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MedKoo Cat#: 525293 | Name: Thiolutin
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Description:

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

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

Thiolutin
Thiolutin
CAS#87-11-6

Theoretical Analysis

MedKoo Cat#: 525293

Name: Thiolutin

CAS#: 87-11-6

Chemical Formula: C8H8N2O2S2

Exact Mass: 228.0027

Molecular Weight: 228.28

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 450.00
10mg USD 750.00
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Related CAS #
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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
Certificate of Analysis
View CoA: current batch, Lot#C8Y01M08
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

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
1: Pillai JR, Wali AF, Shivappa P, Talath S, Attia SM, Nadeem A, Rehman MU. Evaluating the anti-cancer potential and pharmacological in-sights of Physalis angulata Root Extract as a strong candidate for future research. J Genet Eng Biotechnol. 2024 Dec;22(4):100410. doi: 10.1016/j.jgeb.2024.100410. Epub 2024 Aug 22. PMID: 39674639; PMCID: PMC11387689. 2: Cai W, Teng T, Wang X, Li B, Gu X, Zhou Y. Thiolutin Alleviates Cardiotoxic Effects of Doxorubicin by Suppressing NLRP3 Inflammasome in the Mouse Model. Cardiovasc Toxicol. 2024 Dec 11. doi: 10.1007/s12012-024-09947-1. Epub ahead of print. PMID: 39663334. 3: Su L, Huber EM, Westphalen M, Gellner J, Bode E, Köbel T, Grün P, Alanjary MM, Glatter T, Cirnski K, Müller R, Schindler D, Groll M, Bode HB. Isofunctional but Structurally Different Methyltransferases for Dithiolopyrrolone Diversification. Angew Chem Int Ed Engl. 2024 Dec 2;63(49):e202410799. doi: 10.1002/anie.202410799. Epub 2024 Oct 18. PMID: 39185606. 4: Sumang FA, Ward A, Errington J, Dashti Y. Hibiscus acid and hydroxycitric acid dimethyl esters from Hibiscus flowers induce production of dithiolopyrrolone antibiotics by Streptomyces Strain MBN2-2. Nat Prod Bioprospect. 2024 Jul 3;14(1):40. doi: 10.1007/s13659-024-00460-0. PMID: 38955942; PMCID: PMC11219617. 5: Ri-Wen, Yang YH, Zhang TN, Liu CF, Yang N. Targeting epigenetic and post- translational modifications regulating pyroptosis for the treatment of inflammatory diseases. Pharmacol Res. 2024 May;203:107182. doi: 10.1016/j.phrs.2024.107182. Epub 2024 Apr 12. PMID: 38614373. 6: Liu J, Isaji T, Komatsu S, Sun Y, Xu X, Fukuda T, Fujimura T, Takahashi S, Gu J. BRCC36 associates with FLT3-ITD to regulate its protein stability and intracellular signaling in acute myeloid leukemia. Cancer Sci. 2024 Apr;115(4):1196-1208. doi: 10.1111/cas.16090. Epub 2024 Jan 30. PMID: 38288901; PMCID: PMC11007003. 7: Qiu C, Arora P, Malik I, Laperuta AJ, Pavlovic EM, Ugochukwu S, Naik M, Kaplan CD. Thiolutin has complex effects in vivo but is a direct inhibitor of RNA polymerase II in vitro. Nucleic Acids Res. 2024 Mar 21;52(5):2546-2564. doi: 10.1093/nar/gkad1258. PMID: 38214235; PMCID: PMC10954460. 8: Nguyen LTT, Park AR, Van Le V, Hwang I, Kim JC. Exploration of a multifunctional biocontrol agent Streptomyces sp. JCK-8055 for the management of apple fire blight. Appl Microbiol Biotechnol. 2024 Dec;108(1):49. doi: 10.1007/s00253-023-12874-w. Epub 2024 Jan 6. PMID: 38183485. 9: Wang H, Shu L, Lv C, Liu N, Long Y, Peng X, Ling H, Tao T, Tang J, Cheng Y, Liu S, Xiao D, Tao Y. BRCC36 Deubiquitinates HMGCR to Regulate the Interplay Between Ferroptosis and Pyroptosis. Adv Sci (Weinh). 