Disease relevance of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid

• Antibody to cardiolipin was loosely linked to a history, but not the simultaneous presence, of demonstrable lupus anticoagulant or thrombocytopenia, and could be detected as early in pregnancy as either anticoagulant or thrombocytopenia [1].
• Antibody to cardiolipin as a predictor of fetal distress or death in pregnant patients with systemic lupus erythematosus [1].
• In contrast, IgG from a patient with syphilis recognized cardiolipin alone and binding was inhibited by beta 2GPI [2].
• Cardiolipin antibodies in survivors of myocardial infarction [3].
• Our aims were to determine if liver mitochondria become resistant to the MPT during cholestasis and, if so, if the resistance is mediated by Bcl-x and/or increased cardiolipin [4].

Psychiatry related information on [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid

• Following immunization, the mice developed high titers of autoantibodies reacting with cardiolipin, DNA, nuclear extract, 16/6 and anti-16/6 Id, and anticardiolipin antibodies [5].
• Content and fatty acid composition of cardiolipin in the brain of patients with Alzheimer's disease [6].
• Absence of antibodies to cardiolipin in patients with Huntington's chorea, Sydenhams chorea and acute rheumatic fever [7].

High impact information on [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid

• During a prospective study of pregnancies in women with systemic lupus erythematosus, we examined the relation between antibody to cardiolipin, measured by the enzyme-linked immunosorbent assay, and midpregnancy fetal distress, identified by abnormal results of antepartum fetal heart-rate testing or by fetal death [1].
• Increased titers of antibodies to cardiolipin and myeloperoxidase were also noted [8].
• In competitive radioimmunoassays, cardiolipin, phosphatidic acid, and phosphatidyl glycerol blocked the binding of these hybridoma antibodies to denatured DNA [9].
• Cardiolipin provides specificity for targeting of tBid to mitochondria [10].
• We provide evidence that cardiolipin, which is present in mitochondrial membranes, mediates the targeting of tBid to mitochondria through a previously unknown three-helix domain in tBid [10].

Chemical compound and disease context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid

• The phosphatidylglycerol phosphate was made available to the surfactant enzyme in a coupled assay by hydrolysis of cardiolipin [1-(3-sn-phosphatidyl)-3-(3-sn-phosphatidyl)-sn-glycerol] by stereospecific cleavage with phospholipase C (phosphatidylcholine cholinephosphohydrolase, EC 3.1.4.3) from Bacillus cereus [11].
• These antibodies, which were strongly reactive with phosphatidylethanolamine and crossreactive with cardiolipin, had functional lupus anticoagulant activity and were characteristic of autoantibodies common in patients with autoimmune disease [12].
• Doxorubicin in cardiolipin liposomes demonstrated enhanced chemotherapeutic potential against murine ascitic P388 leukemia with a 144% increased life span compared to 55% increased life span with free drug at a dose of 7.5 mg/kg on Days 1, 3, and 7 [13].
• It bound to prothrombin with low affinity, reacted with 3 phospholipids (cardiolipin, phosphatidylethanolamine, and phosphatidylserine), and showed lupus anticoagulant activity [14].
• The results provide evidence that a decrease in cardiolipin levels and altered mitochondrial function are involved in palmitate-induced breast cancer cell death [15].

Biological context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid

• Flow cytometry of isolated hepatocytes incubated with anti-Fas monoclonal antibody showed that ROS production was associated with the collapse of transmembrane potential and loss of cardiolipin content [16].
• Autoimmunity to cardiolipin in infectious mononucleosis [17].
• CONCLUSIONS: These data suggest that an increase in mitochondria cardiolipin content occurs during cholestasis as an adaptive phenomenon to resist cell death by the MPT [4].
• Congenital and acquired anatomical defects of the uterine fundus and cervix, parental chromosomal rearrangements, gene mutations, antibodies to cardiolipin, and luteal phase defects each make a small contribution [18].
• In this system, protein translocation is very low in the absence of divalent cations but can be enhanced by inclusion of Mg2+, Ca2+ or Sr2+ but not by Ba2+ which is unable to sustain growth of the mutant strain and cannot induce a non-bilayer phase in E. coli CL dispersions [19].

