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MedKoo Cat#: 406130 | Name: Sirtinol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Sirtinol
Sirtinol
CAS#410536-97-9

Theoretical Analysis

MedKoo Cat#: 406130

Name: Sirtinol

CAS#: 410536-97-9

Chemical Formula: C26H22N2O2

Exact Mass: 394.1681

Molecular Weight: 394.47

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

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 Weeks
10mg USD 600.00 2 Weeks
25mg USD 750.00 2 Weeks
50mg USD 1,150.00 2 Weeks
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Related CAS #
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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 and DMF
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
        
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Sirtinol is a cell-permeable inhibitor of sirtuin NAD+-dependent deacetylases, inhibiting the yeast sirtuin Sir2p with an IC50 value of 68 μM and the human sirtuins SIRT1 and SIRT2 with IC50 values of 131 and 38 μM, respectively. It does not alter HDAC1 activity. Sirtinol inhibits the growth of cancer cells and suppresses inflammatory signaling in human dermal microvascular endothelial cells. In plants, sirtinol can be metabolized to 2-hydroxy-1-naphthoic acid, which activates auxin signaling and alters plant growth and development.
In vitro activity:
Sirtinol can be used to treat Acanthamoeba infections. Sirtinol inhibited A. castellanii trophozoites proliferation (IC50=61.24 μM) and significantly decreased the encystation rate of cells. Sirtinol suppressed cyst-specific cysteine protease (CSCP) transcription, resulting that the undegraded organelles and large molecules remained in sirtinol-treated cells during encystation. Reference: Korean J Parasitol. 2022 Feb;60(1):1-6. https://pubmed.ncbi.nlm.nih.gov/35247948/
In vivo activity:
Sirtinol in combination with FK506 may be a promising treatment to prevent the rejection reaction of heart transplantation. Allografts from sirtinol-treated recipients showed significantly lower levels of IL-17A expression and higher levels of Foxp3 expression. Sirtinol reduced the proportion of Th17 cells and increased the proportion of Treg cells in splenocytes from recipients. There were synergistic effects of sirtinol and FK506 on prolonging allograft survival, and sirtinol synergized with FK506 to promote Foxp3 expression. Reference: Cell Biosci. 2017 Oct 27;7:55. https://pubmed.ncbi.nlm.nih.gov/29090089/
Solvent mg/mL mM
Solubility
DMF 15.0 38.03
DMSO 10.0 25.35
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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:
1. Petronek MS, Bayanbold K, Amegble K, Tomanek-Chalkley AM, Allen BG, Spitz DR, Bailey CK. Evaluating the iron chelator function of sirtinol in non-small cell lung cancer. Front Oncol. 2023 Jun 15;13:1185715. doi: 10.3389/fonc.2023.1185715. PMID: 37397370; PMCID: PMC10313412. 2. Joo SY, Aung JM, Shin M, Moon EK, Kong HH, Goo YK, Chung DI, Hong Y. Sirtinol Supresses Trophozoites Proliferation and Encystation of Acanthamoeba via Inhibition of Sirtuin Family Protein. Korean J Parasitol. 2022 Feb;60(1):1-6. doi: 10.3347/kjp.2022.60.1.1. Epub 2022 Feb 23. PMID: 35247948; PMCID: PMC8898648. 3. Ye Q, Zhang M, Wang Y, Fu S, Han S, Wang L, Wang Q. Sirtinol regulates the balance of Th17/Treg to prevent allograft rejection. Cell Biosci. 2017 Oct 27;7:55. doi: 10.1186/s13578-017-0182-2. PMID: 29090089; PMCID: PMC5658927. 4. Tsai YF, Yu HP, Chang WY, Liu FC, Huang ZC, Hwang TL. Sirtinol inhibits neutrophil elastase activity and attenuates lipopolysaccharide-mediated acute lung injury in mice. Sci Rep. 2015 Feb 10;5:8347. doi: 10.1038/srep08347. PMID: 25666548; PMCID: PMC4322352.
