Molecular characteristics of water-soluble fullerene derivatives of amino acids and peptides

The diffusion of fullerene derivatives of amino acids and peptides in dilute aqueous solutions has been studied. These derivatives can exist in solution both as separate molecules and as associates. The degree of association depends both on the nature of the amino acid or peptide residue and on the concentration of the solution.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 879–882, April, 1996.     

Synthesis and properties of water-soluble derivatives of fullerene C60

Procedures for synthesized of water-soluble forms of fullerene C₆₀ and its derivatives were developed.     

Polymeric dressing formulations containing water-soluble fullerene derivatives

The effect of small additions of water-soluble fullerene C₆₀ derivatives on the strength properties of polyvinyl alcohol films was examined. Solutions of polyvinyl alcohol and fullerenol were tested as polymeric dressing formulations for glass-reinforced plastics based on a thermoplastic polyethylene or polyamide matrix.     

Synthesis and antiviral activity of highly water-soluble polycarboxylic derivatives of [70]fullerene

We report here a facile preparation of highly water-soluble derivatives C(70)[p-C(6)H(4)(CH(2))(n)COOH](8) (n = 2, 3) starting from readily available chlorinated [70]fullerene precursors C(70)Cl(8) and C(70)Cl(10). The synthesized fullerene derivatives showed pronounced antiviral activity in vitro, particularly against human immunodeficiency virus (HIV) and influenza A virus (subtypes H1N1 and H3N2).     

Synthesis of water-soluble cationic cellulose derivatives with tertiary amino groups

Water-soluble cellulose derivatives with tertiary amino groups up to substitution degree 0.8 (4.2% of coupled nitrogen) were prepared in a controlled manner by the interaction of cellulose acetate with N,N-diethylepoxypropylamine. It was shown that two reactions take place simultaneously, i.e., hydrolysis of acetyl groups and aminoalkylation of free hydroxyl groups of cellulose. The amino groups coupled to the cellulose are of middle basicity with pK _α ~9.5. Solubility of the products was found to be determined by the chemical composition of the cellulose derivative.     

Sugar-functionalized water-soluble cyclotriveratrylene derivatives: preparation and interaction with fullerene

Cyclotriveratrylene (CTV) has attracted much attention because of its good chemical stability, small cavity, stable conformation, and facile modification. In this article, two water-soluble CTV derivatives (CTV-G and CTV-L) functionalized by glucose and lactose residues were synthesized, respectively. Unexpectedly, sugar-bearing CTVs exhibit a distinct photoluminescence, which might be ascribed to the enhanced planar conformation of cyclotriveratrylene ring derived from the spatial effect of bulky branch groups. The interaction between the water-soluble CTV derivatives and C(60) was investigated in organic solvent and aqueous solution, which was further characterized by fluorescence spectra, ultraviolet-visible spectra, and Raman spectra. CTV-G can associate with C(60) to form supramolecular complex with 1:1 molar ratio (K(a) = 1.38 × 10(5) M(-1), 298 K). As for CTV-L, a similar complex with a lower association constant (K(a) = 5.09 × 10(4) M(-1), 298 K) can also be formed.     

Synthesis and characterization of adducts of p-azidostyrene derivatives to fullerene C_(60)

Fullerene C60 reacted with p-azidostyrene derivatives in refluxing chlorobenzene,yielding monoadducts 2a and 2d as well as diadduct 2c with aziridine structure at 6/6-ring junctions.Experimental results showed that the addition of the second azide to the monoadduct was regioselective.The diadduct,of Cs symmetry in C60 moiety,was unstable by opening to be 1,6-imido[10]annulene structure.     

Synthesis and characterization of water-soluble O-succinyl-chitosan

The efficient procedure to prepare novel water-soluble O-succinyl-chitosan was established by using one three-step reaction. Phthaloyl group was firstly chosen as the protection group for the amino group of chitosan, and O-succinylation was then completed. Protection group was removed finally by using hydrazine hydrate. The chemical structure of the modified chitosan was characterized by FTIR, ¹H-NMR, ¹³C-NMR and elemental analysis. Some physical properties were analyzed by X-ray diffraction, differential scanning calorimetry (DSC), thermogravimetry (TG) and solubility test. It indicates that after O-succinylation, the modified chitosan shows much better solubility in water. The study of enzymatic degradation showed that the O-succinyl-chitosan was of low susceptibility to lysozyme. O-succinylation-chitosan is a useful intermediate, which permits further chemical modification for amino group and may be have potential applications in biomedical system.     

Optical circular dichroism of the fullerene amino acid derivatives

The dependence of the circular dichroism spectra of the amino acid derivatives of fullerene C₆₀ on the structure of the initial α-amino acid was studied.     

Interaction of water-soluble pentaamino acid fullerene derivatives with membranes of phosphatidylcholine liposomes

Russian Chemical Bulletin - Regularities of interaction of water-soluble pentaamino acid derivatives of fullerenes (WPDFs) with the lipid bilayer of phosphatidylcholine liposomes were studied using...     

新型水溶性金属酞菁化合物的合成与表征

以含有咪唑阳离子的邻苯二腈为前驱体,通过环合反应分别合成了四咪唑阳离子取代的锌酞菁和铜酞菁,它们的结构均通过了红外光谱、核磁氢谱、元素分析和紫外-可见吸收光谱的表征.这2种酞菁化合物在水、DMF、DMSO及甲醇中均呈现出良好的溶解性.利用紫外-可见吸收光谱法考察了它们在不同种溶剂中、不同浓度下的聚集行为,并利用循环伏安法和方波伏安法测试了它们的电化学性质.     

