A low molecular weight PSMA-based fluorescent imaging agent for cancer

Ying Chen; Surajit Dhara; Sangeeta Ray Banerjee; Youngjoo Byun; Mrudula Pullambhatla; Ronnie C. Mease; Martin G. Pomper

doi:10.1016/j.bbrc.2009.10.017

A low molecular weight PSMA-based fluorescent imaging agent for cancer

Ying Chen, Surajit Dhara, Sangeeta Ray Banerjee, Youngjoo Byun, Mrudula Pullambhatla, Ronnie C. Mease, Martin G. Pomper

School of Medicine

Research output: Contribution to journal › Article › peer-review

100 Scopus citations

Abstract

We synthesized YC-27 3 to provide a fluorescent imaging agent for the prostate-specific membrane antigen (PSMA), a marker for hormone-independent prostate cancer and tumor neovasculature, with suitable pharmacokinetics for use in vivo. Immediate precursor trifluoroacetate salt of 2-(3-{5-[7-(5-amino-1-carboxy-pentylcarbamoyl)-heptanoylamino]-1-carboxy-pentyl}-ureido)-pentanedioic acid 2 was conjugated with a commercially available near-infrared light-emitting dye (IRDye 800CW) to provide 3 in 72% yield. YC-27 3 demonstrated a PSMA inhibitory activity of 0.37 nM and was capable of generating target-to-nontarget ratios of at least 10 in PSMA-expressing PC3-PIP vs. PSMA-negative PC3-flu tumors in vivo. YC-27 3 may be useful for study of PSMA-expressing tissue in preclinical models or for intraoperative guidance.

Original language	English (US)
Pages (from-to)	624-629
Number of pages	6
Journal	Biochemical and Biophysical Research Communications
Volume	390
Issue number	3
DOIs	https://doi.org/10.1016/j.bbrc.2009.10.017
State	Published - Dec 18 2009

Keywords

Fluorescence
Molecular imaging
NAALADase
Prostate-specific membrane antigen
Urea

ASJC Scopus subject areas

Biophysics
Biochemistry
Molecular Biology
Cell Biology

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10.1016/j.bbrc.2009.10.017

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title = "A low molecular weight PSMA-based fluorescent imaging agent for cancer",

abstract = "We synthesized YC-27 3 to provide a fluorescent imaging agent for the prostate-specific membrane antigen (PSMA), a marker for hormone-independent prostate cancer and tumor neovasculature, with suitable pharmacokinetics for use in vivo. Immediate precursor trifluoroacetate salt of 2-(3-{5-[7-(5-amino-1-carboxy-pentylcarbamoyl)-heptanoylamino]-1-carboxy-pentyl}-ureido)-pentanedioic acid 2 was conjugated with a commercially available near-infrared light-emitting dye (IRDye 800CW) to provide 3 in 72% yield. YC-27 3 demonstrated a PSMA inhibitory activity of 0.37 nM and was capable of generating target-to-nontarget ratios of at least 10 in PSMA-expressing PC3-PIP vs. PSMA-negative PC3-flu tumors in vivo. YC-27 3 may be useful for study of PSMA-expressing tissue in preclinical models or for intraoperative guidance.",

keywords = "Fluorescence, Molecular imaging, NAALADase, Prostate-specific membrane antigen, Urea",

author = "Ying Chen and Surajit Dhara and Banerjee, {Sangeeta Ray} and Youngjoo Byun and Mrudula Pullambhatla and Mease, {Ronnie C.} and Pomper, {Martin G.}",

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AU - Chen, Ying

AU - Dhara, Surajit

AU - Banerjee, Sangeeta Ray

AU - Byun, Youngjoo

AU - Pullambhatla, Mrudula

AU - Mease, Ronnie C.

AU - Pomper, Martin G.

PY - 2009/12/18

Y1 - 2009/12/18

N2 - We synthesized YC-27 3 to provide a fluorescent imaging agent for the prostate-specific membrane antigen (PSMA), a marker for hormone-independent prostate cancer and tumor neovasculature, with suitable pharmacokinetics for use in vivo. Immediate precursor trifluoroacetate salt of 2-(3-{5-[7-(5-amino-1-carboxy-pentylcarbamoyl)-heptanoylamino]-1-carboxy-pentyl}-ureido)-pentanedioic acid 2 was conjugated with a commercially available near-infrared light-emitting dye (IRDye 800CW) to provide 3 in 72% yield. YC-27 3 demonstrated a PSMA inhibitory activity of 0.37 nM and was capable of generating target-to-nontarget ratios of at least 10 in PSMA-expressing PC3-PIP vs. PSMA-negative PC3-flu tumors in vivo. YC-27 3 may be useful for study of PSMA-expressing tissue in preclinical models or for intraoperative guidance.

AB - We synthesized YC-27 3 to provide a fluorescent imaging agent for the prostate-specific membrane antigen (PSMA), a marker for hormone-independent prostate cancer and tumor neovasculature, with suitable pharmacokinetics for use in vivo. Immediate precursor trifluoroacetate salt of 2-(3-{5-[7-(5-amino-1-carboxy-pentylcarbamoyl)-heptanoylamino]-1-carboxy-pentyl}-ureido)-pentanedioic acid 2 was conjugated with a commercially available near-infrared light-emitting dye (IRDye 800CW) to provide 3 in 72% yield. YC-27 3 demonstrated a PSMA inhibitory activity of 0.37 nM and was capable of generating target-to-nontarget ratios of at least 10 in PSMA-expressing PC3-PIP vs. PSMA-negative PC3-flu tumors in vivo. YC-27 3 may be useful for study of PSMA-expressing tissue in preclinical models or for intraoperative guidance.

KW - Fluorescence

KW - Molecular imaging

KW - NAALADase

KW - Prostate-specific membrane antigen

KW - Urea

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A low molecular weight PSMA-based fluorescent imaging agent for cancer

Abstract

Keywords

ASJC Scopus subject areas

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