23911-26-4

Usage

Uses

Used in Medical Imaging:
DIETHYLENETRIAMINEPENTAACETIC DIANHYDRIDE is used as a synthetic intermediate for producing DPTA, which is essential in the synthesis of GO-DEN(Gd-DTPA)-mAb. This contrast reagent is utilized for prostate tumor MRI imaging, aiding in the detection and monitoring of prostate cancer.
Used in Cancer Treatment:
DIETHYLENETRIAMINEPENTAACETIC DIANHYDRIDE is used as a component in the development of GO-DEN(Gd-DTPA)-mAb/DOX, an effective delivery system for anti-cancer drugs. This system allows for targeted delivery of drugs, such as DOX, to prostate cancer cells (PC-3) in mice, enhancing the therapeutic efficacy and reducing side effects associated with conventional chemotherapy.

InChI:InChI=1/C14H19N3O8/c18-10(19)5-15(1-3-16-6-11(20)24-12(21)7-16)2-4-17-8-13(22)25-14(23)9-17/h1-9H2,(H,18,19)

Upstream product

• 67-43-6 diethylenetriaminopentaacetic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 265648-73-5 3,9-bis[2-(benzyloxy)-2-oxoethyl]-6-(carboxymethyl)-3,6,9-triazaundecanedioic acid 
• 122404-69-7 N-(4-carboxy-3-hydroxyphenylcarbamoylmethyl)-N,N',N'',N''-diethylenetriaminetetraacetic acid 
• 150922-49-9 (HOOCCH₂)(4-HOOC-3-HO-C₆H₃NHCOCH₂)NCH₂CH₂N(CH₂COOH)CH₂CH₂N(CH₂COOH)(CH₂CONHC₆H₃-3-OH-4-COOH) 

Relevant academic research and scientific papers

Synthesis and study on magnetic resonance imaging performance of Gd(III)-DTPA-bisfuran-2-carbohydrazide as a potential MRI contrast agent

One novel ligand, diethylenetriamine-N, N?-bi(acetyl-furan-2-carbohydrazide)-N, N?, N?-triacetic acid (H3L), has been synthesized in high yield by the reaction of bicyclic anhydride of diethylenetraiaminepentaacetic acid (DTPA) with furan-2-carbohydrazide. It has three carboxylic groups, and the corresponding nonion complex of Gd(III)-L holding promise of magnetic resonance imaging (MRI) was obtained by treating these ligand with Gd2O3 in water. The efficacy of the contrast agent was assessed by measuring the longitudinal relaxivity (r1) and T1 weighted magnetic resonance imaging in vitro. The r1 of Gd(III)-DTPA-bisfuran-2- carbohydrazide was up to 5.92 mM-1￠s-1, which was 1.27 times higher than that of the analogous MRI contrast agent Gd(III)-DTPA(4.65 mM-1￠s-1) in clinical application. T1 weighted magnetic resonance imaging in vitro showed that proton signal intensity increased with Gd(III) complex concentration and the imaging effect of Gd(III)-DTPA-bisfuran-2-carbohydrazide was superior to that of Gd(III)-DTPA in the same condition. These results showed that the complex might be considered as a potential MRI contrast agent.

A dual-excitation fluorescent probe EuIII-dtpa-bis(HBT) for hydrazine detection in aqueous solutions and living cells

Based on the esterification of 2-(2-hydroxyphenyl)benzothiazole (HBT) and a rare-earth metal ion complex EuIII-dtpa, a novel dual-excitation fluorescence probe, EuIII-dtpa-bis(HBT), was developed for the detection of hydrazine (N2H4). The structure of dtpa-bis(HBT) was characterized via FT-IR and NMR, and its optical properties were studied via UV-vis absorption and fluorescence spectroscopy. Influencing factors including solution acidity, interfering substances and N2H4 concentrations were considered for the detection of N2H4 using EuIII-dtpa-bis(HBT). EuIII-dtpa-bis(N2H4) and HBT emit significant fluorescence at 470 nm (λex = 270 nm) and 480 nm (λex = 325 nm), respectively. The detection limit of EuIII-dtpa-bis(HBT) with N2H4 was 0.283 μM (14 ppb) and 0.182 μM (9 ppb) upon excitation at 270 nm and 325 nm, which is close to and lower than the EPA standard (10 ppb), respectively. The mechanism for the detection of N2H4 by EuIII-dtpa-bis(HBT) was deduced from the experimental results and theoretical calculations. Also, cytotoxicity and cell imaging experiments of EuIII-dtpa-bis(HBT) were performed. The experimental results showed that the fluorescent probe EuIII-dtpa-bis(HBT) can be applied to detect N2H4 in aqueous solution and living cells.

