Physicochemical Properties
| Molecular Formula | C10H8N2 |
| Molecular Weight | 156.1839 |
| Exact Mass | 156.068 |
| CAS # | 366-18-7 |
| PubChem CID | 1474 |
| Appearance | White to off-white solid powder |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 272.5±0.0 °C at 760 mmHg |
| Melting Point | 70-73 °C(lit.) |
| Flash Point | 107.2±12.0 °C |
| Vapour Pressure | 0.0±0.5 mmHg at 25°C |
| Index of Refraction | 1.581 |
| LogP | 1.28 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Heavy Atom Count | 12 |
| Complexity | 120 |
| Defined Atom Stereocenter Count | 0 |
| InChi Key | ROFVEXUMMXZLPA-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H |
| Chemical Name | 2-pyridin-2-ylpyridine |
| 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) |
Biological Activity
| ln Vitro |
A CAE/COL-type 2,2'-bipyridine analog, COL H, was tested for neuroprotective activity in an in vivo zebrafish model of oxidative stress. The treatment with 1 µM COL H reduced the appearance of apoptotic cells by approximately 60%. [1] In a parallel experiment, 1 µM COL A treatment in the same zebrafish model reduced the apoptosis rate by 44%. [1] COL H was evaluated for cytotoxic activity against tumor cell lines A549, HCT116, and MDA-MB-231. The half-maximal inhibitory concentration (IC₅₀) values against all three cell lines were reported to be higher than 100 µM, indicating weak cytotoxic activity. [1] Several CAE analogs (cyanogriside E, F, G, H) were tested for cytotoxic effects on various human cancer cell lines. Cyanogriside F and G showed cytotoxicity against HCT116 and HL-60 cells with IC₅₀ values of 0.8/3.6 µM and 3.1/2.0 µM, respectively. Cyanogriside E and H were cytotoxic against K562 cells with IC₅₀ values of 6.0 µM and 0.8 µM, respectively. [1] |
| ln Vivo | 2,2'-Bipyridyl (40 mg/kg; sc; once) causes a temporary hypotension within 24 hours of a hypertensive hyperglycemia (53.8 mg/100 mL rise over 2 hours) without leading to long-term diabetes [2]. |
| Cell Assay |
The neuroprotective effect of COL H was assessed in an in vivo zebrafish model. Zebrafish were treated with COL H at a concentration of 1 µM, and the reduction in the appearance of apoptotic cells was quantified as a measure of neuroprotection against oxidative stress. [1] For cytotoxic activity assays, tumor cell lines (A549, HCT116, MDA-MB-231, HCT116, HL-60, K562) were treated with various CAE/COL-type 2,2'-bipyridine compounds (e.g., COL H, cyanogrisides E-H). Cell viability was measured, and the half-maximal inhibitory concentration (IC₅₀) values were calculated to determine the potency of cytotoxic effects. [1] |
| Animal Protocol |
Animal/Disease Models: Male Holtzman rat (6-8 weeks old)[2]. Doses: 40 mg/kg Route of Administration: subcutaneous injection; once. Experimental Results: Displayed hyperglycemic activity. |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion PYRIDINE & ITS ALKYL DERIVATIVES ARE ABSORBED FROM GI TRACT, INTRAPERITONEAL CAVITY & LUNGS. PERITONEAL ABSORPTION IS APPARENTLY ONLY SLIGHTLY MORE RAPID & COMPLETE THAN GI ABSORPTION ... IN GENERAL THE BASES ARE RAPIDLY ABSORBED THROUGH INTACT SKIN. /ALKYL DERIVATIVES OF PYRIDINE/ Metabolism / Metabolites 2,2'-BIPYRIDINE INHIBITED AROMATIC HYDROXYLATION IN MICROSOMES DERIVED FROM 3-METHYLCHOLANTHRENE TREATED RATS & ENHANCED THIS PROCESS IN MICROSOMES FROM PHENOBARBITAL SODIUM TREATED RATS. 2,2'-BIPYRIDINE PRODUCED A TYPE I BINDING SPECTRUM WITH AEROBIC MICROSOMAL FRACTIONS FROM PHENOBARBITAL SODIUM TREATED RATS & A TYPE II BINDING SPECTRUM WITH MICROSOMES FROM 3-METHYLCHOLANTHRENE TREATED RATS. |
| Toxicity/Toxicokinetics |
