Page last updated: 2024-12-05

4,4'-dimethyl-2,2'-bipyridine

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Description

4,4'-dimethyl-2,2'-bipyridine is a chelating ligand commonly used in coordination chemistry and catalysis. It is synthesized by reacting 2,2'-bipyridine with methyl iodide in the presence of a base. 4,4'-dimethyl-2,2'-bipyridine forms stable complexes with a wide range of transition metals, including ruthenium, osmium, and iron. These complexes exhibit diverse properties, such as luminescence, redox activity, and catalytic activity. For instance, ruthenium complexes of 4,4'-dimethyl-2,2'-bipyridine are employed as photosensitizers in dye-sensitized solar cells. The presence of the methyl groups on the bipyridine backbone enhances the electron-donating ability of the ligand, which influences the electronic properties of the metal complexes and their applications. 4,4'-dimethyl-2,2'-bipyridine is extensively studied due to its ability to fine-tune the properties of metal complexes for various applications, including catalysis, photochemistry, and materials science.'

4,4'-dimethyl-2,2'-bipyridine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID14338
CHEMBL ID101165
SCHEMBL ID181893
MeSH IDM0560448

Synonyms (47)

Synonym
AC-5118
4,4'-dimethyl-[2,2']bipyridinyl
CHEMBL101165 ,
4,2'-dipyridyl
4,2'-bipyridine
2, 4,4'-dimethyl-
2,2'-bi-4-picoline
nsc3261
1134-35-6
nsc-3261
2,2'-bipyridyl, 4,4'-dimethyl-
nsc 3261
einecs 214-483-2
4,4'-dimethyl-2,2'-bipyridine
4,4'-dimethyl-2,2'-bipyridyl
4,4'-dimethyl-2,2'-dipyridyl
2,2'-bipyridine, 4,4'-dimethyl-
4,4'-dimethyl-2,2'-dipyridyl, 99.5%, purified by sublimation
4,4'-dimethyl-2,2'-dipyridyl, 99%
2,2'-di-4-picolyl
B0852
AKOS000344143
4-methyl-2-(4-methylpyridin-2-yl)pyridine
bdbm50401350
FT-0609153
SC11757
AM84345
SCHEMBL181893
SY011392
4,4 inverted exclamation mark -dimethyl-2,2 inverted exclamation mark -dipyridyl
mfcd00006441
4,4' dimethyl 2,2' bipyridine
4,4'-dimethyl 2,2'-bipyridine
4,4'dimethyl 2,2'bipyridine
DTXSID3061552
2,2'-bi(gamma-picoline)
CS-W002003
4,4'-dimethyl-2,2'-dipyridyl, for spectrophotometric det., >=99.0%
4,4/'-dimethyl-2,2/'-bipyridyl
4,4`-dimethyl-2,2`-dipyridyl
2,2-bi-4-picoline
BBL104382
STL558645
AS-17512
EN300-754538
HY-W002003
H79UAE6A72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
C-C chemokine receptor type 1Homo sapiens (human)IC50 (µMol)100.50000.00070.20022.5000AID716289
C-C chemokine receptor type 5Homo sapiens (human)IC50 (µMol)326.61400.00020.25679.0000AID716287
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
C-C chemokine receptor type 1Homo sapiens (human)EC50 (µMol)3.79051.50002.98566.3096AID716296
C-C chemokine receptor type 5Homo sapiens (human)EC50 (µMol)11.79460.00702.09365.0119AID716295
C-C chemokine receptor type 8Homo sapiens (human)EC50 (µMol)3.23110.48003.72297.9433AID716294
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (34)