Synthesis and Characterization of Amphiphilic Gd(III) Complexes: Gd-DTPA-BA

Magnetic resonance imaging (MRI) is widely used to identify different diseases. MRI contrast agents, used to enhance the MRI signal, have been studied extensively for precise diagnosis. Based on the advantages of macromolecular MRI contrast agents of higher contrast imaging ability and a longer cycle time, this article modified the most common micromolecular contrast agent (Gd-diethylene triamine pentaacetic acid [DTPA]). 2 long saturated aliphatic chains were attached to both sides of DTPA. DTPA derivatives with 12, 14, and 16 carbon lengths were synthesized and chelated to Gd3+. 3 amphiphilic MRI contrast agents were obtained and their structures were characterized using mass spectrometry, 1H NMR, and Fourier transform infrared. Furthermore, the surface tension of the compounds was measured, and liposomes were prepared by mixing the synthesized amphiphilic molecules with egg lecithin and cholesterol. The assembly behavior of the liposomes was studied using transmission electron microscopy (TEM), dynamic light scattering (DLS), and zeta potential measurements. TEM showed that the liposomes possessed bilayer vesicle structures. The liposome size distribution determined by DLS was from 10 to 1000 nm, and as the aliphatic chain length increased, the polydispersity index (PDI) and zeta potential increased. No obvious changes in the PDI and zeta potential of the liposomes were observed after 5 days at room temperature, suggesting that they possess good stability.

Synthesis soluble non-ion transition metal manganese(II), cobalt(II), nickel(II) complexes of diethylenetriamine-N,N′,N″-tri(acetyl-p-hydroxybenzoyl hydrazine)- N,N″- bisacetic acid as potential contrast enhancement agent

A novel ligand, diethylenetriamine-N,N′,N″-tri(acetyl-p-hydroxybenzoyl hydrazine)-N,N″-bisacetic acid, and its three soluble non-ion transition metal complexes, ML· nH2O (M = Mn, n = 4; M = Co, Ni, n = 2) have been synthesized and characterized on the basis of elemental analysis, molar conductivities, 1H NMR, FAB-MS, TG-DTA analysis, and IR methods. In addition, relaxivity of complexes are determined, The relaxivity (R1) of MnL, CoL, NiL, and Gd(DTPA)2- used as control are 6.33, 2.71, 2.60, and 4.34L·mmol-1·s-1, respectively. The spin-lattice relaxivity of MnL are larger than that of Gd(DTPA)2-. The results showed that complex of MnL may be a potential MRI contrast agent with high spin-lattice relaxivity, good solubility, low osmotic pressure due to non-ion complex.

Design and synthesis of novel adenine fluorescence probe based on Eu(III) complexes with dtpa-bis(guanine) ligand

A novel adenine (Ad) fluorescence probe (EuIII-dtpa-bis(guanine)) was designed and synthesized by improving experimental method based on the Eu(III) complex and dtpa-bis(guanine) ligand. The dtpa-bis(guanine) ligand was first synthesized by the acylation action between dtpaa and guanine (Gu), and the corresponding Eu(III) complex was successfully prepared through heat-refluxing method with dtpa-bis(guanine) ligand. As a novel fluorescence probe, the EuIII-dtpa-bis(guanine) complex can detect adenine (Ad) with characteristics of strong targeting, high specificity and high recognition ability. The detection mechanism of the adenine (Ad) using this probe in buffer solution was studied by ultraviolet-visible (UV–vis) and fluorescence spectroscopy. When the EuIII-dtpa-bis(guanine) was introduced to the adenine (Ad) solution, the fluorescence emission intensity was significantly enhanced. However, adding other bases such as guanine (Gu), xanthine (Xa), hypoxanthine (Hy) and uric acid (Ur) with similar composition and structure to that of adenine (Ad) to the EuIII-dtpa-bis(guanine) solution, the fluorescence emission intensities are nearly invariable. Meanwhile, the interference of guanine (Gu), xanthine (Xa), hypoxanthine (Hy) and uric acid (Ur) on the detection of the adenine using EuIII-dtpa-bis(guanine) probe was also studied. It was found that presence of these bases does not affect the detection of adenine (Ad). A linear response of fluorescence emission intensities of EuIII-dtpa-bis(guanine) at 570?nm as a function of adenine (Ad) concentration in the range of 0.00–5.00?×?10??5?mol?L??1 was observed. The detection limit is about 4.70?×?10??7?mol?L??1.

Design and synthesis of a novel fluorescent probe, euiii-dtpa-bis(Adenine), and application for the detection of orotic acid in urine

For detection of orotic acid (OA), a novel fluorescent probe, EuIII-dtpa-bis(adenine), was designed and synthesized based on the complementation base pairing principle. The dtpa-bis(adenine) ligand was characterized by nuclear magnetic resonance spectroscopy (1H NMR and13C NMR), Fourier transform infrared spectra (FTIR), and elemental analysis. Then, the effects of solution pH values and some coexisting interfering substances on OA detection using EuIII-dtpa-bis(adenine) as a fluorescent probe were investigated. The linear relationship of F0/F and OA concentration in the range of 10–150 μmol/L was obtained, where F0 and F are the fluorescence intensities of EuIII-dtpa-bis(adenine) at 320 nm in the absence and presence of OA, respectively. The calculated limit of detection is about 0.807 μmol/L. The detection mechanism of OA was proposed. In addition, the detection of OA in urine samples has also been studied. It was found that the designed and synthesized fluorescent probe is effective for the detection of OA in urine samples.

