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SML1576

Sigma-Aldrich

Undecylprodigiosin hydrochloride

≥95% (HPLC)

Synonym(s):

2-[(Z)-[3-Methoxy-5-(1H-pyrrol-2-yl)-2H-pyrrol-2-ylidene]methyl]-5-undecyl-1H-pyrrole hydrochloride, CID 6438379 hydrochloride, Prodigiosin C-25 hydrochloride, Undecylprodiginin hydrochloride, Undecylprodiginine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C25H35N3O · HCl
CAS Number:
56247-02-0
Molecular Weight:
430.03
UNSPSC Code:
12352200
NACRES:
NA.77

biological source

Streptomyces parvulus

Quality Level

100

Assay

≥95% (HPLC)

form

powder

storage condition

desiccated
protect from light

color

, faint red to dark red

storage temp.

−20°C

SMILES string

COC1=CC(C2=CC=CN2)=N/C1=C\C3=CC=C(CCCCCCCCCCC)N3.[H]Cl

Biochem/physiol Actions

Undecylprodigiosin is a tri-pyrolle antibiotic isolated from Streptomyces coelicolor A3 that exhibits immunosuppressive and apoptotic activities as well as antibacterial, antioxidative and UV protective properties. Undecylprodigiosin selectively induces p53 independent apoptosis in cancer cells.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Leirós et al.
Neuroscience, 305, 26-35 (2015-08-08)
Anhydroexfoliamycin (1) and undecylprodigiosin (2) have been previously described as neuroprotective molecules against oxidative stress in neurons. Since oxidative stress is strongly correlated with neurodegenerative diseases, we have evaluated their effects over the principal hallmarks of Alzheimer's disease (AD). Both
Yongxiang Song et al.
Marine drugs, 13(3), 1304-1316 (2015-03-19)
Two new C-glycoside angucyclines, marangucycline A (1) and marangucycline B (2), along with three known compounds, dehydroxyaquayamycin (3), undecylprodigiosin (4) and metacycloprodigiosin (5), have been identified as products of the deep-sea sediment strain Streptomyces sp. SCSIO 11594. New structures were
Marta Leirós et al.
ACS chemical neuroscience, 5(1), 71-80 (2013-11-14)
Oxidative stress is a common point in neurodegenerative diseases, widely connected with mitochondrial dysfunction. In this study, we screened seven natural products from Streptomyces sources against hydrogen peroxide insult in primary cortical neurons, an oxidative stress in vitro model. We

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