Synthesis and characterization of pi-stacked phenothiazine-labeled oligodeoxynucleotides.

  title={Synthesis and characterization of pi-stacked phenothiazine-labeled oligodeoxynucleotides.},
  author={S. A. Nadeem Hashmi and Xi Hu and Chad E. Immoos and Stephen J. Lee and Mark W. Grinstaff},
  journal={Organic letters},
  volume={4 26},
[reaction: see text] A facile procedure for the incorporation of N-methyl phenothiazine as the terminal nucleoside in oligodeoxynucleotides is reported. The phenothiazine nucleoside analogue is synthesized and then incorporated into DNA using an automated DNA solid-phase synthesizer. Phenothiazine-labeled oligodeoxynucleotides form stable B-form duplexes with higher melting temperatures compared to unlabeled DNA duplexes. 
Phenothiazine as a redox-active DNA base substitute: comparison with phenothiazine-modified uridine.
Phenothiazine can be incorporated as a redox-active probe into DNA in two conceptually different ways: the non-nucleosidic DNA base surrogate exhibits similar properties to 10-methylphenothiazine but
Indole in DNA: Comparison of a Nucleosidic with a Non-Nucleosidic DNA Base Substitution
Interestingly, not only the In' and In'' modifications but also the natural-like In base surrogate destabilize the DNA duplex strongly, which supports the approach to apply the acyclic glycol linker to incorporate aromatic molecules as artificial DNA base substitutions.
Reductive electron transfer in phenothiazine-modified DNA is dependent on the base sequence.
It became evident that excess-electron transfer is highly sequence dependent and occurs more efficiently over T-A base pairs than over C-G base pairs.
Phenothiazine-linked nucleosides and nucleotides for redox labelling of DNA.
PT-linked dNTPs are useful additions to the portfolio of nucleotides for enzymatic synthesis of redox-labelled DNA for electrochemical analysis.
Efficient synthesis of novel cyclic fused-phenothiazines via domino cyclization of 2-(benzo[b][1,4]thiazin-3-ylidene)acetate, aromatic aldehydes and cyclic 1,3-diketones
Novel fused and bridged phenothiazine derivatives were selectively synthesized via an acid-promoted reaction of alkyl 2-(benzo[b][1,4]thiazin-3-ylidene)acetate, aromatic aldehydes and cyclic
Cobalt-catalyzed diastereoselective synthesis of C-furanosides. Total synthesis of (-)-isoaltholactone.
An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient
Enhancement of excess electron transfer efficiency in DNA containing a phenothiazine donor and multiple stable phenanthrenyl base pairs.
EET grown ohm: Excess electron transfer (EET) was observed within a DNA duplex containing π-stacked phenothiazine as an electron donor, phenanthrenes as electron carriers and 5-bromouracil as an


Synthesis and characterization of phenothiazine labeled oligodeoxynucleotides: novel 2'-deoxyadenosine and thymidine probes for labeling DNA.
Phenothiazine labeled oligodeoxynucleotides form stable B-form duplexes with similar melting temperatures, CD spectra, and DSC traces compared to unlabeled DNA duplexe.
Synthesis and characterization of fluorenone-, anthraquinone-, and phenothiazine-labeled oligodeoxynucleotides: 5'-probes for DNA redox chemistry.
A facile and automated procedure for the synthesis of oligodeoxynucleotides possessing derivatives of 9-fluoreneone, 9,10-anthraquinone, and phenothiazine is described, which shows a slight enhancement in duplex stability relative to the unlabeled control.
Synthesis and stability of oligodeoxynucleotides containing C8-labeled 2'-deoxyadenosine: novel redox nucleobase probes for DNA-mediated charge-transfer studies.
An efficient and convenient synthetic strategy to redox-labeled C8-derivatives of 2'-deoxyadenosine is described and the resulting labeled oligodeoxynucleotide strands form stable B-form duplexes with melting temperatures and CD spectra similar to those of the unlabeled analogues.
Synthesis and biophysical studies of short oligodeoxynucleotides with novel modifications: a possible approach to the problem of mixed base oligodeoxynucleotide synthesis.
Oligodeoxynucleotides containing these analogues having been synthesised and hybridized to their complementary strands and shown to be less stable than either the totally complementary duplex or those containing A.C.T mismatches.
Automated Solid-Phase DNA Synthesis and Photophysical Properties of Oligonucleotides Labeled at the 5‘-Terminus with Ru(bpy)32+
Photophysical studies of the Ru(II) tris-diimine complex as well as the corresponding labeled oligonucleotides demonstrate that the excited-state electron is localized on one specific bipyridine with the dipole directed toward the linkage to DNA, and that the Ru (II) excited state is long-lived when attached to the DNA.
Solid-Phase Synthesis and Photophysical Properties of DNA Labeled at the Nucleobase with Ru(bpy)(2)(4-m-4'-pa-bpy)(2+).
A facile procedure for incorporating a Ru(diimine)(3)(2+) complex at the nucleobase in an oligonucleotide is reported that combines the advantages of Pd(0) cross-coupling and solid-phase DNA
Automated solid-phase synthesis and photophysical properties of oligodeoxynucleotides labeled at 5'-aminothymidine with Ru(bpy)2(4-m-4'-cam-bpy)2+.
Photophysical studies of the novel ruthenium trisdiimine thymidine complex as well as the corresponding labeled oligodeoxynucleotides demonstrate that the favorable properties associated with the ruthensium complex are retained after covalent attachment to the nucleoside and oligode oxynucleotide.
Preparation of 3-substituted 10-methylphenothiazines
Lithiation at the C-3 position of 10-methylphenothiazine can be achieved by a BusLi–Br exchange reaction starting from 3-bromo-10-methylphenothiazine. Reaction of the lithiated species with different
Automated Solid-Phase Synthesis of Site-Specifically Labeled Ruthenium-Oligonucleotides.
A novel metallonucleoside phosphoramidite is reported for the automated solid-phase synthesis of site-specifically metallolabeled oligonucleotides.
Heterocyclic modifications of oligonucleotides and antisense technology.
  • P. Herdewijn
  • Chemistry, Biology
    Antisense & nucleic acid drug development
  • 2000
The physicochemical factors that are responsible for duplex stabilization through base modification are described and a summary is given of the different heterocyclic modifications that can be used to beneficially influence this duplex stability.