Elaiophylin (also known as Azalomycin-B) shows antiprotozoal activity against Plasmodium falciparum K1a and Trypanosoma brucei brucei GUTat 3.1 strains with IC50 of 0.36 μM and 0.45 μM, respectively. Elaiophylin is a highly characteristic macrolide antibiotic that was first isolated from a culture of Streptomyces melanosporus. Elaiophylin demonstrates antifungal activity when combined with metabolite rapamycin (sc-3504). Elaiophylin shows shown cytotoxicity against mammalian tumor cells, protozoa, nematodes and antibacterial activity aganst gram-positive bacteria. The compound has also displayed immunosuppressive activity through inhibition of B-cell stimulation and inhibiting proliferation of lymphocytes stimulated by mitogens. Elaiophylin has been found to have antihelminthic to inhibit nitric oxide synthesis. Elaiophylin is an inhibitor of 5 α-Reductase and NOS.

Physicochemical Properties

Molecular Formula	C54H88O18
Molecular Weight	1025.27
Exact Mass	1024.597
CAS #	37318-06-2
Related CAS #	37318-06-2
PubChem CID	6444206
Appearance	White to off-white solid powder
Density	1.3±0.1 g/cm3
Boiling Point	1080.5±65.0 °C at 760 mmHg
Flash Point	295.8±27.8 °C
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.569
LogP	2.59
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	18
Rotatable Bond Count	14
Heavy Atom Count	72
Complexity	1730
Defined Atom Stereocenter Count	26
SMILES	CC[C@@H]1[C@@H](C)O[C@](C[C@H]1O[C@H]2C[C@@H]([C@@H]([C@H](C)O2)O)O)([C@@H](C)[C@@H]([C@H](C)[C@@H]3[C@@H](C)C=CC=CC(=O)O[C@@H]([C@@H](C)C=CC=CC(=O)O3)[C@@H](C)[C@H]([C@H](C)[C@]4(C[C@H]([C@H](CC)[C@@H](C)O4)O[C@H]5C[C@@H]([C@@H]([C@H](C)O5)O)O)O)O)O)O
InChi Key	OSERMIPXNLXAPD-MJMYBOKFSA-N
InChi Code	InChI=1S/C54H88O18/c1-13-37-33(9)71-53(63,25-41(37)67-45-23-39(55)49(61)35(11)65-45)31(7)47(59)29(5)51-27(3)19-15-17-22-44(58)70-52(28(4)20-16-18-21-43(57)69-51)30(6)48(60)32(8)54(64)26-42(38(14-2)34(10)72-54)68-46-24-40(56)50(62)36(12)66-46/h15-22,27-42,45-52,55-56,59-64H,13-14,23-26H2,1-12H3/b19-15+,20-16+,21-18+,22-17+/t27-,28-,29-,30-,31-,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42+,45-,46-,47+,48+,49+,50+,51-,52-,53+,54+/m0/s1
Chemical Name	(3E,5E,7S,8S,11E,13E,15S,16S)-8,16-bis((2S,3R,4S)-4-((2R,4R,5R,6R)-4-(((2R,4S,5S,6S)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5-ethyl-2-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)-3-hydroxypentan-2-yl)-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
Synonyms	Azalomycin-B; Azalomycin B; Gopalamicin; Salbomycin
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Elaiophylin-mediated autophagy suppression and lysosomal dysfunction impair ovarian cancer cell survival during hypoxia. Exposure to Elaiophylin (0.025-0.5 μM; 24 hours) produces a considerable increase in ovarian cancer SKOV3 cell mortality in hypoxic conditions[1]. In both the SKOV3 and A2780 cell lines, Elaiophylin (0.25, 0.5, 0.75 μM; 24 hours) treatment leads to considerable activation of cleaved CASP9/caspase-9 and PARP1 and downregulation of BIRC5/survivin in a concentration-dependent manner[1].
ln Vivo	therapy with 2 mg/kg Elaiophylin (given ip every 2 days for 21 days; in BALB/C athymic mice) effectively suppresses ovarian cancer SKOV3 cells growth compared with DMSO therapy, resulting in a 72% drop in the average daily tumor growth rate compared with DMSO treatment [1]. Lower dosages of Elaiophylin as a single agent exert strong anticancer efficacy, but greater levels lead to intestinal damage. Administration of a lower dose (2 mg/kg) of Elaiophylin as a single agent yields a considerable anticancer effect without toxicity in an orthotopic ovarian cancer model with metastases. Toxic responses are reported only in the 8 mg/kg group[1].
Cell Assay	Cell Viability Assay[1] Cell Types: Ovarian cancer SKOV3 cells. Tested Concentrations: 0.025, 0.05, 0.1, 0.2, 0.5 μM Incubation Duration: 24 hrs (hours) Experimental Results: Caused a significant increase in ovarian cancer SKOV3 cells death in hypoxia conditions. Western Blot Analysis[1] Cell Types: Ovarian cancer SKOV3 cells; A2780 cells Tested Concentrations: 0.25, 0.5, 0.75 μM Incubation Duration: 24 hrs (hours) Experimental Results: Treatment led to significant activation of cleaved CASP9/caspase-9 and PARP1 and downregulation of BIRC5/survivin in a concentration-dependent manner .
Animal Protocol	Animal/Disease Models: 4-wk-old BALB/C athymic mice with ovarian cancer SKOV3 cells[1] Doses: 1 or 2 mg/kg Route of Administration: Given ip every 2 days for 21 days Experimental Results: Treatment with 2 mg/kg Dramatically suppressed ovarian cancer SKOV3 cell growth compared with DMSO treatment.
References	[1]. Zhao X, et al Elaiophylin, a novel autophagy inhibitor, exerts antitumor activity as a single agent in ovarian cancer cells. Autophagy. 2015;11(10):1849-63.
Additional Infomation	Elaiophylin is a macrodiolide that is isolated from several bacteria including Streptomyces violaceoniger and other soil actinomycetes. It has a role as a bacterial metabolite, an antifungal agent and an autophagy inhibitor. It is a lactol, a monosaccharide derivative and a macrodiolide. Elaiophylin has been reported in Streptomyces, Streptomyces violaceusniger, and other organisms with data available.

Solubility Data

Solubility (In Vitro)

DMSO:49 mg/mL (47.8 mM) Water:<1 mg/mL Ethanol:5 mg/mL (4.9 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	0.9754 mL	4.8768 mL	9.7535 mL
	5 mM	0.1951 mL	0.9754 mL	1.9507 mL
	10 mM	0.0975 mL	0.4877 mL	0.9754 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.