含糖基水溶性紫外吸收剂的合成与表征

以三聚氯氰(TCT)、2,4-二羟基二苯甲酮(UV-0)、双丙酮葡萄糖为原料,经三步反应合成一种具有反应性基团的水溶性紫外吸收剂3-(2-(2-羟基苯基苯甲酮-4-氧基)-4-氯-1,3,5-三嗪-6-氧基)-1,2-异丙叉-α-D-葡萄糖(UV-DTM),产物的结构经IR、NMR和MS表征。探讨了每一步反应的条件对反应产率的影响。合成3-(4,6-二氯-1,3,5-三嗪-2-氧基)-1,2,5,6-双异丙叉-α-D-葡萄糖(DTDT)的优化反应条件为:n(三聚氯氰)∶n(双丙酮葡萄糖)∶n(Na OH)=0.9∶1∶1.7,在丙酮和水的混合体系中0℃下反应8h,产率73%。合成3-(2-(2-羟基苯基苯甲酮-4-氧基)-4-氯-1,3,5-三嗪-6-氧基)-1,2,5,6双异丙叉-α-D-葡萄糖(UV-DT)的优化条件为:n(DTDT)∶n(UV-0)∶n(Na OH)=1∶1.1∶1,在丙酮和水的混合体系中30℃下反应2h,产率74%。合成UV-DTM的优化条件为:每1mmol UV-DT与0.5m L盐酸(36%)在THF体系中25℃下反应5h,产率74%。UV-DTM的紫外吸收性能在240~400 nm内表现良好,水溶性得到大幅改善。     

"Deconvoluted fullerene" derivatives: synthesis and characterization

We have designed the synthesis of "deconvoluted fullerene" derivatives that present an ordered pattern of hexagons and pentagons in the backbone of the molecule. We not only mimicked the fullerene structure in dihedral planes, but also preserved its electron accepting behavior and enlarged its optical absorption. Moreover, very preliminary photoluminescence (PL) quenching experiments also confirmed the potentiality of these materials as acceptors in the field of organic photovoltaics (OPV)s. A brief discussion of the surface morphology, based on AFM analysis, is also presented.     

Synthesis of novel fullerene amino acids and their multifullerene peptides

[60]-Fullerene functionalized amino acids with 4-6 methylene spacers from α-carbon to the nitrogen atom of fulleropyrolidine and corresponding multifullerene peptides have been synthesized.     

Synthesis and spectroscopic properties of highly water-soluble perylene derivatives

Most known perylene diimides are lipophilic, with few exceptions of hydrophilic derivatives. Even in the latter case, the compounds have limited water solubility and show a strong tendency to self-aggregation. In this paper we present the synthesis of four new perylene derivatives with three and four basic side chains, obtained by functionalizing the bay-area of perylene. These molecules show great solubility in aqueous media as hydrochlorides and their tendency to self-aggregate is remarkably reduced with respect to the previously synthesized two-chained perylene diimides. Their different spectroscopic properties in various solvents and conditions are reported and discussed.     

Synthesis and antineoplastic activity of novel water-soluble curcumol derivatives

6-Succinyl curcumol sodium salt was synthesized by reaction of curcumol with succinic acid. The structure of the derivative was confirmed by NMR spectroscopy and mass spectrometry. Furthermore, the derivative showed antitumor activity, which makes it a promising antitumor drug candidate that overcomes the insolubility in water.     

Synthesis and characterization of PS-block-PEO associative water-soluble polymers

We report the synthesis and structure determination of PS-block-PEO functionalized by fluorocarbon end-group (C₈F₁₇) via an ester bridge. The synthesis was done by an anionic polymerization of PS and POE terminated by grafting 3-perfluorooctylpropanoyle chloride (C₈F₁₇-C₂H₄-COCl) onto PS-POE alcoholate. The structure has been characterized by a number of techniques: size exclusion chromatography, elementary analysis, UV spectroscopy, ¹H nuclear magnetic resonance. Those analyses have allowed the determination of the real molar mass of the copolymers and the percentage functionalization. Because of their well-defined structure, these copolymers can be used as model compounds for the determination of structure-property relationships.     

Heat capacities of aqueous solutions of amino acid and dipeptide derivatives of fullerene

The concentration dependences of heat capacities of aqueous solutions of several amino acid and peptide derivatives of fullerene were measured by scanning differential calorimetry at 298 K. The heat capacities for the arginine, alanylalanine, and glycylvaline derivatives dissolved in water depend slightly on concentration. The concentration dependences of the heat capacities of aqueous solutions of the serine and alanine derivatives display extrema. The calculated contributions of hydration to the heat capacities of the dissolved fullerene derivatives have both positive and negative signs. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2202–2204, November, 1998.     

Synthesis and characterization of water-soluble and photostable L-DOPA dendrimers

A small drug molecule, L-DOPA, was converted into well-defined dendritic macromolecules. Their monodisperse nature was shown by NMR, MALDI-TOF-MS, and PAGE. A third-generation L-Dopa dendrimer contained 30 L-Dopa residues, which made up its core, branches, and periphery. Individual L-Dopa moieties in the dendrimer were connected to one another via hydrolyzable diester linkages. These Dopa dendrimers showed a 20-fold increase in aqueous solubility and enhanced photostability in solutions over L-Dopa under identical conditions.     

Synthesis and properties of pentane amino derivatives

Synthesis of pentane amino derivatives by the reaction of the corresponding amines with 1-bromopentanes of n- and iso-structure by environmentally safe methods in water medium was carried out. The structure of the compounds obtained was confirmed by elemental analysis, IR, ¹H and ¹³C NMR spectroscopy. The products synthesized were tested as reagents for the suppression of growth of the sulfate-reducing bacteria and as the anticorrosive substances. It was found that they are effective bactericides for the sulfate-reducing bacteria and exhibit high anticorrosive properties.