apogossypol: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 454878 |
| CHEMBL ID | 551288 |
| SCHEMBL ID | 2513478 |
| MeSH ID | M0475080 |
| Synonym |
|---|
| cndo-103 |
| nsc-736630 |
| 5-isopropyl-3-methyl-2-(1,6,7-trihydroxy-5-isopropyl-3-methyl-2-naphthyl)naphthalene-1,6,7-triol |
| 1,1',6,6',7,7'-hexahydroxy-3,3'-dimethyl-5,5'-bis(1-methylethyl)-[2,2'-binaphthalene] |
| 66389-74-0 |
| apogossypol |
| racemic apogossypol, stabilized with ascorbic acid |
| nsc736630 |
| bdbm31802 |
| 3-methyl-5-propan-2-yl-2-(1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)naphthalene-1,6,7-triol |
| CHEMBL551288 |
| 5,5'-diisopropyl-3,3'-dimethyl-(2,2'-binaphthalene)-1,1',6,6',7,7'-hexol |
| 475-56-9 |
| (2,2'-binaphthalene)-1,1',6,6',7,7'-hexol, 5,5'-diisopropyl-3,3'-dimethyl- |
| (+)-apogossypol |
| AKOS016013513 |
| (+/-)-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol |
| PBJKWGWHZVXBGU-UHFFFAOYSA-N |
| (+)-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol |
| SCHEMBL2513478 |
| 5,5'-diisopropyl-3,3'-dimethyl-[2,2'-binaphthalene]-1,1',6,6',7,7'-hexaol |
| DTXSID60197162 |
| 3,3'-dimethyl-5,5'-bis(propan-2-yl)-[2,2'-binaphthalene]-1,1',6,6',7,7'-hexol |
| (s)-apogossypol |
| A16316 |
| apogossypol; nsc736630 |
| BCP32267 |
| apogossypol;nsc736630 |
ApoG2 is a semi-synthesized derivative of gossypol.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Apogossypolone (ApoG2) is a semi-synthesized derivative of gossypol. " | ( Apogossypolone, a nonpeptidic small molecule inhibitor targeting Bcl-2 family proteins, effectively inhibits growth of diffuse large cell lymphoma cells in vitro and in vivo. Aboukameel, A; Al-Katib, A; Arnold, AA; Banerjee, S; Chen, J; Lin, Y; Ling, X; Mohammad, RM; Nikolovska-Coleska, Z; Sun, Y; Wang, S; Wu, J; Yang, D, 2008) | 3.23 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Hepatotoxicity and gastrointestinal toxicity represented the major adverse activities of gossypol, with apogossypol far less toxic." | ( Bcl-2 antagonist apogossypol (NSC736630) displays single-agent activity in Bcl-2-transgenic mice and has superior efficacy with less toxicity compared with gossypol (NSC19048). Jia, L; Kitada, S; Krajewska, M; Kress, CL; Pellecchia, M; Reed, JC, 2008) | 0.9 |
Apogossypol and gossypols show similar oral and intravenous pharmacokinetic profiles and in vitro stability. apogossypsol appears to have a slower clearance rate, larger AUC, and better microsomal stability.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Gossypol, apogossypol and apogossypol hexaacetate were incubated in plasma or liver microsomes from various species, or administered to mice, respectively, from which the stability, metabolism and pharmacokinetic profiles of these analogs were quantitatively determined using a liquid chromatography-mass spectrometry (LC/MS/MS) method." | ( Comparison of pharmacokinetic and metabolic profiling among gossypol, apogossypol and apogossypol hexaacetate. Cork, RL; Coward, LC; Gorman, GS; Jia, L; Kerstner-Wood, CD; Kitada, S; Noker, PE; Pellecchia, M; Reed, JC, 2008) | 0.98 |
| " (+/-)-Gossypol and (-)-gossypol showed comparable pharmacokinetic profile and oral bioavailability (12." | ( Comparison of pharmacokinetic and metabolic profiling among gossypol, apogossypol and apogossypol hexaacetate. Cork, RL; Coward, LC; Gorman, GS; Jia, L; Kerstner-Wood, CD; Kitada, S; Noker, PE; Pellecchia, M; Reed, JC, 2008) | 0.58 |
| "Apogossypol and gossypol show similar oral and intravenous pharmacokinetic profiles and in vitro stability although apogossypol appears to have a slower clearance rate, larger AUC, and better microsomal stability." | ( Comparison of pharmacokinetic and metabolic profiling among gossypol, apogossypol and apogossypol hexaacetate. Cork, RL; Coward, LC; Gorman, GS; Jia, L; Kerstner-Wood, CD; Kitada, S; Noker, PE; Pellecchia, M; Reed, JC, 2008) | 2.02 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "5/3-mda-7 alone or in combination with BI-97C1 would be predicted to exert significantly improved therapeutic efficacy in colorectal cancer patients." | ( Enhanced delivery of mda-7/IL-24 using a serotype chimeric adenovirus (Ad.5/3) in combination with the Apogossypol derivative BI-97C1 (Sabutoclax) improves therapeutic efficacy in low CAR colorectal cancer cells. Azab, B; Bhutia, SK; Curiel, DT; Das, SK; Dash, R; Dent, P; Dmitriev, IP; Fisher, PB; Grant, S; Hedvat, M; Pellecchia, M; Quinn, BA; Reed, JC; Sarkar, D; Sarkar, S; Shen, XN; Wang, XY, 2012) | 0.59 