Skip to Content
Merck
All Photos(1)

Documents

S4068

Sigma-Aldrich

Splitomicin

≥98% (HPLC), powder

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

100

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
View All Related Papers

Articles

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service