Superoxide dismutase/catalase mimetics, such as salen Mn complexes and certain metalloporphyrins, catalytically neutralize reactive oxygen and nitrogen species, which have been implicated in the pathogenesis of many serious diseases. Both classes of mimetic are protective in animal models of oxidative stress. However, only AEOL11207 and EUK-418, two uncharged Mn porphyrins, have been shown to be orally bioavailable. In this study, EUK-418 and several new analogs (the EUK-400 series) were synthesized and shown to exhibit superoxide dismutase, catalase, and peroxidase activities in vitro. Some also protected PC12 cells against staurosporine-induced cell death. All EUK-400 compounds were stable in simulated gastric fluid, and most were substantially more lipophilic than the salen Mn complexes EUK-189 and EUK-207, which lack oral activity. Pharmacokinetics studies demonstrate the presence of all EUK-400 series compounds in the plasma of rats after oral administration. These EUK-400 series compounds are potential oral therapeutic agents for cellular damage caused by oxidative stress.

The synthesis of several UO(2)-alaskaphyrin derivatives functionalized with aliphatic chains is described. These compounds are found to be liquid-crystalline and form columnar mesophases, as judged from polarizing optical microscopy studies, and represent the first uranium-containing discotic mesogens.

Aliphatic derivatives of hydrazinophyrin, a new type of tetrapyrrolic macrocycle prepared by the condensation of 2,5-diformylpyrroles with hydrazine, exhibit liquid crystalline properties as judged from polarising optical microscopy; these hydrazinophyrins appear to be the first mesogens derived from an expanded porphyrin core.

In recent years, the field of porphyrin chemistry has expanded to include several new analogs of the original four pyrrole, carbon-bridged systems. This review traces the development of one such class of new macrocycles, namely Schiff-base porphyrin analogs. The review's focus is on the synthesis and properties of these new Schiff-base macrocycles that for ease of division have been divided into four classes: systems with two pyrrole rings, systems with three pyrrole or heterocyclic rings, systems with four pyrrole or heterocyclic rings, and systems with five or more pyrrole or heterocyclic rings. In addition to the role of metal ions as templating agents in the synthesis of these complexes, the rich coordination chemistry of several of the macrocycles is also discussed. X-ray crystallography has played an important role in determining the structures of many of these Schiff-base porphyrin analogs and many of the available structures have been incorporated into this review. Aromaticity of the macrocycles is discussed and has been evaluated from available electronic and NMR spectra. Finally, several potential applications of these molecules are discussed, briefly.