Base-Pair Formation of Self-Organizing RNA Amphiphiles within Two Dimensions

Rädler, Ulf; Heiz, Cornelia; Luisi, Pier Luigi; Tampé, Robert

doi:10.1021/la980515s

Cited by 24 publications

(20 citation statements)

References 36 publications

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“…[11] Another related class of amphiphiles is based on low-molecular-weight hydrophobic groups attached to ODNs or individual nucleotides. The latter are known as nucleolipids and have been extensively studied for their interactions with membranes, potential biomedical applications, [12] and their supramolecular organization, both into monolayers [13] and micelles. [14] The ability of these aggregates to carry information is limited by the presence of only individual nucleotides, but pyrimidine bases modified at the 5-position with a range of hydrophobic moieties have also been integrated into DNA sequences by using solid-phase synthesis.…”

Section: Introductionmentioning

confidence: 99%

Tunable Hydrophobicity in DNA Micelles: Design, Synthesis, and Characterization of a New Family of DNA Amphiphiles

Anaya

Kwak

Musser

et al. 2010

Chemistry A European J

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This work describes the synthesis and characterization of a new family of DNA amphiphiles containing modified nucleobases. The hydrophobicity was imparted by the introduction of a dodec-1-yne chain at the 5-position of the uracil base, which allowed precise and simple tuning of the hydrophobic properties through solid-phase DNA synthesis. The micelles formed from these modified DNA sequences were characterized by atomic force microscopy, dynamic light scattering, and polyacrylamide gel electrophoresis. These experiments revealed the role of the quantity and location of the hydrophobic units in determining the morphology and stability of the micelles. The effects of hybridization on the physical characteristics of the DNA micelles were also studied; these results showed potential for the sequence-specific noncovalent functionalization of the self-assembled aggregates.

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Section: Introductionmentioning

confidence: 99%

Tunable Hydrophobicity in DNA Micelles: Design, Synthesis, and Characterization of a New Family of DNA Amphiphiles

Anaya

Kwak

Musser

et al. 2010

Chemistry A European J

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“…[8][9][10][11][12][13] A variety of synthetic strategies have been used to prepare nucleotide-based amphiphiles, [14][15][16] including coupling reactions of a monoalkylphosphate with a nucleoside 17 and enzymatic catalysis. [18][19][20][21] A significant amount of the literature devoted to this family of amphiphiles describes mainly longchain alkyl ester nucleoside-5 0 -monophosphate derivatives (Scheme 1, i.e. C 16 UMP).…”

Section: Introductionmentioning

confidence: 99%

Nanostructured assemblies from nucleotide-based amphiphiles

Campins¹,

Dieudonné²,

Grinstaff³

et al. 2007

New J. Chem.

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A synthetic route to 3 0 -O-alkyl nucleotides is described that provides easy access to a series of nucleotide-based amphiphiles. Physicochemical experiments demonstrate that these nucleotide amphiphiles possess different aggregating properties compared to both their non-nucleotide analogues and simple nucleotides. The data collected from TEM, SEM, FT-IR and WAXS studies indicate that the aqueous dispersion of these nucleotide amphiphiles provides nanostructured assemblies such as ribbon-like structures for the thymidine derivatives and small aggregates for adenine. These results indicate that the nature of the base has an impact on aggregate morphology. A molecular model illustrating the 3D supramolecular arrangements of a thymidine nucleoamphiphile forming ribbons is proposed.

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“…[11][12][13][14][15][16][17] Moreover, much emphasis is placed upon the interaction between the host monolayers and guest components in the subphase, and no attention is attracted to the competition of the host-host interactions with the host-guest ones. Our recent studies indicated that the monolayer of cytosine-functionalized nucleolipids on the aqueous guanosine subphase underwent an orientation change not only in base moiety but also in alkyl chain in comparison to the monolayer on pure water, 19,20 and these revealed the interconversion of hydrogen bonds between adjacent cytosine moieties and between cytosine and guanosine base pairs in the courses of molecular recognition and the phase transition behaviors of the corresponding LB films.…”

Section: Introductionmentioning

confidence: 99%

Molecular Recognition of Cytosine- and Guanine-Functionalized Nucleolipids in the Mixed Monolayers at the Air−Water Interface and Langmuir−Blodgett Films

Miao

Liang

2006

J. Phys. Chem. B

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Molecular recognition of mixed nucleolipids of 1-(2-octadecyloxycarbonylethyl)cytosine and 7-(2-octadecyloxycarbonylethyl)guanine in the monolayers at the air-water interface and Langmuir-Blodgett (LB) films has been investigated in detail using surface pressure/potential-area isotherms, infrared reflection-absorption spectroscopy (IRRAS), and Fourier transform infrared (FTIR) transmission spectroscopy, respectively. Prior to molecular recognition, the cytosine moieties in the monolayer were hydrogen bonded with an almost flat-on orientation, the alkyl chains were uniaxially oriented with respect to the film normal, the guanine moieties in the monolayer were stacked probably through pi-pi interaction with an end-on orientation, and the C-C-C planes of the alkyl chains were preferentially oriented parallel to the water surface. In the monolayer of equimolar mixture, molecular recognition between the cytosine and guanine moieties occurred together with the ring planes of base pairing and the C-C-C planes of the alkyl chains favorably oriented parallel to the water surface. The guanine moieties underwent an orientation change from an end-on mode before molecular recognition to a flat-on one after molecular recognition. The base pairing between the cytosine and guanine moieties in the monolayers was achieved since the N7-substituted guanine derivatives suppressed the formation of guanine tetramers. Both the IRRAS spectra of the monolayers and the FTIR spectra of the LB films presented the exact sites in the cytosine and guanine moieties for the formation of triple hydrogen bonds. The base pairing resulted in a change in molecular orientation and interaction, and the corresponding LB film exhibited a different phase transition behavior from a typical crystal transition for the cytosine-functionalized nucleolipids and an analogous glass transition for the guanine-functionalized nucleolipids. The thermal stability of the mixed LB film was improved in comparison to the LB films of pure components.

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Base-Pair Formation of Self-Organizing RNA Amphiphiles within Two Dimensions

Cited by 24 publications

References 36 publications

Tunable Hydrophobicity in DNA Micelles: Design, Synthesis, and Characterization of a New Family of DNA Amphiphiles

Tunable Hydrophobicity in DNA Micelles: Design, Synthesis, and Characterization of a New Family of DNA Amphiphiles

Nanostructured assemblies from nucleotide-based amphiphiles

Molecular Recognition of Cytosine- and Guanine-Functionalized Nucleolipids in the Mixed Monolayers at the Air−Water Interface and Langmuir−Blodgett Films

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