A monovalent cation ionophore
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Tetranactin

Item No. 26687

Product Insert (PDF)
Technical Information
Formal Name
(1R,2R,5R,7R,10S,11S,14S,16S,19R,20R,23R,25R,28S,29S,32S,34S)-5,14,23,32-tetraethyl-2,11,20,29-tetramethyl-4,13,22,31,37,38,39,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
CAS Number
33956-61-5
Molecular Formula
C44H72O12
Formula Weight
793.0
Purity
≥85%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: solubleDMSO: solubleEthanol: solubleMethanol: soluble
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
InChi Code
InChI=1S/C44H72O12/c1-9-29-21-33-13-17-38(49-33)26(6)42(46)54-31(11-3)23-35-15-19-40(51-35)28(8)44(48)56-32(12-4)24-36-16-20-39(52-36)27(7)43(47)55-30(10-2)22-34-14-18-37(50-34)25(5)41(45)53-29/h25-40H,9-24H2,1-8H3/t25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-,37-,38+,39+,40-
InChi Key
NKNPHSJWQZXWIX-DCVDGXQQSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Tetranactin is a macrotetrolide and a monovalent cation ionophore that has been found in S. aureus and has antibacterial, insecticidal, and mitogenic activities.1,2 It exhibits an equilibrium permeability ratio 1,000-fold greater for lithium than sodium or cesium ions accross bilayer membranes at low voltages.2 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.1 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).3 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.4 In vivo, tetranactin (10 mg/animal per day) completely inhibits the formation of experimental autoimmune uveoretinitis (EAU) in rats.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ando, K., Oishi, H., Hirano, S., et al. Tetranactin, a new miticidal antibiotic. I. Isolation, characterization and properties of tetranactin. J. Antibiot. (Tokyo) 24(6), 347-352 (1971).

    2. Krasne, S., and Eisenman, G. 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. 30(1), 1-44 (1976).

    3. Walker, G., Kunz, D., Pignat, W., et al. Tetranactin inhibits interleukin 1 β and cAMP induction of group II phospholipase A2 in rat renal mesangial cells. Eur. J. Pharmacol. 306(1-3), 265-270 (1996).

    4. Callewaert, D.M., Radcliff, G., Tanouchi, Y., et al. Tetranactin, a macrotetrolide antibiotic, suppresses in vitro proliferation of human lymphocytes and generation of cytotoxicity. Immunopharmacology 16(1), 25-32 (1988).

    5. Tanouchi, Y., and Shichi, H. Immunosuppressive and anti-proliferative effects of a macrotetrolide antibiotic, tetranactin. Immunology 63(3), 471-475 (1988).