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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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250 μG
$107.10
1 MG
$360.00

$107.10

List Price$119.00Save 10%

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250 μG
$107.10
1 MG
$360.00

About This Item

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

$107.10

List Price$119.00Save 10%

In StockDetails

Request a Bulk Order

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

InChI

1S/C25H35N3O.ClH/c1-3-4-5-6-7-8-9-10-11-13-20-15-16-21(27-20)18-24-25(29-2)19-23(28-24)22-14-12-17-26-22;/h12,14-19,26-27H,3-11,13H2,1-2H3;1H/b24-18-;

Inchi Key

ZZRPZWXEPLULCE-XWASNXTISA-N

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 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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000067858
0000060834
126M4721V

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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
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
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

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