2-(3-carboxy-2-pyridinyl)-3-pyridinecarboxylic acid, also known as **dipicolinic acid (DPA)**, is a small, rigid, bidentate chelating agent with two carboxylic acid groups.
**Importance for Research:**
**1. Biomarker for Bacterial Spores:**
* DPA is a major component of the spore core of many bacterial species, including *Bacillus* and *Clostridium*.
* It is present in high concentrations (up to 15% of dry weight) and is essential for spore resistance to heat, radiation, and chemicals.
* DPA's presence can be used as a biomarker for the presence of bacterial spores, which is crucial in fields like food safety, bioterrorism detection, and medical diagnostics.
**2. Antimicrobial Activity:**
* DPA exhibits antimicrobial activity against a range of bacteria, including *Staphylococcus aureus* and *Escherichia coli*.
* Its mechanism of action involves chelating metal ions essential for bacterial growth, disrupting bacterial metabolism.
* This has led to research on its potential use as an antimicrobial agent in various applications.
**3. Chemical & Material Science Applications:**
* DPA is used as a chelating agent in metal extraction and purification processes.
* It also finds applications in organic synthesis as a catalyst and a ligand in coordination chemistry.
* Its ability to form stable metal complexes is also explored in the development of new materials, including sensors and luminescent materials.
**4. Biological Research Tools:**
* DPA's ability to bind metal ions has made it a valuable tool in biological research.
* It is used to study metal ion transport and metabolism in cells.
* DPA is also a fluorescent probe for metal ion detection in various biological systems.
**5. Environmental Applications:**
* DPA is being investigated for its potential use in environmental remediation.
* It can be used to remove heavy metals from contaminated water and soil.
* Research is ongoing to develop more efficient and environmentally friendly applications of DPA.
In summary, 2-(3-carboxy-2-pyridinyl)-3-pyridinecarboxylic acid (dipicolinic acid) is a versatile molecule with diverse applications in various fields, primarily due to its chelating properties and its unique role in bacterial spore formation.
| ID Source | ID |
|---|---|
| PubMed CID | 681885 |
| CHEMBL ID | 1577802 |
| CHEBI ID | 107744 |
| SCHEMBL ID | 270419 |
| Synonym |
|---|
| OPREA1_020777 |
| CBDIVE_002636 |
| 2,2'-bipyridine-3,3'-dicarboxylic acid |
| smr000021311 |
| MLS000085982 , |
| CHEMDIV2_002789 |
| STK369226 |
| 2,2'-bipyridine-3,3'-dicarboxylic acid, 97% |
| CHEBI:107744 |
| 2-(3-carboxy-2-pyridyl)pyridine-3-carboxylic acid |
| 2,2'-bipyridine-3,3-dicarboxylic acid |
| AKOS000268280 |
| HMS1376O17 |
| 2-(3-carboxypyridin-2-yl)pyridine-3-carboxylic acid |
| 4433-01-6 |
| B3622 |
| 2,2'-binicotinic acid |
| HMS2349A23 |
| [2,2'-bipyridine]-3,3'-dicarboxylic acid |
| F3055-0215 |
| SCHEMBL270419 |
| CHEMBL1577802 |
| W-200588 |
| 2-(3-carboxy-2-pyridinyl)-3-pyridinecarboxylic acid |
| cid_681885 |
| bdbm68526 |
| 2-(3-carboxy-2-pyridyl)nicotinic acid |
| Q27186071 |
| sr-01000091653 |
| SR-01000091653-1 |
| mfcd00226068 |
| 2,2'-bipyridyl-3,3'-dicarboxylic acid |
| DTXSID90350521 |
| AC-8995 |
| LT0045 |
| CS-W004579 |
| FT-0761526 |
| 2,2 inverted exclamation mark -bipyridine-3,3 inverted exclamation mark -dicarboxylic acid |
| SY052696 |
| DS-17417 |
| A918629 |
| YSWG613 |
| Class | Description |
|---|---|
| bipyridines | Compounds containing a bipyridine group. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, TYROSYL-DNA PHOSPHODIESTERASE | Homo sapiens (human) | Potency | 17.7828 | 0.0040 | 23.8416 | 100.0000 | AID485290 |
| Chain A, JmjC domain-containing histone demethylation protein 3A | Homo sapiens (human) | Potency | 19.9526 | 0.6310 | 35.7641 | 100.0000 | AID504339 |
| Chain A, 2-oxoglutarate Oxygenase | Homo sapiens (human) | Potency | 39.8107 | 0.1778 | 14.3909 | 39.8107 | AID2147 |
| phosphopantetheinyl transferase | Bacillus subtilis | Potency | 79.4328 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
| nonstructural protein 1 | Influenza A virus (A/WSN/1933(H1N1)) | Potency | 12.5893 | 0.2818 | 9.7212 | 35.4813 | AID2326 |
| euchromatic histone-lysine N-methyltransferase 2 | Homo sapiens (human) | Potency | 56.2341 | 0.0355 | 20.9770 | 89.1251 | AID504332 |
| DNA polymerase iota isoform a (long) | Homo sapiens (human) | Potency | 89.1251 | 0.0501 | 27.0736 | 89.1251 | AID588590 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| glycogen synthase kinase-3 beta isoform 1 | Homo sapiens (human) | EC50 (µMol) | 300.0000 | 0.2125 | 22.1562 | 83.9400 | AID434954 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
| AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| AID1230192 | Binding affinity to Fe(2) assessed as half maximal concentration required for binding 20 uM Fe(2) in pH 7.0 sodium phosphate buffer | 2015 | Bioorganic & medicinal chemistry, Jul-01, Volume: 23, Issue:13 | Selective inhibition of prolyl 4-hydroxylases by bipyridinedicarboxylates. |
| AID1494470 | Inhibition of Rickettsia prowazekii N-terminal His6-tagged methionine aminopeptidase 1 expressed in Escherichia coli DLB3 Rosetta cells at 10 uM using Met-AMC as substrate preincubated for 1 hr followed by 30 mins incubation after substrate addition measu | 2018 | Bioorganic & medicinal chemistry letters, 05-01, Volume: 28, Issue:8 | The identification of inhibitory compounds of Rickettsia prowazekii methionine aminopeptidase for antibacterial applications. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 1 (14.29) | 29.6817 |
| 2010's | 5 (71.43) | 24.3611 |
| 2020's | 1 (14.29) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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 weak demand-to-supply ratio for research on this compound.
| This Compound (12.29) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 7 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||