Tetranactin
(Synonyms: 杀螨素) 目录号 : GC45022A monovalent cation ionophore
Cas No.:33956-61-5
Sample solution is provided at 25 µL, 10mM.
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Tetranactin is a macrotetrolide and a monovalent cation ionophore that has been found in S. aureus and has antibacterial, insecticidal, and mitogenic activities. It exhibits an equilibrium permeability ratio 1,000-fold greater for lithium than sodium or cesium ions accross bilayer membranes at low voltages. Tetranactin inhibits the growth of Gram-positive bacteria and C. miyabeanus and R. solani fungi when used at concentrations less than 0.9 μg/ml. Tetranactin (0.5-1.5 μg per insect) dose-dependently increases the mortality of adult C. chinensis weevils up to 100% and has mitogenic activity against T. telarius when sprayed onto plants with an LC50 value of 9.2 μg/ml. It reduces IL-1β- and cAMP-induced secretion of phospholipase A2 (PLA2) from rat mesangial cells (IC50s = 43 and 33 nM, respectively). Tetranactin (50 ng/ml) suppresses the proliferation of human T lymphocytes induced by allogeneic cells and IL-2 and supresses the generation of cytotoxic T lymphocytes in mixed lymphocyte cultures. In vivo, tetranactin (10 mg/animal per day) completely inhibits the formation of experimental autoimmune uveoretinitis (EAU) in rats.
Cas No. | 33956-61-5 | SDF | |
别名 | 杀螨素 | ||
Canonical SMILES | O=C(O[C@@H](CC)C[C@@]1([H])O[C@]([C@H]2C)([H])CC1)[C@@H](C)[C@]3([H])CC[C@@](C[C@@H](CC)OC([C@@H]([C@]4([H])O[C@@](C[C@@H](OC([C@@H](C)[C@@]5([H])O[C@@](CC5)([H])C[C@@H](CC)OC2=O)=O)CC)([H])CC4)C)=O)([H])O3 | ||
分子式 | C44H72O12 | 分子量 | 793 |
溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg | |
1 mM | 1.261 mL | 6.3052 mL | 12.6103 mL |
5 mM | 0.2522 mL | 1.261 mL | 2.5221 mL |
10 mM | 0.1261 mL | 0.6305 mL | 1.261 mL |
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Tetranactin, a macrotetrolide antibiotic, suppresses in vitro proliferation of human lymphocytes and generation of cytotoxicity
Immunopharmacology 1988 Jul-Aug;16(1):25-32.PMID:2971634DOI:10.1016/0162-3109(88)90047-1.
Tetranactin, a hydrophobic cyclic antibiotic produced by Streptomyces aureus, has previously been shown to suppress in vitro activation of rat lymphocytes by concanavalin A as well as the onset of experimental autoimmune uveoretinitis in Lewis rats. Here we report the effects of Tetranactin on human T and NK lymphocytes in vitro. Tetranactin, at concentrations up to 100 ng/ml, was not toxic to human lymphocytes but completely abrogated the proliferation of human T lymphocytes in response to allogeneic cells in mixed lymphocyte cultures. Tetranactin also blocked the initiation of proliferation in response to interleukin-2, but did not block proliferation of interleukin-2-activated cells. Tetranactin also blocked generation of cytotoxic T lymphocytes and activated killer cells in the mixed lymphocyte culture. However, up to 100 ng/ml Tetranactin did not alter the lytic activity of cytotoxic T or NK lymphocytes generated in its absence. The ability of low doses of Tetranactin to block the induction of lymphoproliferation is similar to the action of cyclosporin A. Since cyclosporin A is also a cyclic hydrophobic molecule, the immunosuppressive actions of these two agents may involve a similar mechanism.
Tetranactin inhibits interleukin 1 beta and cAMP induction of group II phospholipase A2 in rat renal mesangial cells
Eur J Pharmacol 1996 Jun 13;306(1-3):265-70.PMID:8813640DOI:10.1016/0014-2999(96)00203-8.
Renal mesangial cells express secretory phospholipase A2 in response to two principal classes of activating signals that may interact in a synergistic fashion. These two groups of activators comprise inflammatory cytokines, such as interleukin 1 beta, and agents that elevate cellular levels of cAMP. Treatment of mesangial cells with Tetranactin, a cyclic antibiotic produced by Streptomyces aureus with a molecular structure similar to cyclosporin A inhibits interleukin 1 beta- and cAMP-dependent group II phospholipase A2 secretion in a dose-dependent manner with IC50 values of 43 and 33 nM, respectively. However, Tetranactin does not directly inhibit group II phospholipase A2 activity. Western blot analyses of mesangial cell supernatants reveal that the inhibition of phospholipase A2 activity is due to suppression of phospholipase A2 protein synthesis. This effect is preceded by the reduction of phospholipase A2 mRNA steady-state levels as shown by Northern blot analyses of total cellular RNA isolated from stimulated mesangial cells. Thus, Tetranactin is a potent inhibitor of group II phospholipase A2 expression in cytokine- and cAMP-stimulated mesangial cells and represents a new class of group II phospholipase A2 inhibitors with IC50 values in the low nanomolar range. This compound may be useful in the therapy of diseases associated with increased group II phospholipase A2 secretion.
