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Literature DB >> 17036123

Synthesis and G-quadruplex binding studies of new 4-N-methylpyridinium porphyrins.

Diana P N Gonçalves¹, Sylvain Ladame, Shankar Balasubramanian, Jeremy K M Sanders.

Abstract

A series of cationic porphyrins carrying 1-3 meso-N-pyridinium groups has been synthesised, and their binding to G-quadruplex DNA has been explored by surface plasmon resonance (SPR) and circular dichroism spectroscopy. Two trans substituents appear to be sufficient for tight binding; preferential binding to the anti-parallel intramolecular human telomeric DNA was observed for the A2trans and A3 porphyrins. The A2trans is able to induce the formation of an anti-parallel G-quadruplex in a K+ free solution, mimicking the effect of a molecular chaperone.

Entities: Chemical

Mesh：

Substances：

Year: 2006 PMID： 17036123 PMCID： PMC2195891 DOI： 10.1039/b608494j

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

26 in total

1. Rational synthesis of meso-substituted porphyrins bearing one nitrogen heterocyclic group.

Authors: D Gryko; J S Lindsey
Journal: J Org Chem Date: 2000-04-07 Impact factor: 4.354

2. Telomestatin, a potent telomerase inhibitor that interacts quite specifically with the human telomeric intramolecular g-quadruplex.

Authors: Mu-Yong Kim; Hariprasad Vankayalapati; Kazuo Shin-Ya; Konstanty Wierzba; Laurence H Hurley
Journal: J Am Chem Soc Date: 2002-03-13 Impact factor: 15.419

Review 3. G-quadruplex DNA structures--variations on a theme.

Authors: T Simonsson
Journal: Biol Chem Date: 2001-04 Impact factor: 3.915

4. Direct evidence for a G-quadruplex in a promoter region and its targeting with a small molecule to repress c-MYC transcription.

Authors: Adam Siddiqui-Jain; Cory L Grand; David J Bearss; Laurence H Hurley
Journal: Proc Natl Acad Sci U S A Date: 2002-08-23 Impact factor: 11.205

5. Structure-based design of selective and potent G quadruplex-mediated telomerase inhibitors.

Authors: M Read; R J Harrison; B Romagnoli; F A Tanious; S H Gowan; A P Reszka; W D Wilson; L R Kelland; S Neidle
Journal: Proc Natl Acad Sci U S A Date: 2001-04-17 Impact factor: 11.205

6. Molecular modeling studies on G-quadruplex complexes of telomerase inhibitors: structure-activity relationships.

Authors: M A Read; A A Wood; J R Harrison; S M Gowan; L R Kelland; H S Dosanjh; S Neidle
Journal: J Med Chem Date: 1999-11-04 Impact factor: 7.446

7. Selective interactions of cationic porphyrins with G-quadruplex structures.

Authors: H Han; D R Langley; A Rangan; L H Hurley
Journal: J Am Chem Soc Date: 2001-09-19 Impact factor: 15.419

8. Quadruplex-interactive agents as telomerase inhibitors: synthesis of porphyrins and structure-activity relationship for the inhibition of telomerase.

Authors: D F Shi; R T Wheelhouse; D Sun; L H Hurley
Journal: J Med Chem Date: 2001-12-20 Impact factor: 7.446

9. H(2)D3: a cationic porphyrin designed to intercalate into B-form DNA (H(2)D3 = trans-di(N-methylpyridium-3-yl)porphyrin).

Authors: R K Wall; A H Shelton; L C Bonaccorsi; S A Bejune; D Dubé; D R McMillin
Journal: J Am Chem Soc Date: 2001-11-21 Impact factor: 15.419

Synthesis and G-quadruplex binding studies of new 4-N-methylpyridinium porphyrins.

1. Rational synthesis of meso-substituted porphyrins bearing one nitrogen heterocyclic group.

2. Telomestatin, a potent telomerase inhibitor that interacts quite specifically with the human telomeric intramolecular g-quadruplex.

Review 3. G-quadruplex DNA structures--variations on a theme.

4. Direct evidence for a G-quadruplex in a promoter region and its targeting with a small molecule to repress c-MYC transcription.

5. Structure-based design of selective and potent G quadruplex-mediated telomerase inhibitors.

6. Molecular modeling studies on G-quadruplex complexes of telomerase inhibitors: structure-activity relationships.

7. Selective interactions of cationic porphyrins with G-quadruplex structures.

8. Quadruplex-interactive agents as telomerase inhibitors: synthesis of porphyrins and structure-activity relationship for the inhibition of telomerase.

9. H(2)D3: a cationic porphyrin designed to intercalate into B-form DNA (H(2)D3 = trans-di(N-methylpyridium-3-yl)porphyrin).

Review 10. Telomere maintenance as a target for anticancer drug discovery.

1. "One ring to bind them all"-part I: the efficiency of the macrocyclic scaffold for g-quadruplex DNA recognition.

2. A platinum-quinacridine hybrid as a G-quadruplex ligand.

3. Tetramethylpyridiniumporphyrazines--a new class of G-quadruplex inducing and stabilising ligands.

4. Interaction of human telomeric DNA with N-methyl mesoporphyrin IX.

5. Short LNA-modified oligonucleotide probes as efficient disruptors of DNA G-quadruplexes.

6. Cationic porphyrin induced a telomeric DNA to g-quadruplex form in water.

Review 7. Artificial Intelligence in Aptamer-Target Binding Prediction.