A trithiol bifunctional chelate for 72,77As: A matched pair theranostic complex with high in vivo stability

Feng, Yutian; DeGraffenreid, Anthony J.; Phipps, Michael D.; Rold, Tammy L.; Okoye, Nkemakonam C.; Gallazzi, Fabio A.; Barnes, Charles L.; Cutler, Cathy S.; Ketring, Alan R.; Hoffman, Timothy J.; Jurisson, Silvia S.

doi:10.1016/j.nucmedbio.2018.03.001

Title: A trithiol bifunctional chelate for ^72,77As: A matched pair theranostic complex with high in vivo stability

Abstract

Trithiol chelates are suitable for labeling radioarsenic (⁷²As: 2.49 MeV β⁺, 26 h; ⁷⁷As: 0.683 MeV β^-, 38.8 h) to form potential theranostic radiopharmaceuticals for PET imaging and therapy. In this paper, to investigate the in vivo stability of trithiol chelates complexed with no carrier added (nca) radioarsenic, a bifunctional trithiol chelate was developed, and conjugated to bombesin(7–14)NH₂ as a model peptide. A trithiol-BBN(7–14)NH₂ bioconjugate and its arsenic complex were synthesized and characterized. The trithiol-BBN(7–14)NH₂ conjugate was radiolabeled with ⁷⁷As, its in vitro stability assessed, and biodistribution studies were performed in CF-1 normal mice of free [⁷⁷As]arsenate and ⁷⁷As-trithiol- BBN(7–14)NH₂. The trithiol-BBN(7–14)NH₂ conjugate, its precursors and its As-trithiol-BBN(7–14)NH₂ complex were fully characterized. Radiolabeling studies with nca ⁷⁷As resulted in over 90% radiochemical yield of ⁷⁷As-trithiol-BBN, which was stable for over 48 h. Biodistribution studies were performed with both free [⁷⁷As]arsenate and Sep-Pak® purified ⁷⁷As-trithiol-BBN(7–14)NH₂. Compared to the fast renal clearance of free [⁷⁷As]arsenate, ⁷⁷As-trithiol-BBN(7–14)NH₂ demonstrated increased retention with clearance mainly through the hepatobiliary system, consistent with the lipophilicity of the ⁷⁷As-trithiol-BBN(714)NH₂ complex. Finally, the combined in vitro stability of ⁷⁷As-trithiol-BBN(7–14)NH₂ and the biodistribution results demonstrate its high in vivo stability, making the trithiol a promising platform for developing radioarsenic-based theranosticmore » radiopharmaceuticals.« less

Authors:

Feng, Yutian ^[1]; DeGraffenreid, Anthony J. ^[2]; Phipps, Michael D. ^[1]; Rold, Tammy L. ^[3]; Okoye, Nkemakonam C. ^[1]; Gallazzi, Fabio A. ^[4]; Barnes, Charles L. ^[1]; Cutler, Cathy S. ^[5]; Ketring, Alan R. ^[6]; Hoffman, Timothy J. ^[3];

^[7]

Univ. of Missouri, Columbia, MO (United States). Dept. of Chemistry
Univ. of Missouri, Columbia, MO (United States). Dept. of Chemistry; Brookhaven National Lab. (BNL), Upton, NY (United States). Medical Isotope Research and Production Program (MIRP). Collider-Accelerator Dept.
Harry S. Truman Memorial Veterans' Hospital, Columbia, MO (United States). Research Service
Univ. of Missouri, Columbia, MO (United States). Molecular Interaction Core
Univ. of Missouri, Columbia, MO (United States). Research Reactor Center (MURR); Brookhaven National Lab. (BNL), Upton, NY (United States). Medical Isotope Research and Production Program (MIRP). Collider-Accelerator Dept.
Univ. of Missouri, Columbia, MO (United States). Research Reactor Center (MURR)
Univ. of Missouri, Columbia, MO (United States). Dept. of Chemistry. Research Reactor Center (MURR)

