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Hexadecameric self-assembled dendrimers built from 2'-deoxyguanosine derivatives.

Betancourt JE, Rivera JM - Org. Lett. (2008)

Bottom Line: Herein we describe the construction of hexadecameric self-assembled dendrimers (SADs) using a series of dendronized 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) subunits.The azido-substituted mAG subunits were covalently linked to alkynyl polyester dendrons using a copper-catalyzed 1,3-dipolar cycloaddition reaction.Discrete SADs are formed with high fidelity and thermal stability even with the increased steric hindrance offered by the dendrons.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Puerto Rico, Río Piedras Campus, Río Piedras, Puerto Rico.

ABSTRACT
Herein we describe the construction of hexadecameric self-assembled dendrimers (SADs) using a series of dendronized 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) subunits. The azido-substituted mAG subunits were covalently linked to alkynyl polyester dendrons using a copper-catalyzed 1,3-dipolar cycloaddition reaction. Discrete SADs are formed with high fidelity and thermal stability even with the increased steric hindrance offered by the dendrons.

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Hierarchical formation of a self-assembled dendrimer (SAD). (a) Dendronized mAG subunits self-assemble into (b) disk-like tetramers, which (c) further stack to form hexadecameric SADs. (d) The resulting SADs have a functional core composed of a modified lipophilic G-quadruplex.
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fig1: Hierarchical formation of a self-assembled dendrimer (SAD). (a) Dendronized mAG subunits self-assemble into (b) disk-like tetramers, which (c) further stack to form hexadecameric SADs. (d) The resulting SADs have a functional core composed of a modified lipophilic G-quadruplex.

Mentions: Guanosine and related compounds have a propensity to form planar tetramers (G-tetrads, Figure 1), which are held together by hydrogen bonds and cation complexation; further stacking of such tetrads leads to structures known as G-quadruplexes.(11) Previously we have demonstrated that the self-assembly of lipophilic dG-derivatives could be modulated by replacement of the H8 in the guanine base with a functionalized phenyl group.(12) The position of the functional group in the phenyl ring controlled the stoichiometry, thermal stability, and in some cases their selective binding for metal cations.12,13 Taking advantage of our familiarity with these derivatives, we embarked on the construction of other nanostructures such as dendrimers.(14)


Hexadecameric self-assembled dendrimers built from 2'-deoxyguanosine derivatives.

Betancourt JE, Rivera JM - Org. Lett. (2008)

Hierarchical formation of a self-assembled dendrimer (SAD). (a) Dendronized mAG subunits self-assemble into (b) disk-like tetramers, which (c) further stack to form hexadecameric SADs. (d) The resulting SADs have a functional core composed of a modified lipophilic G-quadruplex.
© Copyright Policy - open-access - ccc-price
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2654094&req=5

fig1: Hierarchical formation of a self-assembled dendrimer (SAD). (a) Dendronized mAG subunits self-assemble into (b) disk-like tetramers, which (c) further stack to form hexadecameric SADs. (d) The resulting SADs have a functional core composed of a modified lipophilic G-quadruplex.
Mentions: Guanosine and related compounds have a propensity to form planar tetramers (G-tetrads, Figure 1), which are held together by hydrogen bonds and cation complexation; further stacking of such tetrads leads to structures known as G-quadruplexes.(11) Previously we have demonstrated that the self-assembly of lipophilic dG-derivatives could be modulated by replacement of the H8 in the guanine base with a functionalized phenyl group.(12) The position of the functional group in the phenyl ring controlled the stoichiometry, thermal stability, and in some cases their selective binding for metal cations.12,13 Taking advantage of our familiarity with these derivatives, we embarked on the construction of other nanostructures such as dendrimers.(14)

Bottom Line: Herein we describe the construction of hexadecameric self-assembled dendrimers (SADs) using a series of dendronized 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) subunits.The azido-substituted mAG subunits were covalently linked to alkynyl polyester dendrons using a copper-catalyzed 1,3-dipolar cycloaddition reaction.Discrete SADs are formed with high fidelity and thermal stability even with the increased steric hindrance offered by the dendrons.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Puerto Rico, Río Piedras Campus, Río Piedras, Puerto Rico.

ABSTRACT
Herein we describe the construction of hexadecameric self-assembled dendrimers (SADs) using a series of dendronized 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) subunits. The azido-substituted mAG subunits were covalently linked to alkynyl polyester dendrons using a copper-catalyzed 1,3-dipolar cycloaddition reaction. Discrete SADs are formed with high fidelity and thermal stability even with the increased steric hindrance offered by the dendrons.

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