Elaiophylin

Specifications / Handling

More Information
Product Details
Synonyms	Antibiotic 255-E; Antibiotic 5001B; Antibiotic 56-62; Antibiotic 846I; Gopalamicin; Salbomycin; Azalomycin B; SNA 4606-3
Product Type	Chemical
Properties
Formula	C₅₄H₈₈O₁₈
MW	1025.3
CAS	37318-06-2
Source/Host Chemicals	Isolated from Streptomyces sp. MT-1.
Purity Chemicals	≥95% (HPLC)
Appearance	White powder.
Solubility	Soluble in 100% ethanol, methanol, dimethyl formamide or DMSO.
Identity	Determined by ¹H-NMR.
Declaration	Manufactured by BioViotica.
Other Product Data	May undergo transformation to methyl ketal on storage in methanol. We recommend the use of fresh solutions.
InChi Key	OSERMIPXNLXAPD-MJMYBOKFSA-N
Smiles	[H][C@@]1(C[C@H](O)[C@H](O)[C@H](C)O1)O[C@@H]1C[C@@](O)(O[C@H](C)[C@H]1CC)[C@@H](C)[C@H](O)[C@H](C)[C@@]1([H])OC(=O)\C=C\C=C\[C@H](C)[C@]([H])(OC(=O)\C=C\C=C\[C@@H]1C)[C@@H](C)[C@@H](O)[C@H](C)[C@@]1(O)C[C@@H](O[C@@]2([H])C[C@H](O)[C@H](O)[C@H](C)O2)[C@H](CC)[C@@H](C)O1
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light when in solution.
Use/Stability	Stable for at least 1 year after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Antibiotic.
Active against Gram-positive bacteria, protozoa and tumors.
Antitumor agent. Autophagy inhibitor and antiangiogenic agent.
Testosterone 5α-reductase inhibitor.
Nitric oxide synthase (NOS) inhibitor.
Immunosuppressive.
Enhances the antifungal activity of rapamycin.

Product References

Isolation and characterization of Niphithricins A, B and Elaiophylin, antibiotics produced by Streptomyces violaceoniger: H.-P. Fiedler et al.; J Antibiot. 34, 1107 (1981)
Strukturaufklärung von Elaiophylin: Spektroskopische Untersuchungen und Abbau: H. Kaiser & W. Keller-Schierlein; Helv. Chim. Acta 64, 407 (1981)
Röntgenstrukturanalyse von Elaiophylin: K. Neupert-Laves & M. Dobler; Helv. Chim. Acta 65, 262 (1982)
Elaiophylin derivatives and their biological activities: P. Hammann et al.; J. Antibiot. 43, 1431 (1990)
The biogenetic origin of the carbon skeleton and the oxygen atoms of Elaiophylin, a symmetric macrodiolide antibiotic: M. Gerlitz et al.; J. Org. Chem. 57, 4030 (1992)
Immunosuppressive activity of elaiophylins: S. Y. Lee et al.; J. Microbiol. Biotechnol. 7, 272 (1997)
SNA-4606-1, a new member of Elaiophylins with enzyme inhibition activity against testosterone 5 α-reductase: M. Nakakoshi et al.; J. Antibiot. 52, 175 (1999)
Enhancement of the antifungal activity of Rapamycin by the coproduced Elaiophylin and Nigericin: A. Fang et al.; J. Antibiot. 53, 158 (2000)
Cation selective ion channels formed by macrodiolide antibiotic Elaiophylin in lipid bilayer membranes: P.A. Grigoriev et al.; Bioelectrochem. 54, 11 (2001)
Elaiophylins, new cell cycle inhibitors and apoptosis inducers, produced by Streptomyces pseudoverticillus II. Structures and biological properties: C. Cui et al.; Chinese J. Antibiot. 26, 165-170 (2001)
In vitro and in vivo antiprotozoal activities of bispolides and their derivatives: K. Otoguru et al.; J. Antibiot. 63, 275 (2010)
Elaiophylin, a novel autophagy inhibitor, exerts antitumor activity as a single agent in ovarian cancer cells: X. Zhao, et al.; Autophagy 11, 1849 (2015)
The novel autophagy inhibitor elaiophylin exerts antitumor activity against multiple myeloma with mutant TP53 in part through endoplasmic reticulum stress-induced apoptosis: G. Wang, et al.; Cancer Biol. Ther. 18, 584 (2017)
Antiangiogenic potential of microbial metabolite elaiophylin for targeting tumor angiogenesis: H.N. Lim, et al.; Molecules 23, 563 (2018)

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