Synthesis, Structure and Antiproliferative Activity of Cationic Porphyrin - Imidazophenazine Conjugate


(*) Corresponding author


Authors' affiliations


DOI's assignment:
the author of the article can submit here a request for assignment of a DOI number to this resource!
Cost of the service: euros 10,00 (for a DOI)

Abstract


New conjugate of G-quadruplex ligand, cationic tris(methylpyridinium)porphyrin, and its Zn(II) and Mn(III) metal complexes with a neutral intercalating agent imidazophenazine were synthesized. The synthesis was based on the coupling of carboxyalkyl derivative of the porphyrin with N1-aminoalkylated dye. Spectral-fluorescent studies and density functional quantum-chemical calculations suggest the formation of intramolecular complexes between the two chromophores for non-metalated hybrid and zinc(II) derivative. The conjugates have been found to inhibit the growth of tumor cells of mouse Lewis lung carcinoma in vitro at micromolar concentrations. Metal complexes were several times more active than the non-metalated hybrid. The most efficient Zn(II) complex suppressed the tumor cells with IC50 5.9 M
Copyright © 2011 Praise Worthy Prize - All rights reserved.

Keywords


Antiproliferative Activity; G-quadruplex; Imidazophenazine; Porphyrin Conjugates

Full Text:

PDF


References


T. R. Cech, Life at the End of the Chromosome: Telomeres and Telomerase, Angewandte Chemie International Edition, Volume 39, (Issue 1), January 2000, Pages 34-43.

C. B. Harley, Telomerase and Cancer Therapeutics, Nature Reviews Cancer, Volume 8, (Issue 3), March 2008, Pages 167-179.

J. L. Huppert, Hunting G-quadruplexes, Biochimie, Volume 90, (Issue 8), August 2008, Pages 1140-1148.

H. J. Lipps, D. Rhodes, G-quadruplex structures: in vivo evidence and function, Trends in Cell Biology, Volume 19, (Issue 8), August 2009, Pages 414-422.

D. Monchaud, M.-P. Teulade-Fichou, A hitchhiker's guide to G-quadruplex ligands, Organic & Biomolecular Chemistry, Volume 6, (Issue 4), February 2008, p. 627-636.

A. De Cian, L. Lacroix, C. Douarre, N. Temime-Smaali, C. Trentesaux, J.-F. Riou, J.-L. Mergny. Targeting telomeres and telomerase. Biochimie, Volume 90, (Issue 1), January 2008, Pages 131-155.

M. Franceschin, G-Quadruplex DNA Structures and Organic Chemistry: More Than One Connection, European Journal of Organic Chemistry, Volume 2009, (Issue 14), May 2009, Pages 2225-2238.

S. Neidle, Human telomeric G-quadruplex: The current status of telomeric G-quadruplexes as therapeutic targets in human cancer, FEBS Journal, Volume 277, (Issue 5), March 2010, Pages 1118-1125.

J. L.-Y. Chen, J. Sperry, N.Y. Ip, M.A. Brimble, Natural products targeting telomere maintenance, MedChemComm, Volume 2, (Issue 4), April 2011, Pages 229-245.

Y. Xu, Chemistry in Human Telomere Biology: Structure, Function and Targeting of Telomere DNA/RNA, Chemical Society Reviews, Volume 40, (Issue 5), May 2011, Pages 2719-2740.

R.T. Wheelhouse, D. Sun, H. Han, F.X. Han, L.H. Hurley, Cationic Porphyrins as Telomerase Inhibitors: the Interaction of Tetra-(N-methyl-4-pyridyl)porphine with Quadruplex DNA, Journal of the American Chemical Society, Volume 120, (Issue 13), 1998, Pages 3261-3262.

N.V. Anantha, M. Azam, R.D. Sheardy, Porphyrin Binding to Quadrupled T4G4, Biochemistry, Volume 37, (Issue 9), March 1998, Pages 2709-2714.

E. Izbicka, R.T. Wheelhouse, E. Raymond, K.K. Davidson, R.A. Lawrence, D. Sun, B.E. Windle, L.H. Hurley, D.D. Von Hoff, Effects of Cationic Porphyrins as G-Quadruplex Interactive Agents in Human Tumor Cells, Cancer Research, Volume 59, February 1999, Pages 639-644.

I.M. Dixon, F. Lopez, A.M. Tejera, J.-P. Estève, M.A. Blasco, G. Pratviel, B. Meunier, A G-Quadruplex Ligand with 10000-Fold Selectivity over Duplex DNA, Journal of the American Chemical Society, Volume 129, (Issue 6), February 2007, Pages 1502-1503.

A. Maraval, S. Franco, C. Vialas, G. Pratviel, M. A. Blasco, B. Meunier, Porphyrin–Aminoquinoline Conjugates as Telomerase Inhibitors, Organic & Biomolecular Chemistry, Volume 1, (Issue 6), March 2003, Pages 921-927.

