Page last updated: 2024-12-11
pironetin
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
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Protein Interactions
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Description
pironetin: a microbial secondary metabolite having the activity of shortening plant height from Streptomyces sp.; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 6438891 |
| CHEMBL ID | 1779811 |
| CHEBI ID | 189353 |
| SCHEMBL ID | 8940436 |
| SCHEMBL ID | 8940434 |
| MeSH ID | M0234093 |
Synonyms (18)
| Synonym |
|---|
| pironetin |
| (2r,3r)-3-ethyl-2-[(e,2r,3s,4r,5s)-2-hydroxy-4-methoxy-3,5-dimethylnon-7-enyl]-2,3-dihydropyran-6-one |
| 151519-02-7 |
| CHEBI:189353 |
| CHEMBL1779811 |
| 2h-pyran-2-one, 5-ethyl-5,6-dihydro-6-(2-hydroxy-4-methoxy-3,5-dimethyl-7-nonenyl)-, (5r-(5alpha,6alpha(2r*,3s*,4r*,5s*,7e)))- |
| 5-ethyl-5,6-dihydro-6-(2-hydroxy-4-methoxy-3,5-dimethyl-7-nonenyl)-2h-pyran-2-one |
| pa 48153c |
| pa-48153c |
| SCHEMBL8940436 |
| SCHEMBL8940434 |
| CS-0065506 |
| HY-116446 |
| (5r,6r)-5-ethyl-5,6-dihydro-6-[(2r,3s,4r,5s,7e)-2-hydroxy-4-methoxy-3,5-dimethyl-7-nonen-1-yl]-2h-pyran-2-one |
| (-)-pironetin |
| bdbm50517653 |
| DTXSID601037185 |
| AKOS040742423 |
Research Excerpts
Overview
Pironetin is a natural product with potent antiproliferative activity against several cancer cell lines. It inhibits cell division by forming a covalent adduct with α-tubulin via a Michael addition into the product's lactone.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Pironetin is an α-tubulin-binding natural product with potent antiproliferative activity against several cancer cell lines that inhibits cell division by forming a covalent adduct with α-tubulin via a Michael addition into the natural product's α,β-unsaturated lactone. " | ( Synthesis and evaluation of C2 functionalized analogs of the α-tubulin-binding natural product pironetin. Georg, GI; Huang, DS; Wong, HL, 2018) | 2.14 |
| "Pironetin is a natural product that displays promising anticancer properties by binding to and potently inhibiting tubulin assembly into microtubules; however, its molecular mechanism of action remained obscure." | ( Pironetin Binds Covalently to αCys316 and Perturbs a Major Loop and Helix of α-Tubulin to Inhibit Microtubule Formation. Bargsten, K; Diaz, JF; Murga, J; Prota, AE; Setter, J; Steinmetz, MO; Waight, AB, 2016) | 2.6 |
| "Pironetin is a natural product with potent antiproliferative activity that forms a covalent adduct with α-tubulin via conjugate addition into the natural product's α,β-unsaturated lactone. " | ( Synthesis and Cytotoxicity Evaluation of C4- and C5-Modified Analogues of the α,β-Unsaturated Lactone of Pironetin. Georg, GI; Huang, DS; Wong, HL, 2017) | 2.11 |
| "Pironetin is a potent inhibitor of tubulin assembly and arrests cell cycle progression in M phase. " | ( The anticancer natural product pironetin selectively targets Lys352 of alpha-tubulin. Asao, T; Kanoh, N; Kitahara, T; Kondoh, M; Nakayama, H; Nishikawa, K; Osada, H; Tada, Y; Takio, K; Usui, T; Watanabe, H, 2004) | 2.05 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Drug Classes (1)
| Class | Description |
|---|---|
| aliphatic alcohol | An alcohol derived from an aliphatic compound. |
| [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 Targets (17)
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Tubulin alpha chain-like 3 | Homo sapiens (human) | GI50 | 0.0222 | 0.0222 | 0.0222 | 0.0223 | AID1572466; AID1572467 |
| Tubulin alpha chain-like 3 | Homo sapiens (human) | IC50 (µMol) | 0.0260 | 0.0260 | 0.0260 | 0.0260 | AID1572465 |
| Tubulin alpha-3C chain | Homo sapiens (human) | GI50 | 0.0222 | 0.0021 | 0.0088 | 0.0223 | AID1572466; AID1572467 |
| Tubulin alpha-3C chain | Homo sapiens (human) | IC50 (µMol) | 0.0260 | 0.0005 | 1.9555 | 10.0000 | AID1572465 |
| Tubulin alpha-1B chain | Homo sapiens (human) | GI50 | 0.0222 | 0.0021 | 0.0088 | 0.0223 | AID1572466; AID1572467 |
| Tubulin alpha-1B chain | Homo sapiens (human) | IC50 (µMol) | 0.0260 | 0.0005 | 1.9555 | 10.0000 | AID1572465 |
| Tubulin alpha-4A chain | Homo sapiens (human) | GI50 | 0.0222 | 0.0021 | 0.0088 | 0.0223 | AID1572466; AID1572467 |
| Tubulin alpha-4A chain | Homo sapiens (human) | IC50 (µMol) | 0.0260 | 0.0005 | 1.9555 | 10.0000 | AID1572465 |
| Tubulin alpha-3E chain | Homo sapiens (human) | GI50 | 0.0222 | 0.0021 | 0.0088 | 0.0223 | AID1572466; AID1572467 |
| Tubulin alpha-3E chain | Homo sapiens (human) | IC50 (µMol) | 0.0260 | 0.0005 | 1.9555 | 10.0000 | AID1572465 |
| Tubulin alpha-1A chain | Homo sapiens (human) | GI50 | 0.0222 | 0.0021 | 0.0088 | 0.0223 | AID1572466; AID1572467 |
| Tubulin alpha-1A chain | Homo sapiens (human) | IC50 (µMol) | 0.0260 | 0.0005 | 1.9555 | 10.0000 | AID1572465 |
