A General Scheme Based on Empirical Increments for the Prediction of Hydrogen‐Bond Associations of Nucleobases and of Synthetic Host–Guest complexes

Sartorius, Joachim; Schneider, Hans‐Jörg

doi:10.1002/chem.19960021118

Cited by 190 publications

(163 citation statements)

References 66 publications

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“…The electrostatic effects have been quantified and it has been shown that each primary hydrogen-bonding interaction showed a contribution of %8 kJ mol À1 to the free energy of complexation. 42 Each attractive or repulsive secondary interaction increases or decreases the free energy with 2.9 kJ mol À1 , respectively. This implies that the keto UPy-tautomer has less repulsive secondary interactions and therefore a higher dimerization constant than the enol UPy-tautomer.…”

Section: The Biomaterialsmentioning

confidence: 99%

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Dankers

Meijer²

2007

Bulletin of the Chemical Society of Japan

123

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Supramolecular chemistry is an exciting area of science that plays a central role in bringing different disciplines together, ranging from molecular medicine to nanotechnology. Materials science based on supramolecular interactions is an emerging field, which has made important steps forward in the past ten years. The self-assembly of small synthetic molecules into long-chain architectures gives rise to the careful design of supramolecular polymers or fibers based on highly directional, reversible, non-covalent interactions. Much afford is put into the development of supramolecular (polymeric) materials with true materials properties, both in solution and in the solid state. These supramolecular materials are beginning to reach the market in all kind of applications. The field of regenerative medicine in general and that of tissue engineering in particular is one of the most challenging areas in which supramolecular materials might have a high potential. In tissue engineering, the biological environment and the interactions of cells with the artificial biomaterial is of utmost importance for the functioning of the implant, i.e. the engineered tissue. Ideal biomaterials do not only have to fulfil the biomaterials trinity of tuneable mechanical properties, regulation of the degradability and the ease for bioactivity incorporation, but also have to mimic the natural environment where the materials are brought into. Therefore, a modular, self-assembly approach using several supramolecular building blocks is an exquisite way to produce such ''responsive'' biomaterials. It is proposed that the artificial materials described in this account have the same type of dynamic ability to adapt its biofunctionality as is so well known for the living cells in the host tissue. This account will highlight two systems, i.e. self-assembling oligopeptide fibers as pioneered by Stupp et al. and Zhang et al., and our hydrogen-bonded supramolecular polymers, to show the potential of a modular approach to dynamic biomaterials for tissue engineering.

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Section: The Biomaterialsmentioning

confidence: 99%

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Dankers

Meijer²

2007

Bulletin of the Chemical Society of Japan

123

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“…Table 1 shows a compilation of methods and thermodynamic parameters, reported for the interaction of thymine and adenine. In addition, Sartorious and Schneider 16 have proposed an empirical rule to determine a K value for the H-bonding interaction in a substrate-receptor system. The K value calculated, by this rule, for the pair thymine-adenine is 56.62 M -1 .…”

Section: Introductionmentioning

confidence: 99%

Enthalpy and entropy contributions to the equilibrium of the hydrogen bonding interaction between 1-octylthymine and 9-octyladenine

Salas¹,

Gordillo²,

González³

2003

Arkivoc

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Hydrogen bonding interaction between 1-octylthymine (1) and 9-octyladenine (2) was analyzed by dynamic proton NMR spectroscopy. A mathematical model that takes into account the independent self-association of 1 and 2 was developed in order to determine the equilibrium constant of the interaction between 1-octylthymine and 9-octyladenine K 1-2 . The measurement of K 1-2 , in CDCl 3 , in the range of temperatures of -30 to 40 o C permitted estimation of the contributions of enthalpy ∆H o = -6.74 kcal/mol, and entropy ∆S o = -13.95 cal mol -1 K -1 , to the hetero-association process. From the enthalpic point of view the association of 1-octylthymine with 9-octyladenine is 0.56 kcal/mol stronger than the self-association of 1-octylthymine, and 0.09 kcal/mol stronger than the self-association of 9-octyladenine. X-ray diffraction of a monocrystal of mixed 1-octylthymine and 9-octyladenine indicated that the interaction between these nucleobases in the solid state resemble Haschemeyer-Sobell more than Watson-Crick hydrogen bonding.

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“…[23][24][25][26][27] Nucleosides A and U, having a symmetric ADA:DAD H-bonding pattern (Figure 4), associate in CHCl3 (or CDCl3) with Ka = 1.8-3.1 x 10 2 M -1 . In the less polar CHCl3 (or …”

Section: Discussionmentioning

confidence: 99%

“…In this work we also study the hydrogen-bonding dimerization and hetero-association processes between complementary units (G-C, iG-iC, G-iC, iG-C and A-U) by both 1 H NMR and absorption spectroscopies, and analyze the binding isotherms by adequate fitting programs in order to obtain the relevant association constants. 22 Guanine-cytosine and adenine or 2-aminoadenineuracile binding has already been studied by a number of authors, [23][24][25][26][27] so this work offers new quantitative data on their association constants studied and analyzed by diverse methods. However, to the best of our knowledge, no data has been reported so far on the association between isoguanine and isocytosine in organic solvents, or on the interactions between these nonnatural bases and cytosine or guanine.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and complementary self-association of novel lipophilic π-conjugated nucleoside oligomers

et al. 2015

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Esta es la versión de autor del artículo publicado en: This is an author produced version of a paper published in: A series of lipophilic nucleosides comprising natural and non-natural bases that are -conjugated to a short oligophenylene-ethynylene fragment has been synthesized. These bases comprise guanosine, isoguanosine, 2-aminoadenosine as purine heterocycles, and cytidine, isocytosine and uridine as complementary pyrimidine bases. The hydrogen-bonding dimerization and association processes between complementary bases were as well studied by 1 H NMR and absorption spectroscopies in order to obtain the relevant association constants.

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A General Scheme Based on Empirical Increments for the Prediction of Hydrogen‐Bond Associations of Nucleobases and of Synthetic Host–Guest complexes

Cited by 190 publications

References 66 publications

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Supramolecular Biomaterials. A Modular Approach towards Tissue Engineering

Enthalpy and entropy contributions to the equilibrium of the hydrogen bonding interaction between 1-octylthymine and 9-octyladenine

Synthesis and complementary self-association of novel lipophilic π-conjugated nucleoside oligomers

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