sirtinol

Cas：410536-97-9

Product Information：

Sirtinol is a SIRT inhibitor. Sirtinol significantly increased the acetylation of p53, which has been reported to be a target of SIRT1/2. Sirtinol significantly increased the G1 phase of the cell cycle.

Chemical Formula: C26H22N2O2

Exact Mass: 394.16813

Molecular Weight: 394.46508

Elemental Analysis: C, 79.16; H, 5.62; N, 7.10; O, 8.11

Synonym: 

Sirtinol

CHEMBL380797

2-[(2-Hydroxynaphthalen-1-ylmethylene)amino]-N-(1-phenethyl)benzamide

2-{[(2-hydroxy-1-naphthyl)methylene]amino}-N-(1-phenylethyl)benzamide

(E)-2-((2-hydroxynaphthalen-1-yl)methyleneamino)-N-(1-phenylethyl)benzamide

2-[[(Z)-(2-oxonaphthalen-1-ylidene)methyl]amino]-N-(1-phenylethyl)benzamide

2-[(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino]-N-(1-phenylethyl)benzamide

2-[(2-oxo-1-naphthalenylidene)methylamino]-N-(1-phenylethyl)benzamide

Sir Two Inhibitor Naphthol

2-[(2-oxonaphthalen-1-ylidene)methylamino]-N-[(1R)-1-phenylethyl]benzamide

AK-16605

Probes1_000047

Probes1_000316

Probes2_000084

Probes2_000518

Oprea1_639422

CBDivE_000728

ARONIS007637

SCHEMBL2543371

SCHEMBL8227466

Sirtinol, >=95% (NMR)

CHEBI:73158

KS-00003ZNW

CHEBI:125379

HMS3413N18

HMS3651B13

HMS3677N18

BCP22454

EX-A4220

BDBM50156760

s2804

STL069068

AKOS000497157

AKOS016842267

AKOS030627556

AB07334

CCG-265000

CS-5291

DS-0089

MCULE-8856934531

VZ23394

SMP2_000018

BR-16605

HY-13515

BCP0726000065

BB0284625

FT-0644594

SW219185-1

W6155

S-5353

BRD-A23747351-001-01-9

Q27140353

Q27215793

2-((2-hydroxynaphthalen-1-yl)methyleneamino)-N-(1-phenylethyl)benzamide

2-[(2-Hydroxynaphthalen-1-ylmethylene)amino]-N-(1-phenethyl) benzamide

(E)-2-(((2-HYDROXYNAPHTHALEN-1-YL)METHYLENE)AMINO)-N-(1-PHENYLETHYL)BENZAMIDE

{2-[(2-Hydroxynaphthalen-1-ylmethylene)amino]}-N-(1-phenethyl)benzamide (Sirtinol

2-[(2-hydroxy-naphthalen-1-ylmethylene)-amino]-N-(1-phenyl-ethyl)-benzamide

2-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]- N -(1-phenylethyl)benzamide

2-[[(2-HYDROXY-1-NAPHTHALENYL)METHYLENE]AMINO]-N-(1-PHENYLETHYL)BENZAMIDE

2-{[(1-(2-hydroxy-naphthalen-1-yl)meth-(E)-ylidene]amino}-N-(1-phenylethyl)-benzamide

2-{[(E)-(2-hydroxynaphthalen-1-yl)methylidene]amino}-N-(1-phenylethyl)benzamide

2-{[1-(2-hydroxynaphthalen-1-yl)meth-(E)-ylene]amino}-N-(1-phenylethyl)benzamide

Chemical Name:

2-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]- N -(1-phenylethyl)benzamide

InChi Key:

UXJFDYIHRJGPFS-WPWMEQJKSA-N

InChi Code:

InChI=1S/C26H22N2O2/c1-18(19-9-3-2-4-10-19)28-26(30)22-13-7-8-14-24(22)27-17-23-21-12-6-5-11-20(21)15-16-25(23)29/h2-18,29H,1H3,(H,28,30)/b27-17+

Smiles Code:

O=C(NC(C1=CC=CC=C1)C)C2=CC=CC=C2/N=C/C3=C4C=CC=CC4=CC=C3O

Technical Data：

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

In Vitro：

Sirtinol reduces the growth of MCF-7 cells in a concentration- and time-dependent manner. The IC50 values of sirtinol are 48.6 μM and 43.5 μM after 24 and 48 h of treatment, respectively. Sirtinol significantly decreases SIRT1 expression and increases the acetylated p53 level. Sirtinol attenuates the proliferation and induces apoptosis of nonsmall cell lung cancer (NSCLC) H1299 cells and causes the significantly increased level of FoxO3a, a proapoptotic transcription factor targeted by Sirt1.

In Vivo：

Sirtinol has anti-inflammatory effects through direct inhibition of HNE activity and attenuates HNE-induced and LPS-mediated tissue or organ injury.

References：

1. Kwak SS, Jeon Y, Yoon JD, Cheong SA, Lee E, Hyun SH. 37 the effects of a class iii histone deacetylase inhibitor (sirtinol) on early development of porcine cloned embryos. Reprod Fertil Dev. 2012 Dec;25(1):166. doi: 10.1071/RDv25n1Ab37. PubMed PMID: 23244871.

2. Wang J, Kim TH, Ahn MY, Lee J, Jung JH, Choi WS, Lee BM, Yoon KS, Yoon S, Kim HS. Sirtinol, a class III HDAC inhibitor, induces apoptotic and autophagic cell death in MCF-7 human breast cancer cells. Int J Oncol. 2012 Sep;41(3):1101-9. doi: 10.3892/ijo.2012.1534. Epub 2012 Jun 26. PubMed PMID: 22751989.

3. Wang TT, Schoene NW, Kim EK, Kim YS. Pleiotropic effects of the sirtuin inhibitor sirtinol involves concentration-dependent modulation of multiple nuclear receptor-mediated pathways in androgen-responsive prostate cancer cell LNCaP. Mol Carcinog. 2012 Apr 11. doi: 10.1002/mc.21906. [Epub ahead of print] PubMed PMID: 22495798.

4. Kozako T, Aikawa A, Shoji T, Fujimoto T, Yoshimitsu M, Shirasawa S, Tanaka H, Honda S, Shimeno H, Arima N, Soeda S. High expression of the longevity gene product SIRT1 and apoptosis induction by sirtinol in adult T-cell leukemia cells. Int J Cancer. 2012 Nov 1;131(9):2044-55. doi: 10.1002/ijc.27481. Epub 2012 Mar 27. PubMed PMID: 22322739.

5. Hsu YF, Sheu JR, Lin CH, Yang DS, Hsiao G, Ou G, Chiu PT, Huang YH, Kuo WH, Hsu MJ. Trichostatin A and sirtinol suppressed survivin expression through AMPK and p38MAPK in HT29 colon cancer cells. Biochim Biophys Acta. 2012 Feb;1820(2):104-15. doi: 10.1016/j.bbagen.2011.11.011. Epub 2011 Dec 1. PubMed PMID: 22155142.

Products are for research use only. Not for human use.