Nonactin | CAS# 6833-84-7 | Ionophore antibiotic

MedKoo Cat#: 571126 | Name: Nonactin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nonactin is an ionophore antibiotic nonactin that permeabilizes cell membranes to NH4+ and K(+). Nonactin, when exposed to erythrocytes, causes erythrocyte shrinkage and subsequent erythrocyte membrane scrambling.

Chemical Structure

Nonactin

CAS#6833-84-7

Theoretical Analysis

MedKoo Cat#: 571126

Name: Nonactin

CAS#: 6833-84-7

Chemical Formula: C40H64O12

Exact Mass: 736.4398

Molecular Weight: 736.94

Elemental Analysis: C, 65.19; H, 8.75; O, 26.05

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 190.00
10mg	USD 320.00
25mg	USD 560.00

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Related CAS #

No Data

Synonym

Nonactin; A-5584; A5584; A 5584

IUPAC/Chemical Name

4,13,22,31,37,38,39,40-Octaoxapentacyclo(32.2.1.1(sup 7,10).1(sup 16,19).1(sup 25,28))tetracontane-3,12,21,30-tetrone, 2,5,11,14,20,23,29,32-octamethyl-, (1R-(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28S*,29S*,32S*,34S*))-

InChi Key

RMIXHJPMNBXMBU-QIIXEHPYSA-N

InChi Code

InChI=1S/C40H64O12/c1-21-17-29-9-13-34(49-29)26(6)38(42)46-23(3)19-31-11-15-36(51-31)28(8)40(44)48-24(4)20-32-12-16-35(52-32)27(7)39(43)47-22(2)18-30-10-14-33(50-30)25(5)37(41)45-21/h21-36H,9-20H2,1-8H3/t21-,22+,23+,24-,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-

