Dipyrido[3,2-a:2′,3′-c]phenazine-Tethered Oligo-DNA: Synthesis and Thermal Stability of Their DNA⋅DNA and DNA⋅RNA Duplexes and DNA⋅DNA⋅DNA Triplexes

Ossipov, Dmitri; Zamaratski, Edouard; Chattopadhyaya, J.

doi:10.1002/(sici)1522-2675(19991215)82:12<2186::aid-hlca2186>3.0.co;2-1

Cited by 29 publications

(7 citation statements)

References 14 publications

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“…There have been few comparative studies on the relative triplex stabilization of intercalators coupled to either a terminal or internal position of the TFO. Except for a strongly triplex stabilizing benzo[ e ]pyridoindole and a benzo[ f ]pyridoquinoxaline attached through an internucleotide pentamethylene and tetramethylene containing linker in the interior of the TFO, respectively, conjugates with a centrally positioned ligand seem generally less effective in triplex stabilization compared to conjugates with terminal modifications , . In addition to the ligand structure, favorable interactions of internally attached intercalators have also been found to be particularly sensitive to the type and length of the linker in line with the present data.…”

Section: Resultssupporting

confidence: 84%

Spectroscopic and Calorimetric Studies on the Triplex Formation with Oligonucleotide−Ligand Conjugates

2010

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Several triplex-forming 9-mer oligonucleotide (TFO) conjugates with a methyl- or methoxy-substituted 5-phenyl-6H-indolo[3,2-b]quinoline (PIQ) attached at the 5'-terminus or 3'-terminus or at an internal C5 thymine position were synthesized and tested for their ability to form and stabilize a triple helix with a double-helical DNA target employing UV melting experiments, fluorescence titrations, and isothermal titration calorimetry (ITC). A considerable thermal stabilization by up to 14 degrees C at pH 6.0 was observed for the 5'- and 3'-conjugates with little influence on the type of substituent but also for a conjugate with the ligand tethered by a short linker to the interior of the 9-mer TFO. A detailed thermodynamic characterization of the unmodified TFO and its 5'-conjugate with a methyl-substituted ligand by ITC experiments yielded a DeltaDeltaG degrees of -1.8 kcal mol(-1) at pH 6.0 for the TFO-attached PIQ-triplex interaction and also revealed a favorable entropic contribution as the major determinant for the free energy of PIQ binding in the conjugate. The pH dependence of triplex thermal stability highlights the importance of ring protonation of the triplex-bound ligand for its effective interaction and triplex stabilization near physiological conditions.

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Section: Resultssupporting

confidence: 84%

Spectroscopic and Calorimetric Studies on the Triplex Formation with Oligonucleotide−Ligand Conjugates

2010

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“…All other commercial reagents were used without further purification. The compounds [Cu(PPh 3 ) 2 ]NO 3 , 1,10-phenantroline-5,6-dione (phendione), dipyrido[3,2- a :2′,3′- h ]quinoxoline (dpq), dipyrido[3,2- a :2′,3′- c ]phenazine (dppz), 11-carboxy-dipyrido(3,2- a :2,3- c )phenazine (dppa), and dipyrido[3,2- a :2′,3′- c ]phenazine-11-carboxylic acid methyl ester (dppme) were synthesized according to reported methods. − C, H and N analyses were performed using a Carlo Erba Model EA1108 elemental analyzer. NMR spectra were obtained from CDCl 3 , trifluoroacetic acid- d , and DMSO- d 6 solutions with a Bruker AVANCE 300 spectrometer.…”

Section: Experimental Sectionmentioning

confidence: 99%

Copper(I)–Phosphine Polypyridyl Complexes: Synthesis, Characterization, DNA/HSA Binding Study, and Antiproliferative Activity

