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MedKoo Cat#: 581001 | Name: Chetomin
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Description:

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

Chetomin is a natural product isolated from Chaetomium species which has antibacterial and antifungal properties. Chetomin induces degradation of XIAP and enhances TRAIL sensitivity in urogenital cancer cells. Chetomin, targeting HIF-1α/p300 complex, exhibits antitumour activity in multiple myeloma.

Chemical Structure

Chetomin
Chetomin
CAS#1403-36-7

Theoretical Analysis

MedKoo Cat#: 581001

Name: Chetomin

CAS#: 1403-36-7

Chemical Formula: C31H30N6O6S4

Exact Mass: 710.1110

Molecular Weight: 710.86

Elemental Analysis: C, 52.38; H, 4.25; N, 11.82; O, 13.50; S, 18.04

Price and Availability

Size Price Availability Quantity
1mg USD 400.00 2 Weeks
5mg USD 1,050.00 2 Weeks
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Synonym
Chetomin; CTM; NSC-289491; NSC 289491; NSC289491.
IUPAC/Chemical Name
2,3S,5aR,6,10bS,11-hexahydro-3-(hydroxymethyl)-10b-[(1S,4S)-3-[[4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]oct-1-yl]methyl]-1H-indol-1-yl]-2-methyl-3,11aS-epidithio-11aH-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
InChi Key
ZRZWBWPDBOVIGQ-YWZWRZHGSA-N
InChi Code
InChI=1S/C31H30N6O6S4/c1-33-25(42)30(15-38)34(2)23(40)28(33,44-46-30)12-17-13-36(21-11-7-4-8-18(17)21)27-14-29-24(41)35(3)31(16-39,47-45-29)26(43)37(29)22(27)32-20-10-6-5-9-19(20)27/h4-11,13,22,32,38-39H,12,14-16H2,1-3H3/t22-,27+,28+,29+,30+,31+/m1/s1
SMILES Code
O=C1N(C)[C@]2(CO)C(N3[C@]1(SS2)C[C@@]4(N5C=C(C[C@]6(N(C)C7=O)SS[C@]7(CO)N(C)C6=O)C8=C5C=CC=C8)[C@]3([H])NC9=C4C=CC=C9)=O
Appearance
Solid powder
Purity
>95% (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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Blocks interaction of HIF-1α, HIF-2α and STAT2 with CBP/p300.
In vitro activity:
Chetomin exposure for 24 hours dose-dependently lowered expression of stem cell biomarkers, SRY (sex determining region Y)-box 2 (Sox2), homeobox protein Nanog, and octamer-binding transcription factor 4 (Oct4), in H1299 monolayer cultures (Figure 2A). Reference: Cancer Biol Ther. 2020; 21(8): 698–708. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7515479/
In vivo activity:
Chetomin partially rescued the integrity of DA neurons in PPL2 cluster as this study observed a significant increase in the number of TH+ neurons in Chetomin treated G2019S flies compared to without treatment (p<0.05) (Figure 5A, 5B). Chetomin treated G2019S flies fared better in climbing compared to G2019S flies without drug treatment, indicating a rescue of pathogenic phenotype by Chetomin (p<0.05) (Figure 5C). There was also an improvement in the number of flies that survived after 60 days in Chetomin treated G2019S flies compared to G2019S flies without treatment (Figure 5D). The results collectively show that Chetomin is able to rescue the pathogenic phenotype of G2019S LRRK2 mutation in flies. Reference: Aging (Albany NY). 2020 Sep 24;12(18):18561-18570. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7585092/
Solvent mg/mL mM
Solubility
DMSO 5.0 7.03
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 710.86 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:
