Bryostatin 1
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-04098 |
| CAS | 83314-01-6 |
| Molecular Weight | 905.04 |
| Molecular Formula | C47H68O17 |
| Purity | ≥99% |
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Description
Bryostatin 1, a structurally unique macrolactone marine natural product, is a protein kinase C (PKC) activator that binds with high affinity (Ki = 1.35 nM). Bryostatin 1 fails to mimic many effects caused by PMA and actually blocks some PMA-induced response in a variety of cells and tissues. Animal tests have shown bryostatin 1 may alleviate brain damage after a stroke.
Specification
| Synonyms | Bryostatin-1; Bryostatin1; NSC-339555; NSC 339555; NSC339555; AC1L8WCW |
| Storage | Store at -20°C |
| IUPAC Name | [(1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-25-acetyloxy-1,11,21-trihydroxy-17-[(1R)-1-hydroxyethyl]-5,13-bis(2-methoxy-2-oxoethylidene)-10,10,26,26-tetramethyl-19-oxo-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] (2E,4E)-octa-2,4-dienoate |
| Canonical SMILES | CCCC=CC=CC(=O)OC1C(=CC(=O)OC)CC2CC(OC(=O)CC(CC3CC(C(C(O3)(CC4CC(=CC(=O)OC)CC(O4)C=CC(C1(O2)O)(C)C)O)(C)C)OC(=O)C)O)C(C)O |
| InChI | InChI=1S/C47H68O17/c1-10-11-12-13-14-15-39(51)62-43-31(22-41(53)58-9)21-34-25-37(28(2)48)61-42(54)24-32(50)23-35-26-38(59-29(3)49)45(6,7)46(55,63-35)27-36-19-30(20-40(52)57-8)18-33(60-36)16-17-44(4,5)47(43,56)64-34/h12-17,20,22,28,32-38,43,48,50,55-56H,10-11,18-19,21,23-27H2,1-9H3 |
| InChI Key | MJQUEDHRCUIRLF-UHFFFAOYSA-N |
| Source | marine bryozoan Bugula neritina (Order Cheilostomata) |
Properties
| Appearance | White lyophilised Solid |
| Application | Adjuvants, Immunologic |
| Boiling Point | 954.7°C at 760 mmHg |
| Flash Point | 270.0±27.8 °C |
| Density | 1.27 g/cm3 |
| Solubility | Soluble in DMSO, ethanol |
Reference Reading
1.Short Communication: Preferential Killing of HIV Latently Infected CD4(+) T Cells by MALT1 Inhibitor.
Li H1,2, He H3, Gong L4, Fu M3, Wang TT2. AIDS Res Hum Retroviruses. 2016 Feb;32(2):174-7. doi: 10.1089/AID.2015.0343.
We report that the addition of an host paracaspase MALT1 inhibitor, MI-2, to HIV latently infected ACH-2, Jurkat E4, and J-LAT cells accelerated cell death in the presence of cell stimuli or the protein kinase C agonist, bryostatin 1. MI-2-mediated cell death correlated with the induction of the cellular RNase MCPIP1 and requires the presence of viral component(s). Altogether, the combination of MI-2 and bryostatin 1 displays selective killing of HIV latently infected CD4(+) T cells.
2.Isolation, analytical measurements, and cell line studies of the iron-bryostatin-1 complex.
Plummer S1, Manning T2, Baker T1, McGreggor T1, Patel M1, Wylie G3, Phillips D4. Bioorg Med Chem Lett. 2016 Mar 30. pii: S0960-894X(16)30333-X. doi: 10.1016/j.bmcl.2016.03.099. [Epub ahead of print]
Bryostatin-1 is a marine natural product that has demonstrated medicinal activity in pre-clinical and clinical trials for the treatment of cancer, Alzheimer's disease, effects of stroke, and HIV. In this study, iron-bryostatin-1 was obtained using a pharmaceutical aquaculture technique developed by our lab that cultivates marine bacteria for marine natural product extraction. Analytical measurements 1H and 13C NMR, mass spectrometry, and flame atomic absorption were utilized to confirm the presence of an iron-bryostatin-1 complex. The iron-bryostatin-1 complex produced was then tested against the National Cancer Institute's 60 cell line panel. Adding iron to bryostatin-1 lowered the anti-cancer efficacy of the compound.
3.Rescue of Synaptic Phenotypes and Spatial Memory in Young Fragile X Mice.
Sun MK1, Hongpaisan J2, Alkon DL2. J Pharmacol Exp Ther. 2016 May;357(2):300-10. doi: 10.1124/jpet.115.231100. Epub 2016 Mar 3.
Fragile X syndrome (FXS) is characterized by synaptic immaturity, cognitive impairment, and behavioral changes. The disorder is caused by transcriptional shutdown in neurons of thefragile X mental retardation 1gene product, fragile X mental retardation protein. Fragile X mental retardation protein is a repressor of dendritic mRNA translation and its silencing leads to dysregulation of synaptically driven protein synthesis and impairments of intellect, cognition, and behavior, and FXS is a disorder that currently has no effective therapeutics. Here, young fragile X mice were treated with chronic bryostatin-1, a relatively selective protein kinase Cεactivator, which induces synaptogenesis and synaptic maturation/repair. Chronic treatment with bryostatin-1 rescues young fragile X mice from the disorder phenotypes, including normalization of most FXS abnormalities in 1) hippocampal brain-derived neurotrophic factor expression, 2) postsynaptic density-95 levels, 3) transformation of immature dendritic spines to mature synapses, 4) densities of the presynaptic and postsynaptic membranes, and 5) spatial learning and memory.
4.Bryostatin-1 for latent virus reactivation in HIV-infected patients on antiretroviral therapy: a phase i, double-blind clinical trial.
Gutiérrez C1, Serrano-Villar S, Madrid-Elena N, Pérez-Elías MJ, Martín ME, Barbas C, Ruipérez J, Muñoz E, Muñoz-Fernández MA, Castor T, Moreno S. AIDS. 2016 Feb 17. [Epub ahead of print]
OBJECTIVE: The protein kinase C-(PKC) agonist bryostatin-1 has shown significant ex vivo potency to revert HIV-1 latency, compared to other latency reversing agents-(LRA). The safety of this candidate LRA remains to be proven in treated HIV-1 infected-patients.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
