Synthesis of New Polymerizable Metal-Chelating Lipids

Roy, B. C.; Mallik, Sanku

doi:10.1021/jo982397j

Cited by 21 publications

(28 citation statements)

References 18 publications

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“…4 B ) (45). From a commercially available N 6 carboxybenzyl (Cbz) protected lysine 2 , tribasic acid 3 was obtained via S N 2 reaction with 2-bromo acetic acid in NaOH aqueous solution, followed by Fischer esterification with methanol in the presence of p -toluenesulfonic acid (TsOH) and deprotection of Cbz group via hydrogenolysis with palladium on carbon (46). Intermediate 5 containing a free amino group was conjugated with 3, 5-didodecyoxyl benzoic acid 6 via 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and N -methylmorpholine (NMM) in THF to obtain compound 7 (67% yield).…”

Section: Resultsmentioning

confidence: 99%

Encapsulation of hydrophobic components in dendrimersomes and decoration of their surface with proteins and nucleic acids

Torre

Xiao

Buzzacchera

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

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Reconstructing the functions of living cells using nonnatural components is one of the great challenges of natural sciences. Compartmentalization, encapsulation, and surface decoration of globular assemblies, known as vesicles, represent key early steps in the reconstitution of synthetic cells. Here we report that vesicles self-assembled from amphiphilic Janus dendrimers, called dendrimersomes, encapsulate high concentrations of hydrophobic components and do so more efficiently than commercially available stealth liposomes assembled from phospholipid components. Multilayer onion-like dendrimersomes demonstrate a particularly high capacity for loading low-molecular weight compounds and even folded proteins. Coassembly of amphiphilic Janus dendrimers with metal-chelating ligands conjugated to amphiphilic Janus dendrimers generates dendrimersomes that selectively display folded proteins on their periphery in an oriented manner. A modular strategy for tethering nucleic acids to the surface of dendrimersomes is also demonstrated. These findings augment the functional capabilities of dendrimersomes to serve as versatile biological membrane mimics.

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Section: Resultsmentioning

confidence: 99%

Encapsulation of hydrophobic components in dendrimersomes and decoration of their surface with proteins and nucleic acids

Torre

Xiao

Buzzacchera

et al. 2019

Proc. Natl. Acad. Sci. U.S.A.

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“…33,34 NMR spectra were measured on Bruker DPX300, AV400, or AMX500 instruments and were assigned using COSY, HMBC, HMQC and DEPT spectra where appropriate. Phospholipids were obtained from Avanti Polar Lipids.…”

Section: Methodsmentioning

confidence: 99%

Fructose controlled ionophoric activity of a cholate–boronic acid

2014

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Wulff-type boronic acids have been shown to act as ionophores at pH 8.2 by transporting Na(+) through phospholipid bilayers. A cholate-boronic acid conjugate was synthesised and shown to be an ionophore, although the hydroxyl-lined face of the cholate moiety did not enhance ion transport. Mechanistic studies suggested a carrier mechanism for Na(+) transport. The addition of fructose (>5 mM) strongly inhibited ionophoric activity of the cholate-boronic acid conjugate, mirrored by a strong decrease in the ability of this compound to partition into an organic phase. Modelling of the partitioning and ion transport data, using a fructose/boronic acid binding constant measured at pH 8.2, showed a good correlation with the extent of fructose/boronic acid complexation and suggested high polarity fructose/boronic acid complexes are poor ionophores. The sensitivity of ion transport to fructose implies that boronic acid-based antibiotic ionophores with activity modulated by polysaccharides in the surrounding environment may be accessible.

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“…Silica gel NM Kieselgel 60 (70Ϫ230 mesh ASTM) was obtained from MachereyϪNagel and Merck. The syntheses of 4, [16] 5 [17] and 17 [21] were performed as described in the literature. Synthesis of 6: ZCl (7.5 mL, 44.8 mmol) in 40 mL of CH 2 Cl 2 was added to a solution of 5 (8.1 g, 20.3 mmol) in dichloromethane (60 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Scheme 3. i: Bromoacetyl bromide, TEA, CH 2 Cl 2 ; ii: 7, TEA, CH 2 Cl 2 ; iii: H 2 , Pd/C, methanol; iv: C 60 , paraformaldehyde, toluene, ∆ To better evaluate the effect of fullerene derivative 3 as a neuroprotecting agent, the branched chain without C 60 (16) was synthesized for use as a control in the biological assays (Scheme 4). Scheme 4. i: 13, TEA, CH 2 Cl 2 ; ii: H 2 , Pd/C, methanol; iii: HCl, methanol Derivative 13 was used as alkylating agent with N-(benzyloxycarbonyl)-2,2Ј-bis(ethylenedioxydiethylene)-diamine (17) [21] to obtain 18, which gave 19 after hydrogenolysis. Total deprotection of 19 by HCl/methanol afforded the desired triamino compound 16 as its hydrochloride salt.…”

Section: Synthesismentioning

confidence: 99%