In vitro protocol:
1. Petronek MS, Bayanbold K, Amegble K, Tomanek-Chalkley AM, Allen BG, Spitz DR, Bailey CK. Evaluating the iron chelator function of sirtinol in non-small cell lung cancer. Front Oncol. 2023 Jun 15;13:1185715. doi: 10.3389/fonc.2023.1185715. PMID: 37397370; PMCID: PMC10313412. 2. Joo SY, Aung JM, Shin M, Moon EK, Kong HH, Goo YK, Chung DI, Hong Y. Sirtinol Supresses Trophozoites Proliferation and Encystation of Acanthamoeba via Inhibition of Sirtuin Family Protein. Korean J Parasitol. 2022 Feb;60(1):1-6. doi: 10.3347/kjp.2022.60.1.1. Epub 2022 Feb 23. PMID: 35247948; PMCID: PMC8898648.
In vivo protocol:
1. Ye Q, Zhang M, Wang Y, Fu S, Han S, Wang L, Wang Q. Sirtinol regulates the balance of Th17/Treg to prevent allograft rejection. Cell Biosci. 2017 Oct 27;7:55. doi: 10.1186/s13578-017-0182-2. PMID: 29090089; PMCID: PMC5658927. 2. Tsai YF, Yu HP, Chang WY, Liu FC, Huang ZC, Hwang TL. Sirtinol inhibits neutrophil elastase activity and attenuates lipopolysaccharide-mediated acute lung injury in mice. Sci Rep. 2015 Feb 10;5:8347. doi: 10.1038/srep08347. PMID: 25666548; PMCID: PMC4322352.
1: Bernhardt A, Jamil A, Morshed MT, Ponnath P, Gille V, Stephan N, Sauer H, Wartenberg M. Oxidative stress and regulation of adipogenic differentiation capacity by sirtuins in adipose stem cells derived from female patients of advancing age. Sci Rep. 2024 Aug 27;14(1):19885. doi: 10.1038/s41598-024-70382-x. PMID: 39191852; PMCID: PMC11349916. 2: Tanhapour M, Nourbakhsh M, Panahi G, Golestani A. The role of Sirtuin 1 in regulation of fibrotic genes expression in pre-adipocytes. J Diabetes Metab Disord. 2024 Mar 7;23(1):1081-1091. doi: 10.1007/s40200-024-01389-4. PMID: 38932833; PMCID: PMC11196476. 3: Chen L, Cai X, Shao L, Wang Y, Hong L, Zhan Y. Sirtuin 2 Exerts Regulatory Functions on Radiation-Induced Myocardial Fibrosis in Mice by Mediating H3K27 Acetylation of Galectin-3 Promoter. Acta Cardiol Sin. 2024 Mar;40(2):214-224. doi: 10.6515/ACS.202403_40(2).20231026B. PMID: 38532816; PMCID: PMC10961639. 4: Chen Y, Zhao S, Xiao H. Sirt1 Inhibits Atrial Fibrosis by Downregulating the Expression of the Transforming Growth Factor-β1/Smad Pathway. Acta Cardiol Sin. 2024 Mar;40(2):225-234. doi: 10.6515/ACS.202403_40(2).20230925B. PMID: 38532813; PMCID: PMC10961634. 5: Ji KB, Wan W, Yang Y, He XJ, Xing YQ, Hu Z. Ameliorative effect of resveratrol on acute ocular hypertension induced retinal injury through the SIRT1/NF-κB pathway. Neurosci Lett. 2024 Mar 15;826:137712. doi: 10.1016/j.neulet.2024.137712. Epub 2024 Mar 4. PMID: 38447888. 6: Taheripak G, Sabeti N, Najar N, Razavi Z, Saharkhiz S, Alipourfard I. SIRT1 activation attenuates palmitate induced apoptosis in C2C12 muscle cells. Mol Biol Rep. 2024 Feb 24;51(1):354. doi: 10.1007/s11033-024-09250-w. PMID: 38400872. 7: Sharma S, Mehan S, Khan Z, Gupta GD, Narula AS. Icariin prevents methylmercury-induced experimental neurotoxicity: Evidence from cerebrospinal fluid, blood plasma, brain samples, and in-silico investigations. Heliyon. 2024 Jan 6;10(1):e24050. doi: 10.1016/j.heliyon.2024.e24050. PMID: 38226245; PMCID: PMC10788811. 8: Song YJ, Huang Q, Chen L, Wang YY, Zhou YD, Liang FX. Electroacupuncture improving obesity-induced insulin resistance via regulating intestinal SIRT1/TLR4 signaling pathway. Zhen Ci Yan Jiu. 2023 Nov 25;48(11):1125-1133. English, Chinese. doi: 10.13702/j.1000-0607.20221057. PMID: 37984910. 