83314-01-6

83314-01-6 structure

Name: Bryostatin 1
Chemical Name: Bryostatin 1,(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-y
CAS Number: 83314-01-6
Molecular Formula: C₄₇H₆₈O₁₇
Molecular Weight: 905.033
Catalog: Signaling Pathways Anti-infection HIV
Create Date: 2016-01-06 19:11:52
Modify Date: 2024-01-04 10:52:21
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].

Name	Bryostatin 1,(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-y
Synonyms	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

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.

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

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

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

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