1229609-38-4

Basic information

• Product Name: C₁₆₈H₃₁₇N₃₁O₄₄
• Synonyms: C₁₆₈H₃₁₇N₃₁O₄₄
• CAS NO: 1229609-38-4
• Molecular Weight: 3475.55
• Mol File: 1229609-38-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₁₆₈H₃₁₇N₃₁O₄₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₆₈H₃₁₇N₃₁O₄₄(1229609-38-4)
• EPA Substance Registry System: C₁₆₈H₃₁₇N₃₁O₄₄(1229609-38-4)

Safety Data

• Hazardous Substances Data: 1229609-38-4(Hazardous Substances Data)

Upstream product

• 87530-14-1 N-(3-aminopropyl)-N-(3-tert-butyloxycarbonyl-aminopropyl)-N-methylamine 
• 200133-18-2 benzyl N-{tris[(2-{[(tris{[2-carboxyethoxy]methyl}methyl)amino]carbonyl}ethoxy)methyl]methyl}carbamate 

Relevant articles and documents

Quantifying the effect of surface ligands on dendron-DNA interactions: Insights into multivalency through a combined experimental and theoretical approach

We report the synthesis, DNA binding ability and preliminary gene delivery profiles of dendrons with different amine surface groups, 1,3-diaminopropane (DAP), N,N-di-(3-aminopropyl)-N-(methyl)amine (DAPMA) and spermine (SPM). By using a combination of ethidium bromide displacement, gel electrophoresis and transfection assays, it is shown that the dendrons with SPM groups are the most effective DNA binders, while the DAPMA-functionalised dendrons were the most effective systems for gene delivery (although the gene delivery profiles were still modest). In order to provide deeper insight into the experimental data, we performed a molecular dynamics simulation of the interactions between the dendrons and DNA. The results of these simulations demonstrated that, in general terms, the enthalpic contribution to binding was roughly proportional to the dendron surface charge, but that dendrons with DAP (and DAPMA) surface amines had significant entropie costs of binding to DNA. In the case of DAP, this is a consequence of the fact that the entire dendron structure has to be organised in order for each individual monoamine charge to make effective contact with DNA. For SPM, however, each surface ligand is already a multivalent triamine, therefore, each individual charge has a much lower entropie cost of binding. For DAPMA, we observed that strong binding of the hindered tertiary amine to the DNA double helix led to ligand back-folding and significant geometric distortion of DNA. Although this weakens the overall binding, we suggest that this distortion might be an explanation for the experimentally observed enhanced gene delivery, in which DNA compaction is an important step. Overall, this paper demonstrates how structure-activity relationships can be developed for multivalent dendritic ligands and provides insights into the thermodynamics of multivalent interactions.