In vitro cellular uptake and dimerization of signal transducer and activator of transcription-3 (STAT3) identify the photosensitizing and imaging-potential of isomeric photosensitizers derived from chlorophyll-a and bacteriochlorophyll-a

J Med Chem. 2011 Oct 13;54(19):6859-73. doi: 10.1021/jm200805y. Epub 2011 Sep 6.

Abstract

Among the photosensitizers investigated, both ring-D and ring-B reduced chlorins containing the m-iodobenzyloxyethyl group at position-3 and a carboxylic acid functionality at position-17(2) showed the highest uptake by tumor cells and light-dependent photoreaction that correlated with maximal tumor-imaging [positron emission tomography (PET) and fluorescence] and long-term photodynamic therapy (PDT) efficacy in BALB/c mice bearing Colon26 tumors. However, among the ring-D reduced compounds, the isomer containing the 1'-m-iobenzyloxyethyl group at position-3 was more effective than the corresponding 8-(1'-m-iodobenzyloxyethyl) derivative. All photosensitizers showed maximum uptake by tumor tissue 24 h after injection, and the tumors exposed with light at low fluence and fluence rates (128 J/cm(2), 14 mW/cm(2)) produced significantly enhanced tumor eradication than those exposed at higher fluence and fluence rate (135 J/cm(2), 75 mW/cm(2)). Interestingly, dose-dependent cellular uptake of the compounds and light-dependent STAT3 dimerization have emerged as sensitive rapid indicators for PDT efficacy in vitro and in vivo and could be used as in vitro/in vivo biomarkers for evaluating and optimizing the in vivo treatment parameters of the existing and new PDT candidates.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Bacteriochlorophyll A / chemical synthesis*
  • Bacteriochlorophyll A / chemistry
  • Bacteriochlorophyll A / pharmacology
  • Cell Line, Tumor
  • Chlorophyll / chemical synthesis*
  • Chlorophyll / chemistry
  • Chlorophyll / pharmacology
  • Chlorophyll A
  • Humans
  • Iodine Radioisotopes
  • Isomerism
  • Mice
  • Mice, Inbred BALB C
  • Neoplasm Transplantation
  • Neoplasms, Experimental / diagnostic imaging
  • Neoplasms, Experimental / drug therapy
  • Photosensitizing Agents / chemical synthesis*
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacology
  • Positron-Emission Tomography
  • Protein Multimerization
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacology
  • STAT3 Transcription Factor / metabolism*
  • Structure-Activity Relationship
  • Transplantation, Heterologous

Substances

  • Bacteriochlorophyll A
  • Iodine Radioisotopes
  • Photosensitizing Agents
  • Radiopharmaceuticals
  • STAT3 Transcription Factor
  • Chlorophyll
  • Chlorophyll A