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Trinactin Sale

(Synonyms: 三活菌素) 目录号 : GC45089

A non-selective monovalent cation ionophore

Trinactin Chemical Structure

Cas No.:7561-71-9

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产品描述

Trinactin is a macrotetrolide antibiotic produced by Streptomyces and an ionophore for monovalent cations, such as sodium, potassium, and ammonium. It is commonly used to facilitate the movement of monovalent cations through natural and artificial lipid membranes.

Chemical Properties

Cas No. 7561-71-9 SDF
别名 三活菌素
Canonical SMILES O=C(O[C@@H](C)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 C43H70O12 分子量 779
溶解度 DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble 储存条件 Store at -20°C
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1 mM 1.2837 mL 6.4185 mL 12.837 mL
5 mM 0.2567 mL 1.2837 mL 2.5674 mL
10 mM 0.1284 mL 0.6418 mL 1.2837 mL
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Research Update

Steady-state ion transport by nonactin and Trinactin

Biochim Biophys Acta 1975 Feb 14;375(3):350-62.PMID:1173049DOI:10.1016/0005-2736(75)90352-1.

The steady-state fluxes of Na+, K+, and NH4+ carried by nonactin and Trinactin across thin lipid membranes have been measured as functions of ion activity, carrier concentration, and the applied potential. In agreement with earlier studies the conductance, G(O), is found to be proportional to the carrier concentration and, for low activities, to the ion activity. The determination of the dependence of G(O) on activity at high activities is, however, apparently obscured by changes in the concentration of carrier in the membrane. Using the values for the rate constants at zero potential which were determined in the preceding paper, it is possible to adjust the potential dependence of the constants so as to achieve a reasonable fit to the current-voltage relations. The data presented provide further evidence that a single molecule of nonactin or Trinactin acts cyclicly as a carrier of univalent cations.

Tests of the carrier model for ion transport by nonactin and Trinactin

Biochim Biophys Acta 1975 Feb 14;375(3):327-49.PMID:1173048DOI:10.1016/0005-2736(75)90351-x.

The fluxes of K+ and NH+4 carried by nonactin and Trinactin across thin lipid membranes have been measured as functions of ion activity, electric potential and time. In agreement with the predictions of a version of the carrier model in common use, the shape of the initial current-voltage relation is independent of the activity of the electrolyte, alpha-i, while the ratio of the initial conductance, G-o, to the steady-state conductance, G infinity, increases according to G-o/G infinity equals const1+const2 times alpha-i. For Trinactin the data presented allow the estimation of the rate constants of the carrier process (in the limit of zero potential) in a manner which does not assume any particular variation with potential for the constants. Using empirically determined functions of potential, a complete set of values is also available for nonactin. The curve fitting which is necessary is described in the following paper. The data presently available for valinomycin are sufficient neither to test the model nor to determine a complete set of constants.

Immunosuppressive effects of polynactins (tetranactin, Trinactin and dinactin) on experimental autoimmune uveoretinitis in rats

Jpn J Ophthalmol 1987;31(2):218-29.PMID:3499534doi

Macrotetrolide antibiotic polynactins [dinactin, Trinactin and tetranactin (1:4:5)] are hydrophobic cyclic esters produced by Streptomyces aureus. Polynactins (PN) and their major component tetranactin (TN) delayed or suppressed the onset of S-antigen-induced experimental autoimmune uveoretinitis (EAU) in Lewis rats. Termination of treatment with PN or TN before day 14 of immunization resulted in a delayed onset of EAU in many animals. Thus, the immunosuppressive effect of PN and TN was not lasting. PN and TN suppressed anti-S-antigen antibody formation. Skin hypersensitivity tests indicated suppression by PN of the delayed-type rather than Arthus type hypersensitivity to S-antigen. PN, TN and Trinactin all inhibited 3H-thymidine incorporation into concanavalin A-treated lymphocytes at the early stage of cell activation. For each drug, 50% inhibition was obtained at about 0.1 ng/ml. Under the incubation condition that the cells were exposed to TN for 21 hours, cell viability remained unchanged up to 100 ng/ml of TN. It is evident that PN and TN suppress T-lymphocyte proliferation without cell injury. These results suggest that PN and TN inhibit the onset of EAU primarily through the suppression of cell-mediated immunity but also by affecting humoral immunity.