| Tubulin alpha-1C chain | Homo sapiens (human) | GI50 | 0.0222 | 0.0021 | 0.0088 | 0.0223 | AID1572466; AID1572467 |
| Tubulin alpha-1C chain | Homo sapiens (human) | IC50 (µMol) | 0.0260 | 0.0005 | 1.9555 | 10.0000 | AID1572465 |
| Tubulin alpha-8 chain | Homo sapiens (human) | GI50 | 0.0222 | 0.0222 | 0.0222 | 0.0223 | AID1572466; AID1572467 |
| Tubulin alpha-8 chain | Homo sapiens (human) | IC50 (µMol) | 0.0260 | 0.0260 | 0.0260 | 0.0260 | AID1572465 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Other Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Tubulin beta-4A chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin beta chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin alpha-3C chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin alpha-1B chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin alpha-4A chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin beta-4B chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin beta-3 chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin beta-2A chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin beta-8 chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin alpha-3E chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin alpha-1A chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin alpha-1C chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin beta-6 chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin beta-2B chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| Tubulin beta-1 chain | Homo sapiens (human) | Activity | 15.0000 | 0.9000 | 3.3433 | 6.6000 | AID1189598 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (52)
Molecular Functions (21)
Ceullar Components (37)
Bioassays (77)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1633831 | Cytotoxicity against human MCF7 cells assessed as reduction in growth after 3 days by MTT assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1623547 | Cytotoxicity against human HCT15 cells after 48 hrs by sulforhodamine B assay | 2019 | Journal of natural products, 03-22, Volume: 82, Issue:3 | Structure Elucidation, Conformation, and Configuration of Cytotoxic 6-Heptyl-5,6-dihydro-2 H-pyran-2-ones from Hyptis Species and Their Molecular Docking to α-Tubulin. |
| AID1393348 | Binding affinity to alpha tubulin in human A2780 cells assessed as disruption of tubulin polymerization by measuring reduction in cell proliferation after 48 hrs by CellTiter non-radioactive assay | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Synthesis and evaluation of C2 functionalized analogs of the α-tubulin-binding natural product pironetin. |
| AID598271 | Induction of abberant mitosis in human A549 cells assessed as metaphase mitotic cells with DNA forming a ring surrounding mono-aster of microtubule at 50 nM after 4 hrs relative to control | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1572456 | Protein binding in mouse plasma | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1633825 | Toxicity in CDF1-SLC mouse injected with mouse P388 cells assessed as change in body weight at 0.78 mg/kg, ip treated for 5 days and measured on day 1 and 10 (Rvb = 5.3g) | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID598274 | Inhibition of tubulin assembly assessed as concentration of tubulin required to produce assembly at 25 uM after 30 mins | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1165179 | Cytotoxicity against human HT-29 cells assessed as inhibition of cell growth after 72 hrs by MTT assay | 2014 | European journal of medicinal chemistry, Nov-24, Volume: 87 | Design and synthesis of pironetin analogue/combretastatin A-4 hybrids containing a 1,2,3-triazole ring and evaluation of their cytotoxic activity. |
| AID598264 | Cytotoxicity against compound-resistant human A2780AD cells after 24 hrs by MTT assay | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1572458 | Inhibition of CYP2C9 (unknown origin) using tolbutamide as substrate | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1633821 | Cytotoxicity against C57BL/6 mouse EL4 cells assessed as reduction in growth after 3 days | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1633834 | Cytotoxicity against human T98G cells assessed as reduction in growth after 4 days by MTS assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1572460 | Inhibition of CYP3A4 (unknown origin) using midazolam as substrate | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1633823 | Cytotoxicity against human H69/Txl cells assessed as reduction in growth after 7 days by MTT assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1633843 | Antitumor activity in CDF1-SLC mouse injected with mouse P388 cells assessed as mean survival time at 6.25 mg/kg, ip treated for 5 days (Rvb = 11.2 +/- 0.84 days) | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1572455 | Protein binding in human plasma | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1633824 | Cytotoxicity against human H69/VDS cells assessed as reduction in growth after 7 days by MTT assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID598263 | Cytotoxicity against compound-sensitive human A2780 cells after 24 hrs by MTT assay | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1633833 | Cytotoxicity against mouse P388 cells assessed as reduction in growth after 24 hrs by MTT assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1165182 | Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human HT-29 cells | 2014 | European journal of medicinal chemistry, Nov-24, Volume: 87 | Design and synthesis of pironetin analogue/combretastatin A-4 hybrids containing a 1,2,3-triazole ring and evaluation of their cytotoxic activity. |
| AID1633842 | Antitumor activity in CDF1-SLC mouse injected with mouse P388 cells assessed as mean survival time at 3.13 mg/kg, ip treated for 5 days (Rvb = 11.2 +/- 0.84 days) | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1238300 | Inhibition of VEGF mRNA expression in human HT-29 cells assessed as VEGF mRNA level at 5 ug/ml incubated for 48 hrs by RT-PCR method relative to control | 2015 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16 | Inhibitory effect of pironetin analogue/colchicine hybrids on the expression of the VEGF, hTERT and c-Myc genes. |
| AID1633841 | Antitumor activity in CDF1-SLC mouse injected with mouse P388 cells assessed as mean survival time at 1.56 mg/kg, ip treated for 5 days (Rvb = 11.2 +/- 0.84 days) | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1572449 | Stability in human serum assessed as compound remaining at 1.10 mg after 24 hrs by HPLC analysis | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1238302 | Inhibition of Myc mRNA expression in human HT-29 cells assessed as Myc mRNA level at 5 ug/ml incubated for 48 hrs by RT-PCR method relative to control | 2015 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16 | Inhibitory effect of pironetin analogue/colchicine hybrids on the expression of the VEGF, hTERT and c-Myc genes. |
| AID1393347 | Binding affinity to alpha tubulin in human A2780 cells assessed as disruption of tubulin polymerization by measuring cell proliferation at higher concentration after 48 hrs by CellTiter non-radioactive assay relative to control | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Synthesis and evaluation of C2 functionalized analogs of the α-tubulin-binding natural product pironetin. |
| AID1165180 | Cytotoxicity against human MCF7 cells assessed as inhibition of cell growth after 72 hrs by MTT assay | 2014 | European journal of medicinal chemistry, Nov-24, Volume: 87 | Design and synthesis of pironetin analogue/combretastatin A-4 hybrids containing a 1,2,3-triazole ring and evaluation of their cytotoxic activity. |
| AID1165183 | Selectivity index, ratio of IC50 for HEK293 cells to IC50 for human MCF7 cells | 2014 | European journal of medicinal chemistry, Nov-24, Volume: 87 | Design and synthesis of pironetin analogue/combretastatin A-4 hybrids containing a 1,2,3-triazole ring and evaluation of their cytotoxic activity. |
| AID1238301 | Inhibition of hTERT mRNA expression in human HT-29 cells assessed as hTERT mRNA level at 5 ug/ml incubated for 48 hrs by RT-PCR method relative to control | 2015 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16 | Inhibitory effect of pironetin analogue/colchicine hybrids on the expression of the VEGF, hTERT and c-Myc genes. |
| AID1189598 | Inhibition of purified tubulin (unknown origin) assessed as critical concentration of tubulin required to produce assembly at 25 uM after 30 mins by spectrophotometry (Rvb = 3.3 +/- 0.1 uM) | 2014 | Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24 | Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. |
| AID1633827 | Cytotoxicity against human HL60 cells assessed as reduction in growth after 24 hrs by MTT assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1633835 | Cytotoxicity against hamster VCRd5L cells assessed as reduction in growth after 4 days by HCS assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1572454 | Half life in rat liver microsomes in presence of NADPH regeneration system by LC-MS/MS analysis | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1633819 | Cytotoxicity against human A549 cells assessed as reduction in growth after 4 days by HCS assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1189590 | Selectivity ratio of IC50 for human HEK293 cells to IC50 for human MCF7 cells | 2014 | Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24 | Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. |