P. Zhao, L.-C. Xu, J.-W. Huang, B. Fu, H.C. Yu, L.-N. Ji, Cationic Porphyrin-Antraquinone Dyads: Modes of Interaction with G-Quadruplex DNA, Dyes and Pigments, Volume 83, (Issue 1), October 2009, Pages 81-87.

P. Zhao, L.-C. Xu, J.-W. Huang, B. Fu, H.C. Yu, W.-H. Zhang, J. Chen, J.-H. Yao, L.-N. Ji, DNA-binding and photocleavage properties of cationic porphyrin–anthraquinone hybrids with different lengths of links, Bioorganic Chemistry Volume 36, (Issue 6), December 2008, Pages 278-287.

V. Zozulya, A. Shcherbakova, I. Dubey, Calculating Helix-to-Coil Transitions of Duplexes Formed by Phenazine-Conjugated Oligonucleotide, Using Flourescence Melting Data, Journal of Fluorescence, Volume 10, (Issue 1), March 2000, Pages 49-54.

V. Zozulya, Yu. Blagoi, I. Dubey, D. Fedoryak, V. Makitruk, O. Ryazanova, A. Shcherbakova, Anchorage of an Oligonucleotide Hybridization by a Tethered Phenazine Nucleoside Analogue, Biopolymers (Biospectroscopy), Volume 72, (Issue 4), 2003, Pages 264-273.

I. Ya. Dubey, D.M. Fedoryak, Novel Reagents for Oligonucleotide Labeling with Imidazophenazine, Ukrainica Bioorganica Acta, Volume 4, (Issue 2), 2006, Pages 3-9.

C. Casas, B. Saint-Jalmes, C. Loup, C. J. Lacey, B. Meunier, Synthesis of Cationic Metalloporphyrin Precursors Related to the Design of DNA Cleavers, Journal of Organic Chemistry, Volume 58, (Issue 10), May 1993, Pages 2913-2917.

I. Dubey, G. Pratviel, B. Meunier, Preparation of Cationic Non-metallated- or Zinc-porphyrin-oligonucleotide Fluorescent Conjugates, Comptes Rendus de l'Académie des Sciences (Paris), Ser. IIC, Volume 1, (Issue 4), April 1998, Pages 259-267.

V. N. Zozulya, O.A. Ryazanova, I.M. Voloshin, L.V. Dubey, I.Ya. Dubey, Spectroscopic Studies on Binding of Porphyrin-Phenazine Conjugate to Intramolecular G-Quadruplex Formed by 22-mer Oligonucleotide, Submitted to Internationall Review of Biophysical chemistry, July 2011.

Y. Zhao, D.G. Truhlar, Comparative DFT Study of van der Waals Complexes: Rare-Gas Dimers, Alkaline-Earth Dimers, Zinc Dimer, and Zinc-Rare-Gas Dimers, Journal of Physical Chemistry A, Volume 110, (Issue 15), March 2006, Pages 5121-5129.

http://www.mcsr.olemiss.edu

V. Barone, M. Cossi, J. Tomasi, Geometry Optimization of Molecular Structures in Solution by the Polarizable Continuum Model, Journal of Computational Chemistry, Volume 19, (Issue 4), March 1998, Pages 404-417.

M. Cossi, G. Scalmani, N. Rega, V. Barone, New Developments in the Polarizable Continuum Model for Quantum Mechanical and Classical Calculations on Molecules in Solution, Journal of Chemical Physics, Volume 117, (Issue 1), July 2002, Pages 43-54.

W.A. Aherne, R.S. Camplejohn, M. Al-Wiswasy, D. Ford, A.M. Kellerer, Assessment of inherent fluctuations of mitotic and labelling indices of human tumours, British Journal of Cancer, Volume 36, (Issue 5), November 1977, Pages 577-582.

C.M. Quinn, N.A. Wright, The clinical assessment of proliferation and growth in human tumours: evaluation of methods and applications as prognostic variables, Journal of Pathology, Volume 160, (Issue 2), February 1990, Pages 93-102.

B, Mestre, G. Pratviel, B. Meunier, Preparation and nuclease activity of hybrid “metallotris(methylpyridinium)porphyrin oligonucleotide” molecules having a 3'-loop for protection against 3'-exonucleases, Bioconjugate Chemistry, Volume 6, (Issue 4), July 1995, Pages 466-472.

D.Y. Lu, M. Huang, C.H. Xu, W.Y. Yang, C.X. Hu, L.P. Lin, L.J. Tong, W. Lu, X.W. Zhang, J. Ding, Anti-proliferative Effects, Cell Cycle C2/M Phase Arrest and Blocking of Chromosome Segregation by Probinane and MST-16 in Human Tumor Cell Lines, BMC Pharmacology, Volume 5, (Paper 11), June 2005, Pages 1-11.


Refbacks

  • There are currently no refbacks.


Please send any question about this web site to info@praiseworthyprize.com
Copyright © 2005-2024 Praise Worthy Prize