Edtmp

Base Information

• Chemical Name: Edtmp
• CAS No.: 1429-50-1
• Deprecated CAS: 54579-31-6,66300-26-3,85497-53-6,103333-76-2,244775-21-1,103333-76-2,244775-21-1,66300-26-3,85497-53-6
• Molecular Formula: C6H20N2O12P4
• Molecular Weight: 436.126
• Hs Code.: HOSPHONIC ACID PRODUCT IDENTIFICATION
• European Community (EC) Number: 215-851-5,244-742-5,263-254-3,239-204-1
• UNII: V4CP8RSX7V
• DSSTox Substance ID: DTXSID3061689
• Nikkaji Number: J56.130D
• Wikipedia: EDTMP
• Wikidata: Q3045881
• NCI Thesaurus Code: C90830
• ChEMBL ID: CHEMBL1208647
• Mol file: 1429-50-1.mol

Synonyms:(68Ga)-EDTMP;(ethylenedinitrilo)-tetramethylenephosphonic acid;(ethylenedinitrilo)-tetramethylenephosphonic acid, ammonium salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, calcium (1:1) salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, calcium (1:2) salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, calcium, sodium (1:1:4) salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, hexasodium salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, octaammonium salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, pentasodium salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, potassium salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, sodium salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, tetrapotassium salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, tetrasodium salt;(ethylenedinitrilo)-tetramethylenephosphonic acid, trisodium salt;68Ga-EDTMP;Dequest 2041;editempa;editempa acid;EDTPO;ethylenediaminetetra(methylenephosphonic)acid;ethylenediaminetetramethylenephosphonate, gallium salt;gallium-68 labeled ethylenediamine tetramethylene phosphonate;N,N,N',N' ethylenediamine tetra(methylenephosphonic acid)

Chemical Property of Edtmp

Chemical Property:

• Vapor Pressure: 2.43E-34mmHg at 25°C
• Melting Point: 247 °C
• Refractive Index: 1.622
• Boiling Point: 878.7 °C at 760 mmHg
• PKA: 0.13±0.10(Predicted)
• Flash Point: 485.2 °C
• PSA: 275.84000
• Density: 1.993 g/cm³
• LogP: -1.86880
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Base (Slightly)
• Water Solubility.: 19.6g/L at 20℃
• XLogP3: -11.2
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 11
• Exact Mass: 435.99667207
• Heavy Atom Count: 24
• Complexity: 486

Purity/Quality:

99% ^*data from raw suppliers

Ethylenediaminetetra(methylenephosphonicacid) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphate Compounds
• Canonical SMILES: C(CN(CP(=O)(O)O)CP(=O)(O)O)N(CP(=O)(O)O)CP(=O)(O)O
• General Description: Ethylenebis(nitrilodimethylene)tetraphosphonic acid (EDTP) is a multiphosphonate ligand that forms stable complexes with cerium ions (Ce^III/Ce^IV), enabling site-selective DNA hydrolysis when conjugated to oligonucleotides. This complex facilitates targeted cleavage of phosphodiester bonds in complementary DNA strands through a hydrolytic mechanism, avoiding oxidative damage and preserving nucleoside integrity. The Ce^III/EDTP system, upon oxidation to Ce^IV, demonstrates enhanced efficiency and selectivity compared to traditional Ce^IV-based cutters, making it a promising tool for precise DNA scission in molecular biology applications.

Technology Process of Edtmp

There total 11 articles about Edtmp which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + ethylenediamine (107-15-3,85404-18-8) → 1,2-ethanediylbistetraphosphonic acid (1429-50-1)

Guidance literature:

ethylenediamine; With hydrogenchloride; phosphonic Acid; In water; for 0.0333333h; Microwave irradiation;

formaldehyd; In water; for 0.166667h; Microwave irradiation;

DOI:10.1080/10426501003724897

Reference yield: 48.2%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + ethylenediamine (107-15-3,85404-18-8) → 1,2-ethanediylbistetraphosphonic acid (1429-50-1) + N-methylethylenediamine-N,N',N'-trimethylenetris(phosphonic acid)

Guidance literature:

ethylenediamine; With phosphorous acid; In water; at 136 ℃; Reflux;

formaldehyd; In water; at 130 - 136 ℃; for 4.33333h;

Reference yield: 36.7%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + ethylenediamine (107-15-3,85404-18-8) → 1,2-ethanediylbistetraphosphonic acid (1429-50-1) + <<(2-aminoethyl)imino>bis(methylene)>biphosphonic acid

Guidance literature:

With hydrogenchloride; phosphoric acid; In water; at 100 ℃; for 3h;

upstream raw materials:

chloromethylphosphonic acid

ethylenediamino tris(methylenephosphonic acid)

formaldehyd

ethylenediamine

Refernces

Oxidation of an oligonucleotide-bound Ce^III/Multiphosphonate complex for site-selective DNA scission

10.1002/chem.200902169

The research focuses on the development of a novel strategy for the preparation of site-selective DNA cutters using a CeIII/multiphosphonate complex. The main objective was to improve the site selectivity and scission efficiency of DNA cleavage tools, which have potential applications in molecular biology and therapy. The experiments involved conjugating an oligonucleotide with ethylenediamine-N,N,N',N'-tetrakis(methylenephosphonic acid) (EDTP) to place a CeIII/EDTP complex near predetermined phosphodiester linkages of a complementary target oligonucleotide. The CeIII was then oxidized to CeIV in the presence of atmospheric oxygen, which efficiently cleaved the target phosphodiester linkage without affecting other single-stranded regions, suggesting a hydrolytic pathway. The reactions were monitored using emission spectra to confirm the oxidation of CeIII to CeIV, and the scission fragments were analyzed using denaturing polyacrylamide gel electrophoresis. Scavengers for hydroxyl radicals and singlet oxygen were used to rule out an oxidative pathway, and the integrity of nucleosides was assessed after incubation with the CeIV/EDTP complex to further support the hydrolytic mechanism. The study concluded that the use of a CeIII salt resulted in a more effective and selective DNA cutter compared to previously reported CeIV salt-derived cutters.

Prompt site-selective DNA hydrolysis by Ce(iv)-EDTA using oligonucleotide multiphosphonate conjugates

10.1039/b807789d

The study focuses on the development of a method for site-selective DNA hydrolysis using Ce(IV)–EDTA complex with the aid of oligonucleotide multiphosphonate conjugates. The researchers synthesized oligodeoxyribonucleotide conjugates functionalized with nitrilotris(methylenephosphonic acid) (NTP) and ethylenediaminetetrakis(methylenephosphonic acid) (EDTP) ligands. These conjugates were designed to hybridize with a longer substrate DNA, creating a single-stranded gap site that could be selectively hydrolyzed by the Ce(IV)–EDTA complex. The purpose of using NTP and EDTP was to enhance the catalytic activity and selectivity of the Ce(IV)–EDTA complex towards the gap sites, allowing for efficient and specific DNA cleavage at lower Ce(IV) concentrations while leaving other single-stranded regions intact. The study demonstrated that the presence of two NTP or EDTP ligands on either side of the gap site was crucial for efficient hydrolysis, and the system allowed for site-selective hydrolysis of single-stranded DNA targets of arbitrary length using short additive oligonucleotide conjugates.