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " (+/-)-Gossypol and (-)-gossypol showed comparable pharmacokinetic profile and oral bioavailability (12." | ( Comparison of pharmacokinetic and metabolic profiling among gossypol, apogossypol and apogossypol hexaacetate. Cork, RL; Coward, LC; Gorman, GS; Jia, L; Kerstner-Wood, CD; Kitada, S; Noker, PE; Pellecchia, M; Reed, JC, 2008) | 0.58 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Daily oral dosing studies showed that mice tolerate doses of apogossypol 2- to 4-times higher than gossypol." | ( Bcl-2 antagonist apogossypol (NSC736630) displays single-agent activity in Bcl-2-transgenic mice and has superior efficacy with less toxicity compared with gossypol (NSC19048). Jia, L; Kitada, S; Krajewska, M; Kress, CL; Pellecchia, M; Reed, JC, 2008) | 0.93 |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Apoptosis regulator Bcl-2 | Homo sapiens (human) | IC50 (µMol) | 20.1200 | 0.0010 | 0.5763 | 4.3000 | AID1799173; AID421426 |
| Apoptosis regulator Bcl-2 | Homo sapiens (human) | Ki | 0.6400 | 0.0000 | 0.1901 | 2.9000 | AID1599454 |
| Bcl-2-like protein 1 | Homo sapiens (human) | IC50 (µMol) | 4.3333 | 0.0003 | 1.0482 | 9.5400 | AID1799173; AID421416; AID421425 |
| Bcl-2-like protein 1 | Homo sapiens (human) | Ki | 2.8000 | 0.0000 | 0.4581 | 9.0000 | AID1599455 |
| Induced myeloid leukemia cell differentiation protein Mcl-1 | Homo sapiens (human) | IC50 (µMol) | 4.6400 | 0.0044 | 2.9235 | 10.0000 | AID1799173; AID421427 |
| Induced myeloid leukemia cell differentiation protein Mcl-1 | Homo sapiens (human) | Ki | 3.3500 | 0.0010 | 1.4653 | 9.5400 | AID1599457 |
| Bcl-2-related protein A1 | Homo sapiens (human) | IC50 (µMol) | 6.1200 | 0.0044 | 1.6514 | 4.3000 | AID1799173; AID421417 |
| Bcl-2-like protein 2 | Homo sapiens (human) | Ki | 2.1000 | 0.0010 | 1.2590 | 8.1900 | AID1599456 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID437157 | Ratio of compound IC50 to (-)-gossypol IC50 for human HeLa cells | 2009 | European journal of medicinal chemistry, Oct, Volume: 44, Issue:10 | Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. |
| AID421422 | Cytotoxicity against human PC3-ML cells assessed as cell viability after 72 hrs by ATP-LITE assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID437161 | Ratio of compound IC50 to cisplatin IC50 for human U87 cells | 2009 | European journal of medicinal chemistry, Oct, Volume: 44, Issue:10 | Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. |
| AID437155 | Anticancer activity against human U87 cells after 48 hrs by MTT assay | 2009 | European journal of medicinal chemistry, Oct, Volume: 44, Issue:10 | Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. |
| AID1599455 | Inhibition of Bcl-xL (unknown origin) | 2019 | European journal of medicinal chemistry, Sep-01, Volume: 177 | The chemical biology of apoptosis: Revisited after 17 years. |
| AID437159 | Ratio of compound IC50 to (-)-gossypol IC50 for human M85 cells | 2009 | European journal of medicinal chemistry, Oct, Volume: 44, Issue:10 | Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. |
| AID421439 | Toxicity in human Bcl2 expressing B6 transgenic mouse administered as single dose at 72 umol/kg, ip after 24 hrs | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID437158 | Ratio of compound IC50 to (-)-gossypol IC50 for human U87 cells | 2009 | European journal of medicinal chemistry, Oct, Volume: 44, Issue:10 | Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. |
| AID421423 | Induction of apoptosis in human RS11846 cells after 1 to 2 days by FITC-annexin V and propidium iodide assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID421418 | Chemical stability assessed as decomposition after 60 days at room temperature in absence of ascorbic acid by HPLC/LC-MS analysis | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID421425 | Displacement of F-BakBH3 from Bcl-xL by fluorescence polarization assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID1599456 | Inhibition of Bcl-w (unknown origin) | 2019 | European journal of medicinal chemistry, Sep-01, Volume: 177 | The chemical biology of apoptosis: Revisited after 17 years. |
| AID421433 | Stability in rat plasma after 1 hr at 37.5 degC | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID437162 | Ratio of compound IC50 to cisplatin IC50 for human M85 cells | 2009 | European journal of medicinal chemistry, Oct, Volume: 44, Issue:10 | Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. |
