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Journal of Chemical Sciences

, 130:133 | Cite as

Synthesis and in vitro photobiological studies of porphyrin capped gold nanoparticles\(^{\S }\)

  • Albish K Paul
  • Dhanya T Jayaram
  • P S Saneesh Babu
  • Nagappanpillai Adarsh
  • Shameel Thurakkal
  • Asha S Nair
  • Danaboyina Ramaiah
Regular Article
  • 122 Downloads

Abstract

We describe the synthesis and characterization of a thiol-functionalized porphyrin derivative 2 and its gold nanoparticle conjugates. The porphyrin 2 exhibited its characteristic intense Soret absorption at 420 nm with a molar extinction coefficient value of \(3.6\times 10^{5}\, \hbox {M}^{-1}\, \hbox {cm}^{-1}\) and good fluorescence in the region of 650–660 nm. The porphyrin-capped gold nanoparticles (POPNPs) were synthesized from the citrate-capped gold nanoparticles by the ligand exchange method and characterized by spectroscopic and morphological analyses (UV–Vis, DLS and TEM). The broadening of the absorption spectrum and quenching of the fluorescence intensity for the porphyrin gold nanoconjugates suggest efficient incorporation of the porphyrin moiety onto the gold surface. The results of DLS and TEM analyses indicate that the nanoconjugate POPNPs are uniformly spherical in shape with a size of ca. \(25 \pm 5\, \hbox {nm}\) and exhibits a negative zeta potential value of \(-\,16.0 \pm 2\, \hbox {mV}\). The singlet oxygen generation efficiency of the porphyrin 2 and POPNPs was calculated and are found to be ca. \(0.53 \pm 0.02\) and \(0.43 \pm 0.03\), respectively. The in vitro photobiological studies revealed that POPNPs exhibited enhanced photodynamic activity compared to their parent porphyrin derivative 2 with an \(\hbox {IC}_{50}\) value of \(5\, \upmu \hbox {M}\) in MDA MB 231 cell lines. The mechanism of the cell destruction was studied by Annexin-FITC and confirmed through TMRM assay. We observed the increase in the percentage of cell population corresponding to the late apoptotic stage ca. 37.7% and 51.2% for 5 and \(10\, \upmu \hbox {M}\) of POPNPs, respectively, thereby demonstrating their apoptotic-mediated cell destruction and use in PDT applications.

Graphical Abstract

Synopsis We synthesized a thiol-functionalized porphyrin-based sensitizer 2 and its gold nanoparticles (POPNPs) and have investigated their photophysical properties, singlet oxygen generation and in vitro photobiological efficacy. Our results demonstrate that the incorporation of the sensitizer onto the surface of nanoparticles not only improved its solubility in the aqueous medium, photophysical and photobiological properties but also its potential as a novel sensitizer for photodynamic therapeutical applications.

Keywords

Gold nanoparticles porphyrin MTT assay singlet oxygen apoptosis 

Notes

Supplementary material

12039_2018_1539_MOESM1_ESM.pdf (470 kb)
Supplementary material 1 (pdf 469 KB)

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Copyright information

© Indian Academy of Sciences 2018

Authors and Affiliations

  1. 1.Photosciences and Photonics Section, Chemical Sciences and Technology DivisionCSIR-National Institute for Interdisciplinary Science and TechnologyThiruvananthapuramIndia
  2. 2.Rajiv Gandhi Centre for BiotechnologyThiruvananthapuramIndia
  3. 3.Academy of Scientific and Innovative Research (AcSIR), CSIR-NIIST CampusThiruvananthapuramIndia
  4. 4.CSIR-North East Institute of Science and TechnologyJorhatIndia

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