Gd-complexes of DTPA-bis(amides) functionalized by pyridine and picolinamide: Synthesis, thermodynamic stability, and relaxivity properties

Sk Md Nasiruzzaman; Ji Ae Park; Yongmin Chang; Tae Jeong Kim

doi:10.5012/bkcs.2008.29.6.1211

Gd-complexes of DTPA-bis(amides) functionalized by pyridine and picolinamide: Synthesis, thermodynamic stability, and relaxivity properties

Sk Md Nasiruzzaman, Ji Ae Park, Yongmin Chang, Tae Jeong Kim

Department of Medicine

Kyungpook National University

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

2 Scopus citations

Abstract

A series of DTPA-bis(amides) functionalized by pyridine (1a-c) and N-phenylpicolinamide) (1d-e) and their Gd(III)-complexes of the type [Gd(1)(H₂O)]·xH₂O (2a-e) were prepared and characterized by analytical and spectroscopic techniques. Potentiality of 2a-e as contrast agents for magnetic resonance imaging (MRI CA) was investigated by measuring relevant physicochemical properties and relaxivities and compared with [Gd(DTPA-BMA)(H₂O)] (DTPA-BMA=N,N″-di(methylcarbamoylmethyl) diethylenetriamine-N,N′,N″-triacetate) (Omniscan®). The R ₁ relaxivities of aqueous solutions of 2a-c are in the range of 3.33 -5.02 mM^-1sec^-1, which are comparable with those of Omniscan® (r₁ = 4.58 mM^-1sec^-1). Complexes 2d-e, insoluble in water, exhibit relatively higher R₁ values (8.1- 8.3 mM^-1sec^-1) in HP-β-CD solutions.

Original language	English
Pages (from-to)	1211-1216
Number of pages	6
Journal	Bulletin of the Korean Chemical Society
Volume	29
Issue number	6
DOIs	https://doi.org/10.5012/bkcs.2008.29.6.1211
State	Published - 20 Jun 2008

Keywords

Gd(DTPA-bisamide)
MRI CA
Picolinamide
Pyridine
T1 relaxivity

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title = "Gd-complexes of DTPA-bis(amides) functionalized by pyridine and picolinamide: Synthesis, thermodynamic stability, and relaxivity properties",

abstract = "A series of DTPA-bis(amides) functionalized by pyridine (1a-c) and N-phenylpicolinamide) (1d-e) and their Gd(III)-complexes of the type [Gd(1)(H2O)]·xH2O (2a-e) were prepared and characterized by analytical and spectroscopic techniques. Potentiality of 2a-e as contrast agents for magnetic resonance imaging (MRI CA) was investigated by measuring relevant physicochemical properties and relaxivities and compared with [Gd(DTPA-BMA)(H2O)] (DTPA-BMA=N,N″-di(methylcarbamoylmethyl) diethylenetriamine-N,N′,N″-triacetate) (Omniscan{\textregistered}). The R 1 relaxivities of aqueous solutions of 2a-c are in the range of 3.33 -5.02 mM-1sec-1, which are comparable with those of Omniscan{\textregistered} (r1 = 4.58 mM-1sec-1). Complexes 2d-e, insoluble in water, exhibit relatively higher R1 values (8.1- 8.3 mM-1sec-1) in HP-β-CD solutions.",

keywords = "Gd(DTPA-bisamide), MRI CA, Picolinamide, Pyridine, T1 relaxivity",

author = "Nasiruzzaman, {Sk Md} and Park, {Ji Ae} and Yongmin Chang and Kim, {Tae Jeong}",

year = "2008",

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T1 - Gd-complexes of DTPA-bis(amides) functionalized by pyridine and picolinamide

T2 - Synthesis, thermodynamic stability, and relaxivity properties

AU - Nasiruzzaman, Sk Md

AU - Park, Ji Ae

AU - Chang, Yongmin

AU - Kim, Tae Jeong

PY - 2008/6/20

Y1 - 2008/6/20

N2 - A series of DTPA-bis(amides) functionalized by pyridine (1a-c) and N-phenylpicolinamide) (1d-e) and their Gd(III)-complexes of the type [Gd(1)(H2O)]·xH2O (2a-e) were prepared and characterized by analytical and spectroscopic techniques. Potentiality of 2a-e as contrast agents for magnetic resonance imaging (MRI CA) was investigated by measuring relevant physicochemical properties and relaxivities and compared with [Gd(DTPA-BMA)(H2O)] (DTPA-BMA=N,N″-di(methylcarbamoylmethyl) diethylenetriamine-N,N′,N″-triacetate) (Omniscan®). The R 1 relaxivities of aqueous solutions of 2a-c are in the range of 3.33 -5.02 mM-1sec-1, which are comparable with those of Omniscan® (r1 = 4.58 mM-1sec-1). Complexes 2d-e, insoluble in water, exhibit relatively higher R1 values (8.1- 8.3 mM-1sec-1) in HP-β-CD solutions.

AB - A series of DTPA-bis(amides) functionalized by pyridine (1a-c) and N-phenylpicolinamide) (1d-e) and their Gd(III)-complexes of the type [Gd(1)(H2O)]·xH2O (2a-e) were prepared and characterized by analytical and spectroscopic techniques. Potentiality of 2a-e as contrast agents for magnetic resonance imaging (MRI CA) was investigated by measuring relevant physicochemical properties and relaxivities and compared with [Gd(DTPA-BMA)(H2O)] (DTPA-BMA=N,N″-di(methylcarbamoylmethyl) diethylenetriamine-N,N′,N″-triacetate) (Omniscan®). The R 1 relaxivities of aqueous solutions of 2a-c are in the range of 3.33 -5.02 mM-1sec-1, which are comparable with those of Omniscan® (r1 = 4.58 mM-1sec-1). Complexes 2d-e, insoluble in water, exhibit relatively higher R1 values (8.1- 8.3 mM-1sec-1) in HP-β-CD solutions.

KW - Gd(DTPA-bisamide)

KW - MRI CA

KW - Picolinamide

KW - Pyridine

KW - T1 relaxivity

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ER -

Gd-complexes of DTPA-bis(amides) functionalized by pyridine and picolinamide: Synthesis, thermodynamic stability, and relaxivity properties

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