| AID437160 | Ratio of compound IC50 to cisplatin IC50 for human HeLa cells | 2009 | European journal of medicinal chemistry, Oct, Volume: 44, Issue:10 | Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. |
| AID421416 | Binding affinity to Bcl-xL by isothermal titration calorimetry assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID437154 | Anticancer activity against human HeLa cells after 48 hrs by MTT assay | 2009 | European journal of medicinal chemistry, Oct, Volume: 44, Issue:10 | Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. |
| AID421426 | Displacement of F-BakBH3 from Bcl-2 by fluorescence polarization assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID421421 | Cytotoxicity against human H460 cells assessed as cell viability after 72 hrs by ATP-LITE assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID421434 | Stability in rat liver microsome at 4 uM after 1 hr | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID421436 | Reduction of spleen weight in human Bcl2 expressing B6 transgenic mouse at 72 umol/kg, ip administered as single dose after 24 hrs | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID437156 | Anticancer activity against human M85 cells after 48 hrs by MTT assay | 2009 | European journal of medicinal chemistry, Oct, Volume: 44, Issue:10 | Chiral gossypol derivatives: evaluation of their anticancer activity and molecular modeling. |
| AID421424 | Induction of apoptosis in human BP3 cells after 1 to 2 days by FITC-annexin V and propidium iodide assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID1755521 | Half life in mouse plasma at 5 ug/ml incubated for 1 to 24 hrs by LC/MS/MS method | 2020 | Journal of medicinal chemistry, 12-10, Volume: 63, Issue:23 | Curse or Cure? A Perspective on the Developability of Aldehydes as Active Pharmaceutical Ingredients. |
| AID1755520 | Half life in dog plasma at 5 ug/ml incubated for 1 to 24 hrs by LC/MS/MS method | 2020 | Journal of medicinal chemistry, 12-10, Volume: 63, Issue:23 | Curse or Cure? A Perspective on the Developability of Aldehydes as Active Pharmaceutical Ingredients. |
| AID421420 | Cytotoxicity against human H1299 cells assessed as cell viability after 72 hrs by ATP-LITE assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID421435 | Membrane permeability assessed as drug permeation at 100 uM at pH 7.2 after 8 hrs by PAMPA | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID1599457 | Inhibition of MCl-1 (unknown origin) | 2019 | European journal of medicinal chemistry, Sep-01, Volume: 177 | The chemical biology of apoptosis: Revisited after 17 years. |
| AID421437 | Induction of spleen weight shrinkage in human Bcl2 expressing B6 transgenic mouse at 72 umol/kg, ip administered as single dose after 24 hrs | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID1599454 | Inhibition of Bcl2 (unknown origin) | 2019 | European journal of medicinal chemistry, Sep-01, Volume: 177 | The chemical biology of apoptosis: Revisited after 17 years. |
| AID421417 | Displacement of F-BakBH3 from Bfl-1 by fluorescence polarization assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID421419 | Inhibition of Bcl-xL at 200 uM by 1D 1H NMR binding assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID421431 | Chemical stability after 60 days at room temperature by HPLC/LC-MS analysis | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID1755519 | Half life in human plasma at 5 ug/ml incubated for 1 to 24 hrs by LC/MS/MS method | 2020 | Journal of medicinal chemistry, 12-10, Volume: 63, Issue:23 | Curse or Cure? A Perspective on the Developability of Aldehydes as Active Pharmaceutical Ingredients. |
| AID421427 | Displacement of F-BakBH3 from Mcl-1 by fluorescence polarization assay | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| AID1799173 | Fluorescence Polarization Assay from Article 10.1021/jm900472s: \\Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins.\\ | 2009 | Journal of medicinal chemistry, Jul-23, Volume: 52, Issue:14 | Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins. |
| [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 | 9 (42.86) | 29.6817 |
| 2010's | 11 (52.38) | 24.3611 |
| 2020's | 1 (4.76) | 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 moderate demand-to-supply ratio for research on this compound.
| This Compound (16.62) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 2 (9.52%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 19 (90.48%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||