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Novel amphiphilic cationic porphyrin and its Ag(II) complex as potential anticancer agents.

Publication ,  Journal Article
Tovmasyan, A; Babayan, N; Poghosyan, D; Margaryan, K; Harutyunyan, B; Grigoryan, R; Sarkisyan, N; Spasojevic, I; Mamyan, S; Sahakyan, L ...
Published in: J Inorg Biochem
November 2014

In the present study we have synthesized a novel amphiphilic porphyrin and its Ag(II) complex through modification of water-soluble porphyrinic structure in order to increase its lipophilicity and in turn pharmacological potency. New cationic non-symmetrical meso-substituted porphyrins were characterized by UV-visible, electrospray ionization mass spectrometry (ESI-MS), (1)H NMR techniques, lipophilicity (thin-layer chromatographic retention factor, Rf), and elemental analysis. The key toxicological profile (i.e. cytotoxicity and cell line- (cancer type-) specificity; genotoxicity; cell cycle effects) of amphiphilic Ag porphyrin was studied in human normal and cancer cell lines of various tissue origins and compared with its water-soluble analog. Structural modification of the molecule from water-soluble to amphiphilic resulted in a certain increase in the cytotoxicity and a decrease in cell line-specificity. Importantly, Ag(II) porphyrin showed less toxicity to normal cells and greater toxicity to their cancerous counterparts as compared to cisplatin. The amphiphilic complex was also not genotoxic and demonstrated a slight cytostatic effect via the cell cycle delay due to the prolongation of S-phase. As expected, the performed structural modification affected also the photocytotoxic activity of metal-free amphiphilic porphyrin. The ligand tested on cancer cell line revealed a dramatic (more than 70-fold) amplification of its phototoxic activity as compared to its water-soluble tetracationic metal-free analog. The compound combines low dark cytotoxicity with 5 fold stronger phototoxicity relative to Chlorin e6 and could be considered as a potential photosensitizer for further development in photodynamic therapy.

Duke Scholars

Published In

J Inorg Biochem

DOI

EISSN

1873-3344

Publication Date

November 2014

Volume

140

Start / End Page

94 / 103

Location

United States

Related Subject Headings

  • Spectrometry, Mass, Electrospray Ionization
  • Silver
  • Proton Magnetic Resonance Spectroscopy
  • Porphyrins
  • Inorganic & Nuclear Chemistry
  • Humans
  • Drug Screening Assays, Antitumor
  • Cell Line, Tumor
  • Cations
  • Antineoplastic Agents
 

Citation

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Tovmasyan, A., Babayan, N., Poghosyan, D., Margaryan, K., Harutyunyan, B., Grigoryan, R., … Gasparyan, G. (2014). Novel amphiphilic cationic porphyrin and its Ag(II) complex as potential anticancer agents. J Inorg Biochem, 140, 94–103. https://doi.org/10.1016/j.jinorgbio.2014.06.013
Tovmasyan, Artak, Nelli Babayan, David Poghosyan, Kristine Margaryan, Boris Harutyunyan, Rusanna Grigoryan, Natalia Sarkisyan, et al. “Novel amphiphilic cationic porphyrin and its Ag(II) complex as potential anticancer agents.J Inorg Biochem 140 (November 2014): 94–103. https://doi.org/10.1016/j.jinorgbio.2014.06.013.
Tovmasyan A, Babayan N, Poghosyan D, Margaryan K, Harutyunyan B, Grigoryan R, et al. Novel amphiphilic cationic porphyrin and its Ag(II) complex as potential anticancer agents. J Inorg Biochem. 2014 Nov;140:94–103.
Tovmasyan, Artak, et al. “Novel amphiphilic cationic porphyrin and its Ag(II) complex as potential anticancer agents.J Inorg Biochem, vol. 140, Nov. 2014, pp. 94–103. Pubmed, doi:10.1016/j.jinorgbio.2014.06.013.
Tovmasyan A, Babayan N, Poghosyan D, Margaryan K, Harutyunyan B, Grigoryan R, Sarkisyan N, Spasojevic I, Mamyan S, Sahakyan L, Aroutiounian R, Ghazaryan R, Gasparyan G. Novel amphiphilic cationic porphyrin and its Ag(II) complex as potential anticancer agents. J Inorg Biochem. 2014 Nov;140:94–103.
Journal cover image

Published In

J Inorg Biochem

DOI

EISSN

1873-3344

Publication Date

November 2014

Volume

140

Start / End Page

94 / 103

Location

United States

Related Subject Headings

  • Spectrometry, Mass, Electrospray Ionization
  • Silver
  • Proton Magnetic Resonance Spectroscopy
  • Porphyrins
  • Inorganic & Nuclear Chemistry
  • Humans
  • Drug Screening Assays, Antitumor
  • Cell Line, Tumor
  • Cations
  • Antineoplastic Agents