Design and development of soft nanomaterials from biobased amphiphiles

John, George; Vemula, Praveen Kumar

doi:10.1039/b609422h

Cited by 76 publications

(63 citation statements)

References 28 publications

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“…In this manner, the balance of a hydrophilic group and a hydrophobic group is important to form a supramolecular aggregate like other LWMGs. 11 It has been reported that guanidinium chloride forms a fibrous nanostructure with 12-hydroxystearic acid in water. 29 In place of arginine, guanidinium chloride was mixed with DDA.…”

Section: 1nmmentioning

confidence: 99%

“…[3][4][5][6][7][8][9] Noncovalent interactions such as hydrogen-bonding, van der Waals, p-p and electrostatic interactions function as driving forces to stabilize these supramolecular nanostructures. 10,11 Polymerization of constituent molecules in supramolecular selfassemblies 12 will provide stable covalent assemblies. In particular, polymerization of the LWMGs with diacetylene groups has been actively investigated, [13][14][15][16] as simple photoirradiation induces polymerization or oligomerization if they arrange and align in a good order.…”

Section: Introductionmentioning

confidence: 99%

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Supramolecular nanofiber formation from commercially available arginine and a bola-type diacetylenic diacid via hydrogelation

Mukai

Kogiso

Aoyagi

et al. 2012

Polym J

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A diacetylenic-acid arginine salt gelated water. The supramolecular structure and optical properties of the resultant hydrogel were examined by optical microscopy, electron microscopy, X-ray diffraction and ultraviolet (UV)-absorption and circular dichroism (CD) spectroscopies. Microscopic images showed that 10, 12-docosadiynedioic acid arginine salt formed a fibrous structure. X-ray diffraction and nuclear magnetic resonance measurements indicated guanidinium-carboxylate interaction. Upon UV irradiation, the gel polymerized to diacetylene oligomers, with a concomitant color change from white to orange. After the removal of arginine, CD spectra indicated that the diacetylene oligomers maintained chirality. Polymer Journal (2012) 44, 646-650; doi:10.1038/pj.2012.46; published online 4 April 2012Keywords: arginine; diacetylene; hydrogel; polymerization; self-assembly INTRODUCTION Low-molecular-weight gelators (LMWGs) have attracted much interest because of their unique features and potential applications as new soft materials. 1,2 The LMWGs construct supramolecular 3D networks consisting of nanofibrous assemblies of amphiphilic molecules. [3][4][5][6][7][8][9] Noncovalent interactions such as hydrogen-bonding, van der Waals, p-p and electrostatic interactions function as driving forces to stabilize these supramolecular nanostructures. 10,11 Polymerization of constituent molecules in supramolecular selfassemblies 12 will provide stable covalent assemblies. In particular, polymerization of the LWMGs with diacetylene groups has been actively investigated, [13][14][15][16] as simple photoirradiation induces polymerization or oligomerization if they arrange and align in a good order. The connection of amide, aromatic or ionic groups to diyne motives through synthetic derivation enables one to attain appropriate molecular arrangement to the polymerization. In most cases, however, the derivation requires several tedious steps. Moreover, a careful handling is necessary at every step to avoid photopolymerization of the synthetic intermediates under light.We have widely investigated the supramolecular nanostructures self-assembled from bola-amphiphiles. [16][17][18][19][20][21][22][23] For example, we previously reported that butadiyne 1-glucosamide connected bolaamphiphiles self-assemble to form nanofibers, and polymerization by photoirradiation causes the gelation of supramolecular networks in organic solvents. 16 In this synthesis, we always needed multistep derivation to attain the gelation.In the present work, we propose a new simple bola-type diacetylenic gelator. Inspired by the reports on gel-like systems of fatty acids and arginine, 24,25 we examined a salt of arginine and bola-type diacetylene diacid 10, 12-docosadiynedioic acid (DDA) for hydrogelation ( Figure 1). The salt gelator requires no multistep synthetic derivation. The hydrogel system showed formation of nanofibers and their stabilization by photo-oligomerization as well as chirality transfer to the nanofibers after the removal of the chiral amino acid. ...

