Illudin S
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MedKoo CAT#: 598259

CAS#: 1149-99-1

Description: Illudin S is a fungal sesquiterpene that, through their unique DNA alkylating actions, have anticancer potential. Illudin S is a cytotoxic illudin that is converted, intracellularly, to metabolites that cause a complete block of cell cycling at the G1-S phase interface, particularly in myeloid and T-lymphocyte leukemia cells (IC50 = 6-11 nM). T-lymphocyte leukemia CEM cells that are resistant to doxorubicin (Item No. 15007), epipodophyllotoxins, and 1-β-D-arabinofuranosylcytosine display only 2-fold increased resistance to illudin S. Illudin S metabolites induce DNA damage that is not repaired by the processes that counter conventional DNA alkylating agents.


Chemical Structure

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Illudin S
CAS# 1149-99-1

Theoretical Analysis

MedKoo Cat#: 598259
Name: Illudin S
CAS#: 1149-99-1
Chemical Formula: C15H21O4
Exact Mass: 265.144
Molecular Weight: 265.32
Elemental Analysis: C, 67.90; H, 7.98; O, 24.12

Price and Availability

Size Price Availability Quantity
1.0mg USD 430.0 2 Weeks
5.0mg USD 1290.0 2 Weeks
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Synonym: Illudin S; DR-15978; DR 15978; DR15978; NSC 626369; NSC-626369; NSC626369; Lunamycin; Lampterol;

IUPAC/Chemical Name: 2',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-2',3'-dihydro-2'l5-spiro[cyclopropane-1,5'-inden]-7'(6'H)-one

InChi Key: OPBKMFNTACLDAN-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H21O4/c1-9-10-6-15(3,19,8-16)7-11(10)12(17)13(2,18)14(9)4-5-14/h7,16,18-19H,4-6,8H2,1-3H3

SMILES Code: O=C1C(C)(O)C2(C(C)=C3CC(C)(CO)(O)C=C13)CC2

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: >3 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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 265.32 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

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1: Glatt H, Pietsch KE, Sturla SJ, Meinl W. Sulfotransferase-independent genotoxicity of illudin S and its acylfulvene derivatives in bacterial and mammalian cells. Arch Toxicol. 2014 Jan;88(1):161-9. doi: 10.1007/s00204-013-1097-2. Epub 2013 Jul 24. PubMed PMID: 23881331.

2: Pietsch KE, van Midwoud PM, Villalta PW, Sturla SJ. Quantification of acylfulvene- and illudin S-DNA adducts in cells with variable bioactivation capacities. Chem Res Toxicol. 2013 Jan 18;26(1):146-55. doi: 10.1021/tx300430r. Epub 2012 Dec 19. PubMed PMID: 23227857; PubMed Central PMCID: PMC3858472.

3: Tanaka K, Inoue T, Kadota S, Kikuchi T. Metabolism by rat liver cytosol of illudin S, a toxic substance of Lampteromyces japonicus. II. Characterization of illudin S-metabolizing enzyme. Xenobiotica. 1992 Jan;22(1):33-9. PubMed PMID: 1377439.

4: Tanaka K, Miyasaka S, Inoue T. Histopathological effects of illudin S, a toxic substance of poisonous mushroom, in rat. Hum Exp Toxicol. 1996 Apr;15(4):289-93. PubMed PMID: 8845217.

5: Tanaka K, Inoue T, Tezuka Y, Kikuchi T. Metabolism of illudin S, a toxic substance of Lampteromyces japonicus: urinary excretion of mercapturic acids in rat. Xenobiotica. 1996 Mar;26(3):347-54. PubMed PMID: 8730925.

6: Tanaka K, Inoue T, Kanai M, Kikuchi T. Metabolism of illudin S, a toxic substance of Lampteromyces japonicus. IV. Urinary excretion of an illudin S metabolite in rat. Xenobiotica. 1994 Dec;24(12):1237-43. PubMed PMID: 7771110.

7: Liu X, Sturla SJ. Profiling patterns of glutathione reductase inhibition by the natural product illudin S and its acylfulvene analogues. Mol Biosyst. 2009 Sep;5(9):1013-24. doi: 10.1039/b904720d. Epub 2009 Jul 8. PubMed PMID: 19668867; PubMed Central PMCID: PMC2841359.

