Development of PEGylated peptide probes conjugated with (18)F-labeled BODIPY for PET/optical imaging of MT1-MMP activity

J Control Release. 2015 Dec 28;220(Pt A):476-483. doi: 10.1016/j.jconrel.2015.11.012. Epub 2015 Nov 11.

Abstract

Since the processing activity of the matrix metalloproteinase MT1-MMP regulates various cellular functions such as motility, invasion, growth, differentiation and apoptosis, precise in vivo evaluation of MT1-MMP activity in cancers can provide beneficial information for both basic and clinical studies. For this purpose, we designed a cleavable Positron Emission Tomography (PET)/optical imaging probe consisting of BODIPY650/665 and polyethylene glycol (PEG) conjugated to opposite ends of MT1-MMP substrate peptides. We used in vitro and in vivo fluorescence experiments to select suitable substrate peptide sequences and PEG sizes for the MT1-MMP probes and obtained an optimized structure referred to here as MBP-2k. Radiofluorinated MBP-2k ([(18)F]MBP-2k) was then successfully synthesized via an (18)F-(19)F isotopic exchange reaction in BODIPY650/665. After intravenous injection into mice with xenografted tumors, [(18)F]MBP-2k showed significantly higher accumulation in HT1080 tumors with high MT1-MMP activity than in A549 tumors that have low MT1-MMP activity. Moreover, PET images showed better contrast in HT1080 tumors. These results show that [(18)F]MBP-2k can be used as a hybrid PET/optical imaging agent and is a promising probe for non-invasive monitoring of MT1-MMP activity in cancers. This probe may also efficiently combine targeted tumor imaging with image-guided surgery that could be beneficial for patients in the future.

Keywords: MT1-MMP; Optical imaging; Peptide; Polyethylene glycol (PEG); Positron emission tomography (PET).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biomarkers, Tumor / metabolism*
  • Boron Compounds / administration & dosage*
  • Boron Compounds / chemistry
  • Boron Compounds / pharmacokinetics
  • Cell Line, Tumor
  • Fibrosarcoma / diagnostic imaging*
  • Fibrosarcoma / enzymology
  • Fibrosarcoma / pathology
  • Fluorescent Dyes / administration & dosage*
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / pharmacokinetics
  • Fluorine Radioisotopes / administration & dosage*
  • Fluorine Radioisotopes / chemistry
  • Fluorine Radioisotopes / pharmacokinetics
  • Heterografts
  • Humans
  • Injections, Intravenous
  • Lung Neoplasms / diagnostic imaging*
  • Lung Neoplasms / enzymology
  • Lung Neoplasms / pathology
  • Male
  • Matrix Metalloproteinase 14 / metabolism*
  • Mice, Inbred BALB C
  • Mice, Nude
  • Microscopy, Fluorescence
  • Optical Imaging / methods*
  • Peptides / administration & dosage*
  • Peptides / chemical synthesis
  • Peptides / pharmacokinetics
  • Polyethylene Glycols / administration & dosage*
  • Polyethylene Glycols / chemical synthesis
  • Positron-Emission Tomography / methods*
  • Predictive Value of Tests
  • Radiopharmaceuticals / administration & dosage*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacokinetics
  • Substrate Specificity
  • Tissue Distribution

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Biomarkers, Tumor
  • Boron Compounds
  • Fluorescent Dyes
  • Fluorine Radioisotopes
  • Peptides
  • Radiopharmaceuticals
  • Polyethylene Glycols
  • MMP14 protein, human
  • Matrix Metalloproteinase 14