Publication Date:: Sat Mar 10 00:00:00 EST 2018

Research Org.:: Brookhaven National Lab. (BNL), Upton, NY (United States); Univ. of Missouri, Columbia, MO (United States); Harry S. Truman Memorial Veterans' Hospital, Columbia, MO (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Nuclear Physics (NP); National Inst. of Health (NIH) (United States); Dept. of Veterans Affairs (VA) (United States)

OSTI Identifier:: 1464108

Alternate Identifier(s):: OSTI ID: 1544917

Report Number(s):: BNL-207952-2018-JAAM
Journal ID: ISSN 0969-8051; TRN: US1902361

Grant/Contract Number:: SC0012704; SC0003851; SC0010283; 5 T32-EB004822

Resource Type:: Accepted Manuscript

Journal Name:: Nuclear Medicine and Biology

Additional Journal Information:: Journal Volume: 61; Journal ID: ISSN 0969-8051

Publisher:: Elsevier

Country of Publication:: United States

Language:: English

Subject:: 38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY; 62 RADIOLOGY AND NUCLEAR MEDICINE; trithiol bioconjugate; arsenic trithiol; no carrier added 77As; radiolabeling; biodistributions

Citation Formats


                    Feng, Yutian, DeGraffenreid, Anthony J., Phipps, Michael D., Rold, Tammy L., Okoye, Nkemakonam C., Gallazzi, Fabio A., Barnes, Charles L., Cutler, Cathy S., Ketring, Alan R., Hoffman, Timothy J., and Jurisson, Silvia S. A trithiol bifunctional chelate for 72,77As: A matched pair theranostic complex with high in vivo stability.  United States: N. p., 2018. 
Web.  doi:10.1016/j.nucmedbio.2018.03.001.

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                    Feng, Yutian, DeGraffenreid, Anthony J., Phipps, Michael D., Rold, Tammy L., Okoye, Nkemakonam C., Gallazzi, Fabio A., Barnes, Charles L., Cutler, Cathy S., Ketring, Alan R., Hoffman, Timothy J., & Jurisson, Silvia S. A trithiol bifunctional chelate for 72,77As: A matched pair theranostic complex with high in vivo stability.  United States.  https://doi.org/10.1016/j.nucmedbio.2018.03.001

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                    Feng, Yutian, DeGraffenreid, Anthony J., Phipps, Michael D., Rold, Tammy L., Okoye, Nkemakonam C., Gallazzi, Fabio A., Barnes, Charles L., Cutler, Cathy S., Ketring, Alan R., Hoffman, Timothy J., and Jurisson, Silvia S. Sat .  
"A trithiol bifunctional chelate for 72,77As: A matched pair theranostic complex with high in vivo stability".  United States.  https://doi.org/10.1016/j.nucmedbio.2018.03.001.  https://www.osti.gov/servlets/purl/1464108.

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@article{osti_1464108,

  title        = {A trithiol bifunctional chelate for 72,77As: A matched pair theranostic complex with high in vivo stability},

  author       = {Feng, Yutian and DeGraffenreid, Anthony J. and Phipps, Michael D. and Rold, Tammy L. and Okoye, Nkemakonam C. and Gallazzi, Fabio A. and Barnes, Charles L. and Cutler, Cathy S. and Ketring, Alan R. and Hoffman, Timothy J. and Jurisson, Silvia S.},

