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Fatty acids resources:

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Biochemistry. 1999 Mar 16;38(11):3393-400.
Mutations at four active site residues of biotin carboxylase abolish substrate-induced synergism by biotin.

Blanchard CZ, Lee YM, Frantom PA, Waldrop GL.

Division of Biochemistry and Molecular Biology, Louisiana State University, Baton Rouge 70803-1806, USA.

Acetyl-CoA carboxylase catalyzes the first committed step in the biosynthesis of long-chain fatty acids. The Escherichia coli form of the enzyme consists of a biotin carboxylase protein, a biotin carboxyl carrier protein, and a carboxyltransferase protein. In this report a system for site-directed mutagenesis of the biotin carboxylase component is described. The wild-type copy of the enzyme, derived from the chromosomal gene, is separated from the mutant form of the enzyme which is coded on a plasmid. Separation of the two forms is accomplished using a histidine-tag attached to the amino terminus of the mutant form of the enzyme and nickel affinity chromatography. This system was used to mutate four active site residues, E211, E288, N290, and R292, to alanine followed by their characterization with respect to several different reactions catalyzed by biotin carboxylase. In comparison to wild-type biotin carboxylase, all four mutant enzymes gave very similar results in all the different assays, suggesting that the mutated residues have a common function. The mutations did not affect the bicarbonate-dependent ATPase reaction. In contrast, the mutations decreased the maximal velocity of the biotin-dependent ATPase reaction 1000-fold but did not affect the Km for biotin. The activity of the ATP synthesis reaction catalyzed by biotin carboxylase where carbamoyl phosphate reacts with ADP was decreased 100-fold by the mutations. The ATP synthesis reaction required biotin to stimulate the activity in the wild-type; however, biotin did not stimulate the activity of the mutant enzymes. The results showed that the mutations have abolished the ability of biotin to increase the activity of the enzyme. Thus, E211, E288, N290, and R292 were responsible, at least in part, for the substrate-induced synergism by biotin in biotin carboxylase.

online pharmacy ref. source: www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10079084&dopt=Abstract

Jpn J Cancer Res. 1998 Dec;89(12):1318-25.
Anti-cachectic effect of FK317, a novel anti-cancer agent, in colon26 and LX-1 models in mice.

Naoe Y, Kawamura I, Inami M, Matsumoto S, Nishigaki F, Tsujimoto S, Manda T, Shimomura K.

Department of Pharmacology, Fujisawa Pharmaceutical Co., Ltd., Osaka.

The effects of FK317 (11-acetyl-8-carbamoyloxymethyl-4-formyl-6- methoxy-14-oxa-1,11-diazatetracyclo[7.4.1.0(2, 7). 0(10, 2] tetradeca-2,4,6-trien-9-yl acetate), a novel anti-cancer agent, on murine adenocarcinoma colon26- and human lung carcinoma LX-1-induced cachexia were investigated in mice. Mice bearing colon26 or LX-1 s.c. lost weight and became cachectic, associated with tumor growth. FK317 and mitomycin C (MMC) inhibited the growth of both tumors. FK317 ameliorated the weight loss induced by the presence of colon26 or LX-1, while MMC enhanced it. An attenuation of the reduction in the weights of epididymal fat, gastrocnemius muscle and carcass was observed in FK317-treated tumor-bearing mice in both cachexia models, but not in MMC-treated mice. The decreases in the circulating levels of triglyceride, glucose and non-esterified fatty acid, which were induced by the presence of colon26, was partially inhibited by treatment with FK317. Overall, this study revealed that FK317 is a potent anti-cancer drug with anti-cachectic activity, suggesting that FK317 has potential utility for the treatment of cancer.

online pharmacy ref. source: www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10081493&dopt=Abstract

Bioconjug Chem. 1999 Mar-Apr;10(2):221-30.
Methods for dual, site-specific derivatization of bovine pancreatic trypsin inhibitor: trypsin protection of lysine-15 and attachment of fatty acids or hydrophobic peptides at the N-terminus.

