title: Iodo-bis(quaternary ammonium) salts. Potential cartilage-selective x-ray contrast agents.
abstract: Bis(quaternary ammonium) compounds in which one or both quaternary nitrogens bear iodinated benzyl moieties and the charged centers are separated by 2, 4, 6, or 10 methylene units have been synthesized and evaluted for (a) binding to cartilaginous material, (b) radiocontrast characteristics, and (c) in vitro pharmacological effects. Also prepared was 1,5-diiodo-2,4-bis(beta-trimethylammonioethyl)benzene diiodide, an analogue in which the iodinated aryl group lies between the charged nitrogen centers. Biological studies show that these compounds bind to cartilage but at relatively slow rates and with low persistence, resulting in low and transient levels of radiopacity. In common with simpler bisquaternary compounds, these compounds block synaptic transmission.
mesh_terms: D000818:Animals; D002356:Cartilage / Q000000981:diagnostic imaging*; D002809:Chondroitin Sulfates / Q000378:metabolism; D003287:Contrast Media / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D004285:Dogs; D005260:Female; D066298:In Vitro Techniques; D008297:Male; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D011859:Radiography; D051381:Rats; D013569:Synapses / Q000187:drug effects; D009435:Synaptic Transmission / Q000187:drug effects
chemical_list: D003287:Contrast Media; D000644:Quaternary Ammonium Compounds; D002809:Chondroitin Sulfates