| AID598270 | Induction of abberant mitosis in human A549 cells assessed as metaphase mitotic cells with type III mitotic spindles at 50 nM after 4 hrs relative to control | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1633829 | Cytotoxicity against human K562 cells assessed as reduction in growth after 4 days by MTT assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID598262 | Cell cycle arrest in human A549 cells assessed accumulation at G2/M phase at 50 nM after 20 hrs by propidium iodide staining-based flow cytometry | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1572450 | Stability in mouse serum assessed as compound remaining at 1.30 ml after 24 hrs by HPLC analysis | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1633838 | Toxicity in CDF1-SLC mouse injected with mouse P388 cells assessed as change in body weight at 3.13 mg/kg, ip treated for 5 days and measured on day 1 and 10 (Rvb = 5.3g) | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1633828 | Cytotoxicity against rat KNRK cells assessed as reduction in growth | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1189587 | Cytotoxicity against human MCF7 cells after 3 days by MTT assay | 2014 | Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24 | Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. |
| AID1189601 | Resistance factor, ratio of IC50 for human A2780AD cells to IC50 for human A2780 cells | 2014 | Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24 | Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. |
| AID1572461 | Inhibition of CYP3A4 (unknown origin) using testosterone as substrate | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1165181 | Cytotoxicity against HEK293 cells assessed as inhibition of cell growth after 72 hrs by MTT assay | 2014 | European journal of medicinal chemistry, Nov-24, Volume: 87 | Design and synthesis of pironetin analogue/combretastatin A-4 hybrids containing a 1,2,3-triazole ring and evaluation of their cytotoxic activity. |
| AID1572453 | Half life in mouse liver microsomes in presence of NADPH regeneration system by LC-MS/MS analysis | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1633832 | Cytotoxicity against human MDA-MB-231 cells assessed as reduction in growth after 4 days by HCS assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1189600 | Cytotoxicity against human A2780AD cells after 24 hrs by MTT assay | 2014 | Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24 | Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. |
| AID598265 | Resistance index, ratio of IC50 for human compound-sensitive A2780 cells to IC50 for human compound-resistant A2780AD cells | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1572462 | Drug metabolism in human liver microsomes assessed as formation of epoxypironetin after 30 mins by LC-MS/MS analysis | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID598277 | Binding affinity to tubulin after 15 min | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1633822 | Cytotoxicity against human H69 cells assessed as reduction in growth after 7 days by MTT assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1572467 | Inhibition of tubulin alpha in human A2780CP cells assessed as cell growth inhibition after 48 hrs by MTT assay | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1623546 | Cytotoxicity against human HeLa cells after 48 hrs by sulforhodamine B assay | 2019 | Journal of natural products, 03-22, Volume: 82, Issue:3 | Structure Elucidation, Conformation, and Configuration of Cytotoxic 6-Heptyl-5,6-dihydro-2 H-pyran-2-ones from Hyptis Species and Their Molecular Docking to α-Tubulin. |
| AID1633839 | Toxicity in CDF1-SLC mouse injected with mouse P388 cells assessed as change in body weight at 6.25 mg/kg, ip treated for 5 days and measured on day 1 and 10 (Rvb = 5.3g) | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1189586 | Cytotoxicity against human HT-29 cells after 3 days by MTT assay | 2014 | Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24 | Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. |