Interactions 2,2'-BIPYRIDINE AT CONCENTRATIONS OF 1.0-5.0 MILLIMOLE GREATLY INCREASED THE COVALENT BINDING OF (14)C-LABELED CARBON TETRACHLORIDE TO RAT LIVER MICROSOMES. BIOTRANSFORMATION OF M-FLUOROTYROSINE BY TYROSINE METABOLIC PATHWAY OF THE LIVER PLAYED AN IMPORTANT ROLE IN THE ELICITATION OF CONVULSIONS IN MICE BY M-FLUOROTYROSINE. SIMULTANEOUS ADMINISTRATION OF M-FLUOROTYROSINE & ALPHA,ALPHA-DIPYRIDYL PREVENTED THE APPEARANCE OF M-FLUOROTYROSINE INDUCED SEIZURES. Non-Human Toxicity Values LD50 Rat oral 256 mg/kg LD50 Rat sc 155 mg/kg LD50 Rat oral 100 mg/kg LD50 Rat ip 150 mg/kg For more Non-Human Toxicity Values (Complete) data for 2,2'-BIPYRIDINE (6 total), please visit the HSDB record page. |
| References |
[1]. Discovery of caerulomycin/collismycin-type 2,2'-bipyridine natural products in the genomic era. J Ind Microbiol Biotechnol. 2019;46(3-4):459-468. [2]. The hyperglycemic activity of 2, 2'-bipyridine. Journal of Pharmacology and Experimental Therapeutics, 1962, 135(3): 317-322. |
| Additional Infomation |
2,2'-bipyridine is a bipyridine in which the two pyridine moieties are linked by a bond between positions C-2 and C-2'. It has a role as a ferroptosis inhibitor and a chelator. 2,2'-Bipyridine has been reported in Dichilus gracilis, Dichilus lebeckioides, and other organisms with data available. A reagent used for the determination of iron. Mechanism of Action 2,2'-DIPYRIDYL, A CHELATOR OF IRON(+2) & INHIBITOR OF PLATELET AGGREGATION WAS STUDIED TO DETERMINE THE MECHANISM OF ITS EFFECTS ON PLATELETS. AT LOW CONCENTRATIONS REQUIRED TO INHIBIT ARACHIDONIC ACID-MEDIATED AGGREGATION, 2,2'-DIPYRIDYL & 4,4'DIPYRIDYL-2HCL INHIBITED THE PLATELET CYCLOOXYGENASE. THE MECHANISM OF INHIBITION OF ADP-INDUCED AGGREGATION WAS INDUCED AGGREGATION, 2,2'-DIPYRIDYL DID NOT ALTER CELL ULTRASTRUCTURE, SEROTONIN OR NUCLEOTIDE CONTENT, OR INTERFERE WITH RELEASE OF ARACHIDONIC ACID-(14)C OR CALCIUM MOVEMENTS. APPARENTLY, THE INHIBITION OF CYCLOOXYGENASE BY LOW CONCENTRATIONS OF THESE COMPOUNDS IS NOT DUE TO BIDENTATE IRON CHELATION, SINCE 4,4'-DIPYRIDYL WAS ALMOST AS EFFECTIVE AS 2,2'-DIPYRIDYL, BUT IS COMPATIBLE WITH BINDING OF THESE INHIBITORS TO THE FE IN THE HEME OF THE CYCLOOXYGENASE. The core chemical scaffold of CAE (Caerulomycin) and COL (Collismycin) natural products is a 2,2'-bipyridine (2,2'-BP) heterocycle. These are a class of microbial natural products. [1] The review discusses strategies for discovering new members of the CAE/COL-type 2,2'-bipyridine family, including traditional isolation, biosynthetic pathway engineering, and bioinformatics-guided genome mining. [1] Biosynthetic studies have elucidated the genetic basis and enzymatic steps for constructing the 2,2'-bipyridine scaffold, which involves a hybrid polyketide synthase-nonribosomal peptide synthetase (PKS-NRPS) assembly line. [1] By engineering the tailoring modification steps in the biosynthetic pathways (e.g., via gene inactivation), multiple novel analogs of COL (e.g., COL SN, SC, C, DH, H, DA, D, DN, DS, H1-H5) and CAE (e.g., cyanogriside E-G, H) were generated to expand structural diversity. [1] COL H, one of the pathway intermediates/analogs, has been identified as having potential neuroprotective activity. [1] Some synthetic analogs of CAE (Caerulomycin A) have been patented for use as immunosuppressive agents, and COL (Collismycin) derivatives have been patented as oxidative stress inhibitors, indicating broader therapeutic potential beyond the specific activities reported in this review. [1] |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~640.29 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 3 mg/mL (19.21 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 30.0 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: ≥ 3 mg/mL (19.21 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 30.0 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. Solubility in Formulation 3: ≥ 3 mg/mL (19.21 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 30.0 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 | 6.4029 mL | 32.0143 mL | 64.0287 mL | |
| 5 mM | 1.2806 mL | 6.4029 mL | 12.8057 mL | |
| 10 mM | 0.6403 mL | 3.2014 mL | 6.4029 mL |