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S4068

Sigma-Aldrich

Splitomicin

≥98% (HPLC), powder

Synonym(s):

1,2-Dihydro-3H-naphtho[2,1-b]pyran-3-one

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About This Item

Empirical Formula (Hill Notation):
C13H10O2
CAS Number:
5690-03-9
Molecular Weight:
198.22
MDL number:
MFCD08705254
UNSPSC Code:
12352200
PubChem Substance ID:
24724608
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage temp.

2-8°C

SMILES string

O=C1CCc2c(O1)ccc3ccccc23

InChI

1S/C13H10O2/c14-13-8-6-11-10-4-2-1-3-9(10)5-7-12(11)15-13/h1-5,7H,6,8H2

InChI key

ISFPDBUKMJDAJH-UHFFFAOYSA-N

Application

Splitomicin was used to inhibit SIRT1 in human aortic endothelial cells and sirtuins in human breast cancer cells. Mouse leukaemic monocyte macrophage cell line was treated with Splitomicin prior to cholesterol efflux studies.

Biochem/physiol Actions

Splitomicin, a derivative of β-naphthol is an inhibitor of Silent Information Regulator 2 (SIR2). It inhibits the NAD+-dependent deacetylase activity of Sir2 in vitro. It increases the levels of cyclic AMP by inhibiting the activity of cyclic AMP phosphodiesterase, interferes with mobilization of intracellular Ca+2 and ATP release. This results in inhibition of platelet aggregation that is effective in cardiovascular and cerebrovascular diseases.
Sir2p (silent information regulator) and HDAC inhibitor.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Gil Blander et al.
Annual review of biochemistry, 73, 417-435 (2004-06-11)
The yeast SIR protein complex has been implicated in transcription silencing and suppression of recombination. The Sir complex represses transcription at telomeres, mating-type loci, and ribosomal DNA. Unlike SIR3 and SIR4, the SIR2 gene is highly conserved in organisms ranging
Fu-Chao Liu et al.
Thrombosis research, 124(2), 199-207 (2009-03-31)
Splitomicin is derived from beta-naphthol and is an inhibitor of Silent Information Regulator 2 (SIR2). Its naphthoic moiety might be responsible for its inhibitory effects on platelets. The major goal of our study was to examine possible mechanisms of action
Evi X Stavrou et al.
Blood, 125(4), 710-719 (2014-10-24)
The precise mechanism for reduced thrombosis in prekallikrein null mice (Klkb1(-/-)) is unknown. Klkb1(-/-) mice have delayed carotid artery occlusion times on the rose bengal and ferric chloride thrombosis models. Klkb1(-/-) plasmas have long-activated partial thromboplastin times and defective contact
Hestia S Mellert et al.
The Journal of biological chemistry, 286(6), 4264-4270 (2010-12-15)
In unstressed cells, the p53 tumor suppressor is highly unstable. DNA damage and other forms of cellular stress rapidly stabilize and activate p53. This process is regulated by a complex array of post-translational modifications that are dynamically deposited onto p53.
Sokrates Stein et al.
Aging, 2(6), 353-360 (2010-07-08)
Excessive production of reactive oxygen species (ROS) contributes to progression of atherosclerosis, at least in part by causing endothelial dysfunction and inflammatory activation. The class III histone deacetylase SIRT1 has been implicated in extension of lifespan. In the vasculature,SIRT1 gain-of-function
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