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MedKoo Cat#: 573548 | Name: Aureothricin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Aureothricin is a dithiolopyrrolone antibiotic that exhibits broad-spectrum antimicrobial activity against many Gram-positive and Gram-negative bacteria as well as strains of M. tuberculosis. It is also reported to inhibit tumor angiogenesis, blocking activity of the vitronectin receptor integrin αvβ3.

Chemical Structure

Aureothricin
Aureothricin
CAS#574-95-8

Theoretical Analysis

MedKoo Cat#: 573548

Name: Aureothricin

CAS#: 574-95-8

Chemical Formula: C9H10N2O2S2

Exact Mass: 242.0184

Molecular Weight: 242.31

Elemental Analysis: C, 44.61; H, 4.16; N, 11.56; O, 13.21; S, 26.46

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 Weeks
5mg USD 1,300.00 2 Weeks
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Related CAS #
No Data
Synonym
Aureothricin; Farcinicin; Propionylpyrrothione
IUPAC/Chemical Name
N-(4-methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)propionamide
InChi Key
UGZYFXMSMFMTSM-UHFFFAOYSA-N
InChi Code
1S/C9H10N2O2S2/c1-3-6(12)10-7-8-5(4-14-15-8)11(2)9(7)13/h4H,3H2,1-2H3,(H,10,12)
SMILES Code
CCC(=O)Nc1c-2sscc2n(c1=O)C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 242.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Sturdíková M, Proksa B, Uhrín D, Fuska J. Regulation of biosynthesis of thiolutin and aureothricin in Streptomyces kasugaensis. Folia Microbiol (Praha). 1990;35(4):278-83. doi: 10.1007/BF02821279. PMID: 2262169. 2: Albini F, Bormann S, Gerschel P, Ludwig VA, Neumann W. Dithiolopyrrolones are Prochelators that are Activated by Glutathione. Chemistry. 2023 Jan 18;29(4):e202202567. doi: 10.1002/chem.202202567. Epub 2022 Nov 27. PMID: 36214647; PMCID: PMC10099403. 3: Qin Z, Huang S, Yu Y, Deng H. Dithiolopyrrolone natural products: isolation, synthesis and biosynthesis. Mar Drugs. 2013 Oct 17;11(10):3970-97. doi: 10.3390/md11103970. PMID: 24141227; PMCID: PMC3826145. 4: Liras P. Holomycin, a dithiolopyrrolone compound produced by Streptomyces clavuligerus. Appl Microbiol Biotechnol. 2014 Feb;98(3):1023-30. doi: 10.1007/s00253-013-5410-z. Epub 2013 Dec 10. PMID: 24323287. 5: Li B, Wever WJ, Walsh CT, Bowers AA. Dithiolopyrrolones: biosynthesis, synthesis, and activity of a unique class of disulfide-containing antibiotics. Nat Prod Rep. 2014 Jul;31(7):905-23. doi: 10.1039/c3np70106a. Erratum in: Nat Prod Rep. 2015 Feb;32(2):348-9. PMID: 24835149; PMCID: PMC4132845. 6: Furumai T, Takeda K, Okanishi M. Function of plasmids in the production of aureothricin. I. Elimination of plasmids and alteration of phenotypes caused by protoplast regeneration in Streptomyces kasugaensis. J Antibiot (Tokyo). 1982 Oct;35(10):1367-73. doi: 10.7164/antibiotics.35.1367. PMID: 6757228. 7: Huang S, Yu Y. [Biosynthesis and metabolic engineering of dithiolopyrrolone - A review]. Wei Sheng Wu Xue Bao. 2016 Mar 4;56(3):383-96. Chinese. PMID: 27382782. 8: Zhai Y, Bai S, Liu J, Yang L, Han L, Huang X, He J. Identification of an unusual type II thioesterase in the dithiolopyrrolone antibiotics biosynthetic pathway. Biochem Biophys Res Commun. 2016 Apr 22;473(1):329-335. doi: 10.1016/j.bbrc.2016.03.105. Epub 2016 Mar 24. PMID: 27018252. 9: MARTIN JH, GROTH WC, HAUSMANN WK. IDENTIFICATION BY X-RAY POWDER DIFFRACTION OF THIOLUTIN AND AUREOTHRICIN ISOLATED BY PAPER CHROMATOGRAPHY. Antimicrob Agents Chemother (Bethesda). 1963;15:130-3. PMID: 14275485. 10: MAEDA K. Chemical studies on antibiotic substances. IV. A crystalline toxic substance of Streptomyces thioluteus producing aureothricin. J Antibiot (Tokyo). 1953 Jul;6(3):137-8. PMID: 13096448. 11: Merrouche R, Bouras N, Coppel Y, Mathieu F, Monje MC, Sabaou N, Lebrihi A. Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis. J Nat Prod. 2010 Jun 25;73(6):1164-6. doi: 10.1021/np900808u. PMID: 20507156. 12: NISHIMURA H, KIMURA T. [On a yellow crystalline antibiotic, identical with aureothricin isolated from a new species of streptomyces, 39a, and its taxonomic study]. J Antibiot (Tokyo). 1953 Apr;6(2):57-65. Undetermined Language. PMID: 13084502. 13: Yamazaki M, Maebayashi Y, Kato F, Koyama Y. [Application of 13C-NMR to the biosynthetic investigations. III. Incorporation of propionate-3-13C into aureothricin (author's transl)]. Yakugaku Zasshi. 1975 Mar;95(3):347-9. Japanese. doi: 10.1248/yakushi1947.95.3_347. PMID: 1171186. 14: Minamiguchi K, Kumagai H, Masuda T, Kawada M, Ishizuka M, Takeuchi T. Thiolutin, an inhibitor of HUVEC adhesion to vitronectin, reduces paxillin in HUVECs and suppresses tumor cell-induced angiogenesis. Int J Cancer. 2001 Aug 1;93(3):307-16. doi: 10.1002/ijc.1321. PMID: 11433393.

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MCL0129

MCL0129