Anatomical context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid

• These occurred infrequently in nonautoantibody Ig, but quite commonly in lupus-related autoantibodies such as antibodies to DNA, cardiolipin, and erythrocytes [20].
• Preadsorption of patient serum with cardiolipin reduced monocyte adhesion by 60% [21].
• In contrast to the mitochondria, peroxisomal membranes contain no cardiolipin [22].
• BACKGROUND: Antibodies to endothelial cells (aECs) and to cardiolipin (aCLs) are implicated in autoimmune diseases like systemic lupus erythematosus vasculitis [23].
• In this study, x-ray crystallography has been used to examine the structural details of an interaction between cardiolipin and the photoreaction center, a key light-driven electron transfer protein complex found in the cytoplasmic membrane of photosynthetic bacteria [24].

Associations of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid with other chemical compounds

• A significant increase in functional affinity for purified megalin was observed when beta2-glycoprotein-I was bound to the acidic phospholipids, phosphatidylserine and cardiolipin [25].
• In addition to a cardiolipin that has previously been reported [McAuley, K. E., Fyfe, P. K., Ridge, J. P., Isaacs, N. W., Cogdell, R. J. & Jones, M. R. (1999) Proc. Natl. Acad. Sci. USA 96, 14706-14711], two other major lipids of the cell membrane are found, a phosphatidylcholine and a glucosylgalactosyl diacylglycerol [26].
• Specific rabbit anti-cardiolipin (anti-CL) antibodies were used to investigate the hypothesis that cardiolipin, associated with mitochondrial membrane proteins, binds C1 and facilitates activation of the complement cascade following reperfusion of ischemic myocardium [27].
• Circulating autoantibodies to oxidized cardiolipin correlate with isoprostane F(2alpha)-VI levels and the extent of atherosclerosis in ApoE-deficient mice: modulation by vitamin E [28].
• The effect of cholic acid on both cardiolipin-mediated Na+ partition and Na+ translocation across the chloroform phase showed a marked dependence on pH, being greater at pH 7.4.(ABSTRACT TRUNCATED AT 250 WORDS)[29]

Gene context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid

• Translational regulation of nuclear gene COX4 expression by mitochondrial content of phosphatidylglycerol and cardiolipin in Saccharomyces cerevisiae [30].
• In mice lacking alpha-synuclein (Snca-/-), total brain steady-state mass of the mitochondria-specific phospholipid, cardiolipin, is reduced 22% and its acyl side chains show a 51% increase in saturated FAs and a 25% reduction in essential n-6, but not n-3, polyunsaturated FAs [31].
• tBid interaction with cardiolipin primarily orchestrates mitochondrial dysfunctions and subsequently activates Bax and Bak [32].
• Phosphatidylglycerophosphate synthase catalyzes the committed step in the synthesis of the mitochondrial phospholipid cardiolipin [33].
• Interestingly, the growth defect of isc1Delta strains resembled that of pgs1Delta strains, lacking the committed step in the synthesis of phosphatidylglycerol (PG) and cardiolipin (CL), which were shown to activate Isc1p in vitro [34].

Analytical, diagnostic and therapeutic context of [(2R)-2,3-dioctadecanoyloxypropoxy]-[3-[[(2R)-2,3-dioctadecanoyloxypropoxy]-hydroxy-phosphoryl]oxy-2-hydroxy-propoxy]phosphinic acid

• Incubation of sperm in capacitating medium supplemented with 32P-labeled phosphate, followed by lipid extraction, thin-layer chromatography, and autoradiography, revealed a radioactive band comigrating with cardiolipin and phosphatidic acid [35].
• Site-directed mutagenesis of ligating residues confirmed the importance of the phosphatidylinositol- and cardiolipin-binding sites [36].
• A [3H]azido-UDBT-cardiolipin adduct, identified after separation of the phospholipid fraction by high performance liquid chromatography, has 6-azido-UDBT linked to an acyl group, not to the head group of the cardiolipin molecule [37].
• The reactivity of HCAL to cardiolipin and to beta2-glycoprotein I (beta2GPI) was studied using a solid-phase enzyme immunoassay [38].
• Thin-layer and gas-liquid chromatography showed that the two contact site-enriched fractions contain predominantly phosphatidylcholine (31%), phosphatidylethanolamine (27%, half-unsaturated), and cardiolipin (27%, fully unsaturated) [39].

References