1558953-52-8

Basic information

• Product Name: 1-(N-(N^α,N^ε-di-Boc-Lys)-N-dodecylamino)methylbenzene
• Synonyms: 1-(N-(N^α,N^ε-di-Boc-Lys)-N-dodecylamino)methylbenzene
• CAS NO: 1558953-52-8
• Molecular Weight: 603.886
• Mol File: 1558953-52-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-(N-(N^α,N^ε-di-Boc-Lys)-N-dodecylamino)methylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(N-(N^α,N^ε-di-Boc-Lys)-N-dodecylamino)methylbenzene(1558953-52-8)
• EPA Substance Registry System: 1-(N-(N^α,N^ε-di-Boc-Lys)-N-dodecylamino)methylbenzene(1558953-52-8)

Safety Data

• Hazardous Substances Data: 1558953-52-8(Hazardous Substances Data)

Upstream product

• 2483-46-7 Boc-Lys(Boc)-OH 
• 1687-68-9 dodecylbenzylamine 
• 20172-42-3 N-(benzylidene)dodecylimine 
• 100-52-7 benzaldehyde 
• 124-22-1 n-Dodecylamine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 657-27-2 L-Lysine hydrochloride 
• 2090-62-2 N-dodecyl-1-aminomethylbenzene hydrochloride 

Relevant articles and documents

Aryl-alkyl-lysines: Membrane-Active Fungicides That Act against Biofilms of Candida albicans

Mortality due to pathogenic fungi has been exacerbated by the rapid development of resistance to frontline antifungal drugs. Fungicidal compounds with novel mechanisms of action are urgently needed. Aryl-alkyl-lysines, which are membrane-active small molecules, were earlier shown to be broad-spectrum antibacterial agents with potency in vitro and in vivo. Herein, we report the antifungal properties of aryl-alkyl-lysines. After identifying the most active compound (NCK-10), we tested its activity against a panel of clinically relevant pathogenic fungi and examined NCK-10's effect against immature and mature biofilms of Candida albicans. NCK-10 was capable of inhibiting the growth of various species of fungi (including Candida spp., Cryptococcus spp., and Aspergillus fumigatus) at concentrations similar to those of antifungal drugs used clinically. It was observed that polarization and permeability of the fungal cell membrane were compromised upon addition of NCK-10, indicating its mechanism is disruption of the fungal cell membrane. In addition to interfering with the growth of planktonic fungi, NCK-10 demonstrated the ability to both inhibit biofilm formation and reduce the metabolic activity of cells in C. albicans biofilm. Additionally, our compound was capable of crossing the blood-brain barrier in an in vitro model, expanding the potential antifungal applications for NCK-10. Overall, aryl-alkyl-lysines were found to be excellent compounds that warrant further investigation as novel antifungal agents.

Small molecular antibacterial peptoid mimics: The simpler the better!

The emergence of multidrug resistant bacteria compounded by the depleting arsenal of antibiotics has accelerated efforts toward development of antibiotics with novel mechanisms of action. In this report, we present a series of small molecular antibacterial peptoid mimics which exhibit high in vitro potency against a variety of Gram-positive and Gram-negative bacteria, including drug-resistant species such as methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecium. The highlight of these compounds is their superior activity against the major nosocomial pathogen Pseudomonas aeruginosa. Nontoxic toward mammalian cells, these rapidly bactericidal compounds primarily act by permeabilization and depolarization of bacterial membrane. Synthetically simple and selectively antibacterial, these compounds can be developed into a newer class of therapeutic agents against multidrug resistant bacterial species.