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| Targets |
The primary targets of Tomatidine hydrochloride are NF-κB and JNK signaling pathways. It suppresses NF-κB signaling in LPS-stimulated macrophages by inhibiting I-κBα phosphorylation, blocking NF-κB nuclear translocation, and modulating binding activity. The compound also inhibits JNK activation, which in turn inhibits c-jun phosphorylation and Oct-2 expression. This leads to reduced expression of inducible nitric oxide synthase (iNOS) and COX-2. Tomatidine hydrochloride also targets autophagy pathways, activating autophagy in both mammalian cells and C. elegans.
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| ln Vitro |
Tomatidine inhibits NF-κB nuclear translocation, JNK activation, and I-κBα phosphorylation, which in turn inhibits c-jun phosphorylation and Oct-2 expression, hence reducing inducible NO synthase and COX-2 expression. At 40 μM, the formation of nitrite was suppressed by 66%, 22%, and 41% of tomate, solanine, and diosgenin, respectively. Tomatine generated a dose-dependent suppression of LPS-induced iNOS expression, and iNOS protein was hardly detectable in unstimulated cells but rose considerably following LPS treatment. Since p65 is a key component of NF-κB in LPS-stimulated macrophages, it was determined how tomatidine affected p65's ability to bind DNA. A dose-dependent inhibition of NF-κB binding activity was observed at tomatine doses of 10–40 μM. Tomatidine suppresses I-κB phosphorylation, prevents I-κB synthesis, and further suppresses the translocation of p65 NF-κB to the nucleus, controlling binding activity [1].
In vitro, Tomatidine hydrochloride decreases inducible NO synthase and COX-2 expression through suppression of I-κBα phosphorylation, NF-κB nuclear translocation, and JNK activation. At 40 μM, tomatidine shows 66% inhibition of nitrite production, compared to 22% for solasodine and 41% for diosgenin. The iNOS protein is barely detectable in unstimulated cells but markedly increases after LPS treatment, and tomatidine causes dose-dependent inhibition of LPS-induced iNOS expression. In the presence of tomatidine at 10-40 μM, the binding activity of NF-κB is suppressed in a dose-dependent manner. |
| ln Vivo |
Tomatidine hydrochloride activates autophagy either in mammalian cells or C. elegans. It has been shown to protect against ischemic neuronal injury by improving lysosomal function. The compound also exhibits antioxidant and anticancer activities. Tomatidine protects against muscle atrophy and promotes muscle growth. Its anti-inflammatory effects have been demonstrated in various in vivo models, although specific detailed in vivo protocols are limited in the available literature.
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| Enzyme Assay |
In vitro enzyme assays for Tomatidine hydrochloride involve measuring its inhibition of NF-κB DNA-binding activity. RAW 264.7 macrophages are cultured and stimulated with LPS in the presence of varying concentrations of tomatidine (10-40 μM). The DNA-binding activity of p65, the major component of NF-κB, is determined using an electrophoretic mobility shift assay (EMSA). The inhibition of I-κBα phosphorylation is assessed by Western blotting. JNK activation is measured by detecting phosphorylated JNK levels.
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| Cell Assay |
In vitro cell-based assays for Tomatidine hydrochloride are performed using RAW 264.7 murine macrophages. Cells are cultured in DMEM supplemented with 10% fetal calf serum, penicillin (100 units/mL), and streptomycin (100 μg/mL) in a 5% CO₂ atmosphere at 37 °C. Cells are plated at 2×10⁵ cells/cm² and treated with vehicle (0.1% DMSO or 0.1% ethanol), test compounds, and/or LPS under serum-free conditions. Nitrite production is measured using the Griess assay. iNOS and COX-2 expression are assessed by Western blotting.
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| Animal Protocol |
In vivo animal experiments for Tomatidine hydrochloride are conducted using rodent models of inflammation and ischemic injury. The compound has been shown to protect against ischemic neuronal injury by improving lysosomal function. However, specific detailed protocols for in vivo studies are limited in the available literature. The compound is typically administered orally or intraperitoneally in preclinical studies. Efficacy is evaluated by measuring inflammatory markers and tissue damage.
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| ADME/Pharmacokinetics |
Pharmacokinetic (PK) properties of Tomatidine hydrochloride indicate that it is the water-soluble form of tomatidine. The compound has a molecular weight of 452.11 and a molecular formula of C27H46ClNO2. It has a LogP of 4.9. The powder is stable when stored at -20°C for up to 3 years or at 4°C for up to 2 years. In solvent, it can be stored at -80°C for 6 months or at -20°C for 1 month. The compound is soluble in DMSO and other organic solvents.
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| Toxicity/Toxicokinetics |
Toxicology (toxicology) data for Tomatidine hydrochloride indicate that it is generally well-tolerated in preclinical studies. As a steroidal alkaloid, it has a favorable safety profile at moderate doses. The compound does not inhibit the hedgehog pathway, unlike its structural analog cyclopamine. This suggests a potentially lower risk of certain developmental toxicities. However, long-term safety data are limited. The compound is for research use only and not for human therapeutic use.
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| References | |
| Additional Infomation |
Other information: Tomatidine hydrochloride is also known as Tomatidine HCl. It is a steroidal alkaloid structurally similar to cyclopamine but does not inhibit the hedgehog pathway and may be used as a negative control for cyclopamine and KAAD-cyclopamine. The compound is present in the skins and leaves of tomatoes. It has been shown to protect against muscle atrophy and promote muscle growth. Its CAS number is 6192-62-7.
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| Molecular Formula |
C27H46CLNO2
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| Molecular Weight |
452.12
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| Exact Mass |
451.321
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| CAS # |
6192-62-7
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| Related CAS # |
Tomatidine;77-59-8
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| PubChem CID |
60196284
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| Appearance |
White to yellow solid powder
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| Boiling Point |
551.1ºC at 760 mmHg
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| Melting Point |
281-284ºC (dec.)
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| Flash Point |
287.1ºC
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| LogP |
6.497
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
31
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| Complexity |
696
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| Defined Atom Stereocenter Count |
12
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| SMILES |
C[C@H]1CC[C@]2([C@H]([C@H]3[C@@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)O)C)C)C)NC1.Cl
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| InChi Key |
SXXHVPYRDFJKPG-VXJLCZPPSA-N
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| InChi Code |
InChI=1S/C27H45NO2.ClH/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4;/h16-24,28-29H,5-15H2,1-4H3;1H/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-;/m0./s1
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| Chemical Name |
(1R,2S,4S,5'S,6S,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-piperidine]-16-ol;hydrochloride
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| Synonyms |
5alpha-Tomatidan-3beta-ol HCl Tomatidine HCl Tomatidine hydrochloride
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~5 mg/mL (~11.06 mM)
Ethanol : ~3.45 mg/mL (~7.63 mM) H2O : < 0.1 mg/mL |
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2118 mL | 11.0590 mL | 22.1180 mL | |
| 5 mM | 0.4424 mL | 2.2118 mL | 4.4236 mL | |
| 10 mM | 0.2212 mL | 1.1059 mL | 2.2118 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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