Sirtinol
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Hodoodo CAT#: H406130

CAS#: 410536-97-9

Description: 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 Structure

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Sirtinol
CAS# 410536-97-9
Instruction

Theoretical Analysis

Hodoodo Cat#: H406130
Name: Sirtinol
CAS#: 410536-97-9
Chemical Formula: C26H22N2O2
Exact Mass: 394.17
Molecular Weight: 394.465
Elemental Analysis: C, 79.16; H, 5.62; N, 7.10; O, 8.11

Price and Availability

Size Price Availability Quantity
200mg USD 450 2 Weeks
500mg USD 950 2 Weeks
1g USD 1650 2 Weeks
2g USD 2950 2 Weeks
5g USD 6550 2 Weeks
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Synonym: Sirtinol;

IUPAC/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

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

More Info:         

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 394.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

6: Orecchia A, Scarponi C, Di Felice F, Cesarini E, Avitabile S, Mai A, Mauro ML, Sirri V, Zambruno G, Albanesi C, Camilloni G, Failla CM. Sirtinol treatment reduces inflammation in human dermal microvascular endothelial cells. PLoS One. 2011;6(9):e24307. doi: 10.1371/journal.pone.0024307. Epub 2011 Sep 12. Erratum in: PLoS One. 2011;6(10). doi:10.1371/annotation/0174b439-c62b-42e8-a420-3defbfe5c8e9. PubMed PMID: 21931678; PubMed Central PMCID: PMC3171404.

7: Pasco MY, Rotili D, Altucci L, Farina F, Rouleau GA, Mai A, Néri C. Characterization of sirtuin inhibitors in nematodes expressing a muscular dystrophy protein reveals muscle cell and behavioral protection by specific sirtinol analogues. J Med Chem. 2010 Feb 11;53(3):1407-11. doi: 10.1021/jm9013345. PubMed PMID: 20041717.

8: Liu FC, Day YJ, Liao CH, Liou JT, Mao CC, Yu HP. Hemeoxygenase-1 upregulation is critical for sirtinol-mediated attenuation of lung injury after trauma-hemorrhage in a rodent model. Anesth Analg. 2009 Jun;108(6):1855-61. doi: 10.1213/ane.0b013e3181a1a194. PubMed PMID: 19448212.

9: Liu FC, Liao CH, Chang YW, Liou JT, Day YJ. A new insight of anti-platelet effects of sirtinol in platelets aggregation via cyclic AMP phosphodiesterase. Biochem Pharmacol. 2009 Apr 15;77(8):1364-73. doi: 10.1016/j.bcp.2009.01.011. Epub 2009 Jan 29. PubMed PMID: 19426675.

10: Liu FC, Day YJ, Liou JT, Lau YT, Yu HP. Sirtinol attenuates hepatic injury and pro-inflammatory cytokine production following trauma-hemorrhage in male Sprague-Dawley rats. Acta Anaesthesiol Scand. 2008 May;52(5):635-40. doi: 10.1111/j.1399-6576.2008.01592.x. PubMed PMID: 18419717.

11: Mai A, Massa S, Lavu S, Pezzi R, Simeoni S, Ragno R, Mariotti FR, Chiani F, Camilloni G, Sinclair DA. Design, synthesis, and biological evaluation of sirtinol analogues as class III histone/protein deacetylase (Sirtuin) inhibitors. J Med Chem. 2005 Dec 1;48(24):7789-95. PubMed PMID: 16302818.

12: Ota H, Tokunaga E, Chang K, Hikasa M, Iijima K, Eto M, Kozaki K, Akishita M, Ouchi Y, Kaneki M. Sirt1 inhibitor, Sirtinol, induces senescence-like growth arrest with attenuated Ras-MAPK signaling in human cancer cells. Oncogene. 2006 Jan 12;25(2):176-85. PubMed PMID: 16170353.

13: Dai X, Hayashi K, Nozaki H, Cheng Y, Zhao Y. Genetic and chemical analyses of the action mechanisms of sirtinol in Arabidopsis. Proc Natl Acad Sci U S A. 2005 Feb 22;102(8):3129-34. Epub 2005 Feb 14. PubMed PMID: 15710899; PubMed Central PMCID: PMC549487