Pool CT, Thompson TE.

Department of Biochemistry and Molecular Genetics, University of Virginia, Charlottesville, Virginia 22908, USA. chadler_t_pooroton.pfizer.com

To produce a series of model membrane proteins, bovine pancreatic trypsin inhibitor (BPTI) has been modified by specifically attaching reporter groups to Lys-15 and fatty acids or hydrophobic peptides at the N-terminus. Lys-15 of BPTI was protected by trypsin bound to BPTI, then O-methylisourea (OMIU) was used to guanidinate all unprotected lysines. The N-terminal amine was then reacted with several saturated fatty acid anhydrides from 8 to 18 carbons in length, or with an SMCC cross-linker. Cysteine-containing hydrophobic peptides, cleaved from resin in the presence of sodium dodecyl sulfate (SDS), were then attached to the protein via the N-terminal cross-linker. The methods described yield a unique, chemically modified protein which can carry site-specific modifications at two distinct residues. The resulting proteins are ideal for diffusional or partitioning studies on model and biological membranes.

online pharmacy ref. source: www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10077471&dopt=Abstract

Mol Endocrinol. 1999 Mar;13(3):410-7.
A novel method for analysis of nuclear receptor function at natural promoters: peroxisome proliferator-activated receptor gamma agonist actions on aP2 gene expression detected using branched DNA messenger RNA quantitation.

Burris TP, Pelton PD, Zhou L, Osborne MC, Cryan E, Demarest KT.

Department of Drug Discovery, The R.W. Johnson Pharmaceutical Research Institute, Raritan, New Jersey 08869, USA. tburririus.jnj.com

Peroxisome proliferator-activated receptor-gamma (PPARgamma), a member of the nuclear hormone receptor superfamily, plays an essential role in the mediation of the actions of antidiabetic drugs known as thiazolidinediones (TZDs). PPARgamma activates many target genes involved in lipid anabolism including the adipocyte fatty acid binding protein (aP2). In this study, induction of aP2 gene expression by PPARgamma agonists was examined in both cultured cells and diabetic mice using branched DNA (bDNA)-mediated mRNA quantitation. bDNA technology allows for the direct measurement of a particular mRNA directly within cellular lysate using a 96-well plate format in a time frame comparable to a reporter gene assay. In cultured human subcutaneous preadipocytes, the TZDs, troglitazone and BRL-49653, both rapidly induced aP2 mRNA as detected with the bDNA method. In these cells, the effect of BRL-49653 on aP2 mRNA levels was detectable as early as 30 min after treatment (47% increase) and was maximal after 24 h of treatment (12-fold increase). The effects of troglitazone on aP2 mRNA induction were similar to those of BRL-49653 except that the maximal level of induction was consistently lower (e.g. 24 h treatment = 4-fold increase). Dose-response relationships for both of the TZDs were also determined using the 24-h treatment time point. EC50s for both BRL-49653 and troglitazone were estimated to be 80 nM and 690 nM, respectively. A natural PPARgamma ligand, 15-deoxy-delta12,14-PGJ2, was also active in this assay with a maximal induction of aP2 mRNA of approximately 5-fold when tested at 1 microM. Since the PPARgamma:retinoid X receptor (RXR) heterodimer has been characterized as a permissive heterodimer with respect to RXR ligands, the ability of 9-cis-retinoic acid (9-cis-RA) to induce aP2 mRNA was examined. Although 9-cis-RA had very low efficacy (2-fold induction), the maximal effect was reached at 100 nM. No synergism or additivity in aP2 mRNA induction was detected when 9-cis-RA was included with either of the TZDs used in this study. Significant induction of aP2 mRNA in bone marrow of db/db mice treated with either troglitazone or BRL-49653 was also detected, indicating that the bDNA assay may be a simple method to monitor nuclear receptor target gene induction in vivo.

online pharmacy ref. source: www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=10076998&dopt=Abstract

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