Auto-induction

Wulff and coworkers have applied their aluminum catalyst 2 containing a vaulted biphenanthrol ligand (VAPOL, Section 2.1) to the Diels-Alder reaction between methyl acrylate and cyclopentadiene [25] (Scheme 1.32). In this Diels-Alder reaction auto-induction is observed, because of a cooperative interaction between the product... 

Nevirapine has been shown to be an inducer of hepatic cytochrome P450 metabolic enzymes 3A4 and 2B6. The pharmacokinetics of autoinduction are characterized by an approximately 1.5- to 2-fold increase in the apparent oral clearance of nevirapine as treatment continues from a single dose to 2 to 4 weeks of dosing with 200 to 400 mg/day. Auto-induction also results in a corresponding decrease in the terminal phase half-life of nevirapine in plasma from approximately 45 hours (single dose) to approximately 25 to 30 hours following multiple dosing with 200 to 400 mg/day. 

Auto-induction protocol using OnEx Solutions from Merck Biosciences... 

Sreenath, H. K., Bingman, C. A., Buchan, B. W., Seder, K. D., Burns, B. T., Geetha, H. V, et al. (2005). Protocols for production of selenomethionine-labeled proteins in 2-L polyethylene terephthalate bottles using auto-induction medium. Protein Expr. Purif. 40,256-267. 

Studier, F. W. (2005). Protein production by auto-induction in high density shaking cultures. Protein Expr. Purif. 41, 207-234. 

Carbamazepine stimulates antidiuretic hormone activity and has been used for the treatment of neurohypophyseal diabetes insipidus. Carbamazepine induces microsomal enzymes and its metabolism is subject to auto-induction. Frequently occurring adverse effects are sedation, dry mouth, dizziness and gastrointestinal disturbances. Photosensitivity reactions, urticaria and Stevens-Johnson syndrome have been described. The elderly are more prone to mental confusion, cardiac abnormalities and problems due to inappropriate ADH secretion. 

Potent inductor of CYP3A4, leading to auto-induction requiring periodic dose adjustment... 

Nicoll-Griffith DA, Silva JM, Chauret N, et al. Application of rat hepatocyte culture to predict in vivo metabolic auto-induction studies with DEP, a cyclooxygenase-2 inhibitor. Drug Metab Dispos 2001 29 159-165. 

The observations made for the VAPOL-aluminum catalyst in Table 15 are suggestive of asymmetric auto-induction similar to that for catalysis of the same reaction by a chiral aluminum catalyst prepared from the diol 225 (Sch. 24 Fig. 1) [48]. Because the Diels-Alder reaction between methacrolein and cyclopentadiene was too fast, monitoring of the time course of asymmetric induction, thus this was done for the reaction between methyl acrylate and cyclopentadiene [53]. The VAPOL-aluminum catalyst catalyzes the reaction of methyl acrylate and cyclopentadiene with asymmetric auto-induction as indicated in Fig. 2. The first data point that was collected was after 20 % conversion, at which point the cycloadduct 141 was 47 % ee when the last data point was collected at the end of the reaction it was found that 141 was 82 % ee. 

It was proposed that auto-induction was a consequence of the coordination of two carbonyl compounds to the aluminum. The aluminum could have two molecules of dienophile, two molecules of product or one of each these are illustrated by structures... 

A recent study by Purse et al. (125) demonstrated that LPS-stimulated EL-lp release is further increased by EL-1, and this process is known as auto-induction. GLA inhibits EL-lp release from LPS-stimulated monocytes mainly by inhibiting the auto-induction process. This information may suggest that GLA may be inhibiting excessive release of EL-lp to prevent inflammation but may not interfere with basal release of EL-lp, which plays a role in host defense. 

The rate of auto-induction of cyclophosphamide was 23% lower and exposure to the active metabolite 4-hydroxycyelophosphamide was 5% lower in 6 patients receiving aprepitant with a 4-day course of high-dose CTC (cyclophosphamide, thiotepa, carboplatin) when compared with 49 patients receiving high-dose CTC without aprepitant. ... 

With combined therapy, it was suggested that the effects of rifampicin might be more apparent during the initial 7 days, but that by week 4 the effect of isoniazid might predominate, because of its reduced inactivation by rifampicin combined with a reduction in the effect of rifampicin by auto-induction of its own metabolism. High theophylline levels in the isolated ease above may have been due to liver impairment brought about by the eombined use of rifampicin and isoniazid, or alcoholism. ... 

Machado, R., Azevedo-Silva, J., Correia, C. et al. (2013) High level expression and facile purification of recombinant silk-elastin-like polymers in auto induction shake flask cultures. AMB Express, doi 10.1186/2191-0855-3-11... 

Svensson US, Maki-JouppUa M, Hoffinann KJ, Ashton M. Characterisation of the human liver in vitro metabolic pattern of artemisinin and auto-induction in the rat by use of nonlinear mixed effects modelling. Biopharm Drug Dispos 2003 24(2) 71 —85. 

Equation 2.6 has been established for well-defined conditions pseudo first-order in substrate (but any order in chiral auxiliary, stoichiometric or catalytic) and no change of mechanism during the course of the reaction, for example, no autoinduction by the products. Reactions with chiral catalysts are especially susceptible to auto-induction. It is then useful to give the calculated x values with an indication of the correspondence between conversion and ee j or eCp j [1 Ij. We advise running experiments for at least two values of conversion and subsequent verification that the X values obtained are identical or similar. If not, this can indicate a change in the structure of the reagent during the reaction or a non-first-order reaction in substrate. TTie extrapolation of x at initial conversion is a characteristic value for a... 

F. 12.1 Proposed mechanism of the two-component agr auto-induction system in S. aureus (reproduced from [14], by permission of The Royal Society of Chemistry, http // dx.doi.org/10.1039/... 

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