201984-76-1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 71-44-3 Spermine 
• 501-53-1 benzyl chloroformate 
• 201984-66-9 1-trifluoroacetyl-5,10,14-tris-Boc-spermine 
• 202145-88-8 N-(3-((4-((3-aminopropyl)amino)butyl)amino)propyl)-2,2,2-trifluoroacetamide 
• 34637-22-4 3-[(N-benzyloxycarbonyl)amino]propanol 

Downstream Products

• 128550-06-1 (N¹,N⁴,N⁹,N¹³-tetra-tert-butoxycarbonyl)-1,16-diamino-4,9,13-triazahexadecane 
• 196704-28-6 (3-Benzyloxycarbonylamino-propyl)-[3-(tert-butoxycarbonyl-{4-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-butyl}-amino)-propyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

A polyamine-modified near-infrared fluorescent probe for selective staining of live cancer cells

We report the synthesis of novel polyamine-modified near-infrared (NIR) probes, which show excellent water-solubility and good optical properties. One probe was taken up efficiently by living cancer cell lines whereas no staining of the non-cancer cells was observed.

Effect of spermine conjugation on the cytotoxicity and cellular transport of acridine

Polyamines are believed to be potent vectors for the selective delivery of chemotherapeutic agents into cancer cells. In this paper, we report the effect of spermine conjugation on the cytotoxic and transport properties of acridine. Six derivatives, composed of a spermine chain attached at its N1 position to an acridine via an aliphatic chain, were synthesized. The aliphatic linker, comprised of 3-5 methylene units, was connected to the position-9 of the heterocycle through either an amide (amidoacridines 8-10) or an amine (aminoacridines 11-13) linkage. Independently of their architecture, all ligands showed a high affinity for DNA binding but a limited DNA sequence selectivity. In a whole cell assay with L1210 and Chinese hamster ovary (CHO) cells, the aminoacridines (IC50 values around 2 μM) were more potent than the amidoacridines (IC50 values between 20 and 40 μM). This was related to a less efficient transport for the latter. As determined from competitive uptake studies with [14C] spermidine, all conjugates had a high affinity for the polyamine transport system (PTS). However, on the basis of competitive studies with an excess of spermidine and on the differential effect on cell growth and accumulation in CHO and in the mutant PTS deficient CHO-MG cells, the accumulation of the conjugates through the PTS was found to be poor but still more efficient for the aminoacridines. α-Difluoromethylornithine (DFMO), an inhibitor of ornithine decarboxylase, which induces an up-regulation of the activity of the PTS, enhanced accumulation of all acridine conjugates through the PTS and had a synergistic effect on the potency of the acridine conjugates to inhibit cell growth. Despite their high affinity for the PTS, the low amount of derivatives transiting through the PTS is likely to be related to their ability to repress rapidly and efficiently the activity of the PTS and, consequently, to inhibit their own uptake via this system.

Homologation of polyamines in the rapid synthesis of lipospermine conjugates and related lipoplexes

Lipopolyamine amides are useful cationic lipids, synthetic vectors for non-viral gene delivery. Desymmetrisation of readily available symmetrical polyamines is an important first step in the synthesis of such compounds. The application of trifluoroacetyl

Homologation of polyamines in the synthesis of lipo-spermine conjugates and related lipoplexes

Polyamine amides are useful in gene delivery as synthetic (non-viral) vectors or mimics of polycationic histones. The application of a homologation strategy, based upon reductive alkylation, allows unsymmetrical polyamine amides to be prepared in good yie