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B7431

Sigma-Aldrich

Bryostatin 1

≥99%, solid

Synonym(s):

NSC 339555

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About This Item

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

Quality Level

Assay

≥99%

form

solid

color

white

solubility

DMSO: soluble
ethanol: soluble

storage temp.

−20°C

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

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

InChI key

MJQUEDHRCUIRLF-TVIXENOKSA-N

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bryostatin effects on cognitive function and PKC? in Alzheimer?s disease phase IIa and expanded access trials
Nelson TJ, et al.
Journal of Alzheimer'S Disease, 58(2), 521-535 (2017)
P Yi et al.
Journal of molecular neuroscience : MN, 48(1), 234-244 (2012-06-16)
Activation of the α-secretase processing pathway of amyloid precursor protein (APP) is recognized as an important mechanism which diverts APP processing from production of beta-amyloid (Aβ) to non toxic sAPPα, decreasing Alzheimer's disease (AD) plaque formation and AD-associated cognitive deficits.
Bryostatin-1 ameliorated experimental colitis in Il-10-/- Mice by protecting the intestinal barrier and limiting immune dysfunction
Zuo L, et al.
Journal of Cellular and Molecular Medicine, 23(8), 5588-5599 (2019)
Effect of bryostatin-1 as an anthelmintic drug on adult Syphacia muris infection in rats
Harras SF, et al.
Journal of Basic & Applied Sciences, 78(1), 8-8 (2017)
Gary E Keck et al.
Journal of the American Chemical Society, 133(4), 744-747 (2010-12-24)
Bryostatin 1 is a marine natural product that is a very promising lead compound because of the potent biological activity it displays against a variety of human disease states. We describe herein the first total synthesis of this agent. The

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