illudin M
illudin M Basic information
- Product Name:
- illudin M
- Synonyms:
-
- illudin M
- (3S)-2,3-Dihydro-3α,6β-dihydroxy-2,2,4,6-tetramethylspiro[5H-indene-5,1'-cyclopropan]-7(6H)-one
- (3'S,6'R)-2',3'-Dihydro-3',6'-dihydroxy-2',2',4',6'-tetramethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one
- Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 2',3'-dihydro-3',6'-dihydroxy-2',2',4',6'-tetramethyl-, (3'S,6'R)-
- (3'S,6'R)-3',6'-dihydroxy-2',2',4',6'-tetramethyl-2',3',6',7'-tetrahydrospiro[cyclopropane-1,5'-inden]-7'-one
- CAS:
- 1146-04-9
- MF:
- C15H20O3
- MW:
- 248.32
- Product Categories:
-
- ADC
- Mol File:
- 1146-04-9.mol
illudin M Chemical Properties
- Melting point:
- 120-122.5° (Matsumoto); mp 128-130° (McMorris)
- Boiling point:
- 452.4±45.0 °C(Predicted)
- Density
- 1.24±0.1 g/cm3(Predicted)
- storage temp.
- Store at -20°C
- solubility
- DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble
- form
- A solid
- pka
- 12.57±0.70(Predicted)
- color
- Off-white to light yellow
- InChI
- InChI=1S/C15H20O3/c1-8-10-9(7-13(2,3)12(10)17)11(16)14(4,18)15(8)5-6-15/h7,12,17-18H,5-6H2,1-4H3/t12-,14+/m1/s1
- InChIKey
- QVMDIQLUNODCTG-OCCSQVGLSA-N
- SMILES
- C12([C@](O)(C)C(=O)C3C(=C1C)[C@@H](O)C(C)(C)C=3)CC2
illudin M Usage And Synthesis
Description
Illudin M is a cytotoxic sesquiterpene from the fungus O. illudens that alkylates DNA. It is cytotoxic to HL-60 human leukemia cells at 6-100 nM. Illudin M was used as a base structure for the development of potential anticancer agents with less toxicity and improved efficacy. It is closely related to illudin S , which has been the focus of additional studies.
Uses
Illudin M is a cytotoxic sesquiterpene from Omphalotus illudens and Granulobasidium vellereum. It acts as an alkylating agent that can cause inhibition of cell growth or replication.
Definition
ChEBI: Illudin M is a sesquiterpenoid.
References
[1] J. JACOBSON. Pharmacokinetics, Safety, and Antiviral Effects of Hypericin, a Derivative of St. John’s Wort Plant, in Patients with Chronic Hepatitis C Virus Infection[J]. Antimicrobial Agents and Chemotherapy, 2001, 45 1: 517-524. DOI: 10.1128/aac.45.2.517-524.2001
[2] M J KELNER. Preclinical evaluation of illudins as anticancer agents.[J]. Cancer research, 1987, 47 12: 3186-3189.
[3] R SCHOBERT. Anticancer active illudins: recent developments of a potent alkylating compound class.[J]. Current medicinal chemistry, 2011, 18 6: 790-807. DOI: 10.2174/092986711794927766
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