs, pentamidine and netropsin. Furthermore, unlike the artificial metallonuclease, [Cu(phen)2]2+, the [Cu(PDT)2]2+ complex does not cleave DNA in the presence of added reductant indicating unique interaction with DNA.",

author = "\{Mc Cann\}, Malachy and \{Mc Ginley\}, John and Kaijie Ni and Mark O{\textquoteright}connor and Kevin Kavanagh and \{Mc Kee\}, Vickie and John Colleran and Michael Devereux and Nicholas Gathergood and Niall Barron and Andreea Prisecaru and Andrew Kellett",

year = "2013",

month = feb,

day = "21",

doi = "10.1039/c3cc38710k",

language = "English",

volume = "49",

pages = "2341--2343",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "23",

}

TY - JOUR

T1 - A new phenanthroline–oxazine ligand

T2 - Synthesis, coordination chemistry and atypical DNA binding interaction

AU - Mc Cann, Malachy

AU - Mc Ginley, John

AU - Ni, Kaijie

AU - O’connor, Mark

AU - Kavanagh, Kevin

AU - Mc Kee, Vickie

AU - Colleran, John

AU - Devereux, Michael

AU - Gathergood, Nicholas

AU - Barron, Niall

AU - Prisecaru, Andreea

AU - Kellett, Andrew

PY - 2013/2/21

Y1 - 2013/2/21

N2 - 1,10-Phenanthroline-5,6-dione and l-tyrosine methyl ester react to form phenanthroline–oxazine (PDT) from which [Cu(PDT)2](ClO4)2 and [Ag(PDT)2]ClO4·2MeOH are obtained. Binding to calf-thymus DNA by Ag(i) and Cu(ii) PDT complexes exceed bis-1,10-phenanthroline analogues and the minor groove binding drugs, pentamidine and netropsin. Furthermore, unlike the artificial metallonuclease, [Cu(phen)2]2+, the [Cu(PDT)2]2+ complex does not cleave DNA in the presence of added reductant indicating unique interaction with DNA.

AB - 1,10-Phenanthroline-5,6-dione and l-tyrosine methyl ester react to form phenanthroline–oxazine (PDT) from which [Cu(PDT)2](ClO4)2 and [Ag(PDT)2]ClO4·2MeOH are obtained. Binding to calf-thymus DNA by Ag(i) and Cu(ii) PDT complexes exceed bis-1,10-phenanthroline analogues and the minor groove binding drugs, pentamidine and netropsin. Furthermore, unlike the artificial metallonuclease, [Cu(phen)2]2+, the [Cu(PDT)2]2+ complex does not cleave DNA in the presence of added reductant indicating unique interaction with DNA.

UR - https://www.scopus.com/pages/publications/84875960682

U2 - 10.1039/c3cc38710k

DO - 10.1039/c3cc38710k

M3 - Article

C2 - 23407675

AN - SCOPUS:84875960682

SN - 1359-7345

VL - 49

SP - 2341

EP - 2343

JO - Chemical Communications

JF - Chemical Communications

IS - 23

ER -

A new phenanthroline–oxazine ligand: Synthesis, coordination chemistry and atypical DNA binding interaction

Abstract

Access to Document

Fingerprint

Cite this