Self-Assembly of aGuanosine DerivativeToForm Nanostructures
Rabindra Nath Das,
Y. Pavan Kumar,
S. Arun Kumar,
Ole Mathis Schütte,
Abstract: We herein report the self-assembly of alipophil-
ic bromoguanosine derivative (G1)inhomogeneous solu-
tion, in the solid state and in planar bilayer membranes.
The self-assembly of G1,driven by H-bonding and p–p
stackinginteractions can form different nano-structures
depending on incubation time. The G1 nanostructure is
able to bind abioactive dyelike Rose Bengal. In crystal
state, it shows ribbon type H-bonding pattern and exhib-
its birefringence in polarized light. And further, the self-as-
sembled nanostructureofG1 can form discretetransmem-
brane ion channels in lipid bilayer membranes, enabling
Guanosine derivatives, owing to their self-assembling proper-
ties, have been used as buildingblocks for fabricating well-de-
fined nanostructures, hydrogels and synthetic ion channels.
Guanosine derivatives can self-assemble using Hoogsteen-type
hydrogen bonding and p–p stacking interactions to generate
tunable three-dimensional highly ordered structures.
philic guanosine derivatives, dependingonthe substituents
and the experimental conditions, are able to form supramolec-
ular architectureslike ribbons, sheets and helices.
In the pres-
ence of metal ions, guanosine derivatives self-assemble to
form macrocyclic G-quartets,
which are building block of
biologically relevant four stranded DNA and RNA secondary
The G-quartet like assembly has been demonstrat-
ed to incorporate aromatic dyes and drug molecules;useful
for industrial and biomedicinal applications.
It has been re-
ported that 8-substitutedguanosinederivatives form stable
cleobasetopreferentially adopt the syn-conformation and ena-
bles Hoogsteen type H-bonding. In our previous report, we
have used acombinationofguanosine 1 and 8-bromoguano-
sine 2 to preparestable hydrogels.
We herein report the self-
assembling and ion passage properties of a8-bromosubstitut-
ed lipophilic guanosine derivative G1.
The lipophilic tert-butyldimethylsilyl (TBDMS) protected bro-
moguanosine derivative G1 was prepared from guanosine nu-
cleoside 1 (Figure 1, Scheme S1, see Supporting Information).
The self-assembling property of G1 on solid surfaces was stud-
ied using AFM and TEM imaging.
The imagesshowedthat the TBDMS protected bromogua-
nosine, G1 formed circular honeycombtype supramolecular
structures after 1h incubation (Figure 2a,b).
heightofthe ring was determined to be 30 nm and the aver-
age width was 125 nm. The images also showedthat some of
Figure 1. Guanosine and its derivatives.
Figure 2. AFM and TEM images of G1 after 1h(a, b);4days(c, d) incubation
(scale bar 400 nm).
[a] R. N. Das, Y. P. Kumar,S.A.Kumar, Prof. Dr.J.Dash
Department of Organic Chemistry
Indian Association for the Cultivation of Science
Jadavpur Kolkata, 700032(India)
[b] O. M. Schütte, Prof. Dr.C.Steinem
Institute for Organic and Biomolecular Chemistry
Georg August University Gçttingen
Supporting information and the ORCID identification number(s) for the au-
thor(s) of this article can be found under:
Chem. Eur.J.2018, 24,4002 –4005 2018 Wiley-VCH Verlag GmbH &Co. KGaA, Weinheim4002