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Merck
CN

B7431

Bryostatin 1

≥99%, Protein kinase C activator, solid

Synonym(s):

NSC 339555

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About This Item

Empirical Formula (Hill Notation):
C47H68O17
CAS Number:
83314-01-6
Molecular Weight:
905.03
UNSPSC Code:
12352200
PubChem Substance ID:
24891991
NACRES:
NA.77
MDL number:
MFCD00893832

Key Documents

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Product Name

Bryostatin 1, ≥99%, solid

SMILES string

[H]\C(C(=O)OC)=C1/C[C@@]2([H])C[C@]3(O)O[C@]([H])(C[C@@H](O)CC(=O)O[C@H](C[C@]4([H])C\C(=C(\[H])C(=O)OC)[C@H](OC(=O)\C=C\C=C\CCC)[C@@](O)(O4)C(C)(C)\C=C\[C@@]([H])(C1)O2)[C@@H](C)O)C[C@H](OC(C)=O)C3(C)C

InChI key

MJQUEDHRCUIRLF-TVIXENOKSA-N

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

assay

≥99%

form

solid

color

white

solubility

DMSO: soluble
ethanol: soluble

storage temp.

−20°C

Quality Level

100

Related Categories

Application

Bryostatin 1 has been used to study its effects on spontaneous Crohn′s disease (CD) like colitis in mice. It has also been used to study its effects as an anthelmintic drug on adult Syphacia muris infection in rats.

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.
Macrolactone isolated from the marine bryozoan Bugula neritina that initially activates and subsequently down-regulates protein kinase C (PKC). More potent than phorbol myristate acetate for translocating PKCδ and ε.

Other Notes

Binds to glass and plastic in aqueous solutions

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ6729
MKCZ6728
MKCX7100
MKCV6265
MKCW8251

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Yasuyuki Ogawa et al.
The Journal of organic chemistry, 78(1), 104-115 (2012-11-06)
The Prins cyclization of syn-β-hydroxy allylsilanes and aldehydes gives cis-2,6-disubstituted 4-alkylidenetetrahydropyrans as sole products in excellent yields regardless of the aldehyde (R″) or syn-β-hydroxy allylsilane substituent (R') used. By reversing the R″ and R' groups, complementary exocyclic stereocontrol can be
Dan Zhao et al.
Cellular immunology, 271(2), 392-400 (2011-09-10)
The majority of melanoma cells express detectable levels of HLA class II proteins, and an increased threshold of cell surface class II is crucial for the stimulation of CD4+ T cells. Bryostatin-1, a protein kinase C (PKC) activator, has been
N Kedei et al.
Biochemical pharmacology, 85(3), 313-324 (2012-11-14)
Bryostatin 1, like the phorbol esters, binds to and activates protein kinase C (PKC) but paradoxically antagonizes many but not all phorbol ester responses. Previously, we have compared patterns of biological response to bryostatin 1, phorbol ester, and the bryostatin
Robert J Morgan et al.
Investigational new drugs, 30(2), 723-728 (2010-10-12)
The California Cancer Consortium has performed a Phase II trial of infusional bryostatin, a protein kinase C inhibitor isolated from the marine invertebrate bryozoan, Bugula Neritina, a member of the phylum Ectoprocta, in combination with cisplatin, in patients (pts) with
Gary E Keck et al.
Bioorganic & medicinal chemistry letters, 22(12), 4084-4088 (2012-05-15)
The role of the C(8) gem-dimethyl group in the A-ring of bryostatin 1 has been examined through chemical synthesis and biological evaluation of a new analogue. Assays for biological function using U937, K562, and MV4-11 cells as well as the
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