Illudin S | CAS#1149-99-1 | fungal sesquiterpene

MedKoo Cat#: 598259 | Name: Illudin S

Description:

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

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 , 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

Illudin S

CAS#1149-99-1

Theoretical Analysis

MedKoo Cat#: 598259

Name: Illudin S

CAS#: 1149-99-1

Chemical Formula: C15H20O4

Exact Mass: 264.1362

Molecular Weight: 264.32

Elemental Analysis: C, 68.16; H, 7.63; O, 24.21

Price and Availability

Size	Price	Availability
1mg	USD 250.00	Ready to Ship
5mg	USD 750.00	Ready to Ship
10mg	USD 1,250.00	Ready to Ship
25mg	USD 1,950.00	Ready to Ship
50mg	USD 3,650.00	2 weeks

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Related CAS #

No Data

Synonym

Illudin S; DR-15978; DR 15978; DR15978; NSC 626369; NSC-626369; NSC626369; Lunamycin; Lampterol;

IUPAC/Chemical Name

(2'S,3'R,6'R)-3',6'-dihydroxy-2'-(hydroxymethyl)-2',4',6'-trimethyl-2',3'-dihydrospiro[cyclopropane-1,5'-inden]-7'(6'H)-one

InChi Key

DDLLIYKVDWPHJI-RDBSUJKOSA-N

InChi Code

InChI=1S/C15H20O4/c1-8-10-9(6-13(2,7-16)12(10)18)11(17)14(3,19)15(8)4-5-15/h6,12,16,18-19H,4-5,7H2,1-3H3/t12-,13+,14+/m1/s1

SMILES Code

CC1=C2[C@H]([C@](CO)(C=C2C([C@](O)(C13CC3)C)=O)C)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

>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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A22T11K03

QC Data

View QC data: current batch, Lot#A22T11K03

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Illudin S, a cytotoxic Illudin, is a natural sesquiterpene with strong anti-tumour and antiviral activities. Illudin S has genotoxic activities. Illudin S blocks the G1-S phase interface of the cell cycle in human leukemia cells.

In vitro activity:

Illudin S and its derivatives induce alkyl DNA adducts, which are repaired by transcription-coupled nucleotide excision repair (TC-NER). Reference: Life Sci Alliance. 2022 Jul 29;5(12):e202201584. https://pubmed.ncbi.nlm.nih.gov/35905994/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	50.0	189.16

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 264.32 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.

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. Kanao R, Kawai H, Taniguchi T, Takata M, Masutani C. RFWD3 and translesion DNA polymerases contribute to PCNA modification-dependent DNA damage tolerance. Life Sci Alliance. 2022 Jul 29;5(12):e202201584. doi: 10.26508/lsa.202201584. PMID: 35905994; PMCID: PMC9348633. 2. Goulielmaki E, Tsekrekou M, Batsiotos N, Ascensão-Ferreira M, Ledaki E, Stratigi K, Chatzinikolaou G, Topalis P, Kosteas T, Altmüller J, Demmers JA, Barbosa-Morais NL, Garinis GA. The splicing factor XAB2 interacts with ERCC1-XPF and XPG for R-loop processing. Nat Commun. 2021 May 26;12(1):3153. doi: 10.1038/s41467-021-23505-1. PMID: 34039990; PMCID: PMC8155215.

In vitro protocol:

In vivo protocol:

TBD

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.