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MedKoo Cat#: 525347 | Name: Chaetocin

Description:

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

Chaetocin is an inducer of apoptosis in human melanoma cells, generating reactive oxygen species and the intrinsic mitochondrial pathway.

Chemical Structure

Chaetocin
Chaetocin
CAS#28097-03-2

Theoretical Analysis

MedKoo Cat#: 525347

Name: Chaetocin

CAS#: 28097-03-2

Chemical Formula: C30H28N6O6S4

Exact Mass: 696.0953

Molecular Weight: 696.83

Elemental Analysis: C, 51.71; H, 4.05; N, 12.06; O, 13.78; S, 18.40

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Chaetocin
IUPAC/Chemical Name
(3S,3'S,5aR,5aR,10bR,10'bR,11aS,11'aS)-2,2',3,3',5a,5'a,6,6'-octahydro-3,3'-bis(hydroxymethyl)-2,2'-dimethyl-[10b,10'b(11H,11'H)-bi3,11a-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole]-1,1',4,4'-tetrone
InChi Key
CNTRDQLQYLGSKO-KPCONVMXSA-N
InChi Code
InChI=1S/C30H28N6O6S4/c1-32-23(39)27-11-16-20-17(31-21(16)35(27)25(41)29(32,12-37)45-43-27)7-5-9-19(20)34-18-8-4-3-6-14(18)15-10-28-24(40)33(2)30(13-38,46-44-28)26(42)36(28)22(15)34/h3-9,15-16,21-22,31,37-38H,10-13H2,1-2H3/t15?,16-,21-,22?,27?,28+,29+,30+/m1/s1
SMILES Code
O=C1N(C)[C@]2(CO)C(N3C1(SS2)C[C@@]4([H])[C@]3([H])NC5=C4C(N6C(N7[C@](C(N(C)[C@]8(CO)C7=O)=O)(SS8)C9)C9C%10=C6C=CC=C%10)=CC=C5)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 696.83 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: Vo MC, Nguyen-Pham TN, Lee HJ, Jung SH, Choi NR, Hoang MD, Kim HJ, Lee JJ. Chaetocin enhances dendritic cell function via the induction of heat shock protein and cancer testis antigens in myeloma cells. Oncotarget. 2017 Apr 29. doi: 10.18632/oncotarget.17517. [Epub ahead of print] PubMed PMID: 28512265. 2: Chen TT, Wu SM, Ho SC, Chuang HC, Liu CY, Chan YF, Kuo LW, Feng PH, Liu WT, Chen KY, Hsiao TC, Juang JN, Lee KY. SUV39H1 Reduction Is Implicated in Abnormal Inflammation in COPD. Sci Rep. 2017 Apr 20;7:46667. doi: 10.1038/srep46667. PubMed PMID: 28425504; PubMed Central PMCID: PMC5397975. 3: Han X, Han Y, Zheng Y, Sun Q, Ma T, Zhang J, Xu L. Chaetocin induces apoptosis in human melanoma cells through the generation of reactive oxygen species and the intrinsic mitochondrial pathway, and exerts its anti-tumor activity in vivo. PLoS One. 2017 Apr 18;12(4):e0175950. doi: 10.1371/journal.pone.0175950. eCollection 2017. PubMed PMID: 28419143; PubMed Central PMCID: PMC5395229. 4: Wang Y, Hu P, Pan Y, Zhu Y, Liu X, Che Y, Liu G. Identification and characterization of the verticillin biosynthetic gene cluster in Clonostachys rogersoniana. Fungal Genet Biol. 2017 Apr 1;103:25-33. doi: 10.1016/j.fgb.2017.03.007. [Epub ahead of print] PubMed PMID: 28376389. 5: Yang G, Weng X, Zhao Y, Zhang X, Hu Y, Dai X, Liang P, Wang P, Ma L, Sun X, Hou L, Xu H, Fang M, Li Y, Jenuwein T, Xu Y, Sun A. The histone H3K9 methyltransferase SUV39H links SIRT1 repression to myocardial infarction. Nat Commun. 2017 Mar 31;8:14941. doi: 10.1038/ncomms14941. PubMed PMID: 28361889; PubMed Central PMCID: PMC5381011. 6: Zuma AA, Santos JO, Mendes I, de Souza W, Machado CR, Motta MCM. Chaetocin-A histone methyltransferase inhibitor-Impairs proliferation, arrests cell cycle and induces nucleolar disassembly in Trypanosoma cruzi. Acta Trop. 2017 Jun;170:149-160. doi: 10.1016/j.actatropica.2017.02.007. Epub 2017 Feb 6. PubMed PMID: 28185826. 7: Zhang S, Yin J, Zhong J. Chaetocin reactivates the lytic replication of Epstein-Barr virus from latency via reactive oxygen species. Sci China Life Sci. 2017 Jan;60(1):66-71. doi: 10.1007/s11427-016-0286-7. Epub 2017 Jan 5. PubMed PMID: 28063010. 8: Ono T, Kamimura N, Matsuhashi T, Nagai T, Nishiyama T, Endo J, Hishiki T, Nakanishi T, Shimizu N, Tanaka H, Ohta S, Suematsu M, Ieda M, Sano M, Fukuda K, Kaneda R. The histone 3 lysine 9 methyltransferase inhibitor chaetocin improves prognosis in a rat model of high salt diet-induced heart failure. Sci Rep. 2017 Jan 4;7:39752. doi: 10.1038/srep39752. PubMed PMID: 28051130; PubMed Central PMCID: PMC5209701. 