2,2'-Bipyridine   中文名称: 2,2'-联吡啶

一种 CAE/COL 型 2,2'-联吡啶类似物 COL H 在斑马鱼氧化应激体内模型中测试了神经保护活性。用 1 µM COL H 处理可使凋亡细胞的出现减少约 60%。[1]
在平行实验中，在同一斑马鱼模型中，1 µM COL A 处理使细胞凋亡率降低了 44%。[1]
评估了 COL H 对肿瘤细胞系 A549、HCT116 和 MDA-MB-231 的细胞毒活性。据报道，其对所有三种细胞系的半数抑制浓度 (IC₅₀) 值均高于 100 µM，表明细胞毒活性较弱。[1]
测试了几种 CAE 类似物 (cyanogriside E, F, G, H) 对各种人类癌细胞系的细胞毒作用。Cyanogriside F 和 G 对 HCT116 和 HL-60 细胞显示出细胞毒性，IC₅₀ 值分别为 0.8/3.6 µM 和 3.1/2.0 µM。Cyanogriside E 和 H 对 K562 细胞具有细胞毒性，IC₅₀ 值分别为 6.0 µM 和 0.8 µM。[1]

2,2'-联吡啶（40 mg/kg；皮下注射；一次）在高血压高血糖（2 小时内升高 53.8 mg/100 mL）后 24 小时内引起暂时性低血压，但不会导致长期糖尿病 [2]。

在斑马鱼体内模型中评估了 COL H 的神经保护作用。用浓度为 1 µM 的 COL H 处理斑马鱼，并量化凋亡细胞出现的减少，作为其对氧化应激神经保护作用的衡量指标。[1]
对于细胞毒活性测定，用各种 CAE/COL 型 2,2'-联吡啶化合物 (例如 COL H，cyanogrisides E-H) 处理肿瘤细胞系 (A549, HCT116, MDA-MB-231, HCT116, HL-60, K562)。测量细胞活力，并计算半数抑制浓度 (IC₅₀) 值以确定细胞毒作用的效力。[1]

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.

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/

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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.

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.

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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.

[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.

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.

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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.

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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]

C10H8N2

156.1839

156.068

366-18-7

1474

White to off-white solid powder

1.1±0.1 g/cm3

272.5±0.0 °C at 760 mmHg

70-73 °C(lit.)

107.2±12.0 °C

0.0±0.5 mmHg at 25°C

1.581

1.28

25.78

0

2

1

12

120

0

ROFVEXUMMXZLPA-UHFFFAOYSA-N

InChI=1S/C10H8N2/c1-3-7-11-9(5-1)10-6-2-4-8-12-10/h1-8H

2-pyridin-2-ylpyridine

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~100 mg/mL (~640.29 mM)

配方 1 中的溶解度: ≥ 3 mg/mL (19.21 mM) (饱和度未知) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将100 μL 30.0 mg/mL 澄清的 DMSO 储备液加入到400 μL PEG300中，混匀；再向上述溶液中加入50 μL Tween-80，混匀；然后加入450 μL 生理盐水定容至1 mL。
*生理盐水的制备：将 0.9 g 氯化钠溶解在 100 mL ddH₂O中，得到澄清溶液。

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配方 2 中的溶解度: ≥ 3 mg/mL (19.21 mM) (饱和度未知) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 30.0 mg/mL澄清DMSO储备液加入900 μL 20% SBE-β-CD生理盐水溶液中，混匀。
*20% SBE-β-CD 生理盐水溶液的制备（4°C，1 周）：将 2 g SBE-β-CD 溶解于 10 mL 生理盐水中，得到澄清溶液。

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配方 3 中的溶解度: ≥ 3 mg/mL (19.21 mM) (饱和度未知) in 10% DMSO + 90% Corn Oil (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 30.0 mg/mL 澄清 DMSO 储备液加入到 900 μL 玉米油中并混合均匀。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
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