et al. 2017

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A series of copper(I)-phosphine polypyridyl complexes have been investigated as potential antitumor agents. The complexes [Cu(PPh)dpq]NO (2), [Cu(PPh)dppz]NO (3), [Cu(PPh)dppa]NO (4), and [Cu(PPh)dppme]NO (5) were synthesized by the reaction of [Cu(PPh)NO] with the respective planar ligand under mild conditions. These copper complexes were fully characterized by elemental analysis, molar conductivity, FAB-MS, and NMR, UV-vis, and IR spectroscopies. Interactions between these copper(I)-phosphine polypyridyl complexes and DNA have been investigated using various spectroscopic techniques and analytical methods, such as UV-vis titrations, thermal denaturation, circular dichroism, viscosity measurements, gel electrophoresis, and competitive fluorescent intercalator displacement assays. The results of our studies suggest that these copper(I) complexes interact with DNA in an intercalative way. Furthermore, their high protein binding affinities toward human serum albumin were determined by fluorescence studies. Additionally, cytotoxicity analyses of all complexes against several tumor cell lines (human breast, MCF-7; human lung, A549; and human prostate, DU-145) and non-tumor cell lines (Chinese hamster lung, V79-4; and human lung, MRC-5) were performed. The results revealed that copper(I)-phosphine polypyridyl complexes are more cytotoxic than the corresponding planar ligand and also showed to be more active than cisplatin. A good correlation was observed between the cytostatic activity and lipophilicity of the copper(I) complexes studied here.

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“…The respective solid supports 113a to 113i, where the distance between the amino group and the nearest hydroxy group was extended to seven single bonds, were substantially more reliable than 111. A number of reporter groups including fluorescein, R 66 (Theisen et al, 1992), cholesterol, R 14 (Vu et al, 1993(Vu et al, , 1994, adamantoyl, R 5 (Habus et al, 1995), 9-(2-methoxy-6-chloroacridinyl), R 48 (Asseline et al, 1996), dipyrido[3,2-a:2 ,3 -c]phenazine-11carbonyl, R 73 (dppz; Ossipov et al, 1999), folic acid attached via αor γ-carboxy group of L-glutamate fragment, R 57 and R 58 , respectively (Kazanova et al, 2007), dabsyl, R 28 (Nakayama et al, 2008), and dabcyl, R 29 (Matsumoto et al, 2010). In addition to the standard deprotection conditions using AH at 55 • C, alternative conditions were used under special circumstances.…”

Section: 132mentioning

confidence: 99%

“…A relatively simple synthetic access to 1‐ O ‐aminoalkylated glycerols prompted preparation of solid supports 114a to 114e where a protected amino group or a reporter was separated from the backbone by long hydrophilic tri‐ and penta(ethyleneoxide) spacer arms. In 114a and 114b , the amino group in the side chain was acylated with dipyrido[3,2‐ a :2′,3′‐ c ]phenazine‐11‐carboxylic acid, R 73 (Ossipov et al, ). In the ensuing publications, the authors succeeded in preparation of 114c and 114d and their use for the synthesis of oligonucleotides labeled with ruthenium complexes [Ru(1,10‐phenantroline) 2 (dipyrido[3,2‐ a :2′,3′‐ c ]phenazine)] 2+ , R 74 (Ossipov et al, ), and [Ru(2,2′:6′,2″‐terpyridine)(dipyrido[3,2‐ a :2′,3′‐ c ]phenazine)Cl] + , R 75 (Ossipov et al, ), respectively.…”

Section: Solid Support Linkers For Oligonucleotide Synthesismentioning

confidence: 99%

Solid‐Phase Supports for Oligonucleotide Synthesis

Guzaev¹

2013

CP Nucleic Acid Chemistry

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This unit attempts to provide a reasonably complete inventory of over 280 solid supports available to oligonucleotide chemists for preparation of natural and 3'-modified oligonucleotides. Emphasis is placed on non-nucleosidic solid supports. The relationship between the structural features of linkers and their behavior in oligonucleotide synthesis and deprotection is discussed wherever the relevant observations are available.

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Dipyrido[3,2-a:2′,3′-c]phenazine-Tethered Oligo-DNA: Synthesis and Thermal Stability of Their DNA⋅DNA and DNA⋅RNA Duplexes and DNA⋅DNA⋅DNA Triplexes

Cited by 29 publications

References 14 publications

Spectroscopic and Calorimetric Studies on the Triplex Formation with Oligonucleotide−Ligand Conjugates

Spectroscopic and Calorimetric Studies on the Triplex Formation with Oligonucleotide−Ligand Conjugates

Copper(I)–Phosphine Polypyridyl Complexes: Synthesis, Characterization, DNA/HSA Binding Study, and Antiproliferative Activity

Solid‐Phase Supports for Oligonucleotide Synthesis

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