Rapid insertion of bismuth radioactive isotopes into texaphyrin in aqueous media

Thiabaud, Grégory; Radchenko, Valery; Wilson, Justin J.; John, Kevin D.; Birnbaum, Eva R.; Sessler, Jonathan L.

doi:10.1142/S1088424617500870

Title: Rapid insertion of bismuth radioactive isotopes into texaphyrin in aqueous media

Abstract

Radioisotopes ²¹³Bi and ²⁰⁷Bi were successfully inserted into a water-soluble and tumor-targeting texaphyrin ligand. The reaction with ²⁰⁷Bi(OAc)₃ proceeds in about 15 min in aqueous media without the use of any organic base. The Bi(III) texaphyrin complex formed (3) is stable in aqueous media even in the presence of an excess of competitive chelators (EDTA or citric acid), as well as in human blood plasma. Finally, these results validate texaphyrins as potential candidates for coordinating bismuth radionuclides and set the stage for their use in targeted alpha therapy (TAT).

Authors:

Thiabaud, Grégory ^[1]; Radchenko, Valery ^[2]; Wilson, Justin J. ^[2]; John, Kevin D. ^[2]; Birnbaum, Eva R. ^[2]; Sessler, Jonathan L. ^[1]

Univ. of Texas, Austin, TX (United States). Dept. of Chemistry
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

Publication Date:: 2017-12-31

Research Org.:: Los Alamos National Lab. (LANL), Los Alamos, NM (United States); Univ. of Texas, Austin, TX (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES); LANL Laboratory Directed Research and Development (LDRD) Program; Robert A. Welch Foundation (United States)

OSTI Identifier:: 1484672

Report Number(s):: LA-UR-18-31066
Journal ID: ISSN 1088-4246

Grant/Contract Number:: 89233218CNA000001; FG02-01ER15186; F-0018

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Porphyrins and Phthalocyanines

Additional Journal Information:: Journal Volume: 21; Journal Issue: 12; Journal ID: ISSN 1088-4246

Publisher:: World Scientific

Country of Publication:: United States

Language:: English

Subject:: 38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY; bismuth radioisotopes; targeted alpha-emitter therapy; texaphyrin

Citation Formats


                    Thiabaud, Grégory, Radchenko, Valery, Wilson, Justin J., John, Kevin D., Birnbaum, Eva R., and Sessler, Jonathan L. Rapid insertion of bismuth radioactive isotopes into texaphyrin in aqueous media.  United States: N. p., 2017. 
Web.  doi:10.1142/S1088424617500870.

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                    Thiabaud, Grégory, Radchenko, Valery, Wilson, Justin J., John, Kevin D., Birnbaum, Eva R., & Sessler, Jonathan L. Rapid insertion of bismuth radioactive isotopes into texaphyrin in aqueous media.  United States.  https://doi.org/10.1142/S1088424617500870

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                    Thiabaud, Grégory, Radchenko, Valery, Wilson, Justin J., John, Kevin D., Birnbaum, Eva R., and Sessler, Jonathan L. Sun .  
"Rapid insertion of bismuth radioactive isotopes into texaphyrin in aqueous media".  United States.  https://doi.org/10.1142/S1088424617500870.  https://www.osti.gov/servlets/purl/1484672.

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@article{osti_1484672,

  title        = {Rapid insertion of bismuth radioactive isotopes into texaphyrin in aqueous media},

  author       = {Thiabaud, Grégory and Radchenko, Valery and Wilson, Justin J. and John, Kevin D. and Birnbaum, Eva R. and Sessler, Jonathan L.},

  abstractNote = {Radioisotopes 213Bi and 207Bi were successfully inserted into a water-soluble and tumor-targeting texaphyrin ligand. The reaction with 207Bi(OAc)3 proceeds in about 15 min in aqueous media without the use of any organic base. The Bi(III) texaphyrin complex formed (3) is stable in aqueous media even in the presence of an excess of competitive chelators (EDTA or citric acid), as well as in human blood plasma. Finally, these results validate texaphyrins as potential candidates for coordinating bismuth radionuclides and set the stage for their use in targeted alpha therapy (TAT).},

  doi          = {10.1142/S1088424617500870},

  journal      = {Journal of Porphyrins and Phthalocyanines},

  number       = 12,

  volume       = 21,

  place        = {United States},

  year         = {2017},

  month        = {12}

}

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Journal Article:

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https://doi.org/10.1142/S1088424617500870

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Cited by: 5 works

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Figures / Tables:

Scheme 1.: Protocols for metallation of texaphyrin macrocycles. Method 1: Stepwise strategy (“onepot”) that consists in oxidizing first using a ferrocenium salt to form as an intermediate (isolable species), and then inserting the metallic ion Bi³⁺ to form complex; Method 2 (shunting arrow on the left side): Concerted strategy usingmore »

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Works referenced in this record:

Synthesis and structural characterization of lanthanide(III) texaphyrins
journal, July 1993

Sessler, Jonathan L.; Mody, Tarak D.; Hemmi, Gregory W.
Inorganic Chemistry, Vol. 32, Issue 14
DOI: 10.1021/ic00066a032

Synthesis of a Metal-Free Texaphyrin
journal, November 2001

Hannah, Sharon; Lynch, Vincent M.; Gerasimchuk, Nikolay
Organic Letters, Vol. 3, Issue 24
DOI: 10.1021/ol016757s

Targeted alpha therapy using short-lived alpha-particles and the promise of nanobodies as targeting vehicle
journal, May 2016

Dekempeneer, Yana; Keyaerts, Marleen; Krasniqi, Ahmet
Expert Opinion on Biological Therapy, Vol. 16, Issue 8
DOI: 10.1080/14712598.2016.1185412

Bismuth– and lead–texaphyrin complexes: towards potential α-core emitters for radiotherapy
journal, January 2010

Preihs, Christian; Arambula, Jonathan F.; Lynch, Vincent M.
Chemical Communications, Vol. 46, Issue 42
DOI: 10.1039/c0cc03528a

Density Functional Theory Studies of Actinide(III) Motexafins (An-Motex ²⁺ , An = Ac, Cm, Lr). Structure, Stability, and Comparison with Lanthanide(III) Motexafins
journal, April 2006

Cao, Xiaoyan; Li, Quansong; Moritz, Anna
Inorganic Chemistry, Vol. 45, Issue 8
DOI: 10.1021/ic052128t

Pt(IV) Prodrugs Designed to Bind Non-Covalently to Human Serum Albumin for Drug Delivery
journal, June 2014

Zheng, Yao-Rong; Suntharalingam, Kogularamanan; Johnstone, Timothy C.
Journal of the American Chemical Society, Vol. 136, Issue 24
DOI: 10.1021/ja5038269

Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review
journal, March 2000

Maeda, H.; Wu, J.; Sawa, T.
Journal of Controlled Release, Vol. 65, Issue 1-2
DOI: 10.1016/S0168-3659(99)00248-5

An overview of targeted alpha therapy
journal, December 2011

Kim, Young-Seung; Brechbiel, Martin W.
Tumor Biology, Vol. 33, Issue 3
DOI: 10.1007/s13277-011-0286-y

Figures / Tables found in this record:

Scheme 1. (p. 3)

Fig. 1. (p. 5)

Fig. 2. (p. 7)

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Similar Records

Title: Rapid insertion of bismuth radioactive isotopes into texaphyrin in aqueous media

Abstract

Citation Formats

Figures / Tables:

Synthesis and structural characterization of lanthanide(III) texaphyrins journal, July 1993

Synthesis of a Metal-Free Texaphyrin journal, November 2001

Targeted alpha therapy using short-lived alpha-particles and the promise of nanobodies as targeting vehicle journal, May 2016

Bismuth– and lead–texaphyrin complexes: towards potential α-core emitters for radiotherapy journal, January 2010

Density Functional Theory Studies of Actinide(III) Motexafins (An-Motex 2+ , An = Ac, Cm, Lr). Structure, Stability, and Comparison with Lanthanide(III) Motexafins journal, April 2006

Pt(IV) Prodrugs Designed to Bind Non-Covalently to Human Serum Albumin for Drug Delivery journal, June 2014

Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review journal, March 2000

An overview of targeted alpha therapy journal, December 2011

Synthesis and structural characterization of lanthanide(III) texaphyrins
journal, July 1993

Synthesis of a Metal-Free Texaphyrin
journal, November 2001

Targeted alpha therapy using short-lived alpha-particles and the promise of nanobodies as targeting vehicle
journal, May 2016

Bismuth– and lead–texaphyrin complexes: towards potential α-core emitters for radiotherapy
journal, January 2010

Density Functional Theory Studies of Actinide(III) Motexafins (An-Motex ²⁺ , An = Ac, Cm, Lr). Structure, Stability, and Comparison with Lanthanide(III) Motexafins
journal, April 2006

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Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review
journal, March 2000

An overview of targeted alpha therapy
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