Bryostatin 1

For research use only. Not for therapeutic Use.

  • CAT Number: M020085
  • CAS Number: 83314-01-6
  • Molecular Formula: C47H68O17
  • Molecular Weight: 905.04
  • Purity: ≥95%
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Bryostatin 1(Cat No.:M020085)is a potent macrocyclic lactone derived from the marine organism Bugula neritina, known for its ability to activate protein kinase C (PKC). This compound has demonstrated potential in cancer treatment, particularly in enhancing the efficacy of chemotherapy and immunotherapy by modulating cell signaling pathways and promoting apoptosis in tumor cells. Additionally, bryostatin 1 shows promise in neurological research, as it may aid in synaptic plasticity and neuroprotection, offering potential therapeutic benefits in conditions like Alzheimer’s disease. Its unique mechanism of action makes it a valuable candidate for further therapeutic exploration.


Catalog Number M020085
CAS Number 83314-01-6
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.

Molecular Formula C47H68O17
Purity ≥95%
Target PKC
Solubility Soluble in DMSO > 10 mM
Storage Store at -20°C
IUPAC Name [(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-yl] (2E,4E)-octa-2,4-dienoate
InChI 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
InChIKey MJQUEDHRCUIRLF-TVIXENOKSA-N
SMILES CCC/C=C/C=C/C(=O)O[C@H]1/C(=C/C(=O)OC)/C[C@H]2C[C@@H](OC(=O)C[C@@H](C[C@@H]3C[C@@H](C([C@@](O3)(C[C@@H]4C/C(=C/C(=O)OC)/C[C@@H](O4)/C=C/C([C@@]1(O2)O)(C)C)O)(C)C)OC(=O)C)O)[C@@H](C)O
Reference

1: Making Bryostatin 1 through Smart Chemistry. Cancer Discov. 2017 Oct 24. doi:
10.1158/2159-8290.CD-NB2017-148. [Epub ahead of print] PubMed PMID: 29066536.
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2: Wender PA, Hardman CT, Ho S, Jeffreys MS, Maclaren JK, Quiroz RV, Ryckbosch
SM, Shimizu AJ, Sloane JL, Stevens MC. Scalable synthesis of bryostatin 1 and
analogs, adjuvant leads against latent HIV. Science. 2017 Oct
13;358(6360):218-223. doi: 10.1126/science.aan7969. PubMed PMID: 29026042.
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3: López-Huertas MR, Jiménez-Tormo L, Madrid-Elena N, Gutiérrez C, Rodríguez-Mora
S, Coiras M, Alcamí J, Moreno S. The CCR5-antagonist Maraviroc reverses HIV-1
latency in vitro alone or in combination with the PKC-agonist Bryostatin-1. Sci
Rep. 2017 May 24;7(1):2385. doi: 10.1038/s41598-017-02634-y. PubMed PMID:
28539614; PubMed Central PMCID: PMC5443841.
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4: Alkon DL, Hongpaisan J, Sun MK. Effects of chronic bryostatin-1 on
treatment-resistant depression in rats. Eur J Pharmacol. 2017 Jul 15;807:71-74.
doi: 10.1016/j.ejphar.2017.05.001. Epub 2017 May 2. PubMed PMID: 28472666.
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5: Dental C, Proust A, Ouellet M, Barat C, Tremblay MJ. HIV-1 Latency-Reversing
Agents Prostratin and Bryostatin-1 Induce Blood-Brain Barrier
Disruption/Inflammation and Modulate Leukocyte Adhesion/Transmigration. J
Immunol. 2017 Feb 1;198(3):1229-1241. doi: 10.4049/jimmunol.1600742. Epub 2016
Dec 19. PubMed PMID: 27994072.
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6: Mizutani K, Sonoda S, Wakita H, Okazaki H, Katoh Y, Chihara T, Shimpo K.
Effects of exercise and bryostatin-1 on serotonin dynamics after cerebral
infarction. Neuroreport. 2016 Jun 15;27(9):659-64. doi:
10.1097/WNR.0000000000000592. PubMed PMID: 27128726.

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7: Plummer S, Manning T, Baker T, McGreggor T, Patel M, Wylie G, Phillips D.
Isolation, analytical measurements, and cell line studies of the
iron-bryostatin-1 complex. Bioorg Med Chem Lett. 2016 May 15;26(10):2489-97. doi:
10.1016/j.bmcl.2016.03.099. Epub 2016 Mar 30. PubMed PMID: 27068183.

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