Thiolutin
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MedKoo CAT#: 525293

CAS#: 87-11-6

Description: Thiolutin, also known as Acetopyrrothin aand NSC-3927, is an antibiotic and anti-angiogenic agent, acting as a zinc chelator that inhibits the Rpn11 and other JAMM metalloproteases.

Chemical Structure

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Thiolutin
CAS# 87-11-6
Instruction

Theoretical Analysis

MedKoo Cat#: 525293
Name: Thiolutin
CAS#: 87-11-6
Chemical Formula: C8H8N2O2S2
Exact Mass: 228.00
Molecular Weight: 228.284
Elemental Analysis: C, 42.09; H, 3.53; N, 12.27; O, 14.02; S, 28.09

Price and Availability

Size Price Availability Quantity
5mg USD 350
10mg USD 650
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Synonym: Thiolutin; Acetopyrrothin; NSC 3927; NSC-3927; NSC3927.

IUPAC/Chemical Name: N-(4-methyl-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)acetamide

InChi Key: MHMRAFONCSQAIA-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H8N2O2S2/c1-4(11)9-6-7-5(3-13-14-7)10(2)8(6)12/h3H,1-2H3,(H,9,11)

SMILES Code: CN1C2=CSSC2=C(NC(C)=O)C1=O

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: >2 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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 228.28 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Lauinger L, Li J, Shostak A, Cemel IA, Ha N, Zhang Y, Merkl PE, Obermeyer S, Stankovic-Valentin N, Schafmeier T, Wever WJ, Bowers AA, Carter KP, Palmer AE, Tschochner H, Melchior F, Deshaies RJ, Brunner M, Diernfellner A. Thiolutin is a zinc chelator that inhibits the Rpn11 and other JAMM metalloproteases. Nat Chem Biol. 2017 May 1. doi: 10.1038/nchembio.2370. [Epub ahead of print] PubMed PMID: 28459440.

2: Huang S, Yu Y. [Biosynthesis and metabolic engineering of dithiolopyrrolone - A review]. Wei Sheng Wu Xue Bao. 2016 Mar 4;56(3):383-96. Review. Chinese. PubMed PMID: 27382782.

3: 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):329-35. doi: 10.1016/j.bbrc.2016.03.105. Epub 2016 Mar 24. PubMed PMID: 27018252.

4: Saker S, Chacar S, Mathieu F. The final acylation step in aromatic dithiolopyrrolone biosyntheses: identification and characterization of the first bacterium N-benzoyltransferase from Saccharothrix algeriensis NRRL B-24137. Enzyme Microb Technol. 2015 May;72:35-41. doi: 10.1016/j.enzmictec.2015.02.005. Epub 2015 Feb 25. PubMed PMID: 25837505.

5: Peccarelli M, Kebaara BW. Measurement of mRNA decay rates in Saccharomyces cerevisiae using rpb1-1 strains. J Vis Exp. 2014 Dec 13;(94). doi: 10.3791/52240. PubMed PMID: 25549102; PubMed Central PMCID: PMC4396921.

6: Huang S, Tong MH, Qin Z, Deng Z, Deng H, Yu Y. Identification and characterization of the biosynthetic gene cluster of thiolutin, a tumor angiogenesis inhibitor, in Saccharothrix algeriensis NRRL B-24137. Anticancer Agents Med Chem. 2015;15(3):277-84. PubMed PMID: 25353334.

7: 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. Review. Erratum in: Nat Prod Rep. 2015 Feb;32(2):348-9. PubMed PMID: 24835149; PubMed Central PMCID: PMC4132845.

8: Saker S, Lebrihi A, Mathieu F. Identification of two putative acyltransferase genes potentially implicated in dithiolopyrrolone biosyntheses in Saccharothrix algeriensis NRRL B-24137. Appl Biochem Biotechnol. 2014 Jun;173(3):787-802. doi: 10.1007/s12010-014-0896-0. Epub 2014 Apr 11. PubMed PMID: 24723205.