1. Min S, Wang X, Du Q, Gong H, Yang Y, Wang T, Wu N, Liu X, Li W, Zhao C, Shen Y, Chen Y, Wang X. Chetomin, a Hsp90/HIF1α pathway inhibitor, effectively targets lung cancer stem cells and non-stem cells. Cancer Biol Ther. 2020 Aug 2;21(8):698-708. doi: 10.1080/15384047.2020.1763147. Epub 2020 Jun 3. PMID: 32489150; PMCID: PMC7515479. 2. Dewangan J, Srivastava S, Mishra S, Pandey PK, Divakar A, Rath SK. Chetomin induces apoptosis in human triple-negative breast cancer cells by promoting calcium overload and mitochondrial dysfunction. Biochem Biophys Res Commun. 2018 Jan 8;495(2):1915-1921. doi: 10.1016/j.bbrc.2017.11.199. Epub 2017 Dec 5. PMID: 29208466. 3. Chua LL, Ho P, Toh J, Tan EK. Chetomin rescues pathogenic phenotype of LRRK2 mutation in drosophila. Aging (Albany NY). 2020 Sep 24;12(18):18561-18570. doi: 10.18632/aging.103843. Epub ahead of print. PMID: 32990658; PMCID: PMC7585092.
In vitro protocol:
1. Min S, Wang X, Du Q, Gong H, Yang Y, Wang T, Wu N, Liu X, Li W, Zhao C, Shen Y, Chen Y, Wang X. Chetomin, a Hsp90/HIF1α pathway inhibitor, effectively targets lung cancer stem cells and non-stem cells. Cancer Biol Ther. 2020 Aug 2;21(8):698-708. doi: 10.1080/15384047.2020.1763147. Epub 2020 Jun 3. PMID: 32489150; PMCID: PMC7515479. 2. Dewangan J, Srivastava S, Mishra S, Pandey PK, Divakar A, Rath SK. Chetomin induces apoptosis in human triple-negative breast cancer cells by promoting calcium overload and mitochondrial dysfunction. Biochem Biophys Res Commun. 2018 Jan 8;495(2):1915-1921. doi: 10.1016/j.bbrc.2017.11.199. Epub 2017 Dec 5. PMID: 29208466.
In vivo protocol:
1. Chua LL, Ho P, Toh J, Tan EK. Chetomin rescues pathogenic phenotype of LRRK2 mutation in drosophila. Aging (Albany NY). 2020 Sep 24;12(18):18561-18570. doi: 10.18632/aging.103843. Epub ahead of print. PMID: 32990658; PMCID: PMC7585092.
1: Wu Q, Li G, Deng S, Ouyang L, Li L, Liu L, Luo N, Song X, He G, Gong C, Wei Y. Enhanced antitumor activity and mechanism of biodegradable polymeric micelles-encapsulated chetomin in both transgenic zebrafish and mouse models. Nanoscale. 2014 Oct 21;6(20):11940-52. doi: 10.1039/c4nr02978j. Epub 2014 Sep 1. PubMed PMID: 25175172. 2: Yano K, Horinaka M, Yoshida T, Yasuda T, Taniguchi H, Goda AE, Wakada M, Yoshikawa S, Nakamura T, Kawauchi A, Miki T, Sakai T. Chetomin induces degradation of XIAP and enhances TRAIL sensitivity in urogenital cancer cells. Int J Oncol. 2011 Feb;38(2):365-74. doi: 10.3892/ijo.2010.874. Epub 2010 Dec 15. PubMed PMID: 21165560. 3: Welch TR, Williams RM. Studies on the Biosynthesis of Chetomin: Enantiospecific Synthesis of a Putative, Late-Stage Biosynthetic Intermediate. Tetrahedron. 2013 Jan 1;69(2):770-773. PubMed PMID: 24489414; PubMed Central PMCID: PMC3908826. 4: Viziteu E, Grandmougin C, Goldschmidt H, Seckinger A, Hose D, Klein B, Moreaux J. Chetomin, targeting HIF-1α/p300 complex, exhibits antitumour activity in multiple myeloma. Br J Cancer. 2016 Mar 1;114(5):519-23. doi: 10.1038/bjc.2016.20. Epub 2016 Feb 11. PubMed PMID: 26867162; PubMed Central PMCID: PMC4782210. 5: Staab A, Loeffler J, Said HM, Diehlmann D, Katzer A, Beyer M, Fleischer M, Schwab F, Baier K, Einsele H, Flentje M, Vordermark D. Effects of HIF-1 inhibition by chetomin on hypoxia-related transcription and radiosensitivity in HT 1080 human fibrosarcoma cells. BMC Cancer. 2007 Nov 13;7:213. PubMed PMID: 17999771; PubMed Central PMCID: PMC2200672. 6: Jin Z, Aixi Y, Baiwen Q, Zonghuan L, Xiang H. Inhibition of hypoxia-inducible factor-1 alpha radiosensitized MG-63 human osteosarcoma cells in vitro. Tumori. 2015 Sep-Oct;101(5):578-84. doi: 10.5301/tj.5000243. Epub 2015 Aug 4. PubMed PMID: 26350185. 7: Kessler J, Hahnel A, Wichmann H, Rot S, Kappler M, Bache M, Vordermark D. HIF-1α inhibition by siRNA or chetomin in human malignant glioma cells: effects on hypoxic radioresistance and monitoring via CA9 expression. BMC Cancer. 