| Size | Price | |
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| Other Sizes |
| Targets |
Not applicable as a drug. This compound is used as a chemical reagent that targets and reacts with free sulfhydryl (thiol) groups in peptides and proteins. [1]
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| ln Vitro |
Intramolecular S-S bond formation can be greatly accelerated by adding 2,2'-dipyridyl disulfide (2-PDS) solution to a mixture of air-oxidized cysteine-containing peptides [1].
The compound is not studied for pharmacological activity. Its primary described in vitro use is to rapidly and completely convert linear peptides containing two reduced cysteine residues into their oxidized cyclic form containing an intramolecular disulfide bond. This reaction is demonstrated with several peptides including salmon calcitonin (sCT), bombyxin IV A chain intermediates, and SCP-1 fragments. [1] In experiments with salmon calcitonin (reduced form, 1 mg in 3 ml buffer), adding 0.3 ml of a 1 mM 2-PDS solution in methanol resulted in complete oxidation within 5 minutes, as shown by RP-HPLC. This rapid formation was observed at both pH 8.0 (50 mM Tris-HCl) and pH 4.0 (50 mM sodium acetate). [1] For bombyxin IV A chain intermediates (reduced form, 0.3 mg in 1 ml of 0.1 M NaHCO₃, pH 7.8), adding 1 ml of a 0.15 mM 2-PDS solution in 10% aqueous methanol led to complete intramolecular disulfide bond formation within 5 minutes. This was significantly faster than air oxidation, which took 4-5 days. [1] For SCP-1 fragments, specifically SCP-1(74-89) (10 mg in 10 ml of 50 mM Tris-HCl, pH 8.0) and SCP-1(113-128) (5 mg in 10 ml of same buffer), adding 2-PDS solutions (5 mM in methanol, 1.2 ml for the former, 0.7 ml for the latter) resulted in complete cyclization within 5 minutes. Air oxidation for these fragments was incomplete even after 5 days or took at least 2 days. [1] The broad pH range (pH 3.4-8.1) over which 2-PDS is effective as a sulfhydryl reagent was noted, highlighting its applicability under acidic conditions. [1] |
| References | |
| Additional Infomation |
Aldehydes and thiols are pyridine compounds with a structure in which pyridine is replaced at the 2-position by a pyridin-2-yldithiodialkyl group. They are commonly used oxidizing agents in molecular biology and are also used in peptide synthesis and the detection of thiols. They are organic disulfides belonging to the pyridine class of compounds. 2,2'-Dithiodipyridine has been reported in Marsypopetalum modestum and Allium stipitatum, and relevant data are available.
2,2'-Bispyridyl disulfide is also known as 2,2'-dipyridyl disulfide or 2,2'-dithiodipyridine. It is a common reagent in peptide chemistry. [1] It reacts selectively with free sulfhydryl (SH) groups over a broad pH range (pH 3.4-8.1). [1] The proposed mechanism involves a thiol-disulfide exchange reaction. First, a free SH group in the peptide reduces 2-PDS, forming a mixed disulfide between the peptide and a pyridyl group (peptide-S-S-pyridyl), and releasing 2-thiopyridine. Second, another free SH group in the same peptide attacks this mixed disulfide, completing the exchange and forming the intramolecular disulfide bond, with 2-thiopyridine as the final byproduct. [1] Both 2-PDS and its byproduct, 2-thiopyridine, can be easily separated from the peptide product by reverse-phase HPLC. [1] This method is presented as a rapid, simple, and SH-selective way to introduce intramolecular disulfide bonds in conventional buffer solutions, with wide applications in synthesizing cystine-containing bioactive polypeptides and in introducing artificial disulfide bonds to stabilize desirable conformations of polypeptides. [1] The salmon calcitonin synthesized using the 2-PDS method was found to be indistinguishable from a commercially available sample when assessed by RP-HPLC retention time, mass spectrometry, and a bioassay measuring inhibition of osteoclastic bone resorption. [1] |
| Molecular Formula |
C10H8N2S2
|
|---|---|
| Molecular Weight |
220.3
|
| Exact Mass |
220.012
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| CAS # |
2127-03-9
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| PubChem CID |
65093
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
356.1±17.0 °C at 760 mmHg
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| Melting Point |
56-58 °C(lit.)
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| Flash Point |
169.2±20.9 °C
|
| Vapour Pressure |
0.0±0.8 mmHg at 25°C
|
| Index of Refraction |
1.694
|
| LogP |
2.53
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
14
|
| Complexity |
148
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
HAXFWIACAGNFHA-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H
|
| Chemical Name |
2-(pyridin-2-yldisulfanyl)pyridine
|
| Synonyms |
OPSS2,2'-Dipyridyl disulfide Aldrithiol 2 Orthopyridyl disulfide
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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)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~453.91 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.35 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 (11.35 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (11.35 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.5393 mL | 22.6963 mL | 45.3926 mL | |
| 5 mM | 0.9079 mL | 4.5393 mL | 9.0785 mL | |
| 10 mM | 0.4539 mL | 2.2696 mL | 4.5393 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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