Improved synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N',N'',N'''-tris(acetic acid)cyclododecane (PA-DOTA)

Lara L. Chappell; Buck E. Rogers; M. B. Khazaeli; Matthew S. Mayo; Donald J. Buchsbaum; Martin W. Brechbiel

doi:10.1016/S0968-0896(99)00171-6

Improved synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N',N'',N'''-tris(acetic acid)cyclododecane (PA-DOTA)

Lara L. Chappell, Buck E. Rogers, M. B. Khazaeli, Matthew S. Mayo, Donald J. Buchsbaum, Martin W. Brechbiel

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

40 Scopus citations

Abstract

A concise synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N','',N'''-tris(acetic acid)cyclododecane (PA-DOTA) is reported. Difficulties involving the production of partially alkylated products and their removal have been addressed and obviated. After the pure nitro form of PA-DOTA was obtained, conversion to the isothiocyanato form PA-DOTA (1, conjugation to HuCC49 and HuCC49ΔCH2 monoclonal antibodies was achieved. Subsequent radiolabeling with ¹⁷⁷Lu was performed, demonstrating a useful bifunctional chelating agent suitable for clinical radioimmunotherapy applications. (C) 1999 Published by Elsevier Science Ltd.

Original language	English
Pages (from-to)	2313-2320
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	7
Issue number	11
DOIs	https://doi.org/10.1016/S0968-0896(99)00171-6
State	Published - Nov 1999

Keywords

Biodistribution
DOTA
Lutetium-177
Radioimmono-conjugate

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Chappell, L. L., Rogers, B. E., Khazaeli, M. B., Mayo, M. S., Buchsbaum, D. J., & Brechbiel, M. W. (1999). Improved synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N',N'',N'''-tris(acetic acid)cyclododecane (PA-DOTA). Bioorganic and Medicinal Chemistry, 7(11), 2313-2320. https://doi.org/10.1016/S0968-0896(99)00171-6

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title = "Improved synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N',N'',N'''-tris(acetic acid)cyclododecane (PA-DOTA)",

abstract = "A concise synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N','',N'''-tris(acetic acid)cyclododecane (PA-DOTA) is reported. Difficulties involving the production of partially alkylated products and their removal have been addressed and obviated. After the pure nitro form of PA-DOTA was obtained, conversion to the isothiocyanato form PA-DOTA (1, conjugation to HuCC49 and HuCC49ΔCH2 monoclonal antibodies was achieved. Subsequent radiolabeling with 177Lu was performed, demonstrating a useful bifunctional chelating agent suitable for clinical radioimmunotherapy applications. (C) 1999 Published by Elsevier Science Ltd.",

keywords = "Biodistribution, DOTA, Lutetium-177, Radioimmono-conjugate",

author = "Chappell, {Lara L.} and Rogers, {Buck E.} and Khazaeli, {M. B.} and Mayo, {Matthew S.} and Buchsbaum, {Donald J.} and Brechbiel, {Martin W.}",

year = "1999",

month = nov,

doi = "10.1016/S0968-0896(99)00171-6",

language = "English",

volume = "7",

pages = "2313--2320",

journal = "Bioorganic and Medicinal Chemistry",

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Improved synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N',N'',N'''-tris(acetic acid)cyclododecane (PA-DOTA). / Chappell, Lara L.; Rogers, Buck E.; Khazaeli, M. B. et al.
In: Bioorganic and Medicinal Chemistry, Vol. 7, No. 11, 11.1999, p. 2313-2320.

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

TY - JOUR

T1 - Improved synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N',N'',N'''-tris(acetic acid)cyclododecane (PA-DOTA)

AU - Chappell, Lara L.

AU - Rogers, Buck E.

AU - Khazaeli, M. B.

AU - Mayo, Matthew S.

AU - Buchsbaum, Donald J.

AU - Brechbiel, Martin W.

PY - 1999/11

Y1 - 1999/11

N2 - A concise synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N','',N'''-tris(acetic acid)cyclododecane (PA-DOTA) is reported. Difficulties involving the production of partially alkylated products and their removal have been addressed and obviated. After the pure nitro form of PA-DOTA was obtained, conversion to the isothiocyanato form PA-DOTA (1, conjugation to HuCC49 and HuCC49ΔCH2 monoclonal antibodies was achieved. Subsequent radiolabeling with 177Lu was performed, demonstrating a useful bifunctional chelating agent suitable for clinical radioimmunotherapy applications. (C) 1999 Published by Elsevier Science Ltd.

AB - A concise synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N','',N'''-tris(acetic acid)cyclododecane (PA-DOTA) is reported. Difficulties involving the production of partially alkylated products and their removal have been addressed and obviated. After the pure nitro form of PA-DOTA was obtained, conversion to the isothiocyanato form PA-DOTA (1, conjugation to HuCC49 and HuCC49ΔCH2 monoclonal antibodies was achieved. Subsequent radiolabeling with 177Lu was performed, demonstrating a useful bifunctional chelating agent suitable for clinical radioimmunotherapy applications. (C) 1999 Published by Elsevier Science Ltd.

KW - Biodistribution

KW - DOTA

KW - Lutetium-177

KW - Radioimmono-conjugate

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Improved synthesis of the bifunctional chelating agent 1,4,7,10- tetraaza-N-(1-carboxy-3-(4-nitrophenyl)propyl)-N',N'',N'''-tris(acetic acid)cyclododecane (PA-DOTA)

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Keywords

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