THIOLUTIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H8N2O2S2
Molecular Weight	228.291
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

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Structure Search

SMILES

CN1C(=O)C(NC(C)=O)=C2SSC=C12

InChI

InChIKey=MHMRAFONCSQAIA-UHFFFAOYSA-N

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)

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11433393 | https://www.ncbi.nlm.nih.gov/pubmed/17914747

Thiolutin is a naturally occurring bicyclic dithiole that was first isolated from Streptomyces luteorectiuli based on its antibiotic activities. Thiolutin inhibits the growth of Saccharomyces cerevisiae and several gram-positive and -negative bacteria by inhibiting DNA-dependent RNA polymerases. It also inhibits the adhesion of endothelial cells, including adhesion of human umbilical vein endothelial cells (HUVECs) to vitronectin, and restricts tumor cell-induced angiogenesis.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA-directed RNA polymerase 11 Target ID: CHEMBL2364672 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4597739	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
The transcriptional inhibitor thiolutin blocks mRNA degradation in yeast.	2008-02	17914747
New dithiolopyrrolone antibiotics from Saccharothrix sp. SA 233. I. Taxonomy, fermentation, isolation and biological activities.	2002-08	12374382
Thiolutin, an inhibitor of HUVEC adhesion to vitronectin, reduces paxillin in HUVECs and suppresses tumor cell-induced angiogenesis.	2001-08-01	11433393
RNA polymerase inhibitors with activity against rifampin-resistant mutants of Staphylococcus aureus.	2000-11	11036042

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

At concentrations as low as 2 mug/ml, the thiolutin inhibited ribonucleic acid (RNA) and protein synthesis in whole cells and spheroplasts. At these low concentrations, protein synthesis continued for a short period of time after RNA synthesis was completely stopped. With higher drug concentrations (greater than 20 mug/ml) protein synthesis was inhibited; concentrations of thiolutin up to 100 mug/ml did not affect translocation or peptide bond formation in cell-free protein-synthesizing systems from yeast. The effect of thiolutin on the activity of partially purified deoxyribonucleic acid-dependent RNA polymerases was examined, and the drug was found to be a potent inhibitor of RNA synthesis in vitro

Name

Type

Language

THIOLUTIN

Common Name

English

NSC-3927

Preferred Name

English

1,2-DITHIOLO(4,3-B)PYRROL-5(4H)-ONE, 6-ACETAMIDO-4-METHYL-

Systematic Name

English

THIOLUTIN [MI]

Common Name

English

N-(4,5-DIHYDRO-4-METHYL-5-OXO-1,2-DITHIOLO(4,3-B)PYRROL-6-YL)ACETAMIDE

Systematic Name

English

ACETOPYRROTHINE

Common Name

English

3-ACETAMIDO-5-METHYLPYRROLIN-4-ONE(4,3-D)-1,2-DITHIOLE

Common Name

English

6-(ACETAMIDO)-4-METHYL-1,2-DITHIOLO(4,3-B)PYRROL-5(4H)-ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258