Isothiocyanate-Functionalized Bifunctional Chelates and fac -[M I (CO) 3 ] + (M = Re, 99m Tc) Complexes for Targeting uPAR in Prostate Cancer

Kasten, Benjamin B.; Ma, Xiaowei; Cheng, Kai; Bu, Lihong; Slocumb, Winston S.; Hayes, Thomas R.; Trabue, Steven; Cheng, Zhen; Benny, Paul D.

doi:10.1021/acs.bioconjchem.5b00531

Title: Isothiocyanate-Functionalized Bifunctional Chelates and fac -[M ^I (CO) ₃ ] ⁺ (M = Re, ^99m Tc) Complexes for Targeting uPAR in Prostate Cancer

Journal Article · Wed Nov 25 00:00:00 EST 2015 · Bioconjugate Chemistry

DOI:https://doi.org/10.1021/acs.bioconjchem.5b00531· OSTI ID:1467664

Kasten, Benjamin B. ^[1]; Ma, Xiaowei ^[2]; Cheng, Kai ^[3]; Bu, Lihong ^[3]; Slocumb, Winston S. ^[1]; Hayes, Thomas R. ^[1]; Trabue, Steven ^[4]; Cheng, Zhen ^[3]; Benny, Paul D. ^[1]

Washington State Univ., Pullman, WA (United States)
Stanford Univ., CA (United States); Fourth Military Medical Univ., Xi'an (China)
Stanford Univ., CA (United States)
National Soil Tilth Lab., Ames, IA (United States)

Developing new strategies to rapidly incorporate the fac-[MI(CO)₃]⁺. (M = Re, ^99mTc) core into biological targeting vectors in radiopharmaceuticals continues to expand as molecules become more complex and as efforts to minimize nonspecific binding increase. This work examines a novel isothiocyanate-functionalized bifunctional chelate based on 2,2'-dipicolylamine (DPA) specifically designed for complexing the fac-[MI(CO)₃]⁺. core. Two strategies (postlabeling and prelabeling) were explored using the isothiocyanate-functionalized DPA to determine the effectiveness of assembly on the overall yield and purity of the complex with amine containing biomolecules. A model amino acid (lysine) examined (1) amine conjugation of isothiocyanate-functionalized DPA followed by complexation with fac-[MI(CO)₃]⁺. (postlabeling) and (2) complexation of fac-[MI(CO)₃]⁺. with isothiocyanate-functionalized DPA followed by amine conjugation (prelabeling). Conducted with stable Re and radioactive ^99mTc analogs, both strategies formed the product in good to excellent yields under macroscopic and radiotracer concentrations. A synthetic peptide (AE105) which targets an emerging biomarker in CaP prognosis, urokinase-type plasminogen activator receptor (uPAR), was also explored using the isothiocyanate-functionalized DPA strategy. In vitro PC-3 (uPAR+) cell uptake assays with the ^99mTc-labeled peptide (8a) showed 4.2 ± 0.5% uptake at 4 h. In a murine model bearing PC-3 tumor xenografts, in vivo biodistribution of 8a led to favorable tumor uptake (3.7 ± 0.7% ID/g) at 4 h p.i. with relatively low accumulation (<2% ID/g) in normal organs not associated with normal peptide excretion. These results illustrate the promise of the isothiocyanate-functionalized approach for labeling amine containing biological targeting vectors with fac-[MI(CO)₃]⁺.

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Research Organization:: Stanford Univ., CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0008397

OSTI ID:: 1467664

Journal Information:: Bioconjugate Chemistry, Vol. 27, Issue 1; ISSN 1043-1802

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 8 works

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Title: Isothiocyanate-Functionalized Bifunctional Chelates and fac -[M I (CO) 3 ] + (M = Re, 99m Tc) Complexes for Targeting uPAR in Prostate Cancer

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