9: Seervi M, Sobhan PK, Mathew KA, Joseph J, Pillai PR, Santhoshkumar TR. A high-throughput image-based screen for the identification of Bax/Bak-independent caspase activators against drug-resistant cancer cells. Apoptosis. 2014 Jan;19(1):269-84. doi: 10.1007/s10495-013-0921-8. PubMed PMID: 24220853.

10: Saker S, Almousa Almaksour Z, Chorin AC, Lebrihi A, Mathieu F. Enzymatic synthesis of dithiolopyrrolone antibiotics using cell-free extract of Saccharothrix algeriensis NRRL B-24137 and biochemical characterization of two pyrrothine N-acyltransferases in this extract. J Microbiol Biotechnol. 2014 Jan;24(1):26-35. PubMed PMID: 24150498.

11: 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. Review. PubMed PMID: 24141227; PubMed Central PMCID: PMC3826145.

12: Hai L, Huang Y, Liao G, Hu C. [Ribosome engineering of streptomyces sp. FJ3 from Three Gorges reservoir area and metabolic product of the selected mutant strain]. Wei Sheng Wu Xue Bao. 2011 Jul;51(7):934-40. Chinese. PubMed PMID: 22043794.

13: Jia Y, Wu SL, Isenberg JS, Dai S, Sipes JM, Field L, Zeng B, Bandle RW, Ridnour LA, Wink DA, Ramchandran R, Karger BL, Roberts DD. Thiolutin inhibits endothelial cell adhesion by perturbing Hsp27 interactions with components of the actin and intermediate filament cytoskeleton. Cell Stress Chaperones. 2010 Mar;15(2):165-81. doi: 10.1007/s12192-009-0130-0. Epub 2009 Jul 5. PubMed PMID: 19579057; PubMed Central PMCID: PMC2866983.

14: Coller J. Methods to determine mRNA half-life in Saccharomyces cerevisiae. Methods Enzymol. 2008;448:267-84. doi: 10.1016/S0076-6879(08)02614-1. PubMed PMID: 19111181.

15: Dai S, Jia Y, Wu SL, Isenberg JS, Ridnour LA, Bandle RW, Wink DA, Roberts DD, Karger BL. Comprehensive characterization of heat shock protein 27 phosphorylation in human endothelial cells stimulated by the microbial dithiole thiolutin. J Proteome Res. 2008 Oct;7(10):4384-95. doi: 10.1021/pr800376w. Epub 2008 Aug 23. PubMed PMID: 18720982; PubMed Central PMCID: PMC2658774.

16: Pelechano V, Pérez-Ortín JE. The transcriptional inhibitor thiolutin blocks mRNA degradation in yeast. Yeast. 2008 Feb;25(2):85-92. PubMed PMID: 17914747.

17: Guan Q, Zheng W, Tang S, Liu X, Zinkel RA, Tsui KW, Yandell BS, Culbertson MR. Impact of nonsense-mediated mRNA decay on the global expression profile of budding yeast. PLoS Genet. 2006 Nov 24;2(11):e203. Epub 2006 Oct 18. PubMed PMID: 17166056; PubMed Central PMCID: PMC1657058.

18: Kebaara BW, Nielsen LE, Nickerson KW, Atkin AL. Determination of mRNA half-lives in Candida albicans using thiolutin as a transcription inhibitor. Genome. 2006 Aug;49(8):894-9. PubMed PMID: 17036064.

19: Tomson BN, D'Amours D, Adamson BS, Aragon L, Amon A. Ribosomal DNA transcription-dependent processes interfere with chromosome segregation. Mol Cell Biol. 2006 Aug;26(16):6239-47. PubMed PMID: 16880532; PubMed Central PMCID: PMC1592809.

20: Bouras N, Mathieu F, Sabaou N, Lebrihi A. Effect of amino acids containing sulfur on dithiolopyrrolone antibiotic productions by Saccharothrix algeriensis NRRL B-24137. J Appl Microbiol. 2006 Feb;100(2):390-7. PubMed PMID: 16430516.