Synthesis, biological evaluation and molecular docking studies of high-affinity bone targeting N,N'-Bis (alendronate) diethylenetriamene-N,N'-triacetic acid: A bifunctional bone scintigraphy agent

A bisphosphonate derivative DTPA-bis(alendronate) conjugate has been synthesized and evaluated as potential radiopharmaceutical for bone imaging. The compound was synthesized by the covalent coupling of DTPA-bis(anhydride) with alendronate and was char-acterized on the basis of IR, NMR and mass spectroscopy. It was labelled with 99mTc with 96% efficacy and was found stable for about 24 h under physiological conditions. Blood kinetic studies of 99mTc DTPA-bis(alendronate) showed a biexponential pattern as well as quick washout from the blood circulation. The biological t1/2(F) and t1/2(S) were found to be 50 min ± 0.001 and 6 h 30 min ± 0.005, respectively. Imaging and biodistribution studies showed a significant accumulation of 99mTc DTPA-bis(alendronate) conjugate at bone site. Bone-to-muscles ratios were 12.08 ± 0.001 at 1 h, 45.33 ± 0.001 at 4 h and 35.83 ± 0.001 at 24 h after post-injection, respectively. The receptor binding of the 99mTc-DTPA-bis (alendronate) was established on human bone cell line (Soas-2) revealed KD = 0.86 nm. The preliminary result of the 99mTc-DTPA-bis(alendronate) is encouraging to carrying out further in vivo experiment for targeted bone imaging because of good-bone-to-normal-organ contrast. Further docking analysis with molecular targets, farnesyl diphosphate synthase, geranylgeranyl pyrophosphate and osteocalcin revealed the high affinity of -17.419 and thus represents strong potential of bone-imaging agent.

Synthesis of novel macrocyclic lanthanide chelates derived from bis-pyrazolylpyridine.

[structure: see text] New macrocyclic chelates based on bis-pyrazolylpyridine and diethylenetriaminepentaacetic acid are synthesized, and the remarkable luminescence properties of their lanthanide chelates are reported.

Lanthanide-containing polycations for monitoring polyplex dynamics via lanthanide resonance energy transfer

Theranostic nanomaterials have emerged in the past decade that combine therapeutic delivery and diagnostic imaging into one package. Such materials offer the opportunity to aid diagnosis, track therapeutic biodistribution, and monitor drug release. We have developed a series of nucleic acid delivery polymers containing oligoethylene amines that are able to be protonated at physiological pH (for binding/compacting pDNA) and a lanthanide-chelating domain, which imparts diagnostic functionality. Diamine monomers (containing between 3 and 6 Boc-protected ethyleneamines) were prepared via a multistep procedure involving the selective protection and deprotection of primary and secondary amines. The polymer structures were then synthesized by step-growth polymerization of the oligoethylene diamines with a bisanhydride of diethylenetriamine pentaacetic acid (DTPA-BA), yielding degrees of polymerization between 18 and 24. Chelation of the polymers with gadolinium and terbium was performed to offer MRI contrast agent and luminescence properties, respectively. All of the polymer chelates were found to house approximately one water coordination site, as calculated by the Horrocks equation and possess longitudinal relaxivities (r1, on a per Gd basis) at least twice that of Magnevist, a clinical contrast agent. All the structures formed polyplexes with pDNA with highly positive zeta potentials and hydrodynamic diameters around 50-80 nm. Lanthanide resonance energy transfer (LRET) was used to monitor polyplex association and dissociation. Polyplexes were formed using the donor-acceptor pair comprising of terbium-chelated polymer with five ethyleneamines within the repeat unit (6c-Tb) and tetramethyl rhodamine (TMR)-labeled pDNA. Association/dissociation in the presence of heparin and NaCl was monitored. The effect of amine number along the polymer backbone on transfection efficiency and cytotoxicity was also investigated. None of the polymers revealed cytotoxic effects with cultured cells; however, the polymer with six ethyleneamines clearly offered the highest transfection efficiency. This preliminary study offers insight into the development of materials with the ability to monitor polyplex unpackaging over time within the cellular environment.

A caged lanthanide complex as a paramagnetic shift agent for protein NMR

A lanthanide complex, named CLaNP (caged lanthanide NMR probe) has been developed for the characterisation of proteins by paramagnetic NMR spectroscopy. The probe consists of a lanthanide chelated by a derivative of DTPA (diethylene-triaminepentaacetic acid) with two thiol reactive functional groups. The CLaNP molecule is attached to a protein by two engineered, surface-exposed, Cys residues in a bidentate manner. This drastically limits the dynamics of the metal relative to the protein and enables measurements of pseudocontact shifts. NMR spectroscopy experiments on a diamagnetic control and the crystal structure of the probe-protein complex demonstrate that the protein structure is not affected by probe attachment. The probe is able to induce pseudocontact shifts to at least 40 A from the metal and causes residual dipolar couplings due to alignment at a high magnetic field. The molecule exists in several isomeric forms with different paramagnetic tensors; this provides a fast way to obtain long-range distance restraints.