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Section: 1nmmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Supramolecular nanofiber formation from commercially available arginine and a bola-type diacetylenic diacid via hydrogelation

Mukai

Kogiso

Aoyagi

et al. 2012

Polym J

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“…According to Bloise et al (2012), the cardanol consists of a rich amount of phenolic lipids: 3-n-pentadecylphenol (20-30%), 3-(pentadeca-8-enyl) phenol (70 -80%), 3-(pent-deca-8,11-dienyl) phenol (5%), and 3-(pentadeca-8,11,14-trienyl) phenol (< 5%) . The cardol (5-npentadecylresorcinolic acid) has a similar structure of tocopherol and a long chain of saturated hydrocarbons or lacks it (Kozubek and Tyman, 1999;John and Vemula, 2006). Among the phenolic compounds, trienes constitute the greatest amount followed by monoenes, dienes (Nishiyama et al, 2000).…”

Section: Contents Of Cashew and The Extraction Processes Of Cashew LImentioning

confidence: 99%

Pharmacological properties of cashew (Anacardium occidentale)

Leite¹,

Islam²,

Junior³

et al. 2016

Afr. J. Biotechnol.

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Anacardium occidentale L. is a tree native to Brazil, which is rich in phenolic lipids. Nowadays, the cashew bark (Cashew Nut Shell Liquid) has received great attention in the pharmaceutical industry, due to its economy, abundance and important chemical compounds. Net of cashew nut shell is classified according to the method of production of: (1) net of the shell of natural cashew nut (60-65% anacardic acid; 15-20% cardol and 10% of cardanol) and (2) liquid from the technical cashew nut shell (60-65% of cardanol, 15-20% cardol and 10% of polymeric material). This work aims to report the pharmacological properties of liquids from cashew nut shells. Results suggest that both liquids have antifungal, antibacterial, antiparasitic, anti-tumor, antiulcerogenic, molluscicides, antimutagenic and antioxidant activities. Natural cashew nut liquid is non-genotoxic, whereas technical liquid is genotoxic in prokaryotes and eukaryotes, although there is no evidence of their mutagenic effects on eukaryotic cells. In conclusion, the excellent antioxidant and non-mutagenic activities of cashew nut shell liquid (CNSL) provide opportunities for CNSL in the cosmetic and/or pharmaceutical industries, but continuous study is needed to allow safe and efficacious preparations.

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“…Cardanols, an example of sugar-lipid conjugate, consists of a carbohydrate head group and an aliphatic alkyl chain connected through a phenyl moiety. When dispersed in aqueous solution at room temperature, this material forms fibrous aggregation and nanotubular structures [11]. Although related literature on further practical application of cardanol-based glycolipids is absent, its selfassembling properties have promoted the synthesis of several glycolipids such as monosaccharide esters with diamino-aromatic linkers [12], amygdalin-based esters [13] and dialkanoate derivative of sugar alcohols [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of nanoarchitectures from fatty acid derivatives of 2,6-diaminopyridine and 2-aminopyridine

Hassan

Rauf

2014

J Nanostruct Chem

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The self-assembling property of lipids makes it an important building block in the field of supramolecular nanoarchitectures with a variety of applications in chemistry, biochemistry, materials science and medicine. We report here, the synthesis and formation of variety of nanostructures such as nanosheets, nanofibers and nanotubes of fatty acid derivatives of 2,6-diaminopyridine and 2-aminopyridine. These molecules possess a saturated or unsaturated long alkyl-chain group as the self-assembling unit. The molecular recognition property of diaminopyridine linker as a result of H-bonding was confirmed by 1 H-NMR and fluorescence spectroscopy and it plays an important role in monitoring the chemical selectivity of supramolecular aggregates toward guest binding. The chemical structures were characterized by Fourier transform-infrared, 1 H-NMR, 13 C-NMR, mass spectra, whereas the morphologies were imaged using scanning electron microscopy and transmission electron microscopy.

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Design and development of soft nanomaterials from biobased amphiphiles

Cited by 76 publications

References 28 publications

Supramolecular nanofiber formation from commercially available arginine and a bola-type diacetylenic diacid via hydrogelation

Supramolecular nanofiber formation from commercially available arginine and a bola-type diacetylenic diacid via hydrogelation

Pharmacological properties of cashew (Anacardium occidentale)

Synthesis and characterization of nanoarchitectures from fatty acid derivatives of 2,6-diaminopyridine and 2-aminopyridine

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