9: Hwang TL, Lin JY, Kuo LM, Kumar Dhandabani G, Hsieh PW. Design and synthesis of sirtinol analogs as human neutrophil elastase inhibitors. Bioorg Med Chem Lett. 2024 Jan 1;97:129544. doi: 10.1016/j.bmcl.2023.129544. Epub 2023 Nov 7. PMID: 37939864. 10: Liao CH, Hung HC, Lai CN, Liao YH, Liu PT, Lu SM, Huang HC, Tsai CW. Carnosic acid and rosemary extract reversed the lipid accumulation induced by bisphenol A in the 3T3-L1 preadipocytes and C57BL/6J mice via SIRT1/FoxO1 pathway. Food Chem Toxicol. 2023 Sep;179:113996. doi: 10.1016/j.fct.2023.113996. Epub 2023 Aug 19. PMID: 37598852. 11: Petronek MS, Bayanbold K, Amegble K, Tomanek-Chalkley AM, Allen BG, Spitz DR, Bailey CK. Evaluating the iron chelator function of sirtinol in non-small cell lung cancer. Front Oncol. 2023 Jun 15;13:1185715. doi: 10.3389/fonc.2023.1185715. PMID: 37397370; PMCID: PMC10313412. 12: Dzidek A, Czerwińska-Ledwig O, Żychowska M, Pilch W, Piotrowska A. The Role of Increased Expression of Sirtuin 6 in the Prevention of Premature Aging Pathomechanisms. Int J Mol Sci. 2023 Jun 2;24(11):9655. doi: 10.3390/ijms24119655. PMID: 37298604; PMCID: PMC10253323. 13: E Silva LFS, Siena A, Yuzawa JM, Torresi JLB, Ziroldo A, Rosenstock TR. Sirtuins Modulators Counteract Mitochondrial Dysfunction in Cellular Models of Hypoxia: Relevance to Schizophrenia. Neuroscience. 2023 Aug 1;524:269-284. doi: 10.1016/j.neuroscience.2023.04.027. Epub 2023 May 9. PMID: 37169164. 14: Niu K, Yang L, Song W, Liu Z, Yuan J, Zhang H, Zhang W, Wang J, Tao K. A COMPARATIVE ANALYSIS TO DETERMINE THE OPTIMUM HISTONE DEACETYLASE INHIBITORS AND ADMINISTRATION ROUTE FOR IMPROVING SURVIVAL AND ORGAN INJURY IN RATS AFTER HEMORRHAGIC SHOCK. Shock. 2023 Jul 1;60(1):75-83. doi: 10.1097/SHK.0000000000002136. Epub 2023 May 5. PMID: 37141162; PMCID: PMC10417212. 15: El-Ashmawy NE, Khedr EG, Khedr NF, El-Adawy SA. Suppression of epithelial- mesenchymal transition and SIRT1/AKT signaling pathway in breast cancer by montelukast. Int Immunopharmacol. 2023 Jun;119:110148. doi: 10.1016/j.intimp.2023.110148. Epub 2023 Apr 10. PMID: 37044036. 16: Niu K, Qu S, Yang L, Zhang H, Yuan J, Fan H, Li X, Tao K. Protective effect of HDACIs in improves survival and organ injury after CLP-induced sepsis. Surg Open Sci. 2023 Mar 2;12:35-42. doi: 10.1016/j.sopen.2023.03.003. PMID: 36936452; PMCID: PMC10015250. 17: Wu K, Li B, Ma Y, Tu T, Lin Q, Zhu J, Zhou Y, Liu N, Liu Q. Nicotinamide mononucleotide attenuates HIF-1α activation and fibrosis in hypoxic adipose tissue via NAD+/SIRT1 axis. Front Endocrinol (Lausanne). 2023 Jan 26;14:1099134. doi: 10.3389/fendo.2023.1099134. PMID: 36777361; PMCID: PMC9909340. 18: Du L, Chen L, Luo B, Chen YJ, Zhang P, Tang YY, Jiang JM, Zou W. Silent information regulator 1 mediates H 2 S-inhibited chronic restraint stress- induced depressive-like behaviors by regulating hippocampal autophagy. Neuroreport. 2023 Feb 1;34(3):128-136. doi: 10.1097/WNR.0000000000001870. Epub 2022 Dec 26. PMID: 36728843. 19: Liao H, Huang J, Liu J, Zhu H, Chen Y, Li X, Wen J, Yang Q. Sirt1 regulates microglial activation and inflammation following oxygen-glucose deprivation/reoxygenation injury by targeting the Shh/Gli-1 signaling pathway. Mol Biol Rep. 2023 Apr;50(4):3317-3327. doi: 10.1007/s11033-022-08167-6. Epub 2023 Feb 1. PMID: 36725745; PMCID: PMC10042964. 20: Xiu M, Zhao Y, Wang X, Yuan S, Qin B, Sun J, Cui L, Song J. Regulation of SIRT1-TLR2/TLR4 pathway in cell communication from macrophages to hepatic stellate cells contribute to alleviates hepatic fibrosis by Luteoloside. Acta Histochem. 2023 Jan;125(1):151989. doi: 10.1016/j.acthis.2022.151989. Epub 2022 Dec 16. PMID: 36529079.