SMILES Code

O=C(O[C@H](C)C[C@@]1([H])CC[C@@](O1)([H])[C@H](C)C(O[C@@H](C)C[C@]2([H])CC[C@](O2)([H])[C@@H](C)C(O[C@H](C)C[C@@]3([H])CC[C@@](O3)([H])[C@@H]4C)=O)=O)[C@H](C)[C@@](O5)([H])CC[C@@]5([H])C[C@H](C)OC4=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 736.94 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Peter T, Bissinger R, Lang F. Erythrocyte Shrinkage and Cell Membrane Scrambling after Exposure to the Ionophore Nonactin. Basic Clin Pharmacol Toxicol. 2016 Feb;118(2):107-12. doi: 10.1111/bcpt.12455. Epub 2015 Sep 11. PubMed PMID: 26280658. 2: Zhan Y, Zheng S. Efficient production of nonactin by Streptomyces griseus subsp. griseus. Can J Microbiol. 2016 Aug;62(8):711-4. doi: 10.1139/cjm-2016-0248. Epub 2016 Jun 10. PubMed PMID: 27405846. 3: Kusche BR, Phillips JB, Priestley ND. Nonactin biosynthesis: setting limits on what can be achieved with precursor-directed biosynthesis. Bioorg Med Chem Lett. 2009 Feb 15;19(4):1233-5. doi: 10.1016/j.bmcl.2008.12.096. Epub 2008 Dec 30. PubMed PMID: 19167217; PubMed Central PMCID: PMC2854622. 4: Woo AJ, Strohl WR, Priestley ND. Nonactin biosynthesis: the product of nonS catalyzes the formation of the furan ring of nonactic acid. Antimicrob Agents Chemother. 1999 Jul;43(7):1662-8. PubMed PMID: 10390219; PubMed Central PMCID: PMC89340. 5: Rong J, Nelson ME, Kusche B, Priestley ND. Nonactin biosynthesis: unexpected patterns of label incorporation from 4,6-dioxoheptanoate show evidence of a degradation pathway for levulinate through propionate in Streptomyces griseus. J Nat Prod. 2010 Dec 27;73(12):2009-12. doi: 10.1021/np100421v. Epub 2010 Dec 7. PubMed PMID: 21138242. 6: Walczak RJ, Woo AJ, Strohl WR, Priestley ND. Nonactin biosynthesis: the potential nonactin biosynthesis gene cluster contains type II polyketide synthase-like genes. FEMS Microbiol Lett. 2000 Feb 1;183(1):171-5. PubMed PMID: 10650222. 7: Kusche BR, Smith AE, McGuirl MA, Priestley ND. Alternating pattern of stereochemistry in the nonactin macrocycle is required for antibacterial activity and efficient ion binding. J Am Chem Soc. 2009 Dec 2;131(47):17155-65. doi: 10.1021/ja9050235. PubMed PMID: 19902940; PubMed Central PMCID: PMC2879896. 8: Korotkov SM, Glazunov VV, Yagodina OV. Increase in the toxic effects of Tl+ on isolated rat liver mitochondria in the presence of nonactin. J Biochem Mol Toxicol. 2007;21(2):81-91. PubMed PMID: 17427175. 9: Lee JM, Kim JG, Kim TH, Lee DS, Kim JH, Cho SK, Riu KZ, Lee DS, Lee SH. Nonactin hinders intracellular glycosylation in virus-infected baby hamster kidney cells. Mol Med Rep. 2010 Jan-Feb;3(1):115-9. doi: 10.3892/mmr_00000227. PubMed PMID: 21472209. 10: Cox JE, Priestley ND. Nonactin biosynthesis: the product of the resistance gene degrades nonactin stereospecifically to form homochiral nonactate dimers. J Am Chem Soc. 2005 Jun 8;127(22):7976-7. PubMed PMID: 15926797. 11: Steverding D, Kadenbach B. The K(+)-ionophores nonactin and valinomycin interact differently with the protein of reconstituted cytochrome c oxidase. J Bioenerg Biomembr. 1990 Apr;22(2):197-205. PubMed PMID: 2158497. 12: Skulskii IA, Saris NE, Savina MV, Glasunov VV. Uptake of thallous ions by mitochondria is stimulated by nonactin but not by respiration alone. Eur J Biochem. 1981 Nov;120(2):263-6. PubMed PMID: 6895621. 13: Nelson ME, Priestley ND. Nonactin biosynthesis: the initial committed step is the condensation of acetate (malonate) and succinate. J Am Chem Soc. 2002 Mar 27;124(12):2894-902. PubMed PMID: 11902879. 14: Negrin S, Nefelova MV, Gavrilova EM, Morales S, Egorov NS. [Intracellular ATP content and nonactin biosynthesis]. Antibiot Med Biotekhnol. 1987 Aug;32(8):579-83. Russian. PubMed PMID: 3674839. 15: Rezanka T, Prell A, Spízek J, Sigler K. Pilot-plant cultivation of Streptomyces griseus producing homologues of nonactin by precursor-directed biosynthesis and their identification by LC/MS-ESI. J Antibiot (Tokyo). 2010 Aug;63(8):524-9. doi: 10.1038/ja.2010.93. Epub 2010 Jul 28. PubMed PMID: 20664602. 16: Nefelova MV, Sverdlova AN, Karelina IIu, Egorov NS. [Nonactin biosynthesis. The incorporation of precursors into the antibiotic molecule]. Antibiot Med Biotekhnol. 1985 Aug;30(8):572-6. Russian. PubMed PMID: 3840667. 17: Avilés-Moreno JR, Gámez F, Berden G, Oomens J, Martínez-Haya B. Isolated alkali cation complexes of the antibiotic ionophore nonactin: correlation with crystalline structures. Phys Chem Chem Phys. 2017 Jun 14;19(23):14984-14991. doi: 10.1039/c7cp02438j. PubMed PMID: 28569331. 18: Martínez-Haya B, Avilés-Moreno JR, Hamad S, Elguero J. On the ionophoric selectivity of nonactin and related macrotetrolide derivatives. Phys Chem Chem Phys. 2017 Jan 4;19(2):1288-1297. doi: 10.1039/c6cp05324f. PubMed PMID: 27966685. 19: Smejtek P, Paulis-Illangasekare M. Modification of ion transport in lipid bilayer membranes in the presence of 2,4-dichlorophenoxyacetic acid. I. Enhancement of cationic conductance and changes of the kinetics of nonactin-mediated transport of potassium. Biophys J. 1979 Jun;26(3):441-66. PubMed PMID: 263687; PubMed Central PMCID: PMC1328563. 20: Sverdlova AN, Solov'eva IV, Nefelova MV. [UV-spectroscopic study of complex formation between nonactin and picrates of monovalent cations]. Antibiot Khimioter. 1995 Apr;40(4):17-24. Russian. PubMed PMID: 7654094.