Influence of molecular variations of ionophore and lipid on the selective ion permeability of membranes: I. Tetranactin and the methylation of nonactin-type carriers
J Membr Biol 1976 Dec 25;30(1):1-44.PMID:1037004DOI:10.1007/BF01869658.
The manner in which molecular structure of the carrier and the lipid composition of the membrane modulate the membrane selectivity among monovalent cations has been investigated for nonactin, trinactin, and Tetranactin, which differ only in their degrees of methylation, and for membranes made of two lipids, phosphatidyl ethanolamine and glyceryl dioleate, in which "equilibrium" and "kinetic" aspects of permeation, respectively, are emphasized. Bilayer permeability ratios for Li, Na, K, Rb, Cs, Tl,and NH4 have been characterized and resolved into "equilibrium" and "kinetic" components using a model for carrier-mediated membrane transport which includes both a trapezoid energy barrier for translocation of the complex across the membrane interior and a potential-dependence of the loading and unloading of ions at the membrane-solution interfaces. The bilayer permeability properties due to Tetranactin have been characterized in each of these lipids and found not only to be regular but to be systematically related to those of the less methylated homologues, trinactin and nonactin. This analysis has led to the following conclusions: (1) The change in lipid composition alters the relative contributions of "kinetic" vs. "equilibrium" components to the observed carrier-mediated selectivity. (2) Increased methylation of the carrier increases the contribution of the "kinetic" component to the selectivity relative to that of the "equilibrium" component and additionally alters the "equilibrium component sufficiently that an inversion of Cs--Na selectivity occurs between trinactin and Tetranactin. (3) For all ions and carriers examined, the "reaction plane" for ion-carrier complexation and the width for the "diffusion barrier can be represented by the same two parameters, independent of the ion or carrier, so that in all cases the complexation reaction senses 10% of the applied potential and the plateau of the "diffusion barrier" extends across 70% of the membrane interior.
High-resolution solid-state 13C NMR study of free and metal-complexed macrocyclic antibiotic ionophores valinomycin, nonactin, and Tetranactin: conformational elucidation in solid and solution by conformation-dependent 13C chemical shifts
Biochemistry 1985 Dec 17;24(26):7696-702.PMID:3841495DOI:10.1021/bi00347a029.
We recorded high-resolution 13C NMR spectra of the macrocyclic antibiotic ionophores valinomycin, nonactin, and Tetranactin in the solid state by the cross-polarization-magic angle spinning (CP-MAS) method, in order to gain insight into the use of conformation-dependent 13C chemical shifts as a convenient means to delineate a conformational change induced by metal ion complexation. The 13C peak splittings in the solid state are consistent with the symmetry properties of the ionophores as revealed by X-ray diffraction: C2 symmetry in free Tetranactin and S4 or S6 symmetry for a variety of metal complexes of nonactin and Tetranactin or the K+ complex of valinomycin, respectively. Interestingly, many of the 13C NMR peaks of carbons in the skeletal backbones were significantly displaced (up to 8 ppm). The displacements of the peaks were explained by a conformational change as characterized by variations of torsion angles. Accordingly, we were able to obtain conformational features of Na+ and Cs+ complexes of valinomycin, for which X-ray diffraction data are unavailable, on the basis of the displacements of the 13C NMR peaks. Further, we discuss conformational features of these complexes in chloroform solution, with reference to those observed in the solid state.
Immunosuppressive and anti-proliferative effects of a macrotetrolide antibiotic, Tetranactin
Immunology 1988 Mar;63(3):471-5.PMID:3258281doi
The macrotetrolide Tetranactin suppressed the appearance of experimental autoimmune uveoretinitis induced in Lewis rats with a soluble retinal antigen (S-antigen). The drug at 1 ng/ml inhibited the mitogen activation of unfractionated lymphocytes; incorporation of radiolabelled precursors such as thymidine, uridine and leucine into the cells was markedly reduced. The synthesis and release of IL-2 by mitogen-activated lymphocytes was significantly suppressed in the presence of Tetranactin. Incorporation of 45Ca was also inhibited, while intracellular Na+ levels were increased. In view of the ionophore property of Tetranactin, it was suggested that the drug might demonstrate its immunosuppressive effect by affecting intracellular cation concentrations.