8: Lehmann VK, Huang A, Ibanez-Calero S, Wilson GR, Rinehart KL. Illudin S, the sole antiviral compound in mature fruiting bodies of Omphalotus illudens. J Nat Prod. 2003 Sep;66(9):1257-8. PubMed PMID: 14510611.

9: Kelner MJ, McMorris TC, Montoya MA, Estes L, Rutherford M, Samson KM, Taetle R. Characterization of cellular accumulation and toxicity of illudin S in sensitive and nonsensitive tumor cells. Cancer Chemother Pharmacol. 1997;40(1):65-71. PubMed PMID: 9137532.

10: Jaspers NG, Raams A, Kelner MJ, Ng JM, Yamashita YM, Takeda S, McMorris TC, Hoeijmakers JH. Anti-tumour compounds illudin S and Irofulven induce DNA lesions ignored by global repair and exclusively processed by transcription- and replication-coupled repair pathways. DNA Repair (Amst). 2002 Dec 5;1(12):1027-38. PubMed PMID: 12531012.

11: Tanaka K, Inoue T, Tezuka Y, Kikuchi T. Michael-type addition of illudin S, a toxic substance from Lampteromyces japonicus, with cysteine and cysteine-containing peptides in vitro. Chem Pharm Bull (Tokyo). 1996 Feb;44(2):273-9. PubMed PMID: 8998835.

12: Kasahara Y, Itou T. [Determination of illudin S in Omphalotus guepiniformis and foods that caused food poisoning by liquid chromatography with tandem mass spectrometry]. Shokuhin Eiseigaku Zasshi. 2009 Aug;50(4):167-72. Japanese. PubMed PMID: 19745584.

13: Tanaka K, Inoue T, Kadota S, Kikuchi T. Metabolism of illudin S, a toxic principle of Lampteromyces japonicus, by rat liver. I. Isolation and identification of cyclopropane ring-cleavage metabolites. Xenobiotica. 1990 Jul;20(7):671-81. PubMed PMID: 2238702.

14: Liu X, Pietsch KE, Sturla SJ. Susceptibility of the antioxidant selenoenyzmes thioredoxin reductase and glutathione peroxidase to alkylation-mediated inhibition by anticancer acylfulvenes. Chem Res Toxicol. 2011 May 16;24(5):726-36. doi: 10.1021/tx2000152. Epub 2011 Apr 12. PubMed PMID: 21443269; PubMed Central PMCID: PMC3210965.

15: NAKANISHI K, TADA M, YAMADA Y. STEREOCHEMISTRY OF ILLUDIN-S (LAMPTEROL). Chem Pharm Bull (Tokyo). 1964 Jul;12:856-7. PubMed PMID: 14206945.

16: McMorris TC, Kelner MJ, Wang W, Yu J, Estes LA, Taetle R. (Hydroxymethyl)acylfulvene: an illudin derivative with superior antitumor properties. J Nat Prod. 1996 Sep;59(9):896-9. PubMed PMID: 8864242.

17: TADA M, YAMADA Y, BHACCA NS, NAKANISHI K, OHASHI M. STRUCTURE AND REACTIONS OF ILLUDIN-S (LAMPTEROL). Chem Pharm Bull (Tokyo). 1964 Jul;12:853-5. PubMed PMID: 14206944.

18: McMorris TC, Kelner MJ, Wang W, Moon S, Taetle R. On the mechanism of toxicity of illudins: the role of glutathione. Chem Res Toxicol. 1990 Nov-Dec;3(6):574-9. PubMed PMID: 2103329.

19: MCMORRIS TC, ANCHEL M. FUNGAL METABOLITES. THE STRUCTURES OF THE NOVEL SESQUITERPENOIDS ILLUDIN-S AND -M. J Am Chem Soc. 1965 Apr 5;87:1594-600. PubMed PMID: 14302677.

20: Kelner MJ, McMorris TC, Estes L, Rutherford M, Montoya M, Goldstein J, Samson K, Starr R, Taetle R. Characterization of illudin S sensitivity in DNA repair-deficient Chinese hamster cells. Unusually high sensitivity of ERCC2 and ERCC3 DNA helicase-deficient mutants in comparison to other chemotherapeutic agents. Biochem Pharmacol. 1994 Jul 19;48(2):403-9. PubMed PMID: 8053936.