Nidulal

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Nidulal
Category Antibiotics
Catalog number BBF-02603
CAS 185853-14-9
Molecular Weight 276.28
Molecular Formula C15H16O5
Purity 95%

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Description

Nidulal is originally isolated from Nidula candida 87220. Nidulal induces differentiation of human promyelocytic leukemia cells. In COS-7 cells it selectively activates AP-1 dependent signal transduction in a manner which is similar to TPA/PMA.

Specification

Synonyms 4-(8-Methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl)cyclohexanecarbaldehyde
Storage Store at -20°C
IUPAC Name 4-(3-methyl-2,9-dioxo-1,6-dioxaspiro[4.4]nona-3,7-dien-8-yl)cyclohexane-1-carbaldehyde
Canonical SMILES CC1=CC2(C(=O)C(=CO2)C3CCC(CC3)C=O)OC1=O
InChI InChI=1S/C15H16O5/c1-9-6-15(20-14(9)18)13(17)12(8-19-15)11-4-2-10(7-16)3-5-11/h6-8,10-11H,2-5H2,1H3
InChI Key NQSKLGFKNUGTFE-UHFFFAOYSA-N

Properties

Appearance Colorless Oily Matter
Antibiotic Activity Spectrum neoplastics (Tumor)
Boiling Point 512.4±50.0°C at 760 mmHg
Density 1.3±0.1 g/cm3
Solubility Soluble in ethanol, methanol or DMSO.

Reference Reading

1. Nidulal, a novel inducer of differentiation of human promyelocytic leukemia cells from Nidula candida
G Erkel, U Becker, T Anke, O Sterner J Antibiot (Tokyo). 1996 Dec;49(12):1189-95. doi: 10.7164/antibiotics.49.1189.
Nidulal (1), a novel inducer of differentiation of human HL-60 promyelocytic leukemia cells, was isolated from fermentations of the basidiomycete Nidula candida together with low amounts of niduloic acid (2). Both compounds are bisabolane sesquiterpenes. Their structures were elucidated by spectroscopic methods. In reporter gene assays nidulal (1) preferentially activated the transcription factor complex AP-1-mediated expression of secreted alkaline phosphatase in COS-7 cells. In addition nidulal (1) and niduloic acid (2) exhibited weak cytotoxic and antibiotic activities.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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