Processvia Protein(s)Taxonomy
dendritic cell chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
monocyte chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
calcium ion transportC-C chemokine receptor type 1Homo sapiens (human)
intracellular calcium ion homeostasisC-C chemokine receptor type 1Homo sapiens (human)
exocytosisC-C chemokine receptor type 1Homo sapiens (human)
chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
immune responseC-C chemokine receptor type 1Homo sapiens (human)
cell adhesionC-C chemokine receptor type 1Homo sapiens (human)
cell surface receptor signaling pathwayC-C chemokine receptor type 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationC-C chemokine receptor type 1Homo sapiens (human)
cell-cell signalingC-C chemokine receptor type 1Homo sapiens (human)
response to woundingC-C chemokine receptor type 1Homo sapiens (human)
negative regulation of gene expressionC-C chemokine receptor type 1Homo sapiens (human)
cytokine-mediated signaling pathwayC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of cell migrationC-C chemokine receptor type 1Homo sapiens (human)
negative regulation of bone mineralizationC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of osteoclast differentiationC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of calcium ion transportC-C chemokine receptor type 1Homo sapiens (human)
chemokine-mediated signaling pathwayC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeC-C chemokine receptor type 1Homo sapiens (human)
positive regulation of monocyte chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
calcium-mediated signalingC-C chemokine receptor type 1Homo sapiens (human)
cell chemotaxisC-C chemokine receptor type 1Homo sapiens (human)
inflammatory responseC-C chemokine receptor type 1Homo sapiens (human)
MAPK cascadeC-C chemokine receptor type 5Homo sapiens (human)
dendritic cell chemotaxisC-C chemokine receptor type 5Homo sapiens (human)
calcium ion transportC-C chemokine receptor type 5Homo sapiens (human)
chemotaxisC-C chemokine receptor type 5Homo sapiens (human)
cellular defense responseC-C chemokine receptor type 5Homo sapiens (human)
cell surface receptor signaling pathwayC-C chemokine receptor type 5Homo sapiens (human)
G protein-coupled receptor signaling pathwayC-C chemokine receptor type 5Homo sapiens (human)
cell-cell signalingC-C chemokine receptor type 5Homo sapiens (human)
release of sequestered calcium ion into cytosol by sarcoplasmic reticulumC-C chemokine receptor type 5Homo sapiens (human)
calcium-mediated signalingC-C chemokine receptor type 5Homo sapiens (human)
signalingC-C chemokine receptor type 5Homo sapiens (human)
symbiont entry into host cellC-C chemokine receptor type 5Homo sapiens (human)
chemokine-mediated signaling pathwayC-C chemokine receptor type 5Homo sapiens (human)
response to cholesterolC-C chemokine receptor type 5Homo sapiens (human)
cellular response to lipopolysaccharideC-C chemokine receptor type 5Homo sapiens (human)
negative regulation of macrophage apoptotic processC-C chemokine receptor type 5Homo sapiens (human)
inflammatory responseC-C chemokine receptor type 5Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationC-C chemokine receptor type 5Homo sapiens (human)
immune responseC-C chemokine receptor type 5Homo sapiens (human)
cell chemotaxisC-C chemokine receptor type 5Homo sapiens (human)
chemotaxisC-C chemokine receptor type 8Homo sapiens (human)
cell adhesionC-C chemokine receptor type 8Homo sapiens (human)
G protein-coupled receptor signaling pathwayC-C chemokine receptor type 8Homo sapiens (human)
chemokine-mediated signaling pathwayC-C chemokine receptor type 8Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationC-C chemokine receptor type 8Homo sapiens (human)
immune responseC-C chemokine receptor type 8Homo sapiens (human)
cell chemotaxisC-C chemokine receptor type 8Homo sapiens (human)
calcium-mediated signalingC-C chemokine receptor type 8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
phosphatidylinositol phospholipase C activityC-C chemokine receptor type 1Homo sapiens (human)
chemokine receptor activityC-C chemokine receptor type 1Homo sapiens (human)
protein bindingC-C chemokine receptor type 1Homo sapiens (human)
C-C chemokine receptor activityC-C chemokine receptor type 1Homo sapiens (human)
C-C chemokine bindingC-C chemokine receptor type 1Homo sapiens (human)
chemokine (C-C motif) ligand 7 bindingC-C chemokine receptor type 1Homo sapiens (human)
chemokine (C-C motif) ligand 5 bindingC-C chemokine receptor type 1Homo sapiens (human)
virus receptor activityC-C chemokine receptor type 5Homo sapiens (human)
actin bindingC-C chemokine receptor type 5Homo sapiens (human)
phosphatidylinositol phospholipase C activityC-C chemokine receptor type 5Homo sapiens (human)
chemokine receptor activityC-C chemokine receptor type 5Homo sapiens (human)
protein bindingC-C chemokine receptor type 5Homo sapiens (human)
coreceptor activityC-C chemokine receptor type 5Homo sapiens (human)
C-C chemokine receptor activityC-C chemokine receptor type 5Homo sapiens (human)
C-C chemokine bindingC-C chemokine receptor type 5Homo sapiens (human)
identical protein bindingC-C chemokine receptor type 5Homo sapiens (human)
chemokine (C-C motif) ligand 5 bindingC-C chemokine receptor type 5Homo sapiens (human)
chemokine receptor activityC-C chemokine receptor type 8Homo sapiens (human)