Carrier-mediated ion transport in lipid bilayer membranes

Can J Biochem Cell Biol 1984 Aug;62(8):738-51.PMID:6498590DOI:10.1139/o84-096.

The electrical properties predicted by a widely accepted model for carrier-mediated ion transport in lipid bilayers are described. The different steps leading to ion transport and their associated rate constants are reaction at the interface between an ion in the aqueous phase and a carrier in the membrane (kRi), followed by translocation of the ion-carrier complex across the membrane interior (kis) and its dissociation at the other interface (kDi) after which the free carrier crosses back the membrane interior (ks). Results on glyceryl monooleate (GMO) membranes for a family of homologue carriers, the macrotetralide actin antibiotics (nonactin, monactin, dinactin, Trinactin, and tetranactin) and a variety of ions (Na+, Cs+, Rb+, K+, NH4+, and Tl+) are presented. Internally consistent data obtained from steady-state electrical measurements (zero-current potential and conductance, current-voltage relationship) allow us to obtain the equilibrium permeability ratios for the different ions and show that for a given carrier kRi is relatively invariant from one ion to the other, except for Tl+ (larger), which implies that the ionic selectivity is controlled by the dissociation of the complex. The values of the individual rate constants obtained from current relaxation experiments are also presented and confirm the findings from steady-state measurements, as well as the isostericity concept for complexes of different ions with the same carrier (kis invariant). These also allow us to determine the aqueous phase membrane and torus membrane partition coefficients. Finally, the observed increase in kis from nonactin to tetranactin and, for all homologues, from GMO-decane to solvent-free GMO membranes, together with the concomitant decrease in kDi, can be explained in terms of modifications of electrostatic energy profiles induced by variations in carrier size and membrane thickness.

The effects of the macrotetralide actin antibiotics on the electrical properties of phospholipid bilayer membranes

J Membr Biol 1969 Dec;1(1):346-82.PMID:24174056DOI:10.1007/BF01869788.

This paper, the last in a series of three, characterizes the electrical properties of phospholipid bilayer membranes exposed to aqueous solutions containing nonactin, monactin, dinactin, and Trinactin and Li(+), Na(+), K(+), Rb(+), Cs(+), and NH 4 (+) ions. Not only are both the membrane resistance at zero current and the membrane potential at zero current found to depend on the aqueous concentrations of antibiotic and ions in the manner expected from the theory of the first paper, but also these measurements are demonstrated to be related to each other in the manner required by this theory for "neutral carriers". To verify that these antibiotics indeed are free to move as carriers of cations, cholesterol was added to the lipid to increase the "viscosity" of the interior of the membrane. Cholesterol decreased by several orders of magnitude the ability of the macrotetralide antibiotics to lower the membrane resistance; nevertheless, the permeability ratios and conductance ratios remained exactly the same as in cholesterolfree membranes. These findings are expected for the "carrier" mechanism postulated in the first paper and serve to verify it. Lastly, the observed effects of nonactin, monactin, dinactin, and Trinactin on bilayers are compared with those predicted in the preceding paper from the salt-extraction equilibrium constants measured there; and a close agreement is found. These results show that the theory of the first paper satisfactorily predicts the effects of the macrotetralide actin antibiotics on the electrical properties of phospholipid bilayer membranes, using only the thermodynamic constants measured in the second paper. It therefore seems reasonable to conclude that these antibiotics produce their characteristic effects on membranes by solubilizing cations therein as mobile positively charged complexes.