Synthesis of meso-(4′-cyanophenyl) porphyrins: efficient photocytotoxicity against A549 cancer cells and their DNA interactions

We report a facile iodine(III)-mediated synthesis of cyanoporphyrins and their DNA photocleavage activity. Cationic-porphyrin 9a showed intercalative binding towards DNA, whereas Zn(II)-cyanoporphyrinate 9b showed outside electrostatic binding as indicated by their absorption and emission spectra. Porphyrin 9a displayed significant photocytotoxicity against A549 cancer cell line with an IC50 value of 54 nM.

[1]  J. Mateos,et al.  (Metallo)porphyrins as potent phototoxic anti-cancer agents after irradiation with red light. , 2015, Chemistry.

[2]  Anil Kumar,et al.  Remarkable photocytotoxicity of a novel triazole-linked cationic porphyrin-β-carboline conjugate. , 2013, Chemical communications.

[3]  S. Mitra,et al.  Facile Synthesis, Characterization, and Fluorescence Studies of Novel Porphyrin Appended Thiazoles , 2013 .

[4]  S. Kerwin,et al.  G-quadruplex DNA cleavage preference and identification of a perylene diimide G-quadruplex photocleavage agent using a rapid fluorescent assay. , 2012, Bioorganic & medicinal chemistry.

[5]  Zao-ying Li,et al.  Fluorescent Properties of the Amidinophenylporphyrins Interacting with DNA , 2012 .

[6]  C. Hunter,et al.  Macroscopic expansion of tetraphenylporphyrin Langmuir layers stimulated by protonation , 2012 .

[7]  W. Marsden.  I and J , 2012 .

[8]  K. Shah,et al.  Synthesis and in-vitro anticancer activity of 3,5-bis(indolyl)-1,2,4-thiadiazoles. , 2011, Bioorganic & medicinal chemistry letters.

[9]  Xunjin Zhu,et al.  Synthesis, characterization, and DNA-binding and -photocleavage properties of water-soluble lanthanide porphyrinate complexes. , 2011, Chemistry.

[10]  P. Kumari,et al.  Isolation, Synthesis and Biomimetic Reactions of Metalloporphyrinoids in Ionic Liquids , 2011 .

[11]  S. Hossain,et al.  Detoxification of cruciferous phytoalexins in Botrytis cinerea: spontaneous dimerization of a camalexin metabolite. , 2011, Phytochemistry.

[12]  Robert Blumenthal,et al.  Light-sensitive lipid-based nanoparticles for drug delivery: design principles and future considerations for biological applications , 2010, Molecular membrane biology.

[13]  H. Burrows,et al.  A New Nonconjugated Naphthalene Derivative of Meso‐tetra‐(3‐hydroxy)‐phenyl‐porphyrin as a Potential Sensitizer for Photodynamic Therapy , 2010, Photochemistry and photobiology.

[14]  S. Rokita,et al.  Dynamic cross-linking is retained in duplex DNA after multiple exchange of strands. , 2010, Angewandte Chemie.

[15]  M. Laranjo,et al.  In Vitro Photodynamic Activity of 5,15‐bis(3‐Hydroxyphenyl)porphyrin and Its Halogenated Derivatives Against Cancer Cells , 2010, Photochemistry and photobiology.

[16]  K. Akamanchi,et al.  IBX/TEAB-mediated oxidative dimerization of thioamides: synthesis of 3,5-disubstituted 1,2,4-thiadiazoles , 2009 .

[17]  Boris Minaev,et al.  Vibration and Fluorescence Spectra of Porphyrin-Cored 2,2-Bis(methylol)-propionic Acid Dendrimers , 2009, Sensors.

[18]  W. Wong,et al.  Synthesis, Characterization, Singlet‐Oxygen Photogeneration, DNA Photocleavage and Two‐Photon‐Absorption Properties of Some (4‐Cyanophenyl)porphyrins , 2009 .

[19]  Koen Clays,et al.  Amphiphilic porphyrins for second harmonic generation imaging. , 2009, Journal of the American Chemical Society.

[20]  R. Granet,et al.  DNA photocleavage by porphyrin-polyamine conjugates. , 2009, Bioorganic & medicinal chemistry.

[21]  C. Dong,et al.  Study on spectroscopic characterization of Cu porphyrin/Co porphyrin and their interactions with ctDNA. , 2008, Talanta.

[22]  D. Kessel,et al.  Apoptosis and Autophagy After Mitochondrial or Endoplasmic Reticulum Photodamage † , 2007, Photochemistry and photobiology.

[23]  Xiang Zhou,et al.  Dicationic pyridium porphyrins appending different peripheral substituents: synthesis and studies for their interactions with DNA. , 2006, Bioorganic & medicinal chemistry.

[24]  J. W. Wells,et al.  Thermodynamics of interactions of water-soluble porphyrins with RNA duplexes. , 2006, Journal of the American Chemical Society.

[25]  T. Takanami,et al.  Metalloporphyrin Cr(TPP)Cl-catalyzed Claisen rearrangement of simple aliphatic allyl vinyl ethers and its unique stereoselectivity , 2005 .

[26]  S. Nakajima,et al.  Highly regio- and stereoselective rearrangement of epoxides to aldehydes catalyzed by high-valent metalloporphyrin complex, Cr(TPP)OTf. , 2004, Journal of the American Chemical Society.

[27]  S. Gibson,et al.  Current clinical and preclinical photosensitizers for use in photodynamic therapy. , 2004, Journal of medicinal chemistry.

[28]  Afaf R. Genady,et al.  Synthesis of triazole- and pyridine-bridged porphyrin-chlorin and porphyrin dimers , 2003 .

[29]  Margaret E. Kosal,et al.  The materials chemistry of porphyrins and metalloporphyrins , 2000 .

[30]  N. Leontis,et al.  Cationic 5,10,15,20-tetrakis(N-methylpyridinium-4-yl)porphyrin fully intercalates at 5'-CG-3' steps of duplex DNA in solution. , 1999, Biochemistry.

[31]  B. R. Munson,et al.  DNA interaction and photocleavage properties of porphyrins containing cationic substituents at the peripheral position. , 1999, Bioconjugate chemistry.

[32]  R. Wheelhouse,et al.  Cationic Porphyrins as Telomerase Inhibitors: the Interaction of Tetra-(N-methyl-4-pyridyl)porphine with Quadruplex DNA , 1998 .

[33]  F. Anson,et al.  NEW ELECTROCATALYSTS FOR THE FOUR-ELECTRON REDUCTION OF DIOXYGEN BASED ON (5,10,15-TRIS(PENTAAMMINERUTHENIUM(II)-4-CYANOPHENYL)-20-(1-METHYLPYRIDINIUM -4-YL)PORPHYRINATO)COBALT(II) IMMOBILIZED ON GRAPHITE ELECTRODES , 1994 .

[34]  O. Prakash,et al.  Preparation of methyl carbamates from primary alkyl- and arylcarboxamides using hypervalent iodine , 1993 .

[35]  R. Fiel.  Porphyrin-nucleic acid interactions: a review. , 1989, Journal of biomolecular structure & dynamics.

[36]  M. Waring,et al.  DNA sequence preferences for an intercalating porphyrin compound revealed by footprinting. , 1987, Nucleic acids research.

[37]  J. Dabrowiak,et al.  DNA binding specificity of a series of cationic metalloporphyrin complexes. , 1986, Biochemistry.

[38]  R. Fiel,et al.  Interaction of DNA with a porphyrin ligand: evidence for intercalation. , 1979, Nucleic Acids Research.