coreceptor activityC-C chemokine receptor type 8Homo sapiens (human)
C-C chemokine receptor activityC-C chemokine receptor type 8Homo sapiens (human)
C-C chemokine bindingC-C chemokine receptor type 8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
plasma membraneC-C chemokine receptor type 1Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 1Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 1Homo sapiens (human)
cytoplasmC-C chemokine receptor type 1Homo sapiens (human)
cell surfaceC-C chemokine receptor type 5Homo sapiens (human)
endosomeC-C chemokine receptor type 5Homo sapiens (human)
plasma membraneC-C chemokine receptor type 5Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 5Homo sapiens (human)
cell surfaceC-C chemokine receptor type 5Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 5Homo sapiens (human)
cytoplasmC-C chemokine receptor type 5Homo sapiens (human)
plasma membraneC-C chemokine receptor type 8Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 8Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID716299Ratio of ZnBip EC50 to compound EC50 for human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716295Allosteric modulation at human CCR5 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as [3H]IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716296Allosteric modulation at human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as {3H]IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716293Binding affinity to Zn(II) after 2 hrs using FluoZin-3 by fuorescence assay2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716289Displacement of [125I]-CCL3 from human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr after 3 hrs2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID649473Antimycobacterial activity against Mycobacterium tuberculosis H37Rv after 6 days by MTT assay2012Bioorganic & medicinal chemistry, Mar-15, Volume: 20, Issue:6
Anti-mycobacterial activities of some cationic and anionic calix[4]arene derivatives.
AID158223In vitro antimalarial activity against chloroquine-sensitive Plasmodium falciparum D10; Not determined2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
In vitro antimalarial activity of a series of cationic 2,2'-bipyridyl- and 1,10-phenanthrolineplatinum(II) benzoylthiourea complexes.
AID716287Displacement of [125I]-CCL3 from human CCR5 transfected in COS7 cells coexpressing chimeric Gqi4myr after 3 hrs2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716294Allosteric modulation at human CCR8 transfected in COS7 cells assessed as [3H]IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID158225In vitro antimalarial activity against chloroquine-sensitive Plasmodium falciparum K1; Not determined2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
In vitro antimalarial activity of a series of cationic 2,2'-bipyridyl- and 1,10-phenanthrolineplatinum(II) benzoylthiourea complexes.
AID716286Displacement of [125I]-CCL3 from human CCR5 transfected in COS7 cells coexpressing chimeric Gqi4myr after 3 hrs relative to basal level2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716298Allosteric modulation at human CCR5 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as [3H]IP3 turnover by liquid scintillation counting analysis relative to basal level2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716301Ratio of ZnBip EC50 to compound EC50 for human CCR5 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716297Allosteric modulation at human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as [3H]IP3 turnover by liquid scintillation counting analysis relative to basal level2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID218537Inhibition of beta-hematin formation; Not active2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
In vitro antimalarial activity of a series of cationic 2,2'-bipyridyl- and 1,10-phenanthrolineplatinum(II) benzoylthiourea complexes.
AID716290Allosteric modulation at human CCR8 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as [3H]IP3 turnover by liquid scintillation counting analysis relative to basal level2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716288Displacement of [125I]-CCL3 from human CCR1 transfected in COS7 cells coexpressing chimeric Gqi4myr after 3 hrs relative to basal level2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID716292Ratio of ZnBip EC50 to compound EC50 for human CCR8 transfected in COS7 cells coexpressing chimeric Gqi4myr assessed as IP3 turnover by liquid scintillation counting analysis2012Journal of medicinal chemistry, Sep-27, Volume: 55, Issue:18
Modulation in selectivity and allosteric properties of small-molecule ligands for CC-chemokine receptors.
AID72976Ability to associate with Ferriprotoporphyrin IX; No association2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
In vitro antimalarial activity of a series of cationic 2,2'-bipyridyl- and 1,10-phenanthrolineplatinum(II) benzoylthiourea complexes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (7.14)29.6817
2010's13 (92.86)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.34

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index35.34 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.91 (4.65)
Search Engine Demand Index44.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.34)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]