Lonomycin A | CAS#58785-63-0 | polyether antibiotic

MedKoo Cat#: 599193 | Name: Lonomycin A

Description:

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

Lonomycin A is a polyether antibiotic ionophore, polycyclic; lonomycin B is stereoisomer of lonomycin A.

Chemical Structure

Lonomycin A

CAS#58785-63-0

Theoretical Analysis

MedKoo Cat#: 599193

Name: Lonomycin A

CAS#: 58785-63-0

Chemical Formula: C44H76O14

Exact Mass: 828.5235

Molecular Weight: 829.07

Elemental Analysis: C, 63.74; H, 9.24; O, 27.02

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Lonomycin A; Antibiotic TM 481; Antibiotic DE 3936; Emericid; Lonomycin;

IUPAC/Chemical Name

(S)-2-((2R,3R,4S,5R,6S)-2-hydroxy-6-((S)-1-((2S,5R,7S,8R,9S)-2-((2S,2'R,3'S,4'R,5R,5'R)-5'-((2S,3S,4S,5R,6S)-6-hydroxy-4-methoxy-3,5,6-trimethyltetrahydro-2H-pyran-2-yl)-4'-methoxy-2,3'-dimethyloctahydro-[2,2'-bifuran]-5-yl)-9-methoxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl)ethyl)-4-methoxy-3,5-dimethyltetrahydro-2H-pyran-2-yl)propanoic acid

InChi Key

BKZOUCVNTCLNFF-IGXZVFLKSA-N

InChi Code

InChI=1S/C44H76O14/c1-21-29(49-12)20-43(56-31(21)22(2)32-23(3)34(51-14)27(7)44(48,57-32)28(8)39(45)46)19-18-40(9,58-43)30-16-17-41(10,54-30)38-25(5)35(52-15)37(53-38)36-24(4)33(50-13)26(6)42(11,47)55-36/h21-38,47-48H,16-20H2,1-15H3,(H,45,46)/t21-,22-,23+,24+,25+,26-,27-,28-,29+,30-,31+,32-,33+,34+,35-,36+,37-,38-,40+,41+,42+,43-,44-/m1/s1

SMILES Code

CO[C@H]1C[C@@]2(O[C@@H]([C@@H]1C)[C@H]([C@H]3O[C@@]([C@@H](C(O)=O)C)([C@@H]([C@H]([C@H]3C)OC)C)O)C)CC[C@](O2)([C@H]4CC[C@](O4)([C@@H]5O[C@@H]([C@H]6O[C@](O)([C@@H]([C@H]([C@@H]6C)OC)C)C)[C@@H]([C@@H]5C)OC)C)C

