ABSTRACT
Dynamic hydrogels are viscoelastic materials that can be designed to be self-healing, malleable, and injectable, making them particularly interesting for a variety of biomedical applications. To design dynamic hydrogels, dynamic covalent crosslinking reactions are attracting increasing attention. However, dynamic covalent hydrogels tend to swell, and often lack stability. Boronate ester-based hydrogels, which result from the dynamic covalent reaction between a phenylboronic acid (PBA) derivative and a diol, are based on stable precursors, and can therefore address these limitations. Yet, boronate ester formation hardly occurs at physiological pH. To produce dynamic covalent hydrogels at physiological pH, we performed a molecular screening of PBA derivatives in association with a variety of diols, using hyaluronic acid as a polymer of interest. The combination of Wulff-type PBA (wPBA) and glucamine stood out as a unique couple to obtain the desired hydrogels. We showed that optimized wPBA/glucamine hydrogels are minimally- to non-swelling, stable long term (over months), tunable in terms of mechanical properties, and cytocompatible. We further characterized their viscoelastic and self-healing properties, highlighting their potential for biomedical applications.
Subject(s)
Esters , Hydrogels , Hydrogels/chemistry , Polymers/chemistry , Boronic Acids/chemistryABSTRACT
The synthesis of 2-isopropenyl-2,3-dihydrobenzofuranic enantioisomers is described. Ortho-(2-hydroxy-3-methyl-but-3-enyl)phenol synthons are used as precursors to these structures. In vitro antitumor activity against a non-small-cell bronchopulmonary carcinoma line (NSCLC-N6) of these enantioisomers has been investigated.
Subject(s)
Antineoplastic Agents , Benzofurans , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Benzofurans/chemical synthesis , Benzofurans/chemistry , Benzofurans/pharmacology , Carcinoma, Non-Small-Cell Lung/pathology , Cell Survival/drug effects , Humans , Inhibitory Concentration 50 , Lung Neoplasms/pathology , Molecular Structure , Stereoisomerism , Structure-Activity Relationship , Tumor Cells, CulturedABSTRACT
Six coumarins have been isolated from the fruits and the stem bark of Calophyllum dispar (Clusiaceae). The structures of these minor components were established by means of spectroscopic analysis, including extensive 2D NMR studies. Some of these coumarins exhibited a significant cytotoxic activity against KB cells.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Clusiaceae/chemistry , Coumarins/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Coumarins/chemistry , Humans , Spectrum Analysis , Tumor Cells, CulturedABSTRACT
The synthesis of benzopyranic simplified analogues of dibenzopyranic natural compounds is described, together with the access to a precursor of a new furobenzopyranic natural product. These natural products have anti-cancer activity. The 1,3-diacetoxy-2-acetyl-4-(3-hydroxy-3-methylbut-1-enyl)benzene synthone is used as a common precursor to these structures.
Subject(s)
Acetophenones/chemical synthesis , Alcohols/chemistry , Allyl Compounds/chemical synthesis , Benzopyrans/chemical synthesis , Biological Products/chemical synthesis , Biological Products/chemistry , Calophyllum/chemistryABSTRACT
Eight new 4-phenylfuranocoumarins (1-8) have been isolated from the stem bark and the fruits of Calophyllum dispar, together with three known coumarins. The structures of 1-8 were established by means of spectroscopic analysis, including extensive 2D NMR studies. Some of these furanocoumarins exhibited significant cytotoxic activity against KB cells.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Coumarins/isolation & purification , Plants, Medicinal/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Coumarins/pharmacology , Drug Screening Assays, Antitumor , Fruit/chemistry , Humans , KB Cells , Mass Spectrometry , Plant Epidermis/chemistry , Spectrophotometry, UltravioletABSTRACT
Four new xanthones, caledonixanthones A-D (1-4), were isolated from the trunk bark of Calophyllum caledonicum, in addition to 17 known compounds. The structures of 1-4 were determined by means of spectroscopic analysis and chemical derivatization.
