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| ln Vitro |
When exposed to the right wavelengths of light, photochromic compounds undergo significant conformational changes that make them particularly appealing as molecular switching elements. A typical option for chromophores is azobenzene. Irradiation at the π-π* transition wavelength quickly converts the thermodynamically preferred trans isomer to the cis isomer, while thermal relaxation in the dark (slow) or irradiation at the wavelength (fast) n-π* transition can accomplish the opposite operation. Amino acids azobenzene (aa) have the potential to function as light-induced conformational switches in polypeptides. When the azobenzene molecule is switched between its cis and trans forms, exposure to the right wavelengths of light can cause reversible conformational changes in the peptide backbone [1]. The most popular photoinitiator for creating photoresponsive systems, such as poly-α-amino acids and novel materials with light-controlled mechanical and optical characteristics, is azobenzene. By utilizing its reversible photoisomerization to create cyclic peptide structures that constrict conformational space, it can be used to induce well-defined transitions between various conformational states [2]. It is possible to manipulate the functions of peptides, proteins, nucleic acids, lipids, and carbohydrates using azobenzene photoswitches [3].
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Following administration of 500 mg/kg body weight of azobenzene to rabbits, 30% appeared in the feces; of the absorbed azobenzene, approximately 23% was excreted unchanged in the urine… Azobenzene binds to bovine serum albumin. The interaction of azobenzene and other azo compounds with proteins involves secondary valence bonds. Metabolism/Metabolites Following intraperitoneal injection of azobenzene into rats, aniline and a water-soluble compound that, upon acidification, yields benzidine, were detected in the urine… The metabolic pathway is catalyzed by hepatic microsomal enzymes. Azobenzene is reduced to aniline. /Excerpt from Table/ Some compounds are excreted unchanged in the urine, but the majority are present in the urine as metabolites, including hydrazine, benzidine, o-hydroxy and p-hydroxyazobenzene, o-amino and p-aminophenol, and their conjugates. Factors influencing the in vitro metabolism of azo compounds have been investigated, and conditions for maximal metabolism have been determined. Significant species differences exist in the degree of N-oxidation, with the activity order depending on the type of substrate used. For diaryl azo compounds, the activity order is rabbit > hamster > mouse > guinea pig > rat; while for dialkyl and mixed alkyl-aryl azo compounds, the activity order is hamster > guinea pig > mouse > rabbit > rat. The corresponding kinetic parameters Km and Vmax for azobenzene N-oxidation are reported. Sex differences in azobenzene N-oxidase activity were observed in rats, but not in hamsters. For more complete metabolite/metabolite data on azobenzenes (6 in total), please visit the HSDB record page. |
| References |
[1]. Aemissegger A, et al. Synthesis and application of an azobenzene amino acid as a light-switchable turn element in polypeptides. Nat Protoc. 2007;2(1):161-7.
[2]. Renner C, et al. Azobenzene as photoresponsive conformational switch in cyclic peptides. J Pept Res. 2005 Jan;65(1):4-14. [3]. Beharry AA, et al. Azobenzene photoswitches for biomolecules. Chem Soc Rev. 2011 Aug;40(8):4422-37. |
| Additional Infomation |
Azobenzene to the U.S. Environmental Protection Agency (EPA), azobenzene may be carcinogenic. Azobenzene is an orange-red crystal or a dark brown lumpy solid. (NTP, 1992) Azobenzene is a molecule whose structure consists of two benzene rings linked by N=N double bonds; it is the parent compound of azobenzene compounds.
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| Molecular Formula |
C12H10N2
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|---|---|
| Molecular Weight |
182.23
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| Exact Mass |
182.084
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| CAS # |
103-33-3
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| Related CAS # |
Azobenzene-d10;30504-49-5
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| PubChem CID |
2272
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| Appearance |
Orange-red leaflets
Monoclinic crystals Yellow or orange crystals |
| Density |
1.0±0.1 g/cm3
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| Boiling Point |
293.0±9.0 °C at 760 mmHg
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| Melting Point |
66 °C
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| Flash Point |
122.9±19.6 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.575
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| LogP |
3.82
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
14
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| Complexity |
157
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1(/N=N/C2=CC=CC=C2)=CC=CC=C1
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| InChi Key |
DMLAVOWQYNRWNQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H10N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H
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| Chemical Name |
diphenyldiazene
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| Synonyms |
NSC 2102 NSC2102 NSC-2102Azobenzene
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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 |
| 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 : ≥ 150 mg/mL (~823.18 mM)
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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 | 5.4876 mL | 27.4379 mL | 54.8757 mL | |
| 5 mM | 1.0975 mL | 5.4876 mL | 10.9751 mL | |
| 10 mM | 0.5488 mL | 2.7438 mL | 5.4876 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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