Bryostatin 1

Names

[ Name ]:
Bryostatin 1

[Synonym ]:
2,4-Octadienoic acid, (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[21.3.1.1.1]nonacos-8-en-12-yl ester, (2E,4E)-
(1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-25-Acetoxy-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[21.3.1.1.1]nonacos-8-en-12-yl (2E,4E)-2,4-octadienoate
2,4-octadienoic acid, (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[21.3.1.1.1]nonacos-8-en-12-yl ester, (2E,4E)-
MFCD00893832
bryostatin1,0
(1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,21R,23R,25S)-25-Acetoxy-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-tetraoxatetracycl ;o[21.3.1.1.1]nonacos-8-en-12-yl (2E,4E)-2,4-octadienoate
(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[21.3.1.1.1]nonacos-8-en-12-yl (2E,4E)-octa-2,4-dienoate
BRYO 1
bryostatine-1
BRYOSTATIN 1
BRYOSTATIN

Biological Activity

[Description]:

Bryostatin 1 is a natural macrolide isolated from the bryozoan Bugula neritina and is a potent and central nervous system (CNS)-permeable PKC modulator. Bryostatin 1 binds to the isolated C1 domain of Munc13-1 and the full-length Munc13-1 protein with Kis of 8.07 nM and 0.45 nM, respectively. Bryostatin 1 has anti-cancer, anti-inflammatory, neuroprotective, anti-HIV-1 infection properties[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> PKC

Research Areas >> Cancer

Signaling Pathways >> Anti-infection >> HIV

Research Areas >> Infection

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

Signaling Pathways >> TGF-beta/Smad >> PKC

[Target]

PKC[1] HIV-1[4]

[In Vitro]

Bryostatin 1 (1 µM; 5 minutes; HT22 cells) treatment successfully recruits Munc13-1 from the cytosol to the plasma membrane. Effects of Bryostatin 1 on the other Munc13 family members, ubMunc13-2 and bMunc13-2, resembled those of Munc13-1 for translocation [1]. The increased level of expression of Munc13-1 following a 24 h incubation with Bryostatin 1 in both HT22 and primary mouse hippocampal cells is observed[1]. Bryostatin 1 can also affect the immune system by modulating dendritic cells (DCs) via toll-like receptor 4 (TLR4) through the MyD88-independent pathway, which favors an anti-inflammatory environment by inducing a type 2 phenotype that promotes the differentiation of CD4+ T-helper (Th) lymphocytes into Th2 versus Th1 effector cells[2]. Western Blot Analysis[1] Cell Line: HT22 cells Concentration: 1 µM Incubation Time: 5 minutes Result: Caused Munc13-1 to transfer to the membrane fraction.

[In Vivo]

Bryostatin 1 (30 μg/kg; intraperitoneal injection; 3 d per week; for 2 weeks; C57BL/6J mice) treatment abolishes the onset of EAE[2]. Animal Model: Female C57BL/6J mice (8-12-week-old) with MOG35-55[2] Dosage: 30 μg/kg Administration: Intraperitoneal injection; 3 d per week; for 2 weeks Result: Abolished the onset of experimental autoimmune encephalomyelitis (EAE).

[References]

[1]. Blanco FA, et al. Munc13 Is a Molecular Target of Bryostatin 1. Biochemistry. 2019 Jul 9;58(27):3016-3030.

[2]. Kornberg MD, et al. Bryostatin-1 alleviates experimental multiple sclerosis. Proc Natl Acad Sci U S A. 2018 Feb 27;115(9):2186-2191.

[3]. Zeng N, et al. Bryostatin 1 causes attenuation of TPA-mediated tumor promotion in mouse skin. Mol Med Rep. 2018 Jan;17(1):1077-1082.

[4]. Proust A, et al. HIV-1 infection and latency-reversing agents bryostatin-1 and JQ1 disrupt amyloid beta homeostasis in human astrocytes. Glia. 2020 Apr 6.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
954.7±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₄₇H₆₈O₁₇

[ Molecular Weight ]:
905.033

[ Flash Point ]:
270.0±27.8 °C

[ Exact Mass ]:
904.445679

[ PSA ]:
240.11000

[ LogP ]:
5.39

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.565

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EH9455000

CHEMICAL NAME :: Bryostatin 1

CAS REGISTRY NUMBER :: 83314-01-6

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C47-H68-O17

MOLECULAR WEIGHT :: 905.15

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 400 nmol/kg

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 9,555,1988

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
EH9455000

Articles

Bryostatin-1 promotes long-term potentiation via activation of PKCα and PKCε in the hippocampus.

Neuroscience 226 , 348-55, (2012)

Activation of protein kinase C (PKC) by bryostatin-1 affects various functions of the central nervous system. We explored whether bryostatin-1 influenced synaptic plasticity via a process involving PK...

Bryostatin-I: A dendritic cell stimulator for chemokines induction and a promising adjuvant for a peptide based cancer vaccine

Cytokine 52(3) , 238-44, (2010)

Bryostatin-1 (Bryo-1), a PKC modulator, was previously shown to activate monocytes and lymphocytes to produce cytokines. In this report, we investigated the adjuvanticity of Bryo-1 both in vitro and i...

Differentiation therapy in poor risk myeloid malignancies: Results of a dose finding study of the combination bryostatin-1 and GM-CSF.

Leuk. Res. 35(1) , 87-94, (2011)

Pharmacologic differentiating agents have had relatively limited clinical success outside of the use of ATRA in acute promyelocytic leukemia and DNA methyltransferase inhibitors in myelodysplastic syn...