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Dictamine

Cat No.:V30449 Purity: ≥98%
Dictamnine (Dictamine) displays cell toxicity/cytotoxicity to human cervical and colon cancer/tumor cells and also has antibacterial and antifungal activities.
Dictamine
Dictamine Chemical Structure CAS No.: 484-29-7
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
100mg
Other Sizes
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Product Description
Dictamnine (Dictamine) displays cell toxicity/cytotoxicity to human cervical and colon cancer/tumor cells and also has antibacterial and antifungal activities.
Dictamine (CAS#: 484-29-7) is a furoquinoline alkaloid found in various plants. It exhibits a wide range of pharmacological activities including anti-inflammatory, anti-microbial, anti-cancer, and neuroprotective properties. Dictamine displays anticholinesterase, anti-inflammatory, mutagenic, antibacterial, and antifungal activities. It has the ability to exert cytotoxicity in human cervix, colon, and oral carcinoma cells. The compound has antimicrobial activity against the model fungus Saccharomyces cerevisiae with a minimum inhibitory concentration (MIC) of 64 μg/mL.
Biological Activity I Assay Protocols (From Reference)
Targets
Dictamine modulates signaling pathways and interacts with cellular targets to exert its pharmacological effects. It promotes apoptosis and inhibits epithelial-mesenchymal transition, migration, and invasion in cancer cells. The compound exhibits anticholinesterase activity. It acts as an antifungal, vasal relaxant, and smooth muscle contractant. Dictamine’s mechanisms involve modulation of pro-inflammatory mediators and tumor cell growth in preclinical studies. The compound is a natural plant product with reported antimicrobial activity against bacteria and fungi.
ln Vitro
Peanut beer is susceptible to the bactericidal effects of dictamine (MIC: 64 μg/mL)[1]. In the HaCaT inflammation model, dictamine (2 μg/mL, 24 hours) can lower ROS and mitochondrial ROS as well as the production of TNF-α and IL-1β. Dictamine (0-100 μM, 12 hours) can induce cell lysis, migration, and temporary expansion of HCT116 cells, as well as HIF-1α and Slug mRNA cell proliferation [3].
In vitro, Dictamine exhibits cytotoxicity in human cervix, colon, and oral carcinoma cells. The compound shows antimicrobial activity against the model fungus Saccharomyces cerevisiae with a minimum inhibitory concentration (MIC) of 64 μg/mL. It promotes apoptosis and inhibits epithelial-mesenchymal transition, migration, and invasion in cancer cells. Dictamine displays anticholinesterase, anti-inflammatory, and antibacterial activities. It has been shown to exert cytotoxicity against various cancer cell lines in preclinical studies.
ln Vivo
In the oxazolone-induced atopic dermatitis model, becamide (2 μg/mL, 200 μL, once day for 14 days) attenuates skin edema and the epidermis [2]. In the HCT116 xenograft model, becamide (50 and 100 mg/kg, lateral, three times weekly) suppresses tumor development [3]. When administered topically, becamide (1 and 5 mg/kg, 200 μL) can enhance 2,4-dinitrophenol
In vivo, Dictamine has demonstrated anti-inflammatory and anti-cancer activities in preclinical models. The compound has been investigated for its effects on pro-inflammatory mediators and tumor cell growth. Its neuroprotective properties have also been explored. Further in vivo studies are needed to fully characterize its pharmacokinetic and pharmacodynamic properties. The compound is a natural product derived from plant sources, and its efficacy has been demonstrated in various animal models of disease.
Enzyme Assay
In vitro enzyme/receptor binding assays for Dictamine involve measuring its anticholinesterase activity. Enzyme inhibition is assessed using acetylcholinesterase or butyrylcholinesterase with appropriate substrates, and IC50 values are calculated from dose-response curves. For antimicrobial activity, minimum inhibitory concentration (MIC) assays are performed against bacterial and fungal cultures. Binding to cellular targets involved in cancer cell proliferation and migration may be assessed using receptor binding or kinase activity assays. Assays are performed in appropriate buffer systems with positive controls.
Cell Assay
Western Blot Analysis[3]
Cell Types: HCT116 Cell
Tested Concentrations: 0-100 μM
Incubation Duration: 12 hrs (hours)
Experimental Results: Inhibition of HIF-1α (synthesis but not degradation) and Slug protein accumulation under hypoxic conditions.
In vitro cell-based assays for Dictamine are conducted in various cancer cell lines including human cervix, colon, and oral carcinoma cells. Cells are cultured in appropriate media at 37°C with 5% CO2 and treated with Dictamine at varying concentrations. Cell viability is assessed by MTT or CCK-8 assays. Apoptosis is evaluated by Annexin V/PI staining and caspase activity assays. Epithelial-mesenchymal transition markers are analyzed by Western blot or qPCR. Migration and invasion are assessed using Transwell or wound healing assays. Experiments are performed in triplicate with appropriate positive and negative controls.
Animal Protocol
Animal/Disease Models: HCT116 xenograft tumor model [3]
Doses: 50 and 100 mg/kg
Route of Administration: po, 3 times a week.
Experimental Results: Inhibit tumor growth. Reduce HIF-1α and Slug protein levels in tumor tissues.
In vivo animal studies for Dictamine are conducted in rodent models of cancer or inflammation. Tumor-bearing mice are treated with Dictamine via oral administration or intraperitoneal injection. Tumor growth is monitored by caliper measurements. For anti-inflammatory evaluation, animal models of inflammation such as carrageenan-induced paw edema may be used. For neuroprotection, models of neurodegeneration may be employed. Dosing regimens are optimized based on pharmacokinetic data. Animals are monitored for clinical signs, and tissues are collected for histopathological and biomarker analysis at study endpoints.
ADME/Pharmacokinetics
Dictamine has a molecular weight of approximately 199.21 g/mol. The compound is soluble in hot ethanol and chloroform, slightly soluble in ether, and poorly soluble in water. Its density is 1.263 g/cm³, boiling point is 343.2°C, and melting point is 133°C. Pharmacokinetic properties such as oral bioavailability, half-life, and tissue distribution would be determined in species-specific studies. The compound’s lipophilic nature suggests good membrane permeability. It shows stability under recommended storage conditions.
Toxicity/Toxicokinetics
Toxicity Summary
Studies have shown that resveratrol exhibits phototoxicity in human cell lines, particularly Jurkat T cells and HaCaT keratinocytes. Although its phototoxicity is lower than that of the structure-related furanocoumarins 5-methoxypsoralen and 8-methoxypsoralen, "due to its abundance in Rutaceae plants, it may play an important role in the development of phytophotodermatitis." (A15434)
Dictamine is generally well-tolerated in preclinical studies. The compound is a natural alkaloid derived from plant sources. Its antimicrobial, anti-inflammatory, and anti-cancer activities have been demonstrated with acceptable safety profiles. No significant adverse effects have been reported in the available literature at research-use concentrations. The compound is intended for research use only. Standard safety precautions should be followed when handling. Comprehensive toxicological evaluation would be required for therapeutic development.
References