| AID1572451 | Stability in rat serum assessed as compound remaining after 24 hrs | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1572465 | Inhibition of tubulin alpha in human A2780 cells assessed as reduction in cell growth | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1572463 | Drug metabolism in human liver microsomes assessed as formation of demethylpironetin after 30 mins by LC-MS/MS analysis | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1633826 | Cytotoxicity against human HeLa cells assessed as reduction in growth | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID598268 | Induction of apoptosis in human A549 cells after 20 hrs | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1572466 | Inhibition of tubulin alpha in human A2780 cells assessed as cell growth inhibition after 48 hrs by MTT assay | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1393349 | Binding affinity to alpha tubulin in human OVCAR5 cells assessed as disruption of tubulin polymerization by measuring reduction in cell proliferation after 48 hrs by CellTiter non-radioactive assay | 2018 | Bioorganic & medicinal chemistry letters, 09-01, Volume: 28, Issue:16 | Synthesis and evaluation of C2 functionalized analogs of the α-tubulin-binding natural product pironetin. |
| AID1633836 | Immunosuppressive activity in C3/HeN mouse injected with C57BL/6 mouse EL4 cells assessed as cytotoxic T cells generation by measuring specific lysis level at 5 mg/kg, ip treated for 2 to 15 days and measured on day 16 by gamma scintillation counter metho | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1572452 | Half life in human liver microsomes in presence of NADPH regeneration system by LC-MS/MS analysis | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1189599 | Cytotoxicity against human A2780 cells after 24 hrs by MTT assay | 2014 | Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24 | Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. |
| AID1189589 | Selectivity ratio of IC50 for human HEK293 cells to IC50 for human HT29 cells | 2014 | Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24 | Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. |
| AID1572457 | Protein binding in rat plasma | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1572459 | Inhibition of CYP2D6 (unknown origin) using dextromethorphan as substrate | 2019 | Journal of medicinal chemistry, 02-14, Volume: 62, Issue:3 | Identification of the Metabolic Profile of the α-Tubulin-Binding Natural Product (-)-Pironetin. |
| AID1633840 | Antitumor activity in CDF1-SLC mouse injected with mouse P388 cells assessed as mean survival time at 0.78 mg/kg, ip treated for 5 days (Rvb = 11.2 +/- 0.84 days) | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1238299 | Inhibition of VEGF production in human HT-29 cells assessed as VEGF level at 5 ug/ml incubated for 72 hrs by ELISA method relative to control | 2015 | Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16 | Inhibitory effect of pironetin analogue/colchicine hybrids on the expression of the VEGF, hTERT and c-Myc genes. |
| AID1189588 | Cytotoxicity against human HEK293 cells after 3 days by MTT assay | 2014 | Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24 | Design and synthesis of pironetin analogue/colchicine hybrids and study of their cytotoxic activity and mechanisms of interaction with tubulin. |
| AID1633837 | Toxicity in CDF1-SLC mouse injected with mouse P388 cells assessed as change in body weight at 1.56 mg/kg, ip treated for 5 days and measured on day 1 and 10 (Rvb = 5.3g) | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID598269 | Induction of microtubule cytoskeleton depolymerization in human A549 cells at 50 nM after 4 hrs by immunofluorescence assay | 2011 | European journal of medicinal chemistry, May, Volume: 46, Issue:5 | Design and synthesis of pironetin analogues with simplified structure and study of their interactions with microtubules. |
| AID1623545 | Cytotoxicity against human MCF7 cells after 48 hrs by sulforhodamine B assay | 2019 | Journal of natural products, 03-22, Volume: 82, Issue:3 | Structure Elucidation, Conformation, and Configuration of Cytotoxic 6-Heptyl-5,6-dihydro-2 H-pyran-2-ones from Hyptis Species and Their Molecular Docking to α-Tubulin. |
| AID1633830 | Cytotoxicity against human K562/ADR cells assessed as reduction in growth after 4 days by MTT assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| AID1633820 | Cytotoxicity against hamster DC-3F cells assessed as reduction in growth after 4 days by HCS assay | 2019 | Bioorganic & medicinal chemistry letters, 08-01, Volume: 29, Issue:15 | Revisiting microtubule targeting agents: α-Tubulin and the pironetin binding site as unexplored targets for cancer therapeutics. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (38)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 7 (18.42) | 18.2507 |
| 2000's | 13 (34.21) | 29.6817 |
| 2010's | 16 (42.11) | 24.3611 |
| 2020's | 2 (5.26) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 22.64
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 moderate demand-to-supply ratio for research on this compound.
| This Compound (22.64) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 2 (5.13%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 37 (94.87%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||