嘧啶-4,6-二羧酸及其单酯与有机金属面-[M(CO)3]+(M = Re 和 99mTc)核的水络合物作为放射性药物探针:合成与表征

IF 2.1 3区 化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR Journal of Organometallic Chemistry Pub Date : 2024-09-03 DOI:10.1016/j.jorganchem.2024.123348
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引用次数: 0

摘要

目前的研究重点是面-[M(CO)3]+(M = Re 和 99mTc)核心与嘧啶-4,6-二羧酸(H2pmdc)及其单酯 6-(乙氧基羰基)嘧啶-4-羧酸(Hetpmdc)的水络合物的合成和表征,它们是未来设计成像和治疗放射性药物的模型。H2pmdc 与 [Re(CO)5Br] 分别在水和 [99mTc(CO)3(OH2)3]+ 水溶液中反应生成[M(CO)3(OH2)(Hpmdc)]复合物(M = Re (1) 和 99mTc (2))。还研究了[Re(CO)5Br]与 H2pmdc 在乙醇(EtOH)中的反应,并生成了[Re(CO)3(OH2)(etpmdc)] 复合物(3),其中 etpmdc- 是 6-(乙氧羰基)嘧啶-4-羧酸阴离子,它是 H2pmdc 在与面-[Re(CO)3]+ 单元配位的同时发生单酯化反应而形成的。H2pmdc 与[99mTc(CO)3(OH2)3]+ 和乙醇的水溶液反应生成了[99mTc(CO)3(OH2)(etpmdc)]复合物(4)。利用 1H NMR、13C NMR、IR、ESI-MS 和元素分析对 1 和 3 进行了化学鉴定。利用单晶 X 射线晶体学进一步鉴定了络合物 3。通过将两种复合物共同注入带有 UV/Vis 检测器和 γ 检测器的高效液相色谱中,然后比较 2 的 γ 峰和 1 的 UV 峰的保留时间,最终明确地鉴定出了 2,从而评估了 1 和 2 在结构上的相似性。同样,在用于鉴定 2 结构的同一高效液相色谱中,将复合物 1 和 3 与 H2pmdc 与 [99mTc(CO)3(OH2)3]+ 和乙醇的水溶液反应生成的产物共同注入,然后比较 2 和 4 的 γ 峰保留时间以及 1 和 3 的紫外峰保留时间,评估了与 2 同时形成的复合物 [99mTc(CO)3(OH2)(etpmdc)] (4)。
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Aqua-complexes of pyrimidine-4,6-dicarboxylic acid and its monoester with organometallic fac-[M(CO)3]+ (M = Re and 99mTc) core as radiopharmaceutical probes: Synthesis and characterization

The current study highlights on the synthesis and characterization of aqua-complexes of the fac-[M(CO)3]+ (M = Re and 99mTc) core with pyrimidine-4,6-dicarboxylic acid (H2pmdc) and its monoester 6-(ethoxycarbonyl)pyrimidine-4-carboxylic acid (Hetpmdc), which are the model for future design of imaging and therapeutic radiopharmaceuticals. Complexes [M(CO)3(OH2)(Hpmdc)] (M = Re (1) and 99mTc (2)) were formed from the reaction of H2pmdc with [Re(CO)5Br] in water and aqueous solution of [99mTc(CO)3(OH2)3]+ respectively. The reaction of [Re(CO)5Br] with H2pmdc in ethanol (EtOH) has also studied and led to the complex [Re(CO)3(OH2)(etpmdc)] (3), where etpmdcis 6-(ethoxycarbonyl)pyrimidine-4-carboxylate anion which was formed from the mono-esterification of H2pmdc in parallel with its coordination to the fac-[Re(CO)3]+ unit. The complex [99mTc(CO)3(OH2)(etpmdc)] (4) was formed in parallel with 2 by reacting H2pmdc with aqueous solution of [99mTc(CO)3(OH2)3]+ and ethanol. The chemical identification of 1 and 3 was achieved by using 1H NMR, 13C NMR, IR, ESI-MS and elemental analysis. Complex 3 was furtherly identified by using single crystal X-ray crystallography. The structural similarities of 1 and 2 was assessed by coinjection of both complexes in the HPLC with UV/Vis detection coupled with a γ-detector followed by comparison of retention times of the γ-peak of 2 and the UV-peak of 1 which allowed unambiguous identification of 2. Similarly, the formation of complex [99mTc(CO)3(OH2)(etpmdc)] (4) in parallel with 2 was assessed by coinjection of complexes 1 and 3 with the product from the reaction of H2pmdc with aqueous solution of [99mTc(CO)3(OH2)3]+ and ethanol in the same HPLC as one used for the structural identification of 2 followed by comparison of retention times of the γ-peaks of 2 and 4 and the UV-peaks of 1 and 3.

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来源期刊
Journal of Organometallic Chemistry
Journal of Organometallic Chemistry 化学-无机化学与核化学
CiteScore
4.40
自引率
8.70%
发文量
221
审稿时长
36 days
期刊介绍: The Journal of Organometallic Chemistry targets original papers dealing with theoretical aspects, structural chemistry, synthesis, physical and chemical properties (including reaction mechanisms), and practical applications of organometallic compounds. Organometallic compounds are defined as compounds that contain metal - carbon bonds. The term metal includes all alkali and alkaline earth metals, all transition metals and the lanthanides and actinides in the Periodic Table. Metalloids including the elements in Group 13 and the heavier members of the Groups 14 - 16 are also included. The term chemistry includes syntheses, characterizations and reaction chemistry of all such compounds. Research reports based on use of organometallic complexes in bioorganometallic chemistry, medicine, material sciences, homogeneous catalysis and energy conversion are also welcome. The scope of the journal has been enlarged to encompass important research on organometallic complexes in bioorganometallic chemistry and material sciences, and of heavier main group elements in organometallic chemistry. The journal also publishes review articles, short communications and notes.
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