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Ansatrienin B (Mycotrienin II) 82189-04-6

Ansatrienin B (Mycotrienin II) 82189-04-6

CAS No.: 82189-04-6

Ansatrienin B (Mycotrienin II) is an antibiotic extracted from Streptomyces. Ansatrienin B has activity against fungi an
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Ansatrienin B (Mycotrienin II) is an antibiotic extracted from Streptomyces. Ansatrienin B has activity against fungi and yeast, but not against bacteria. Ansatrienin B has anti-tumor activity and works as an ADC toxin molecule.

Physicochemical Properties


Molecular Formula C36H50N2O8
Molecular Weight 638.7908
Exact Mass 638.357
CAS # 82189-04-6
PubChem CID 6440888
Appearance Typically exists as solid at room temperature
LogP 6.311
Hydrogen Bond Donor Count 5
Hydrogen Bond Acceptor Count 8
Rotatable Bond Count 6
Heavy Atom Count 46
Complexity 1110
Defined Atom Stereocenter Count 5
SMILES

CC1C(CC=CC=CC=CC(CC(=O)NC2=CC(=CC(=C2O)CCC=C(C1O)C)O)OC)OC(=O)C(C)NC(=O)C3CCCCC3

InChi Key VVJDHJZQBGWPEQ-NXBJUTJHSA-N
InChi Code

InChI=1S/C36H50N2O8/c1-23-14-13-17-27-20-28(39)21-30(34(27)42)38-32(40)22-29(45-4)18-11-6-5-7-12-19-31(24(2)33(23)41)46-36(44)25(3)37-35(43)26-15-9-8-10-16-26/h5-7,11-12,14,18,20-21,24-26,29,31,33,39,41-42H,8-10,13,15-17,19,22H2,1-4H3,(H,37,43)(H,38,40)/b6-5+,12-7+,18-11+,23-14+/t24-,25-,29+,31+,33+/m1/s1
Chemical Name

[(5R,6E,8E,10E,13S,14S,15R,16E)-15,22,24-trihydroxy-5-methoxy-14,16-dimethyl-3-oxo-2-azabicyclo[18.3.1]tetracosa-1(23),6,8,10,16,20(24),21-heptaen-13-yl] (2R)-2-(cyclohexanecarbonylamino)propanoate
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 Ansatrienin B demonstrates antimicrobial activities against Penicillium chrysogenuin 1AM 7106, Mucor pusillus IAM 6122, Rhizopus delemar IAM 6015, Saccharornyces cerevisiae IFO 0304, Candida utilus IFO 0396, and Candida krusei IFO 0590, with MIC values of 12.5 μg/ml, 12.5 μg/ml, 12.5 μg/ml, 8.0 μg/ml, 4.0 μg/ml, 4.0 μg/ml, and 4.0 μg/ml, respectively[1]. Fetal rat long bones release 45 calcium into the culture medium, and ansatrienin B inhibits this release with an apparent halfmaximal inhibition (IC50) value of 21 nM[2]. By selectively inhibiting L-leucine incorporation (IC50=58 nM) in A549 cells, ansatrienin B prevents the translation of the protein synthesis step. In addition, it has an IC50 of 300 nM, which prevents TNF-α-induced ICAM-1 expression[3].
ln Vivo Ansatrienin B (intraperitoneal; once daily; six days) inhibits the formation of tumors in mice that have received P-388 injections. The LD50 value of MTN-II in male CDF1 mice is 80 mg/kg[2].
References [1]. M Sugita, et al. Studies on Mycotrienin Antibiotics, a Novel Class of Ansamycins. I. Taxonomy, Fermentation, Isolation and Properties of Mycotrienins I and II. J Antibiot (Tokyo). 1982 Nov;35(11):1460-6.
[2]. D Feuerbach, et al. Mycotrienins. A New Class of Potent Inhibitors of Osteoclastic Bone Resorption. J Biol Chem. 1995 Oct 27;270(43):25949-55.
[3]. Yuriko Yamada, et al.Mycotrienin II, a Translation Inhibitor That Prevents ICAM-1 Expression Induced by Pro-Inflammatory Cytokines. J Antibiot (Tokyo). 2011 May;64(5):361-6.
Additional Infomation Mycotrienin II has been reported in Streptomyces seoulensis with data available.

Solubility Data


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 1.5655 mL 7.8273 mL 15.6546 mL
5 mM 0.3131 mL 1.5655 mL 3.1309 mL
10 mM 0.1565 mL 0.7827 mL 1.5655 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.