  abstractNote = {Trithiol chelates are suitable for labeling radioarsenic (72As: 2.49 MeV β+, 26 h; 77As: 0.683 MeV β-, 38.8 h) to form potential theranostic radiopharmaceuticals for PET imaging and therapy. In this paper, to investigate the in vivo stability of trithiol chelates complexed with no carrier added (nca) radioarsenic, a bifunctional trithiol chelate was developed, and conjugated to bombesin(7–14)NH2 as a model peptide. A trithiol-BBN(7–14)NH2 bioconjugate and its arsenic complex were synthesized and characterized. The trithiol-BBN(7–14)NH2 conjugate was radiolabeled with 77As, its in vitro stability assessed, and biodistribution studies were performed in CF-1 normal mice of free [77As]arsenate and 77As-trithiol- BBN(7–14)NH2. The trithiol-BBN(7–14)NH2 conjugate, its precursors and its As-trithiol-BBN(7–14)NH2 complex were fully characterized. Radiolabeling studies with nca 77As resulted in over 90% radiochemical yield of 77As-trithiol-BBN, which was stable for over 48 h. Biodistribution studies were performed with both free [77As]arsenate and Sep-Pak® purified 77As-trithiol-BBN(7–14)NH2. Compared to the fast renal clearance of free [77As]arsenate, 77As-trithiol-BBN(7–14)NH2 demonstrated increased retention with clearance mainly through the hepatobiliary system, consistent with the lipophilicity of the 77As-trithiol-BBN(714)NH2 complex. Finally, the combined in vitro stability of 77As-trithiol-BBN(7–14)NH2 and the biodistribution results demonstrate its high in vivo stability, making the trithiol a promising platform for developing radioarsenic-based theranostic radiopharmaceuticals.},

  doi          = {10.1016/j.nucmedbio.2018.03.001},

  journal      = {Nuclear Medicine and Biology},

  number       = ,

  volume       = 61,

  place        = {United States},

  year         = {Sat Mar 10 00:00:00 EST 2018},

  month        = {Sat Mar 10 00:00:00 EST 2018}

}

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https://doi.org/10.1016/j.nucmedbio.2018.03.001

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Title: A trithiol bifunctional chelate for 72,77As: A matched pair theranostic complex with high in vivo stability

Abstract

Citation Formats

Matched pairs for radionuclide-based imaging and therapy journal, April 2011

Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals journal, July 2016

Radioimmunoimaging with Longer-Lived Positron-Emitting Radionuclides: Potentials and Challenges journal, May 2009

High Yield Production and Radiochemical Isolation of Isotopically Pure Arsenic-72 and Novel Radioarsenic Labeling Strategies for the Development of Theranostic Radiopharmaceuticals journal, December 2015

Chromatographic separation of selenium and arsenic: A potential 72Se/72As generator journal, May 2014

Radioarsenic from a Portable 72Se/72As Generator: A Current Perspective journal, June 2012

A no-carrier-added 72 Se/ 72 As radionuclide generator based on solid phase extraction journal, September 2005

Novel radiochemical separation of arsenic from selenium for 72Se/72As generator journal, May 2012

A no-carrier-added 72 Se/ 72 As radionuclide generator based on distillation journal, April 2004

The separation of carrier-free 72Se from a Germanium oxide target journal, October 1973

Chromatographic separation of germanium and arsenic for the production of high purity 77As journal, April 2016

The role of protein binding of trivalent arsenicals in arsenic carcinogenesis and toxicity journal, March 2008

A new method for the labelling of proteins with radioactive arsenic isotopes journal, December 2006

Vascular Imaging of Solid Tumors in Rats with a Radioactive Arsenic-Labeled Antibody that Binds Exposed Phosphatidylserine journal, March 2008

72/74As-labeling of HPMA based polymers for long-term in vivo PET imaging journal, September 2010

Trithiols and their arsenic compounds for potential use in diagnostic and therapeutic radiopharmaceuticals journal, May 2016

Design, Synthesis, and Biological Evaluation of an Antagonist−Bombesin Analogue as Targeting Vector journal, September 2008

True radiotracers: Cu-64 targeting vectors based upon bombesin peptide journal, August 2009

Optimization, biological evaluation and microPET imaging of copper-64-labeled bombesin agonists, [64Cu-NO2A-(X)-BBN(7–14)NH2], in a prostate tumor xenografted mouse model journal, October 2010