2010 Nov 4;10:605. doi: 10.1186/1471-2407-10-605. PubMed PMID: 21050481; PubMed Central PMCID: PMC2992520. 8: Jen WC, Jones GA. Effects of chetomin on growth and acidic fermentation products of rumen bacteria. Can J Microbiol. 1983 Oct;29(10):1399-404. PubMed PMID: 6686488. 9: Hiraki M, Hwang SY, Cao S, Ramadhar TR, Byun S, Yoon KW, Lee JH, Chu K, Gurkar AU, Kolev V, Zhang J, Namba T, Murphy ME, Newman DJ, Mandinova A, Clardy J, Lee SW. Small-Molecule Reactivation of Mutant p53 to Wild-Type-like p53 through the p53-Hsp40 Regulatory Axis. Chem Biol. 2015 Sep 17;22(9):1206-16. doi: 10.1016/j.chembiol.2015.07.016. Epub 2015 Aug 27. PubMed PMID: 26320861; PubMed Central PMCID: PMC4670040. 10: Reece KM, Richardson ED, Cook KM, Campbell TJ, Pisle ST, Holly AJ, Venzon DJ, Liewehr DJ, Chau CH, Price DK, Figg WD. Epidithiodiketopiperazines (ETPs) exhibit in vitro antiangiogenic and in vivo antitumor activity by disrupting the HIF-1α/p300 complex in a preclinical model of prostate cancer. Mol Cancer. 2014 Apr 28;13:91. doi: 10.1186/1476-4598-13-91. PubMed PMID: 24775564; PubMed Central PMCID: PMC4113146. 11: McInnes AG, Taylor A, Walter JA. The structure of chetomin. J Am Chem Soc. 1976 Oct 13;98(21):6741. PubMed PMID: 972228. 12: Fernandez EV, Reece KM, Ley AM, Troutman SM, Sissung TM, Price DK, Chau CH, Figg WD. Dual targeting of the androgen receptor and hypoxia-inducible factor 1α pathways synergistically inhibits castration-resistant prostate cancer cells. Mol Pharmacol. 2015 Jun;87(6):1006-12. doi: 10.1124/mol.114.097477. Epub 2015 Mar 31. PubMed PMID: 25829060; PubMed Central PMCID: PMC4429716. 13: Lai FF, Niu F, Yang HZ, Zhou WQ, Chen XG. [Development of a novel screening assay for inhibitors targeting HIF-1alpha and P300 interaction]. Yao Xue Xue Bao. 2014 Jun;49(6):849-53. Chinese. PubMed PMID: 25212031. 14: GEIGER WB. Chetomin an antibiotic substance from Chaetomium cochliodes; composition and functional groups. Arch Biochem. 1949 Mar;21(1):125-31. PubMed PMID: 18124507. 15: Indelicato M, Pucci B, Schito L, Reali V, Aventaggiato M, Mazzarino MC, Stivala F, Fini M, Russo MA, Tafani M. Role of hypoxia and autophagy in MDA-MB-231 invasiveness. J Cell Physiol. 2010 May;223(2):359-68. doi: 10.1002/jcp.22041. PubMed PMID: 20112292. 16: Brewer D, Hannah DE, Rahman R, Taylor A. The growth of Bacillus subtilis in media containing chetomin, sporidesmin, and gliotoxin. Can J Microbiol. 1967 Nov;13(11):1451-60. PubMed PMID: 4965004. 17: Xu GB, He G, Bai HH, Yang T, Zhang GL, Wu LW, Li GY. Indole Alkaloids from Chaetomium globosum. J Nat Prod. 2015 Jul 24;78(7):1479-85. doi: 10.1021/np5007235. Epub 2015 Jun 30. PubMed PMID: 26125976. 18: Trown PW. Antiviral activity of N, N'-dimethyl-epidithiapiperazinedione, a synthetic compound related to the gliotoxins, LL-S88alpha and beta, chetomin and the sporidesmins. Biochem Biophys Res Commun. 1968 Nov 8;33(3):402-7. PubMed PMID: 5722231. 19: Brewer D, Duncan JM, Jerram WA, Leach CK, Safe S, Taylor A, Vining LC, Archibald RM, Stevenson RG, Mirocha CJ, Christensen CM. Ovine ill-thrift in Nova Scotia. 5. The production and toxicology of chetomin, a metabolite of chaetomium spp. Can J Microbiol. 1972 Jul;18(7):1129-37. PubMed PMID: 5070711. 20: Park JK, Kang TG, Kang MY, Park JE, Cho IA, Shin JK, Choi WJ, Lee SA, Choi WS, Kwon HM, Lee JH, Paik WY. Increased NFAT5 expression stimulates transcription of Hsp70 in preeclamptic placentas. Placenta. 2014 Feb;35(2):109-16. doi: 10.1016/j.placenta.2013.12.005. Epub 2013 Dec 21. PubMed PMID: 24398013.

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LCH-7749944

LCH-7749944