1332367-79-9

Basic information

• Product Name: dimethyl 6,6′([ethane-1,2-diylbis{benzylazanediyl}]bis[methylene])dipicolinate
• Synonyms: dimethyl 6,6′([ethane-1,2-diylbis{benzylazanediyl}]bis[methylene])dipicolinate
• CAS NO: 1332367-79-9
• Molecular Weight: 538.646
• Mol File: 1332367-79-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: dimethyl 6,6′([ethane-1,2-diylbis{benzylazanediyl}]bis[methylene])dipicolinate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 6,6′([ethane-1,2-diylbis{benzylazanediyl}]bis[methylene])dipicolinate(1332367-79-9)
• EPA Substance Registry System: dimethyl 6,6′([ethane-1,2-diylbis{benzylazanediyl}]bis[methylene])dipicolinate(1332367-79-9)

Safety Data

• Hazardous Substances Data: 1332367-79-9(Hazardous Substances Data)

Upstream product

• 3412-76-8 N,N'-dibenzylethylenediamine dihydrochloride 
• 146462-25-1 methyl 6-(bromomethyl)picolinate 
• 104-71-2 N,N'-bis(benzyliden)ethylendiamine 
• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 
• 100-52-7 benzaldehyde 
• 140-28-3 N,N'-Dibenzylethylenediamine 
• 39977-44-1 methyl 6-(hydroxymethyl)pyridine-2-carboxylate 

Downstream Products

• 1332367-80-2 6,6'-((ethane-1,2-diylbis(benzylazanediyl))bis(methylene))dipicolinic acid 

Relevant articles and documents

Rapid Thermodynamically Stable Complex Formation of [nat/111In]In3+, [nat/90Y]Y3+, and [nat/177Lu]Lu3+ with H6dappa

A phosphinate-bearing picolinic acid-based chelating ligand (H6dappa) was synthesized and characterized to assess its potential as a bifunctional chelator (BFC) for inorganic radiopharmaceuticals. Nuclear magnetic resonance (NMR) spectroscopy was employed to investigate the chelator coordination chemistry with a variety of nonradioactive trivalent metal ions (In3+, Lu3+, Y3+, Sc3+, La3+, Bi3+). Density functional theory (DFT) calculations explored the coordination environments of aforementioned metal complexes. The thermodynamic stability of H6dappa with four metal ions (In3+, Lu3+, Y3+, Sc3+) was deeply investigated via potentiometric and spectrophotometric (UV-vis) titrations, employing a combination of acidic in-batch, joint potentiometric/spectrophotometric, and ligand-ligand competition titrations; high stability constants and pM values were calculated for all four metal complexes. Radiolabeling conditions for three clinically relevant radiometal ions were optimized ([111In]In3+, [177Lu]Lu3+, [90Y]Y3+), and the serum stability of [111In][In(dappa)]3- was studied. Through concentration-, time-, temperature-, and pH-dependent labeling experiments, it was determined that H6dappa radiolabels most effectively at near-physiological pH for all radiometal ions. Furthermore, very rapid radiolabeling at ambient temperature was observed, as maximal radiolabeling was achieved in less than 1 min. Molar activities of 29.8 GBq/μmol and 28.2 GBq/μmol were achieved for [111In]In3+ and [177Lu]Lu3+, respectively. For H6dappa, high thermodynamic stability did not correlate with kinetic inertness-lability was observed in serum stability studies, suggesting that its metal complexes might not be suitable as a BFC in radiopharmaceuticals.

BIFUNCTIONAL CHELATING AGENTS

A bifunctional chelating agent of the formula (I): wherein the variables R1, R1 , Q1, Q2 and M are as defined in the description of the present application. Also described is a complex of the above chelating age