Physicochemical Properties
| Molecular Formula | C17H21NO2S |
| Molecular Weight | 303.4191 |
| Exact Mass | 303.129 |
| CAS # | 926908-04-5 |
| PubChem CID | 16126782 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Index of Refraction | 1.625 |
| LogP | 3.71 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 21 |
| Complexity | 311 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | KPNNXHVGOKRBEF-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C17H21NO2S/c19-17(18-20)9-3-1-2-6-12-21-16-11-10-14-7-4-5-8-15(14)13-16/h4-5,7-8,10-11,13,20H,1-3,6,9,12H2,(H,18,19) |
| Chemical Name | N-hydroxy-7-naphthalen-2-ylsulfanylheptanamide |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | At lower concentrations, HNHA (0-100 μM, 96 h) exhibits substantial inhibitory effects on cancer cell lines, particularly on human MCF-7 and murine FM3A breast cancer cells[1]. HNHA (15 μM, 24 hours) significantly rescues protein acetylation, activates p21, and stops cancer cells in the G1/S phase of the cell cycle [1]. HNHA (15 μM, 12 hours) efficiently inactivates MMP-2, MMP-9, VEGF, and HIF-1α while also inhibiting angiogenic proteins in breast cancer cells[1]. |
| ln Vivo | HNHA (20 μM/mouse, IP, once every two days for six injections) inhibits the expression of MMP-2, MMP-9, HIF-1α, and VEGF protein, increases survival time, and decreases tumor burden[1]. It also activates TIMP-1, TIMP-2, and p21. |
| Cell Assay |
Cell Proliferation Assay Cell Types: FM3A, C1300, LA-N-1, LA-N-2, LA-N-5, NB16, NB19, NB69, SK-N-SH, MCF-7 and HT-29[1] Tested Concentrations: 0-100 μM Incubation Duration: 96 hrs (hours) Experimental Results: All cancer cell lines (FM3A, C1300, LA-N-1, LA-N-2, LA-N-5, NB16, NB19) at lower concentrations demonstrated strong inhibitory effects, NB69, SK-N-SH, MCF-7 and HT-29), with IC50 values of 15.70, 55.63, 22.78, 23.18, 26.70, 19.64, 21.26, 22.31, 65.09, 14.33 and 16.98 μM respectively. . Cell viability assay Cell Types: FM3A and MCF-7[1] Tested Concentrations: 0, 0.1, 1, 5, 10, 15, 20, 25, 30 μM Incubation Duration: 48 hrs (hours) Experimental Results: Shows dose dependence on mouse viability Sexual suppression and human breast cancer cells. Cell cycle analysis Cell Types: FM3A and MCF-7 cells [1] Tested Concentrations: 15 μM Incubation Duration: 24 hrs (hours) Experimental Results: FM3A and MCF-7 cells were arrested in G1/S phase. Western Blot Analysis Cell Types: FM3A and MCF-7 cells [1] Tested Concentrations: 0, 0.1, 1, 10 and 20 μM (24 hrs (hours)) Incubation Duration: 1, 6, 24, 48, and 72 h (15 μM) Experimental Results: Activated a cell proliferation arrestor p21, increased histone and non-histone protein acetylation and inhibited FM3A and MCF-7 proliferation in vitro, and was very effective in increasing the acetylation level of histone H3 protein in FM3A and MCF-7. The most effective dose point for acetylation of histone H3 was 10-20 μM. Histone H3 acetylation peaked after 1 h of exposure to the drugs and remained stable for 1-6 h. Western Blot Analysis Cell Types: FM3A and MCF-7 cells[1] Tested Concentrations: 15 μM Incubation Duration: 12 h Experimental Results: demonstrated a strong induction of TIMP-1 and TIMP-2, and effectively inactivated MMP-2, MMP-9, VEGF and HIF-1α. |
| Animal Protocol |
Animal/Disease Models: C3H/HeJ-FasL mice (FM3A breast cancer cell tumor xenograft, 6 weeks, n = 25/group) [1] Doses: 20 μM/mouse Route of Administration: IP, once every 2 days, co-injection 6 Experimental Results: diminished tumor burden and prolonged survival. Effectively inhibits cancer development and angiogenesis in the body. Increased TIMP-1, TIMP-2 and p21, diminished MMP-2, MMP-9, HIF-1α and VEGF protein expression, and diminished CD34, HIF-1α and VEGF distribution. |
| References |
[1]. Potential anti-cancer activity of N-hydroxy-7-(2-naphthylthio) heptanomide (HNHA), a histone deacetylase inhibitor, against breast cancer both in vitro and in vivo. Cancer Sci. 2011 Feb;102(2):343-50. |
| Additional Infomation | N-hydroxy-7-(2-naphthalenylthio)heptanamide is a member of naphthalenes. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2958 mL | 16.4788 mL | 32.9576 mL | |
| 5 mM | 0.6592 mL | 3.2958 mL | 6.5915 mL | |
| 10 mM | 0.3296 mL | 1.6479 mL | 3.2958 mL |