83314-01-6

Basic information

• Product Name: BRYOSTATIN 1
• Synonyms: BRYOSTATIN 1;BRYO 1;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-tetraoxatetracyclo21.3.1.13,7.111,15nonacos-8-en;BRYOSTATIN;bryostatin1,0;(26R)-Bryostatin 1;NSC-339555;(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-yl2,4-octadienoicacidester
• CAS NO: 83314-01-6
• Molecular Formula: C₄₇H₆₈O₁₇
• Molecular Weight: 905.03
• Product Categories: Cell Signaling and Neuroscience;Kinase/Phosphatase Biology;Protein Kinase ActivatorsSerine/Threonine Kinase Biology;Protein Kinase C (PKC);Serine/Threonine Kinase Activators;inhibitor
• Mol File: 83314-01-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 230-235°
• Boiling Point: 716.44°C (rough estimate)
• Flash Point: 270°C
• Appearance: white/solid
• Density: 1.1245 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5940 (estimate)
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• CAS DataBase Reference: BRYOSTATIN 1(CAS DataBase Reference)
• NIST Chemistry Reference: BRYOSTATIN 1(83314-01-6)
• EPA Substance Registry System: BRYOSTATIN 1(83314-01-6)

Safety Data

• Hazard Codes: Xn
• Statements: 68
• Safety Statements: 22-24/25-36/37
• WGK Germany: 3
• RTECS: EH9455000
• Hazardous Substances Data: 83314-01-6(Hazardous Substances Data)

Usage

Description

Bryostatin 1 is a complex macrocyclic lactone compound that belongs to the class of bryostatins. It is characterized by its unique structure, featuring hydroxy groups, an acetoxy group, methyl groups, and 2-methoxy-2-oxoeylidene groups at specific positions, as well as oxygen bridges linking various positions within the molecule. This makes it one of the most abundant members of the bryostatin class.

Uses

Used in Pharmaceutical Research:
Bryostatin 1 is used as a research compound for studying its effects on various diseases and conditions. It has been particularly useful in investigating its potential role in treating spontaneous Crohn's disease-like colitis in mice.
Used in Veterinary Medicine:
In the field of veterinary medicine, Bryostatin 1 is used as an anthelmintic drug to study its effects on adult Syphacia muris infection in rats. This application helps in understanding its potential use in treating parasitic infections in animals.
Note: The provided materials do not mention any specific industries for the applications of Bryostatin 1. The uses mentioned above are based on the research and pharmaceutical context.

Biological Activity

Protein kinase C (PKC) activator that binds with high affinity (K i = 1.35 nM). Initially activates and subsequently induces downregulation of PKC isozymes. Sensitizes tumor cells to cytotoxic effects of anticancer agents.

Biochem/physiol Actions

Bryostatin 1 (Bry1) is a macrocyclic lactone. This synaptogenic compound is obtained from the marine bryozoan?Bugula neritina. Bry1 is capable of reversing synaptic loss. It can enable synaptic maturation in animal models with several neurological disorders. It possesses antidepressant activity, when administered intracebroventricularly. Bry1 is known to participate in protecting cell tight junctions (TJs), anti-inflammatory functions and immune regulation.

references

[1]. gschwendt m, fürstenberger g, rose-john s, et al. bryostatin 1, an activator of protein kinase c, mimics as well as inhibits biological effects of the phorbol ester tpa in vivo and in vitro. carcinogenesis, 1988, 9(4): 555-562.[2]. stone rm, sariban e, pettit gr, et al. bryostatin 1 activates protein kinase c and induces monocytic differentiation of hl-60 cells. blood, 1988, 72(1): 208-213.[3]. schuchter lm, esa ah, may s, et al. successful treatment of murine melanoma with bryostatin 1. cancer res, 1991, 51(2): 682-687.

InChI:InChI=1/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/b13-12+,15-14+,17-16+,30-20-,31-22+/t28-,32-,33?,34?,35-,36+,37-,38+,43?,46+,47?/m1/s1

Upstream product

• 1028481-99-3 (2E,4E)-octa-2,4-dienoic anhydride 
• 1261423-25-9 (2Z,2'E)-dimethyl 2,2'-((3S,7R,11S,12S,15S,17R,21R,23S,25S,E)-25-acetoxy-17-((R)-1-((benzyloxy)methoxy)ethyl)-1,11-dimethoxy-10,10,26,26-tetramethyl-12-((2E,4E)-octa-2,4-dienyloxy)-19-oxo-21-((triethylsilyl)oxy)-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-ene-5,13-diylidene) diacetate 
• 1261423-23-7 (2Z,2'E)-dimethyl ((3S,7R,11S,12S,15S,17R,21R,23S,25S,E)-12,25-diacetoxy-17-((R)-1-((benzyloxy)methoxy)ethyl)-1,11-dimethoxy-10,10,26,26-tetramethyl-19-oxo-21-((triethylsilyl)oxy)-18,27,28,29-tetraoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-ene-5,13-diylidene) diacetate 
• 136205-45-3 bryostatin 2 26-tert-butyldimethylsilyl ether 
• 136205-46-4 C₅₃H₈₂O₁₇Si 
• 87745-28-6 bryostatin 2 
• 136205-45-3 bryostatin 2 26-(tert-butyl dimethyl silyl ether) 
• 136205-46-4 C₅₃H₈₂O₁₇Si 

Downstream Products

• 87745-28-6 bryostatin 2 

Relevant articles and documents

Antineoplastic Agents. 200. Absolute Configuration of the Bryostatins

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BRYOSTATIN COMPOUNDS AND METHODS OF PREPARING THE SAME

Methods for preparing a variety of bryostatin compounds are provided. The subject methods provide for preparation of bryostatin 1 in multi-gram quantities in a low and unprecedented number of convergent synthetic steps from commercially available materials. The subject methods are scalable with low estimated material costs and can provide enough material to meet clinical needs. Also provided are a variety of bryostatin analog compounds, and prodrug forms thereof, which are synthetically accessible via the subject methods and pharmaceutical compositions including the same.

Biological profile of the less lipophilic and synthetically more accessible bryostatin 7 closely resembles that of bryostatin 1

The bryostatins are a group of 20 macrolides isolated by Pettit and co-workers from the marine organism Bugula neritina. Bryostatin 1, the flagship member of the family, has been the subject of intense chemical and biological investigations due to its remarkably diverse biological activities, including promising indications as therapy for cancer, Alzheimer's disease, and HIV. Other bryostatins, however, have attracted far less attention, most probably due to their relatively low natural abundance and associated scarcity of supply. Among all macrolides in this family, bryostatin 7 is biologically the most potent protein kinase C (PKC) ligand (in terms of binding affinity) and also the first bryostatin to be synthesized in the laboratory. Nonetheless, almost no biological studies have been carried out on this agent. We describe herein the total synthesis of bryostatin 7 based on our pyran annulation technology, which allows for the first detailed biological characterizations of bryostatin 7 with side-by-side comparisons to bryostatin 1. The results suggest that the more easily synthesized and less lipophilic bryostatin 7 may be an effective surrogate for bryostatin 1.