Water-induced gel formation of an oleanlic acid–adenine conjugate and the effects of uracil derivative on the gel stability

Lu, Jinrong; Hu, Jun; Liu, Chulong; Gao, Hongxin; Ju, Yi‐Hsu

doi:10.1039/c2sm26085a

Cited by 41 publications

(32 citation statements)

References 75 publications

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“…0.5–3 μm, and by entanglement of such fibers, a closely packed 3D network structure was created to trap the solvent molecules into its interstices. The fiber sizes of these two-component CT gels were larger than those of one-component organogels obtained by us previously [42–44]. On the other hand, these xerogels also revealed various types of morphologies based on the different solvent systems.…”

Section: Resultsmentioning

confidence: 57%

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

Hu¹,

Wu²,

Wang³

et al. 2013

Beilstein J. Org. Chem.

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SummaryWe describe herein the two-component charge-transfer (CT) interaction induced organogel formation with 18β-glycyrrhetinic acid appended pyrene (GA-pyrene, 3) as the donor, and 2,4,7-trinitrofluorenone (TNF, 4) as the acceptor. The use of TNF (4) as a versatile electron acceptor in the formation of CT gels is demonstrated through the formation of gels in a variety of solvents. Thermal stability, stoichiometry, scanning electron microscopy (SEM), optical micrographs, and circular dichroism (CD) are performed on these CT gels to investigate their thermal and assembly properties. UV–vis, fluorescence, mass spectrometric as well as variable-temperature 1H NMR experiments on these gels suggest that the CT interaction is one of the major driving forces for the formation of these organogels.

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Section: Resultsmentioning

confidence: 57%

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

Hu¹,

Wu²,

Wang³

et al. 2013

Beilstein J. Org. Chem.

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“…Functionally rich naturally occurring triterpenoids with several hydroxyl and carboxyl groups offers innumerable opportunities for the generation of triterpenoid derivatives depending upon ones design and requirements . Some of the triterpenoids also occur in nature as salts or linked with sugars as in triterpenoid saponins in some plants .…”

Section: Self‐assembly Of the Derivatives Of Triterpenoids And Study mentioning

confidence: 99%

Self‐assembly of Renewable Nano‐sized Triterpenoids

Bag

Majumdar

2017

The Chemical Record

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Studies on plant metabolites have gained renewed interest in recent years because these can serve as renewable chemicals for the development of a sustainable society. Among various plant secondary metabolites, terpenoids constitute the major component and triterpenoids are the 30C subset of it. In recent years, triterpenoids have drawn the attention of scientific community due to many of its potential and realized applications in medicine, drug delivery, thermochromic materials, pollutant capture, catalysis, liquid crystals, etc. In this personal review, we have discussed our computational results carried out on sixty representative naturally occurring triterpenoids demonstrating that all the triterpenoids are renewable functional nano-entities. Study of the self-assembly of several triterpenoids such as betulin, betulinic acid, oleanolic acid, glycyrrhetinic acid and arjunolic acid and their derivatives in different liquids have also been discussed. Moreover, the utilization of the resulting supramolecular architectures such as vesicles, spheres, flowers and fibrillar networks of nano- to micrometer dimensions and gels have also been discussed in the perspective of green, renewable and nanos.

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“…[22][23][24][25] Recently, the gelation of adenine with tricarboxylic acid compounds was reported based on hydrogen bonding and π-π stacking. 26,27 We are interested in exploring whether it is possible to achieve gelation by metal coordination with adenine derivatives. Guanine and its derivatives have been mixed with monovalent metal ions to form gels based on quadruplex formation.…”

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confidence: 99%

Self-healing metal-coordinated hydrogels using nucleotide ligands

et al. 2015

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A supramolecular gel formed by Zn 2+ coordination with adenosine monophosphate (AMP) is reported. The adenine base, the monophosphate, and Zn 2+ are all important for gel formation. Mechanically disrupted gels can re-form upon centrifugation; applications of this gel for guest molecule entrapment are explored.Supramolecular gels have received considerable attention in recent years both as intriguing examples of self-assembly and as a means of creating smart materials.1-5 These gels are formed by noncovalent interactions to assemble supramolecular networks that trap solvent. 6Among the various types of supramolecular gels, those crosslinked by metal coordination are particular interesting. A few types of ligands have been developed for this purpose. For example, Craig and coworkers reported organopalladium−pyridine coordination. 16,17 Self-healing is a very interesting and useful feature of metal-coordinated gels; broken gel pieces can seal together with a mild mechanical force.Most of previously reported gels have to use specially designed ligands (e.g. incorporating a segment of PEG chain in addition to the metal ligand) to facilitate solvent trapping and gelation. Few reports are based on pure small molecule ligands. We reason that small molecule ligands will allow a higher metal density and thus may display different properties.Adenine, a purine nucleobase, is an important ligand in supramolecular chemistry. Adenine and its derivatives can form many complexes by coordination (with metal ions) and hydrogen bonding (with organic molecules). [18][19][20] With metal ions, it may form metalorganic frameworks, 21 and nanoparticles. [22][23][24][25] Recently, the gelation of adenine with tricarboxylic acid compounds was reported based on hydrogen bonding and π-π stacking. 26,27 We are interested in exploring whether it is possible to achieve gelation by metal coordination with adenine derivatives. Guanine and its derivatives have been mixed with monovalent metal ions to form gels based on quadruplex formation. 28-31 However, little has been done on adenine derivatives. Nanoparticles are the most common products. [22][23][24][25] Compared to nanoparticles, hydrogels are more attractive materials for making stimuli-responsible materials. [32][33][34][35][36][37][38][39] In this work, we communicate such an example, its property in guest molecule encapsulation, and healing.Since most previous work focused on adenine nucleobase and nucleoside as ligands, we started with nucleotide coordination in this work. Zn 2+ was chosen as the metal because it is a good Lewis acid that can be coordinated by a diverse range of ligands. In addition, it is a relatively biocompatible metal with low toxicity. We first studied the reaction between Zn 2+ and three kinds of nucleotides (AMP, GMP and CMP). TMP was not included since thymine has very weak coordination ability at neutral pH. Zn 2+ was respectively titrated into the solutions of AMP, GMP and CMP, and the UV-vis extinction at 550 nm was recorded. Since none of the products are c...

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Water-induced gel formation of an oleanlic acid–adenine conjugate and the effects of uracil derivative on the gel stability

Cited by 41 publications

References 75 publications

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

Self‐assembly of Renewable Nano‐sized Triterpenoids

Self-healing metal-coordinated hydrogels using nucleotide ligands

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