Lipid oligonucleotide conjugates as responsive nanomaterials for drug delivery

Pokholenko, Oleksandr; Gissot, Arnaud; Vialet, Brune; Bathany, Katell; Thiéry, Alain; Barthélémy, Philippe

doi:10.1039/c3tb20357c

Cited by 42 publications

(35 citation statements)

References 35 publications

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“…Due to the poor solubility of G2 in acetonitrile, tetrahydrofuran (THF) was utilized to dissolve G2 in the initial step. After the self‐assembly procedure in the mixture solution (H 2 O/THF, v/v, 20:1), the hydrodynamic diameter of 49 ± 13 nm was found by DLS (Figure 1D), and the spherical micelles with a diameter of about 30 nm were observed by TEM (Figure 1E), which was consistent with twice the calculated size of the D18‐CB[7]/ G2 (about 23 nm, the calculated size of G2 not including adamantine is about 2.7 nm [ 25 ] , thus the calculated size of D18‐CB[7]/ G2 is 11.4 nm (7.7 nm + 1 nm + 2.7 nm), and the size of the D18‐CB[7]/ G2 micelles was about 23 nm). The AFM image (Figure 1F) showed large spherical micelles with a height of about 20 nm were formed (the insert of Figure 1F).…”

Section: Methodssupporting

confidence: 74%

Self‐Assembly of Supramolecular DNA Amphiphiles through Host–Guest Interaction and Their Stimuli‐Responsiveness

Yuan

Zhao

et al. 2020

Macromol. Rapid Commun.

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micelles, [6] nanofibers, [7] vesicles, [8] and nanosheets. [9] More interestingly, morphological shift of the DNA assemblies has been achieved through external stimuli, such as pH values, [10] temperature, [11] DNA-selective enzymatic activity, [12] and host-guest recognition. [13] Recently, supramolecular host-guest chemistry has been an effective strategy to construct supra-amphiphiles [14] by conjugating hydrophilic and hydrophobic segments. These supra-amphiphiles can assemble into diverse stimuli-responsive nanomaterials, applied in materials science, [15] supramolecular catalysis, [16] and biochemistry. [17] Doubtlessly, the hostguest approach could be an ideal alternative to construct DNA supra-amphiphiles. To date, the construction of DNA supra-amphiphiles through host-guest interactions has been rarely reported. [18] Moreover, the effect of such different topologic guests or stimuli-responsive guests on the assembled morphology is still unknown.Herein, we design and construct two DNA supra-amphiphiles via noncovalent recognition based on the host-guest interaction between cucurbit[7]uril (CB[7]) and the guests (ferrocene derivative or adamantane derivative). The host-guest interaction between CB[7] and guest (ferrocene or adamantane) has been widely investigated in the supramolecular chemistry due to their efficient molecular recognition with a strong association constant (K a = 10 4 -10 6 M −1 for CB [7] and ferrocene analogs, [19] K a = 10 8 -10 13 M −1 for CB [7] and adamantine derivates [20] ). Here, CB[7]-modified DNA (D18-CB[7]) is regarded as the hydrophilic host. Two types of molecules with different guest units and topologic structures are chosen to be the hydrophobic guests. One is ferrocene modified with second-generation poly(benzyl ether) dendron (G1) and the other is adamantane tailed with three 18-carbon alkyl chains (G2). Through host-guest interaction, the supramolecular DNA amphiphiles could be modularly constructed and then undergo their self-assembly process (Scheme 1). The self-assembly mechanism and application of the assembled nanostructures have been further demonstrated. Finally, the stimuli-responsiveness of assemblies induced by competitive guest or by the redox properties of ferrocene has been investigated.After having the host and two different guests obtained, we want to explore the construction of DNA-based supra-amphiphiles (D18-CB[7]/G1 and D18-CB[7]/G2) through host-guest 2000022 (5 of 5) www.advancedsciencenews.com www.mrc-journal.de

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Section: Methodssupporting

confidence: 74%

Self‐Assembly of Supramolecular DNA Amphiphiles through Host–Guest Interaction and Their Stimuli‐Responsiveness

Yuan

Zhao

et al. 2020

Macromol. Rapid Commun.

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“…Two equivalents of 6 were Polymers 2017, 9, 471 6 of 29 coupled with the appropriately functionalized 2,5-dibromo-or 2,5-diiodohydroquinone ethers 7 [87,88], giving the bolapolyphiles C-E after deprotection of the 1,2-diol groups with pyridinium p-toluenesulfonate (PPTS) in methanol and THF [47,89]. For the synthesis of the diiodohydroquinone ethers 7a-i with two identical branched chains (X = I, R 1 = R 2 = -CH 2 CH(C m H 2m+1 ) 2 ), the branched alkyl bromides were obtained from diethyl malonate by a sequence of alkylation [90], dealkoxycarbonylation [91], reduction [92], and bromination [93], were etherified with 2,5-diiodohydroquinone (Scheme S1) [94]. The diiodohydoquinone ether 7k, with two semiperfluorinated chains (X = I, R 1 = R 2 = -(CH 2 ) 4 C 6 F 13 ), was prepared in an analogous way using tridecafluorodecyl bromide (Schemes S2 and S3) [92,93,95].…”

