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Kim HL, Sachin K, Jeong HJ, et al. F-18 Labeled RGD Probes Based on Bioorthogonal Strain-Promoted Click Reaction for PET Imaging. ACS Med Chem Lett. 2015;6(4):402-7doi: 10.1021/ml500464f.
Kim, H. L., Sachin, K., Jeong, H. J., Choi, W., Lee, H. S., & Kim, D. W. (2015). F-18 Labeled RGD Probes Based on Bioorthogonal Strain-Promoted Click Reaction for PET Imaging. ACS medicinal chemistry letters, 6(4), 402-7. https://doi.org/10.1021/ml500464f
Kim, Hye Lan, et al. "F-18 Labeled RGD Probes Based on Bioorthogonal Strain-Promoted Click Reaction for PET Imaging." ACS medicinal chemistry letters vol. 6,4 (2015): 402-7. doi: https://doi.org/10.1021/ml500464f
Kim HL, Sachin K, Jeong HJ, Choi W, Lee HS, Kim DW. F-18 Labeled RGD Probes Based on Bioorthogonal Strain-Promoted Click Reaction for PET Imaging. ACS Med Chem Lett. 2015 Feb 06;6(4):402-7. doi: 10.1021/ml500464f. eCollection 2015 Apr 09. PMID: 25893040; PMCID: PMC4394342.
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ACS Med Chem Lett. 2015 Feb 06;6(4):402-7. doi: 10.1021/ml500464f. eCollection 2015 Apr 09.

F-18 Labeled RGD Probes Based on Bioorthogonal Strain-Promoted Click Reaction for PET Imaging.

ACS medicinal chemistry letters

Hye Lan Kim, Kalme Sachin, Hyeon Jin Jeong, Wonsil Choi, Hyun Soo Lee, Dong Wook Kim

Affiliations

  1. Department of Nuclear Medicine, Chonbuk National University Medical School , Jeonju, Jeonbuk 561-712, Korea.
  2. Department of Chemistry and Chemical Engineering, Inha University , 100 Inha-ro, Nam-gu, Incheon 402-751, Korea.
  3. Department of Chemistry, Sogang University , Seoul 121-742, Korea.

PMID: 25893040 PMCID: PMC4394342 DOI: 10.1021/ml500464f

Abstract

A series of fluorine-substituted monomeric and dimeric cRGD peptide derivatives, such as cRGD-ADIBOT-F (ADIBOT = azadibenzocyclooctatriazole), di-cRGD-ADIBOT-F, cRGD-PEG5-ADIBOT-F, and di-cRGD-PEG5-ADIBOT-F, were prepared by strain-promoted alkyne azide cycloaddition (SPAAC) reaction of the corresponding aza-dibenzocyclooctyne (ADIBO) substituted peptides with a fluorinated azide 3. Among these cRGD derivatives, di-cRGD-PEG5-ADIBOT-F had the highest binding affinity in a competitive binding assay compared to other derivatives and even the original cRGDyk. On the basis of the in vitro study results, di-cRGD-PEG5-ADIBOT-(18)F was prepared from a SPAAC reaction with (18)F-labeled azide and subsequent chemo-orthogonal scavenger-assisted separation without high performance liquid chromatography (HPLC) purification in 92% decay-corrected radiochemical yield (dcRCY) with high specific activity for further in vivo positron emission tomography (PET) imaging study. In vivo PET imaging study and biodistribution data showed that this radiotracer allowed successful visualization of tumors with good tumor-to-background contrast and significantly higher tumor uptake compared to other major organs.

Keywords: F-18 labeling method; PET molecular imaging; RGD peptide; copper-free click chemistry; fluorine-18; radiopharmaceuticals; tumor angiogenesis

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