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

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 829.07 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: Kaneko K, Tsuchida K, Yamazaki R, Otomo S. Hemodynamic effects of a potassium ionophore, lonomycin A. Res Commun Chem Pathol Pharmacol. 1990 Jan;67(1):17-30. PubMed PMID: 2326545. 2: Tsuchida K, Kaneko K, Otomo S. Effects of a monovalent ionophore, lonomycin A, on the contractile force in canine cardiac Purkinje fibers. Arch Int Pharmacodyn Ther. 1991 Nov-Dec;314:25-33. PubMed PMID: 1824188. 3: Tsuchida K, Aihara H. Effects of a K ionophore, lonomycin A, on the action potential in canine cardiac Purkinje fibers. Jpn J Pharmacol. 1986 Jul;41(3):353-61. PubMed PMID: 3761751. 4: Miyagami T, Takei Y, Matsumoto Y, Otake N, Mizoue K, Mizutani T, Omura S, Ozeki M, Suzuki N. An in vitro study on the toxoplasmacidal activity of lonomycin A in host cells. J Antibiot (Tokyo). 1981 Feb;34(2):218-23. PubMed PMID: 7298512. 5: Saito A, Sakurai H, Saito T, Taji S, Miyagami T, Suzuki N, Seitz HM, Osaki H. Correlation between release of reactive oxygen intermediates and inhibition of Toxoplasma multiplication in mouse peritoneal and alveolar macrophages and kidney cells after in vitro incubation with Obioactin, lonomycin A, muramyl dipeptide, lipopolysaccharide or Toxoplasma lysate antigen. Zentralbl Bakteriol Mikrobiol Hyg A. 1987 May;264(3-4):446-54. PubMed PMID: 3660981. 6: Tsuchida K, Kaneko K, Aihara H, Chiba S. Cardiovascular effects of an ionophorous antibiotic, lonomycin A, in anesthetized dogs. Jpn J Pharmacol. 1985 May;38(1):109-12. PubMed PMID: 4021226. 7: Mita M. Release of relaxin-like gonad-stimulating substance from starfish radial nerves by lonomycin. Zoolog Sci. 2013 Jul;30(7):602-6. doi: 10.2108/zsj.30.602. PubMed PMID: 23829221. 8: Ohshima M, Ishizaki N, Abe N, Ukawa M, Marumoto Y. Antibiotic DE-3936, a polyether antibiotic identical with lonomycin. Taxonomy, fermentation, isolation and characterization. J Antibiot (Tokyo). 1976 Apr;29(4):354-65. PubMed PMID: 931804. 9: Seto H, Mizoue K, Otake N. Studies on the ionophorous antibiotics. XXVI. The assignments of the 13C-NMR spectra of lonomycin A and mutalomycin. J Antibiot (Tokyo). 1980 Sep;33(9):979-88. PubMed PMID: 7440419. 10: Satoh H, Tsuchida K. Pharmacological actions of monovalent ionophores on spontaneously beating rabbit sino-atrial nodal cells. Gen Pharmacol. 1999 Aug;33(2):151-9. PubMed PMID: 10461853. 11: Mitani M, Otake N. Studies on the ionophorous antibiotics. XV The monovalent cation selective ionophorous activities of carriomycin, lonomycin and etheromycin. J Antibiot (Tokyo). 1978 Aug;31(8):750-5. PubMed PMID: 690008. 12: Omura S, Shibata M, Machida S, Sawada J. Isolation of a new polyether antibiotic, lonomycin. J Antibiot (Tokyo). 1976 Jan;29(1):15-20. PubMed PMID: 931790. 13: Mizutani T, Yamagishi M, Hara H, Omura S, Ozeki M, Mizoue K, Seto H, Otake N. Lonomycins B and C, two new components of polyether antibiotics. Fermentation, isolation and characterization. J Antibiot (Tokyo). 1980 Nov;33(11):1224-30. PubMed PMID: 6894745. 14: Cruthers LR, Szanto J, Linkenheimer WH, Maplesden DC, Brown WE. Anticoccidial activity of lonomycin (SQ 12,525) in chicks. Poult Sci. 1978 Sep;57(5):1227-33. PubMed PMID: 724593. 15: Cefai D, Cai YC, Hu H, Rudd C. CD28 co-stimulatory regimes differ in their dependence on phosphatidylinositol 3-kinase: common co-signals induced by CD80 and CD86. Int Immunol. 1996 Oct;8(10):1609-16. PubMed PMID: 8921441. 16: Saito A, Igarashi I, Miyahara K, Venturini C, Claveria FG, Hirose T, Suzuki N, Ono K. Effects of reactive oxygen intermediate scavengers on the antitoxoplasmic activity of activated macrophages. Parasitol Res. 1992;78(1):28-31. PubMed PMID: 1584743. 17: Hillaire MC, Jouany JP, Gaboyard C, Jeminet G. In vitro study of the effect of different ionophore antibiotics and of certain derivatives on rumen fermentation and on protein nitrogen degradation. Reprod Nutr Dev. 1989;29(3):247-57. PubMed PMID: 2590388. 18: Simon AK, Auphan N, Schmitt-Verhulst AM. Developmental control of antigen-induced thymic transcription factors. Int Immunol. 1996 Sep;8(9):1421-8. PubMed PMID: 8921420. 19: Dong P, Zhang S, Cai M, Kang N, Hu Y, Cui L, Zhang J, He W. Global characterization of differential gene expression profiles in mouse Vγ1+ and Vγ4+ γδ T cells. PLoS One. 2014 Nov 18;9(11):e112964. doi: 10.1371/journal.pone.0112964. eCollection 2014. PubMed PMID: 25405356; PubMed Central PMCID: PMC4236085. 20: Amano S, Morota T, Kano YK, Narita H, Hashidzume T, Yamamoto S, Mizutani K, Sakuda S, Furihata K, Takano-Shiratori H, Takano H, Beppu T, Ueda K. Promomycin, a polyether promoting antibiotic production in Streptomyces spp. J Antibiot (Tokyo). 2010 Aug;63(8):486-91. doi: 10.1038/ja.2010.68. Epub 2010 Jun 23. PubMed PMID: 20571515.