Ethylenediamine-N,N'-diacetic acid

• CAS: 5657-17-0
• Catalog Number: ACM5657170-1
• Category: Other Products
• Molecular Weight: 176.17
• Molecular Formula: C6H12N2O4
• Description: Ethylenediaminediacetic acid is an ethylenediamine derivative in which two of the four amine protons of ethylenediamine are replaced by carboxymethyl groups. It has a role as a chelator and a bacterial xenobiotic metabolite. It is an ethylenediamine derivative, a glycine derivative, a polyamino carboxylic acid and an amino dicarboxylic acid. It is a conjugate acid of an ethylenediaminediacetate(1-).
• Synonyms: N,N'-Ethylenediglycine
• IUPAC Name: 2-[2-(Carboxymethylamino)ethylamino]acetic acid
• Canonical SMILES: C(CNCC(=O)O)NCC(=O)O
• InChI: InChI=1S/C6H12N2O4/c9-5(10)3-7-1-2-8-4-6(11)12/h7-8H,1-4H2,(H,9,10)(H,11,12)
• InChI Key: IFQUWYZCAGRUJN-UHFFFAOYSA-N
• Boiling Point: 357ºC
• Melting Point: 224 °C
• Flash Point: 203.7ºC
• Density: 1.31 g/mL
• Appearance: White powder.
• Application: Ethylenediamine-N,N'-diacetic acid (EDDA) is a chelating agent that can be used to synthesize:; Binary and ternary copper(II) complexes with potent proteasome inhibitory properties.; Pd(EDDA) complexes which can coordinate with amino acids, peptides, or DNA units.
• Storage: Store at 2-8 ℃
• Complexity: 142
• Covalently-Bonded Unit Count: 1
• EC Number: 227-105-6
• Exact Mass: 176.08
• Hazard Codes: Xi: Irritant
• Hazard Statements: Xi: Irritant
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Heavy Atom Count: 12
• Hydrogen Bond Acceptor Count: 6
• Hydrogen Bond Donor Count: 4
• MDL Number: MFCD00004281
• Monoisotopic Mass: 176.07970687
• Physical State: Solid
• PSA: 98.66
• Refractive Index: 1.509
• Rotatable Bond Count: 7
• Stability: Stable at room temperature in closed containers under normal storage and handling conditions.
• Topological Polar Surface Area: 98.7Å2
• WGK Germany: 3

Case Study

Application of EDDA as a Ligand in the Synthesis of Radioactive Tracers

Najmeh Rahmanian, et al. Medicinal Chemistry Research, 2018, 27, 890-902.

Coligands such as ethylenediamine-N,N'-diacetic acid (EDDA) which also have impacts on pharmacokinetic properties of the resulting radiolabeled peptide have been used to occupy the remaining cores of 99mTc.
Radiolabeling of HYNIC-SSS-GE11 conjugated peptide
· Labeling of HYNIC-(Ser)3-GE11 with 99mTc Labeling of HYNIC-(Ser)3-GE11 with 99mTc using an exchange ligand approach in the presence of both tricine and EDDA at 95°C gave 99mTc-EDDA/tricine-HYNIC- (Ser)3-GE11 with RCP of 99% (n = 10).
· Briefly, 50 µL solution of tricine (200 mg/mL in 0.5 M ammonium acetate buffer of pH 6.5), 200 µL solution of EDDA (25 mg/mL in 0.5 M ammonium acetate buffer of pH 6.5), 40 µL solution of SnCl2.
· 2H2O (1 mg/mL in 0.1 N HCl) and 100-300 MBq solution of the freshly eluted 99mTc-pertecnetate were added to 10 µL solution of peptide (1 mg/mL in water) in a microcentrifuge tube and incubated at 95°C for 10 min.

EDDA-Based Molecular Probes for Micro-SPECT/CT Imaging

Zhang, Yiqiu, et al. Chemical Biology & Drug Design, 2019, 93(4), 447-453.

Ethylenediamine-N,N'-dacetic acid (EDDA) can be used to synthesize a new (99m)Tc-tricine-EDDA-Hynic-c-Met molecular probe, and further used to screen c-Met indicators of NSCLC in the H1993 nude mouse model, for targeted drug therapy.
Preparation of (99m)Tc-tricine-EDDA-Hynic-c-Met
· Tricine-EDDA solution was prepared by dissolving 20 mg/mL triglycine and 10 mg/mL EDDA in water, pH 6.0 to 7.0.
· In a 1.5 mL centrifuge tube, 25 μL Hynic-c-Met solution (1mg/mL) and 100 μL tricine-EDDA solution were added, followed by adding 65 μL Na99mTcO4 eluent 1 mci and 10 μL SnCl2 solution (1 mg/mL dissolved in 0.1 mol/L HCl), which were reacted in water bath at 30°C for 30min.

Synthesis of EDDA-Based (99m)Tc-5-Fluorouracil for Brain Imaging

Ahmed, N., et al. Journal of Radioanalytical and Nuclear Chemistry, 2016, 309, 805-811.

EDDA can modify the labeling surface of (99m)Tc-5-fluorouracil, which is an anti-tumor agent for solid tumors. The obtained EDDA-(99m)Tc-5-fluorouracil can be localized in the brain and therefore can be further used for brain imaging studies.
Synthesis Procedure of EDDA-based (99m)Tc-5-fluorouracil
· The sample vial contained 10 mg/ml of 5-fluorouracil and 300 μg of stannous chloride in 0.5 ml of 0.9 % normal saline (marked as Vial I-A).
· 2.5 mg of EDDA, 300 μg of disodium hydrogen phosphate dodecahydrate and 0.1 ml of 0.05 N Sodium hydroxide were taken in other vial with final volume of 0.5 ml marked as Vial I-B and transferred to the Vial I-A.
· After 15 min, 500 ± 20 MBq/0.5 ml of sodium pertechnetate was added to the vial with a final volume of 1.5 ml; pH was adjusted at 7.0 ± 0.5 and incubated at 80 °C for 15 min.
· The sample vial was then allowed to cool at temperature for 30 min. The solution was sterilized by passing through 0.2 lm syringe filter. Radiochemical purity was checked by ITLC.