Azalomycin

Names

[ Name ]:
Azalomycin

[Synonym ]:
(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 (non-preferred 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-hydroxy-2-pentanyl}-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
5001B
gopalamicin
Azalomycin
Azalomycin-B,Gopalamicin,SNA 4606-3
Antibiotic 56-62
Elaiofilin
Salbomycin
Elaiophylin,Salbomycin,Gopalamicin,SNA 4606-3,Azalomycin-B
(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-methyloxan-2-yl]oxy-5-ethyl-2-hydroxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
Antibiotic 5001B
azalomycin B
Elaiophylin

Biological Activity

[Description]:

Elaiophylin (Azalomycin B; Gopalamicin; Efomycin E) is an autophagy inhibitor, exerts antitumor activity as a single agent in ovarian cancer cells[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Autophagy >> Autophagy

[Target]

Autophagy[1]

[In Vitro]

Elaiophylin-mediated autophagy inhibition and lysosomal dysfunction affect ovarian cancer cell survival during hypoxia. Exposure to Elaiophylin (0.025-0.5 μM; 24 hours) causes a significant increase in ovarian cancer SKOV3 cell death in hypoxia conditions[1]. In both the SKOV3 and A2780 cell lines, Elaiophylin (0.25, 0.5, 0.75 μM; 24 hours) treatment leads to significant activation of cleaved CASP9/caspase-9 and PARP1 and downregulation of BIRC5/survivin in a concentration-dependent manner[1]. Cell Viability Assay[1] Cell Line: Ovarian cancer SKOV3 cells. Concentration: 0.025, 0.05, 0.1, 0.2, 0.5 μM Incubation Time: 24 hours Result: Caused a significant increase in ovarian cancer SKOV3 cells death in hypoxia conditions. Western Blot Analysis[1] Cell Line: Ovarian cancer SKOV3 cells; A2780 cells Concentration: 0.25, 0.5, 0.75 μM Incubation Time: 24 hours Result: Treatment led to significant activation of cleaved CASP9/caspase-9 and PARP1 and downregulation of BIRC5/survivin in a concentration-dependent manner.

[In Vivo]

Treatment with 2 mg/kg Elaiophylin (given i.p. every 2 days for 21 days; in BALB/C athymic mice) significantly suppresses ovarian cancer SKOV3 cells growth compared with DMSO treatment, resulting in a 72% decrease in the average daily tumor growth rate compared with DMSO treatment [1]. Lower doses of Elaiophylin as a single agent exert significant antitumor activity, while higher doses lead to intestinal toxicity. Administration of a lower dose (2 mg/kg) of Elaiophylin as a single agent achieves a significant antitumor effect without toxicity in an orthotopic ovarian cancer model with metastasis. Toxic reactions are observed only in the 8 mg/kg group[1]. Animal Model: 4-wk-old BALB/C athymic mice with ovarian cancer SKOV3 cells[1] Dosage: 1 or 2 mg/kg Administration: Given i.p. every 2 days for 21 days Result: Treatment with 2 mg/kg significantly suppressed ovarian cancer SKOV3 cells 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.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
1080.5±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₅₄H₈₈O₁₈

[ Molecular Weight ]:
1025.27

[ Flash Point ]:
295.8±27.8 °C

[ Exact Mass ]:
1024.597046

[ PSA ]:
269.82000

[ LogP ]:
2.59

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.569

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CL8380000

CHEMICAL NAME :: Azalomycin B

CAS REGISTRY NUMBER :: 37318-06-2

LAST UPDATED :: 198910

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C54-H88-O13

MOLECULAR WEIGHT :: 945.42

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 281 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JAJAAA Journal of Antibiotics, Series A. (Tokyo, Japan) V.6-20, 1953-67. For publisher information, see JANTAJ. Volume(issue)/page/year: 13,51,1960

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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