Section: Synthesismentioning

confidence: 99%

“…For the synthesis of the diiodohydroquinone ethers 7a-i with two identical branched chains (X = I, R1 = R2 = -CH2CH(CmH2m+1)2), the branched alkyl bromides were obtained from diethyl malonate by a sequence of alkylation [90], dealkoxycarbonylation [91], reduction [92], and bromination [93], were etherified with 2,5-diiodohydroquinone (Scheme S1) [94]. The diiodohydoquinone ether 7k, with two semiperfluorinated chains (X = I, R1 = R2 = -(CH2)4C6F13), was prepared in an analogous way using tridecafluorodecyl bromide (Schemes S2 and S3) [92,93,95].…”

Section: Synthesismentioning

confidence: 99%

Effects of Lateral and Terminal Chains of X-Shaped Bolapolyphiles with Oligo(phenylene ethynylene) Cores on Self-Assembly Behaviour. Part 1: Transition between Amphiphilic and Polyphilic Self-Assembly in the Bulk

Poppe

Ebert

et al. 2017

Polymers

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Polyphilic self-assembly leads to compartmentalization of space and development of complex structures in soft matter on different length scales, reaching from the morphologies of block copolymers to the liquid crystalline (LC) phases of small molecules. Whereas block copolymers are known to form membranes and interact with phospholipid bilayers, liquid crystals have been less investigated in this respect. Here, series of bolapolyphilic X-shaped molecules were synthesized and investigated with respect to the effect of molecular structural parameters on the formation of LC phases (part 1), and on domain formation in phospholipid bilayer membranes (part 2). The investigated bolapolyphiles are based on a rod-like π-conjugated oligo(phenylene ethynylene) (OPE) core with two glycerol groups being either directly attached or separated by additional ethylene oxide (EO) units to both ends. The X-shape is provided by two lateral alkyl chains attached at opposite sides of the OPE core, being either linear, branched, or semiperfluorinated. In this report, the focus is on the transition from polyphilic (triphilic or tetraphilic) to binary amphiphilic self-assembly. Polyphilic self-assembly, i.e., segregation of all three or four incorporated units into separate nano-compartments, leads to the formation of hexagonal columnar LC phases, representing triangular honeycombs. A continuous transition from the well-defined triangular honeycomb structures to simple hexagonal columnar phases, dominated by the arrangement of polar columns on a hexagonal lattice in a mixed continuum formed by the lipophilic chains and the OPE rods, i.e., to amphiphilic self-assembly, was observed by reducing the length and volume of the lateral alkyl chains. A similar transition was found upon increasing the length of the EO units involved in the polar groups. If the lateral alkyl chains are enlarged or replaced by semiperfluorinated chains, then the segregation of lateral chains and rod-like cores is retained, even for enlarged polar groups, i.e., the transition from polyphilic to amphiphilic self-assembly is suppressed.

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“…For efficient synthesis and assembly, DNA–lipid micelles (DLMs), consisting of a single-stranded hydrophilic DNA head and a hydrophobic lipid tail, have been reported. [6] By solid-phase DNA synthesis, diacyllipid can be coupled onto the 5’-end of oligonucleotides. [7] Owing to the similarity between the diacyllipid in DLMs and the lipid bilayers in cell membranes, DLMs have shown low critical micelle concentration (CMC), [8] excellent biocompatibility, [7] and compelling membrane permeability.…”

mentioning

confidence: 99%

“…[12] At the same time, however, loss of DLM integrity and arbitrary insertion of disassembled lipid units could interfere with the recognition ability of the aptamer when interacting with cells. [6a,9] Therefore, a more stable micelle structure is required for target-cell recognition in practical applications. Various approaches have been investigated to stabilize copolymer micelles by employing covalent [13] or reducible linkages.…”

mentioning

confidence: 99%

Cross‐Linked Aptamer–Lipid Micelles for Excellent Stability and Specificity in Target‐Cell Recognition

Figg

Wang

et al. 2018

Angew Chem Int Ed

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The specific binding ability of DNA-lipid micelles (DLMs) can be increased by the introduction of an aptamer. However, supramolecular micellar structures based on self-assemblies of amphiphilic DLMs are expected to demonstrate low stability when interacting with cell membranes under certain conditions, which could lead to a reduction in selectivity for targeting cancer cells. We herein report a straightforward cross-linking strategy that relies on a methacrylamide branch to link aptamer and lipid segments. By an efficient photoinduced polymerization process, covalently linked aptamer-lipid units help stabilize the micelle structure and enhance aptamer probe stability, further improving the targeting ability of the resulting nanoassembly. Besides the development of a facile cross-linking method, this study clarifies the relationship between aptamer-lipid concentration and the corresponding binding ability.

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Lipid oligonucleotide conjugates as responsive nanomaterials for drug delivery

Cited by 42 publications

References 35 publications

Self‐Assembly of Supramolecular DNA Amphiphiles through Host–Guest Interaction and Their Stimuli‐Responsiveness

Self‐Assembly of Supramolecular DNA Amphiphiles through Host–Guest Interaction and Their Stimuli‐Responsiveness

Effects of Lateral and Terminal Chains of X-Shaped Bolapolyphiles with Oligo(phenylene ethynylene) Cores on Self-Assembly Behaviour. Part 1: Transition between Amphiphilic and Polyphilic Self-Assembly in the Bulk

Cross‐Linked Aptamer–Lipid Micelles for Excellent Stability and Specificity in Target‐Cell Recognition

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