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Synthesis of novel technetium-99m tricarbonyl-HBED-CC complexes and structural prediction in solution by density functional theory calculation.

ABSTRACT: HBED-CC (N,N'-bis[2-hydroxy-5-(carboxyethyl)benzyl]ethylene diamine-N,N'-diacetic acid, L1 ) is a common bifunctional chelating agent in preparation of 68Ga-radiopharmaceuticals. Due to its high stability constant for the Ga3+ complex (logKGaL = 38.5) and its acyclic structure, it is well known for a rapid and efficient radiolabelling at ambient temperature with Gallium-68 and its high in vivo stability. [99mTc][Tc(CO)3(H2O)3]+ is an excellent precursor for radiolabelling of biomolecules. The aim of this study was to develop a novel preparation method of 99mTc-HBED-CC complexes. In this study, HBED-CC-NI (2,2'-(ethane-1,2-diylbis((2-hydroxy-5-(3-((2-(2-nitro-1H-imidazol-1-yl)ethyl)amino)-3-oxopropyl)benzyl)-azanediyl))-diacetic acid, L2 ), a derivative of HBED-CC, was designed and synthesized. Both L1 and L2 were radiolabelled by [99mTc][Tc(CO)3(H2O)3]+ successfully for the first time. In order to explore the coordination mode of metal and chelates, non-radioactive Re(CO)3 L1 and Re(CO)3 L2 were synthesized and characterized spectroscopically. Tc(CO)3 L1 and Tc(CO)3 L2 in solution were calculated by density functional theory and were analysed with radio-HPLC chromatograms. It showed that [99mTc]Tc(CO)3 L2 forms two stable diastereomers in solution, which is similar to those of [68Ga]Ga-HBED-CC complexes. Natural bond orbital analysis through the natural population charges revealed a charge transfer between [99mTc][Tc(CO)3]+ and L1 or L2 . The experimental results showed that tricarbonyl technetium might form stable complex with HBED-CC derivatives, which is useful for the future application of using HBED-CC as a bifunctional chelating agent in developing new 99mTc-radiopharmaceuticals as diagnostic imaging agents.

SUBMITTER: Shi S

PROVIDER: S-EPMC6894603 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Synthesis of novel technetium-99m tricarbonyl-HBED-CC complexes and structural prediction in solution by density functional theory calculation.

Shi Shengyu S Yao Lifeng L Li Linlin L Wu Zehui Z Zha Zhihao Z Kung Hank F HF Zhu Lin L Fang De-Cai DC

Royal Society open science 20191127 11

HBED-CC (N,N'-bis[2-hydroxy-5-(carboxyethyl)benzyl]ethylene diamine-N,N'-diacetic acid, L1 ) is a common bifunctional chelating agent in preparation of 68Ga-radiopharmaceuticals. Due to its high stability constant for the Ga3+ complex (logKGaL = 38.5) and its acyclic structure, it is well known for a rapid and efficient radiolabelling at ambient temperature with Gallium-68 and its high in vivo stability. [99mTc][T ...[more]

PMID: 31827858

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Project description:Background and purposeNiosomes are nonionic surfactant-based vesicles that exhibit certain unique features which make them favorable nanocarriers for sustained drug delivery in cancer therapy. Biodistribution studies are critical in assessing if a nanocarrier system has preferential accumulation in a tumor by enhanced permeability and retention effect. Radiolabeling of nanocarriers with radioisotopes such as Technetium-99m (99mTc) will allow for the tracking of the nanocarrier noninvasively via nuclear imaging. The purpose of this study was to formulate, characterize, and optimize 99mTc-labeled niosomes.MethodsNiosomes were prepared from a mixture of sorbitan monostearate 60, cholesterol, and synthesized D-?-tocopherol polyethylene glycol 1000 succinate-diethylenetriaminepentaacetic acid (synthesis confirmed by 1H and 13C nuclear magnetic resonance spectroscopy). Niosomes were radiolabeled by surface chelation with reduced 99mTc. Parameters affecting the radiolabeling efficiency such as concentration of stannous chloride (SnCl2·H2O), pH, and incubation time were evaluated. In vitro stability of radiolabeled niosomes was studied in 0.9% saline and human serum at 37°C for up to 8 hours.ResultsNiosomes had an average particle size of 110.2±0.7 nm, polydispersity index of 0.229±0.008, and zeta potential of -64.8±1.2 mV. Experimental data revealed that 30 µg/mL of SnCl2·H2O was the optimal concentration of reducing agent required for the radiolabeling process. The pH and incubation time required to obtain high radiolabeling efficiency was pH 5 and 15 minutes, respectively. 99mTc-labeled niosomes exhibited high radiolabeling efficiency (>90%) and showed good in vitro stability for up to 8 hours.ConclusionTo our knowledge, this is the first study published on the surface chelation of niosomes with 99mTc. The formulated 99mTc-labeled niosomes possessed high radiolabeling efficacy, good stability in vitro, and show good promise for potential use in nuclear imaging in the future.

Dataset Information

Synthesis of novel technetium-99m tricarbonyl-HBED-CC complexes and structural prediction in solution by density functional theory calculation.

Publications

Synthesis of novel technetium-99m tricarbonyl-HBED-CC complexes and structural prediction in solution by density functional theory calculation.

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