A Trithiol Protio-Ligand and Its Fixation to the Periphery of a Carbosilane Dendrimer as Scaffolds for Polynuclear Rhodium and Iridium Complexes and Metallodendrimers journal, October 2005

A Practical Procedure for the Synthesis of Alkyl Azides at Ambient Temperature in Dimethyl Sulfoxide in High Purity and Yield journal, April 1997

A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes journal, July 2002

Cu-Catalyzed Azide−Alkyne Cycloaddition journal, August 2008

A short history of SHELX journal, December 2007

Isolation and structure of bombesin and alytesin, two analogous active peptides from the skin of the european amphibiansBombina andAlytes journal, February 1971

Arsenic toxicity and potential mechanisms of action journal, July 2002

Arsenic Binding to Proteins journal, June 2013

Title: A trithiol bifunctional chelate for ^72,77As: A matched pair theranostic complex with high in vivo stability

Matched pairs for radionuclide-based imaging and therapy
journal, April 2011

Dithiol Aryl Arsenic Compounds as Potential Diagnostic and Therapeutic Radiopharmaceuticals
journal, July 2016

Radioimmunoimaging with Longer-Lived Positron-Emitting Radionuclides: Potentials and Challenges
journal, May 2009

High Yield Production and Radiochemical Isolation of Isotopically Pure Arsenic-72 and Novel Radioarsenic Labeling Strategies for the Development of Theranostic Radiopharmaceuticals
journal, December 2015

Chromatographic separation of selenium and arsenic: A potential 72Se/72As generator
journal, May 2014

Radioarsenic from a Portable 72Se/72As Generator: A Current Perspective
journal, June 2012

A no-carrier-added ⁷² Se/ ⁷² As radionuclide generator based on solid phase extraction
journal, September 2005

Novel radiochemical separation of arsenic from selenium for 72Se/72As generator
journal, May 2012

A no-carrier-added ⁷² Se/ ⁷² As radionuclide generator based on distillation
journal, April 2004

The separation of carrier-free 72Se from a Germanium oxide target
journal, October 1973

Chromatographic separation of germanium and arsenic for the production of high purity 77As
journal, April 2016

The role of protein binding of trivalent arsenicals in arsenic carcinogenesis and toxicity
journal, March 2008

A new method for the labelling of proteins with radioactive arsenic isotopes
journal, December 2006

Vascular Imaging of Solid Tumors in Rats with a Radioactive Arsenic-Labeled Antibody that Binds Exposed Phosphatidylserine
journal, March 2008

72/74As-labeling of HPMA based polymers for long-term in vivo PET imaging
journal, September 2010

Trithiols and their arsenic compounds for potential use in diagnostic and therapeutic radiopharmaceuticals
journal, May 2016

Design, Synthesis, and Biological Evaluation of an Antagonist−Bombesin Analogue as Targeting Vector
journal, September 2008

True radiotracers: Cu-64 targeting vectors based upon bombesin peptide
journal, August 2009

Optimization, biological evaluation and microPET imaging of copper-64-labeled bombesin agonists, [64Cu-NO2A-(X)-BBN(7–14)NH2], in a prostate tumor xenografted mouse model
journal, October 2010

A Trithiol Protio-Ligand and Its Fixation to the Periphery of a Carbosilane Dendrimer as Scaffolds for Polynuclear Rhodium and Iridium Complexes and Metallodendrimers
journal, October 2005

A Practical Procedure for the Synthesis of Alkyl Azides at Ambient Temperature in Dimethyl Sulfoxide in High Purity and Yield
journal, April 1997

A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes
journal, July 2002

Cu-Catalyzed Azide−Alkyne Cycloaddition
journal, August 2008

A short history of SHELX
journal, December 2007

Isolation and structure of bombesin and alytesin, two analogous active peptides from the skin of the european amphibiansBombina andAlytes
journal, February 1971

Arsenic toxicity and potential mechanisms of action
journal, July 2002

Arsenic Binding to Proteins
journal, June 2013