Ascomycin

Names

[ Name ]:
Ascomycin

[Synonym ]:
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Ethyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-propen-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatr ;icyclo[22.3.1.0]octacos-18-ene-2,3,10,16-tetrone
immunomycin
4H-Pyrrolo3,2-dpyrimidin-4-one,7-(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-pyrrolidinyl-1,5-dihydro
(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-ethyl-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone
15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-
(1R,9S,12S,13R,14S,17R,18Z,21S,23S,24R,25S,27R)-17-Ethyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-propen-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatr ;icyclo[22.3.1.0]octacos-18-ene-2,3,10,16-tetrone
(1S)-1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-iMino-D-ribitol,iMMucillin H
7-((2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one
Ascomycin
changchuanmycin
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-Ethyl-1,14-dihydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.0]octacos-18-ene-2,3,10,16-tetrone
7-[(2S,3S,4R,5R)-3,4-Dihydroxy-5-(hydroxymethyl)-2-pyrrolidinyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one
(1S)-1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-imino-D-ribitol
Isopamphos
Immucillin-H
1,4-dideoxy-(1S)-1-C-(4-hydroxypyrrolo[3,2-d]pyrimidin-7-yl)-1,4-imino-D-ribitol
15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-, (3S,4R,5S,8R,9Z,12S,14S,15R,16S,18R,19R,26aS)-
MFCD00467131
Fodosine

Biological Activity

[Description]:

Ascomycin(Immunomycin, FR-900520, FK520) is an ethyl analog of tacrolimus (FK506) with strong immunosuppressant properties. IC50 Value: 0.55 nM [1]Target: in vitro: When we used either CD4+CD8+ thymocytes or peripheral T cells activated by phorbol ester and ionomycin, the cell surface induction of CD5 was also partially blocked by CsA, FK-520 and rapamycin [2]. Ascomycinalso had a 3-fold lower immunosuppressive potency in a popliteal lymph node hyperplasia assay, resulting in an equivalent therapeutic index consistent with a common mechanistic dependence on calcineurin inhibition [3].in vivo: In 14-day studies, nephrotoxicity was not induced by continuous i.p. infusion of ascomycin at 10 mg/kg/day or daily oral administration (up to 50 mg/kg/day) in rats on a normal diet, nor by continuous i.v. infusion (up to 6 mg/kg/day) in rats on a low salt diet to enhance susceptibility [3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

Natural Products >> Others

[References]

[1]. Hatanaka H, Kino T, Miyata S, FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. II. Fermentation, isolation and physico-chemical and biological characteristics. J Antibiot (Tokyo). 1988 Nov;41(11):1592-601.

[2]. Teutsch M, Higer M, Wang D, Induction of CD5 on B and T cells is suppressed by cyclosporin A, FK-520 and rapamycin. Int Immunol. 1995 Mar;7(3):381-92.

[3]. Mollison KW, Fey TA, Krause RA, Nephrotoxicity studies of the immunosuppressants tacrolimus (FK506) and ascomycin in rat models. Toxicology. 1998 Feb 6;125(2-3):169-81.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
868.3±75.0 °C at 760 mmHg

[ Melting Point ]:
153-157ºC

[ Molecular Formula ]:
C₄₃H₆₉NO₁₂

[ Molecular Weight ]:
792.008

[ Flash Point ]:
478.9±37.1 °C

[ Exact Mass ]:
791.481995

[ PSA ]:
178.36000

[ LogP ]:
3.81

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

[ Index of Refraction ]:
1.546

[ Storage condition ]:
−20°C

[ Water Solubility ]:
Soluble in DMSO at 65mg/ml; soluble in ethanol at 50mg/m; with warming. Very poorly soluble in water

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H302 + H332-H319

[ Precautionary Statements ]:
P210-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
36/37

[ RIDADR ]:
UN 1648 3 / PGII

[ WGK Germany ]:
3

[ RTECS ]:
KD4185000

[ HS Code ]:
29419090

Articles

Highly specific targeting of human leukocytes using gold nanoparticle-based biologically active conjugates.

J. Biomed. Nanotechnol. 10(7) , 1259-66, (2014)

In this study we demonstrate for the first time a new approach for highly specific targeting of viable human leukocytes by functionalised gold nanoconjugates made on the basis of citrate-stabilised go...

Effects of calcineurin inhibitors on an in vitro assay for chronic urticaria.

Clin. Exp. Allergy 35(5) , 554-9, (2005)

Chronic urticaria is a common skin disorder, which causes considerable morbidity. In approximately 40% of cases, patients have an autoimmune disorder in which functional antibodies cause degranulation...

The immunosuppressant cyclosporin A antagonizes human formyl peptide receptor through inhibition of cognate ligand binding.

J. Immunol. 177(10) , 7050-8, (2006)

Cyclosporin A (CsA) is a fungus-derived cyclic undecapeptide with potent immunosuppressive activity. Its analog, cyclosporin H (CsH), lacks immunosuppressive function but can act as an antagonist for ...

Related Compounds

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