[12]aneN-based lipid with naphthalimide moiety for enhanced gene transfection efficiency.

Three cationic lipids derived from [12]aneN modified with naphthalimide (1a), oleic acid (1b) and octadecylamine (1c) were designed and synthesized. In vitro transfection showed that all these liposomes can deliver plasmid DNA into the tested cell lines. Among these liposomes, 1a gave the best transfection efficiency (TE) in A549 cells, which was higher than that of lipofectamine 2000.

Effective formation of stable and versatile double-stranded β-sheets templated by a hydrogen-bonded duplex.

We report herein an effective approach that is generally applicable for constructing double-stranded β-sheets composed of tetra- and penta-peptides based on a hydrogen-bonded duplex template, regardless of their amino acid sequences and α-helical or β-sheet propensities.

Gemini-Type Tetraphenylethylene Amphiphiles Containing [12]aneN and Long Hydrocarbon Chains as Nonviral Gene Vectors and Gene Delivery Monitors.

Four gemini amphiphiles decorated with triazole-[12]aneN as the hydrophilic moiety and various long hydrocarbons as hydrophobic moieties, 1-4, were designed to form micelles possessing the aggregation-induced emission (AIE) property for gene delivery and tracing. All four amphiphiles give ultralow critical micelle concentrations, are pH-/photostable and biocompatible, and completely retard the migration of plasmid DNAs at low concentrations. The DNA-binding abilities of the micelles were fully assessed.

Functional lipids based on [12]aneN3 and naphthalimide as efficient non-viral gene vectors.

Small organic non-viral gene vectors with the structural combinations of (aliphatic chain)-naphthalimide-[12]aneN3 (11a, b) and naphthalimide-(aliphatic chain)-[12]aneN3 (12a-c) were synthesized and fully characterized. Agarose gel electrophoresis experiments indicated that the first type of compounds, 11a and 11b, could completely retard DNA at the concentration of 5 μM in the presence of DOPE. Within the second type of compounds, 12c with the decane chain showed a complete retardation of DNA at the concentration of 20 μM, whereas 12a and 12b with the ethyl and hexyl chains could not retard DNA effectively.

[12]aneN3 Modified Tetraphenylethene Molecules as High-Performance Sensing, Condensing, and Delivering Agents toward DNAs.

Four [12]aneN3 modified tetraphenylethene (TPE) compounds with different numbers of polyamine units and structure configurations, namely 1, 2, 3, and 4, were designed and synthesized. All compounds showed strong aggregation-induced emission (AIE) features. Compounds 2 and 4 showed significant emission enhancement after the addition of ssDNAs and dsDNAs of different lengths as well as calf thymus DNA (ctDNA).

1,8-naphthalimide modified [12]aneN₃ compounds as selective and sensitive probes for Cu²⁺ ions and ATP in aqueous solution and living cells.

A new fluorescent probe 1 featuring one 1,8-naphthalimide and two [12]aneN3 units was synthesized. In the presence of Cu(2+) ions, the fluorescence emission of 1 was quenched by a factor of 127-fold and no interference by other metal ions was observed under physiological conditions. By means of titration and a Job's plot it was established that 1 forms a complex with Cu(2+) ions in a 1:2 ratio.

Fluorescent sensors based on [12]aneN3-modified BODIPY: Discrimination of different biological thiols in aqueous solution and living cells.

Two fluorescent probes, 1 and 2, derived from borondipyrromethene (BODIPY) modified with macrocyclic polyamine [12]aneN3, were synthesized and applied in the discrimination of cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) with absorption and fluorescent spectroscopy in comparison. It was found that Boc-protected 1 showed highly sensitive and selective recognition of GSH over Cys and Hcy; while probe 2 was able to distinguish the three different thiols due to their different reactivities. With its water-solubility, rapid responsiveness, high sensitivity and low cytotoxicity, probe 2 was successfully applied in the fast detection of three biothiols in living cells.

A naphthalimide-based [12]aneN3 compound as an effective and real-time fluorescence tracking non-viral gene vector.

A novel bifunctional naphthalimide-based [12]aneN3 compound 1 was successfully applied as an effective non-viral gene vector in cancer cells, the fluorescence properties of 1 clearly demonstrated the process of cellular uptake, DNA translocation and release based on real-time fluorescence tracking.