Designer amphiphiles based on para-acyl-calix[8]arenes.
The synthesis of a series of fully O-derivatised para-acyl-calix[8]arenes is described, where the acyl function is either octanoyl or hexadecanoyl. The groups attached at the phenolic face are, carboxymethoxy (anionic), carboxypropoxy (anionic), 4-sulfonatobutoxy (anionic), ethoxycarboxymethoxy (neutral), ethoxycarboxypropoxy (neutral), 2-methoxyethoxy (neutral) and 2-(2-methoxy)diethoxy (neutral). The use of specific synthetic routes has allowed complete substitution in high yields for all the compounds obtained. The interfacial properties of the compounds have been studied and stable monolayers have been obtained for certain compounds in the series having para-octanoyl substituents; all compounds studied in the series having para-hexadecanoyl substituents formed stable monolayers at the air-water interface. The interactions between O-4-sulfonatobutoxy-para-ocatanoylcalix[8]arene and a series of serum albumins have been studied by dynamic light scattering and specific adsorption of the calix-[8]-arene derivative onto the proteins observed. The anionic derivatives O-4-sulfonatobutoxy-para-ocatanoylcalix[8]arene and O-carboxymethoxy-para-ocatanoylcalix[8]arene have been shown to possess anticoagulant properties but to have no haemolytic toxicity.
Jebors
Saïd
S
Institut de Biologie et Chimie des Protéines, 7 passage du Vercors, Lyon, F-69367, France.
Fache
Fabienne
F
Balme
Sylvain
S
Devoge
Floriane
F
Monachino
Melany
M
Cecillon
Sebastien
S
Coleman
Anthony W
AW
D000818:Animals; D000925:Anticoagulants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001777:Blood Coagulation / Q000187:drug effects; D047250:Calixarenes / Q000138:chemical synthesis* / Q000494:pharmacology; D002417:Cattle; D004912:Erythrocytes / Q000187:drug effects; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D015394:Molecular Structure; D010316:Particle Size; D012710:Serum Albumin, Bovine / Q000737:chemistry / Q000187:drug effects; D012995:Solubility; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013501:Surface-Active Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013997:Time Factors
D000925:Anticoagulants; D013501:Surface-Active Agents; D047250:Calixarenes; D012710:Serum Albumin, Bovine