9: Zhang J, Liang L, Miao X, Wu S, Cao J, Tao B, Mao Q, Mo K, Xiong M, Lutz BM, Bekker A, Tao YX. Contribution of the Suppressor of Variegation 3-9 Homolog 1 in Dorsal Root Ganglia and Spinal Cord Dorsal Horn to Nerve Injury-induced Nociceptive Hypersensitivity. Anesthesiology. 2016 Oct;125(4):765-78. doi: 10.1097/ALN.0000000000001261. PubMed PMID: 27483126; PubMed Central PMCID: PMC5030174. 10: Lin SH, Ho WT, Wang YT, Chuang CT, Chuang LY, Guh JY. Histone methyltransferase Suv39h1 attenuates high glucose-induced fibronectin and p21(WAF1) in mesangial cells. Int J Biochem Cell Biol. 2016 Sep;78:96-105. doi: 10.1016/j.biocel.2016.06.021. Epub 2016 Jun 29. PubMed PMID: 27373678. 11: Zhang X, Wu J, Choiniere J, Yang Z, Huang Y, Bennett J, Wang L. Arsenic silences hepatic PDK4 expression through activation of histone H3K9 methylatransferase G9a. Toxicol Appl Pharmacol. 2016 Aug 1;304:42-7. doi: 10.1016/j.taap.2016.05.015. Epub 2016 May 20. PubMed PMID: 27217333; PubMed Central PMCID: PMC4930740. 12: Rombo R, Weiher H, Schmidt-Wolf IG. Effect of chaetocin on renal cell carcinoma cells and cytokine-induced killer cells. Ger Med Sci. 2016 Apr 18;14:Doc04. doi: 10.3205/000231. eCollection 2016. PubMed PMID: 27141211; PubMed Central PMCID: PMC4836455. 13: Jung HJ, Seo I, Casciello F, Jacquelin S, Lane SW, Suh SI, Suh MH, Lee JS, Baek WK. The anticancer effect of chaetocin is enhanced by inhibition of autophagy. Cell Death Dis. 2016 Feb 18;7:e2098. doi: 10.1038/cddis.2016.15. PubMed PMID: 26890137; PubMed Central PMCID: PMC5399187. 14: Bae JS, Han M, Yao C, Chung JH. Chaetocin inhibits IBMX-induced melanogenesis in B16F10 mouse melanoma cells through activation of ERK. Chem Biol Interact. 2016 Feb 5;245:66-71. doi: 10.1016/j.cbi.2015.12.021. Epub 2015 Dec 31. PubMed PMID: 26748310. 15: Gray LR, On H, Roberts E, Lu HK, Moso MA, Raison JA, Papaioannou C, Cheng WJ, Ellett AM, Jacobson JC, Purcell DF, Wesselingh SL, Gorry PR, Lewin SR, Churchill MJ. Toxicity and in vitro activity of HIV-1 latency-reversing agents in primary CNS cells. J Neurovirol. 2016 Aug;22(4):455-63. doi: 10.1007/s13365-015-0413-4. Epub 2016 Jan 4. PubMed PMID: 26727904. 16: Zhao N, Tsuda H, Murofushi T, Imai K, Ochiai K, Yang P, Suzuki N. Chaetocin inhibits RANKL-induced osteoclast differentiation through reduction of Blimp1 in Raw264.7 cells. Life Sci. 2015 Dec 15;143:1-7. doi: 10.1016/j.lfs.2015.10.027. Epub 2015 Oct 26. PubMed PMID: 26514304. 17: Li MF, Zhang R, Li TT, Chen MY, Li LX, Lu JX, Jia WP. High Glucose Increases the Expression of Inflammatory Cytokine Genes in Macrophages Through H3K9 Methyltransferase Mechanism. J Interferon Cytokine Res. 2016 Jan;36(1):48-61. doi: 10.1089/jir.2014.0172. Epub 2015 Sep 25. PubMed PMID: 26406561. 18: Liu X, Guo S, Liu X, Su L. Chaetocin induces endoplasmic reticulum stress response and leads to death receptor 5-dependent apoptosis in human non-small cell lung cancer cells. Apoptosis. 2015 Nov;20(11):1499-507. doi: 10.1007/s10495-015-1167-4. PubMed PMID: 26349783. 19: Keung EZ, Akdemir KC, Al Sannaa GA, Garnett J, Lev D, Torres KE, Lazar AJ, Rai K, Chin L. Increased H3K9me3 drives dedifferentiated phenotype via KLF6 repression in liposarcoma. J Clin Invest. 2015 Aug 3;125(8):2965-78. doi: 10.1172/JCI77976. Epub 2015 Jul 20. PubMed PMID: 26193637; PubMed Central PMCID: PMC4563740. 20: Xia RH, Wang Z, Zhang CY, Hu YH, Zhou RR, Wang LZ, Tian Z, Li J. Low expression of endothelin receptor B (EDNRB) is related to H3K9me3 binding with the EDNRB promoter region and is associated with the clinical T tumor stage in salivary adenoid cystic carcinoma. Oral Surg Oral Med Oral Pathol Oral Radiol. 2015 Aug;120(2):258-68. doi: 10.1016/j.oooo.2015.04.015. Epub 2015 May 13. PubMed PMID: 26166030.