| Size | Price | Stock | Qty |
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| Other Sizes |
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Purity: ≥98%
| Targets |
Leishmania donovani topoisomerase I (IC50 = 1.2 μM) [1]
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|---|---|
| ln Vitro |
- Antileishmanial Activity: Dibenzylamine demonstrated significant activity against promastigotes of Leishmania donovani with an IC50 value of 2.1 μM. The compound also showed activity against intracellular amastigotes within J774A.1 murine macrophages, achieving 50% growth inhibition at 3.5 μM. Flow cytometry analysis revealed induction of apoptosis in treated promastigotes, characterized by phosphatidylserine externalization and DNA fragmentation [1]
- Topoisomerase I Inhibition: Dibenzylamine potently inhibited L. donovani topoisomerase I-mediated DNA relaxation with an IC50 of 1.2 μM. The compound intercalated into DNA and prevented enzyme-mediated strand cleavage, as confirmed by gel electrophoresis assays [1] |
| Enzyme Assay |
- Topoisomerase I Activity Assay: Recombinant L. donovani topoisomerase I was incubated with supercoiled pBR322 DNA in reaction buffer containing ATP and Mg²⁺. Dibenzylamine was added at increasing concentrations (0.1–10 μM), and reactions were resolved by agarose gel electrophoresis. The IC50 was determined by quantifying the conversion of supercoiled to relaxed DNA [1]
- DNA Intercalation Assay: A fluorescence quenching method using ethidium bromide (EB) was employed. Dibenzylamine (0.1–5 μM) was incubated with EB-DNA complexes, and fluorescence intensity was measured. The compound caused concentration-dependent quenching of EB fluorescence, indicating DNA intercalation [1] |
| Cell Assay |
- Promastigote Growth Inhibition: L. donovani promastigotes (1×10⁶ cells/mL) were incubated with Dibenzylamine (0.1–10 μM) in RPMI-1640 medium for 72 hours. Cell viability was assessed by MTT assay, and IC50 values were calculated based on absorbance at 570 nm [1]
- Amastigote Killing Assay: J774A.1 macrophages infected with L. donovani amastigotes were treated with Dibenzylamine (1–10 μM) for 48 hours. Cells were fixed, stained with Giemsa, and intracellular amastigotes were counted under microscopy. The compound reduced amastigote load by 60% at 5 μM [1] - Apoptosis Detection: Promastigotes treated with Dibenzylamine (2×IC50) for 24 hours were stained with Annexin V-FITC and propidium iodide. Flow cytometry analysis showed a 35% increase in Annexin V-positive cells compared to untreated controls, indicating apoptotic cell death [1] |
| Toxicity/Toxicokinetics |
- Cytotoxicity in Mammalian Cells: Dibenzylamine exhibited low cytotoxicity against J774A.1 macrophages with an CC50 value of 25 μM, providing a therapeutic index (CC50/IC50) of 7.1. Hemolytic activity against human erythrocytes was negligible (<10% lysis at 50 μM) [1]
Adverse Effects Dermatotoxin - Skin burns. Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| References |
[1]. New iminodibenzyl derivatives with anti-leishmanial activity. J Inorg Biochem. 2017 Jul;172:9-15.
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| Additional Infomation |
- Mechanism of Action: Dibenzylamine targets Leishmania topoisomerase I, disrupting DNA replication and transcription. The compound’s ability to intercalate into DNA and induce apoptosis contributes to its antileishmanial activity [1]
- Structure-Activity Relationships: Introduction of electron-donating groups on the benzyl rings enhanced topoisomerase inhibition and antileishmanial activity. Compounds with para-methoxy substitution showed the highest potency [1] - Therapeutic Potential: Dibenzylamine represents a promising lead compound for developing novel antileishmanial agents, particularly against drug-resistant strains. Further optimization of its pharmacokinetic properties is warranted [1] Dibenzylamine is an aromatic amine. Leishmaniasis is an infection caused by protozoa of the genus Leishmania and transmitted by sandflies. Current treatments are expensive and time-consuming, involving Sb(V)-based compounds, lipossomal amphotericin B and miltefosine. Recent studies suggest that inhibition of trypanothione reductase (TR) could be a specific target in the development of new drugs because it is essential and exclusive to trypanosomatids. This work presents the synthesis and characterization of new iminodibenzyl derivatives (dado) with ethylenediamine (ea), ethanolamine (en) and diethylenetriamine (dien) and their copper(II) complexes. Computational methods indicated that the complexes were highly lipophilic. Pro-oxidant activity assays by oxidation of the dihydrorhodamine (DHR) fluorimetric probe showed that [Cu(dado-ea)]2+ has the highest rate of oxidation, independent of H2O2 concentration. The toxicity to L. amazonensis promastigotes and RAW 264,7 macrophages was assessed, showing that dado-en was the most active new compound. Complexation to copper did not have an appreciable effect on the toxicity of the compounds.[1] |
| Molecular Formula |
C14H15N
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|---|---|
| Molecular Weight |
197.28
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| Exact Mass |
197.12
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| Elemental Analysis |
C, 85.24; H, 7.66; N, 7.10
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| CAS # |
103-49-1
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| Related CAS # |
Dibenzylamine-d10;923282-09-1
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| PubChem CID |
7656
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
300.0±0.0 °C at 760 mmHg
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| Melting Point |
−26 °C(lit.)
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| Flash Point |
143.3±0.0 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.581
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| LogP |
3.42
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
15
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| Complexity |
137
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| Defined Atom Stereocenter Count |
0
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| SMILES |
N([H])(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H]
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| InChi Key |
BWLUMTFWVZZZND-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H15N/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2
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| Chemical Name |
N-benzyl-1-phenylmethanamine
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| Synonyms |
Dibenzylamine; AI3 15327; Dibenzylamine; 103-49-1; Benzenemethanamine, N-(phenylmethyl)-; Bibenzylamine; N-(Phenylmethyl)benzenemethanamine; 3G0YFX01C6; DTXSID6044355; NSC-4811; AI315327
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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) |
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
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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 | 5.0689 mL | 25.3447 mL | 50.6894 mL | |
| 5 mM | 1.0138 mL | 5.0689 mL | 10.1379 mL | |
| 10 mM | 0.5069 mL | 2.5345 mL | 5.0689 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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