Phenacetin was used as a model pharmaceutical compound to investigate the impact of solvent choice and crystallization conditions on the crystal habit and size distribution of the final crystallized product. The crystal habit of phenacetin was explored using crash-cooling crystallization (kinetically controlled) and slow evaporative crystallization (thermodynamically controlled) in a wide range of organic solvents. In general, a variety of needle-type shapes (needles, rods, or blades) were recovered from fast-cooling crystallizations, in contrast to hexagonal blocks obtained from slow evaporative crystallizations. The solubility of phenacetin was measured in five solvents from 10−70 °C to allow for the design of larger-scale crystallization experiments. Supersaturation and the nucleation temperature were independently controlled in isothermal desupersaturation experiments to investigate the impact of each on crystal habit and size. The crystal size (needle cross-sectional area) decreased with increasing supersaturation because of higher nucleation rates at higher supersaturation, and elongated needles were recovered. Increasing the nucleation temperature resulted in the production of larger crystals with decreased needle aspect ratios. Antisolvent phenacetin crystallizations were developed for three solvent/antisolvent systems using four different antisolvent addition rates to simultaneously probe the crystal habit and size of the final product. In general, increasing the antisolvent addition rate, associated with increased rate of generation of supersaturation, resulted in the production of shorter needle crystals.
The propensity of a range of different sulfoxides and
sulfones
to cocrystallize with either 1,2- or 1,4-diiodotetrafluorobenzene,
via I···O=S
halogen bonding, was investigated. Cocrystallization occurred exclusively
with 1,4-diiodotetrafluorobenzene in either a 1:1 or 1:2 stoichiometry
of the organohalide and the sulfoxide, respectively, depending on
the sulfoxide used. It was found that the stoichiometry observed was
not necessarily related to whether the oxygen acts as a single halogen
bond acceptor or if it is bifurcated; with I···π
interactions observed in two of the cocrystals synthesized. Only those
cocrystals with a 1:2 stoichiometry exhibit C–H···O
hydrogen bonding in addition to I···O=S halogen bonding.
Examination of the Cambridge Structural Database shows that (i) the
I···O=S interaction is similar to other I···O
interactions, and (ii) the I···π interaction
is significant, with the distances in the two cocrystals among the
shortest known.
Although macrophages are considered the prototype of antigen presenting cells (APC), recent studies have emphasized the potential role of several parenchymal and mesenchymal cells in this process. We have studied the capacity of cultured glomerular visceral epithelial cells (GEC) to act as effective APC and compared this capacity with that demonstrated by peritoneal macrophages. Affinity-purified and in vitro propagated rat GEC were exposed to hen egg lysozyme, keyhole limpet hemocyanin, and cationic ferritin. As effector cells, we used antigen-specific T cell hybridomas; the level of antigen presentation was assessed by determining the level of interleukin 2 (IL-2) present in tissue culture supernatants. Cytokine-treated GEC were capable of processing and presenting all antigens in a dose-dependent manner. Crucial for antigen presentation were intracellular processing of antigen and the presence of Ia on the cell surface. Our findings indicate that GEC can act as effective APC, and further suggest that this capacity may be relevant to cell-mediated immune injury at the level of the glomerular capillaries in vivo.
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