201416-10-6

Upstream product

• 67-56-1 methanol 
• 197906-32-4 2-methoxy-5-methylbenzene-1,3-dicarboxylic acid 
• 91-04-3 2,6-bis(hydroxymethyl)-4-methylphenol 
• 40617-52-5 2,6-dicarboxylic acid-4-methylphenol 
• 74-88-4 methyl iodide 

Downstream Products

• 1612753-24-8 tri-tert-butyl 2,2',2''-(10-(2-((4-methoxy-3,5-bis(methylcarbamoyl)benzyl) amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetate 
• 1612753-25-9 2,2',2''-(10-(2-((4-methoxy-3,5-bis(methylcarbamoyl)benzyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid 
• 1612753-26-0 2,2',2''-(10-(2-((4-hydroxy-3,5-bis(methylcarbamoyl)benzyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)triacetic acid 
• 1612753-19-1 2-methoxy-N¹,N³-dimethyl-5-((2-(4,7,10-tris(2-(benzylamino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)methyl)isophthalamide 
• 1612753-20-4 2-methoxy-N¹,N³-dimethyl-5-((2-(4,7,10-tris(2-(hexylamino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)methyl)isophthalamide 
• 1612753-21-5 2-methoxy-N¹,N³-dimethyl-5-((2-(4,7,10-tris(2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)-1,4,7,10-tetraazacyclododecan-1-yl)acetamido)methyl)isophthalamide 
• 1612753-22-6 triethyl-2,2',2''-((2,2',2''-(10-(2-((4-methoxy-3,5-bis(methylcarbamoyl)benzyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)tris(acetyl))tris(azanediyl))tripropanoate 
• 1612753-23-7 hexaethyl-2,2',2''-((2,2',2''-(10-(2-((4-methoxy-3,5-bis(methylcarbamoyl)benzyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triyl)tris(acetyl))tris(azanediyl))tripentanedioate 
• 1612753-14-6 5-formyl-2-methoxy-N¹,N³-dimethylisophthalamide 
• 1612753-15-7 5-((hydroxyimino)methyl)-2-methoxy-N¹,N³-dimethylisophthalamide 
• 1630981-41-7 5-(aminomethyl)-2-methoxy-N¹,N³-dimethylisophthalamide hydrochloride 
• 1612753-16-8 5-(aminomethyl)-2-methoxy-N¹,N³-dimethylisophthalamide 
• 1612753-17-9 tri-tert-butyl 10-(2-((4-methoxy-3,5-bis(methylcarbamoyl)benzyl)amino)-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-tricarboxylate 
• 1612753-13-5 2-methoxy-N¹,N³,5-trimethylisophthalamide 

Relevant academic research and scientific papers

Effect of lanthanide complex structure on cell viability and association

A systematic study of the effect of hydrophobicity and charge on the cell viability and cell association of lanthanide metal complexes is presented. The terbium luminescent probes feature a macrocyclic polyaminocarboxylate ligand (DOTA) in which the hydrophobicity of the antenna and that of the carboxyamide pendant arms are independently varied. Three sensitizing antennas were investigated in terms of their function in vitro: 2-methoxyisophthalamide (IAM(OMe)), 2-hydroxyisophthalamide (IAM), and 6-methylphenanthridine (Phen). Of these complexes, Tb-DOTA-IAM exhibited the highest quantum yield, although the higher cell viability and more facile synthesis of the structurally related Tb-DOTA-IAM(OMe) platform renders it more attractive. Further modification of this latter core structure with carboxyamide arms featuring hydrophobic benzyl, hexyl, and trifluoro groups as well as hydrophilic amino acid based moieties generated a family of complexes that exhibit high cell viability (ED 50 > 300 μM) regardless of the lipophilicity or the overall complex charge. Only the hexyl-substituted complex reduced cell viability to 60% in the presence of 100 μM complex. Additionally, cellular association was investigated by ICP-MS and fluorescence microscopy. Surprisingly, the hydrophobic moieties did not increase cell association in comparison to the hydrophilic amino acid derivatives. It is thus postulated that the hydrophilic nature of the 2-methoxyisophthalamide antenna (IAM(OMe)) disfavors the cellular association of these complexes. As such, responsive luminescent probes based on this scaffold would be appropriate for the detection of extracellular species.

Hydrogen-bonding-mediated anthranilamide homoduplexes. Increasing stability through preorganization and iterative arrangement of a simple amide binding site

This paper describes the assembly of two new series of self-complementary duplexes by making use of amide units, the simplest assembling units of hydrogen bonding, as binding sites. All the new monomers possess a rigidified anthranilamide skeleton, which is stabilized by intramolecular hydrogen bonding. Amide units are iteratively introduced to one side of the preorganized skeletons to facilitate the formation of intermolecular hydrogen bonding. Compounds 2 and 3 bear two and three CONH2 units, respectively, while 4, 6, and 7 are incorporated with two, three, and four AcNH units, respectively. For comparison, compound 5, which is similar to 4 but contains one AcNH and one CF3CONH unit, is also prepared. X-ray diffraction analysis of 2, 4, and 5 revealed homodimeric motifs in the solid state which are stabilized by two or more intermolecular hydrogen bonds. 1H NMR investigations in CDCl3 indicated that all the compounds form hydrogen-bonded homoduplexes. Duplexes 3-3, 6-6, and 7-7 are highly stable in CDCl3, with a lower Kassoc limit of 2.3 × 10 5 M-1. The Kassoc values of the three duplexes in more polar CDCl3/CD3CN (9:1, v/v) were determined with the 1H NMR dilution method. The result opens the way for the development of new polymeric duplexes of well-ordered structures.