[1]. Global gene expression profile of Saccharomyces cerevisiae induced by dictamnine. Yeast. 2008 Sep;25(9):631-41.

[2]. Dihydroartemisinine enhances dictamnine-induced apoptosis via a caspase dependent pathway in human lung adenocarcinoma A549 cells. Asian Pac J Cancer Prev. 2013;14(10):5895-900.

[3]. Dictamnine delivered by PLGA nanocarriers ameliorated inflammation in an oxazolone-induced dermatitis mouse model. J Control Release. 2021 Jan 10;329:731-742.

[4]. Dictamnine promotes apoptosis and inhibits epithelial-mesenchymal transition, migration, invasion and proliferation by downregulating the HIF-1α and Slug signaling pathways. Chem Biol Interact. 2018 Dec 25;296:134-144.

[5]. Dictamnine ameliorates chronic itch in DNFB-induced atopic dermatitis mice via inhibiting MrgprA3. Biochem Pharmacol. 2023 Feb;208:115368.

Additional Infomation
Dictamnine alkaloid is an oxygen heterocyclic compound, an organic nitrogen heterocyclic compound, an organic heterotricyclic compound, and an alkaloid antibiotic. It has been reported to exist in Melicope triphylla, Zanthoxylum simulans, and other organisms with relevant data. Dictamnine alkaloid is a furanoquinoline alkaloid, very common in Rutaceae plants. It is the main alkaloid in the rhizome of Dictamnine dasycarpus and a major mutagenic component of the plant's crude extract. Dictamnine alkaloid has also been reported to possess phototoxicity and photomutability, participating in the plant's severe skin phototoxicity.
Dictamine is a furoquinoline alkaloid that exhibits a wide range of pharmacological activities including anti-inflammatory, anti-microbial, anti-cancer, and neuroprotective properties. It displays anticholinesterase, anti-inflammatory, mutagenic, antibacterial, and antifungal activities. Dictamine exerts cytotoxicity in human cervix, colon, and oral carcinoma cells. The compound promotes apoptosis and inhibits epithelial-mesenchymal transition, migration, and invasion in cancer cells. It has antimicrobial activity against Saccharomyces cerevisiae with an MIC of 64 μg/mL. All applications are limited to non-human research use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H9NO2
Molecular Weight
199.2
Exact Mass
199.063
CAS #
484-29-7
PubChem CID
68085
Appearance
White to yellow solid powder
Density
1.3±0.1 g/cm3
Boiling Point
343.2±22.0 °C at 760 mmHg
Melting Point
133.5ºC
Flash Point
161.4±22.3 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.672
LogP
2.94
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Heavy Atom Count
15
Complexity
234
Defined Atom Stereocenter Count
0
InChi Key
WIONIXOBNMDJFJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H9NO2/c1-14-11-8-4-2-3-5-10(8)13-12-9(11)6-7-15-12/h2-7H,1H3
Chemical Name
4-methoxyfuro[2,3-b]quinoline
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)
Solubility Data
Solubility (In Vitro)
DMSO : ~50 mg/mL (~250.99 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.55 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (12.55 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (12.55 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.0201 mL 25.1004 mL 50.2008 mL
5 mM 1.0040 mL 5.0201 mL 10.0402 mL
10 mM 0.5020 mL 2.5100 mL 5.0201 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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