2024 Mar;11(11):e2304263. doi: 10.1002/advs.202304263. Epub 2024 Jan 4. PMID: 38178583; PMCID: PMC10953584. 10: Zhu P, Bi X, Su D, Li X, Chen B, Li J, Zhao L, Wang Y, Xu S, Wu X. Thiolutin, a selective NLRP3 inflammasome inhibitor, attenuates cyclophosphamide-induced impairment of sperm and fertility in mice. Immunopharmacol Immunotoxicol. 2024 Apr;46(2):172-182. doi: 10.1080/08923973.2023.2298894. Epub 2024 Jan 4. PMID: 38174705. 11: Chen X, Johnson RM, Li B. A Permissive Amide N-Methyltransferase for Dithiolopyrrolones. ACS Catal. 2023 Feb 3;13(3):1899-1905. doi: 10.1021/acscatal.2c05439. Epub 2023 Jan 18. PMID: 38106463; PMCID: PMC10720983. 12: Yang P, Yang X, Wang D, Yang H, Li Z, Zhang C, Zhang S, Zhu J, Li X, Su P, Zhuang T. PSMD14 stabilizes estrogen signaling and facilitates breast cancer progression via deubiquitinating ERα. Oncogene. 2024 Jan;43(4):248-264. doi: 10.1038/s41388-023-02905-1. Epub 2023 Nov 29. PMID: 38017133; PMCID: PMC10798890. 13: Bora P, Gogoi S, Deshpande MV, Garg P, Bhuyan RP, Altaf N, Saha N, Borah SM, Phukon M, Tanti N, Saikia B, Ahmed SS, Borah SR, Dutta A, Sarmah BK. Rhizospheric Bacillus spp. Exhibit Miticidal Efficacy against Oligonychus coffeae (Acari: Tetranychidae) of Tea. Microorganisms. 2023 Nov 2;11(11):2691. doi: 10.3390/microorganisms11112691. PMID: 38004703; PMCID: PMC10673310. 14: Zhang W, Liu K, Ren GM, Wang Y, Wang T, Liu X, Li DX, Xiao Y, Chen X, Li YT, Zhan YQ, Xiang SS, Chen H, Gao HY, Zhao K, Yu M, Ge CH, Li CY, Ge ZQ, Yang XM, Yin RH. BRISC is required for optimal activation of NF-κB in Kupffer cells induced by LPS and contributes to acute liver injury. Cell Death Dis. 2023 Nov 15;14(11):743. doi: 10.1038/s41419-023-06268-z. PMID: 37968261; PMCID: PMC10651896. 15: He S, Li J, Wang Y, Xiang G, Yang G, Xiao L, Tang M, Zhang H. Phosphorylated heat shock protein 27 improves the bone formation ability of osteoblasts and bone marrow stem cells from patients with adolescent idiopathic scoliosis. JOR Spine. 2023 Apr 20;6(3):e1256. doi: 10.1002/jsp2.1256. PMID: 37780830; PMCID: PMC10540826. 16: Cai W, Teng T, Wang X, Li B, Gu X, Zhou Y. The protective effect of thiolutin on doxorubicin-induced H9c2 cardiomyocyte injury. J Toxicol Sci. 2023;48(8):469-479. doi: 10.2131/jts.48.469. PMID: 37532580. 17: Wang A, Ma X, Wei F, Li Y, Liu Q, Zhang H. Evidence on the therapeutic role of thiolutin in imiquimod-induced psoriasis-like skin inflammation in mice. Immun Inflamm Dis. 2023 Jul;11(7):e877. doi: 10.1002/iid3.877. PMID: 37506136; PMCID: PMC10336655. 18: Chen Y, Tu Y, Pan T, Deng Z, Duan L. A Cysteine-Reloading Process Initiating the Biosynthesis of the Bicyclic Scaffold of Dithiolopyrrolones. Antibiotics (Basel). 2023 Apr 20;12(4):787. doi: 10.3390/antibiotics12040787. PMID: 37107148; PMCID: PMC10134970. 19: Jia Y, Xue K, Luo Y, Liu C. Thiolutin attenuates ischemic stroke injury via inhibition of NLRP3 inflammasome: an in vitro and in vivo study. Exp Brain Res. 2023 Mar;241(3):839-849. doi: 10.1007/s00221-023-06566-0. Epub 2023 Feb 7. PMID: 36749359. 20: Jimbo K, Hattori A, Koide S, Ito T, Sasaki K, Iwai K, Nannya Y, Iwama A, Tojo A, Konuma T. Genetic deletion and pharmacologic inhibition of E3 ubiquitin ligase HOIP impairs the propagation of myeloid leukemia. Leukemia. 2023 Jan;37(1):122-133. doi: 10.1038/s41375-022-01750-7. Epub 2022 Nov 9. PMID: 36352193.