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Bryostatin information


Bryostatin 1
Names
IUPAC name
(1S,3S,5Z,7R,8E,11S,12S,13E,15S,17R,20R,23R,25S)-25-Acetoxy-1,11,20-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)-2,4-octadienoate
Identifiers
CAS Number
  • 1: 83314-01-6
3D model (JSmol)
  • 1: Interactive image
ChEBI
  • 1: CHEBI:88353
ChEMBL
  • 1: ChEMBL449158
ChemSpider
  • 1: 27022418
DrugBank
  • 1: DB11752
KEGG
  • 1: C05149
PubChem CID
  • 1: 5280757
UNII
  • 1: 37O2X55Y9E
InChI
  • InChI=1S/C47H68O17/c1-10-11-12-13-14-15-39(51)62-42-31(24-41(53)58-9)23-34-25-37(28(2)48)61-43(54)36(50)17-16-33-26-38(59-29(3)49)45(6,7)46(55,63-33)27-35-21-30(22-40(52)57-8)20-32(60-35)18-19-44(4,5)47(42,56)64-34/h12-15,18-19,22,24,28,32-38,42,48,50,55-56H,10-11,16-17,20-21,23,25-27H2,1-9H3/b13-12+,15-14+,19-18+,30-22+,31-24+/t28-,32+,33-,34+,35+,36-,37-,38+,42+,46+,47-/m1/s1
    Key: XYXASLYZTKBYQJ-OAUMSBLFSA-N
  • 1: InChI=1/C47H68O17/c1-10-11-12-13-14-15-39(51)62-42-31(24-41(53)58-9)23-34-25-37(28(2)48)61-43(54)36(50)17-16-33-26-38(59-29(3)49)45(6,7)46(55,63-33)27-35-21-30(22-40(52)57-8)20-32(60-35)18-19-44(4,5)47(42,56)64-34/h12-15,18-19,22,24,28,32-38,42,48,50,55-56H,10-11,16-17,20-21,23,25-27H2,1-9H3/b13-12+,15-14+,19-18+,30-22+,31-24+/t28-,32+,33-,34+,35+,36-,37-,38+,42+,46+,47-/m1/s1
    Key: XYXASLYZTKBYQJ-OAUMSBLFBY
SMILES
  • 1: 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@@H](CC[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
Properties
Chemical formula
C47H68O17
Molar mass 905.044 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Bryostatins are a group of macrolide lactones from (bacterial symbionts of) the marine organism Bugula neritina that were first collected and provided to JL Hartwell’s anticancer drug discovery group at the National Cancer Institute (NCI) by Jack Rudloe.[1] Bryostatins are potent modulators of protein kinase C. They have been studied in clinical trials as anti-cancer agents, as anti-AIDS/HIV agents and in people with Alzheimer's disease.

  1. ^ Halford B (24 October 2011). "The Bryostatins' Tale". Chemical and Engineering News. 89 (43): 10–17. doi:10.1021/cen-v089n043.p010.

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Bryostatin

Last Update:

Bryostatins are a group of macrolide lactones from (bacterial symbionts of) the marine organism Bugula neritina that were first collected and provided...

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Bryozoa

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called bryostatins can be extracted from the marine bryozoan Bugula neritina. In 2001 pharmaceutical company GPC Biotech licensed bryostatin 1 from Arizona...

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Krische allylation

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than was previously achieved. For example, total syntheses of roxaticin, bryostatin and cryptocaryol were accomplished via double Krische allylation of 1...

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Protein kinase C

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myricitrin, gossypol. Other PKCIs : Verbascoside, BIM-1, Ro31-8220. Bryostatin 1 can act as a PKC inhibitor; It was investigated for cancer. Tamoxifen...

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Bugula neritina

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Endobugula sertula, produces the bryostatins, a group of around twenty bioactive natural products. The bryostatins are under investigation for their...

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Drug discovery

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cancer, anti-inflammatory use and pain. One class of these agents are bryostatin-like compounds, under investigation as anti-cancer therapy.[citation needed]...

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Mitzi Nagarkatti

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discovery that Bryostatin-1 can be used to treat latent HIV infection and formed the basis for clinical trials on the use of Bryostatin as a latent infection-reversing...

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Bugula

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Bugula neritina attracted interest as a source of cytotoxic chemicals, bryostatins, under clinical investigation as anti-cancer agents. It was first collected...

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Carbonyl olefin metathesis

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carbonyl-olefin metathesis in their preparation of the C-ring fragment of bryostatin 1 In 2012, the Lambert group has reported a ring-opening metathesis of...

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Marine pharmacognosy

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Cancer Hemiasterlin (E7974) N/A Sponge Tripeptide Microtubules 0/3 Cancer Bryostatin 1 N/A Bryozoa Polyketide Protein Kinase C 0/38 Cancer, Alzheimers Pseudopterosins...

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Jon Clardy

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elucidation of numerous marine natural products such as the anticancer agent bryostatin, the insecticidal and antifungal jaspamide, diazonamide A and B, and many...

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Natural product

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dissoluta), eleutherobin (from the coral Erythropodium caribaeorum), and the bryostatins (from the bryozoan Bugula neritina). Natural products sometimes have...

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Diverted total synthesis

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doi:10.1016/j.tet.2011.10.026 Design, synthesis, and evaluation of potent bryostatin analogs that modulate PKC translocation selectivity Paul A. Wender, Jeremy...

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Sponge isolates

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derivative of a dolastatin 10, a compound made by Dolabella auricularia. Bryostatins were first isolated from Bryozoa. Salinosporamides are derived from Salinispora...

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Aplysiatoxin

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development of a synthetically accessible protein kinase C activator with bryostatin-like activity. Journal of the American Chemical Society. 2009 Jun 10;131(22):7573-9...

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Index of oncology articles

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bronchoscope – bronchoscopy – bronchus – brostallicin – broxuridine – bryostatin 1 – buccal mucosa – budesonide – bupropion – burdock – Burkitt's leukemia...

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Jack Rudloe

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Bugula neritina used by the National Cancer Institute (NCI) to develop the bryostatin family of drugs used for treatment of cancer, HIV, Alzheimer's disease...

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Keck asymmetric allylation

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enantioselectively, moieties found in products such as phorboxazole and bryostatin 1. Although the groups of E. Tagliavini[who?] and K. Mikami[who?] reported...

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Aplidium californicum

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relationship with the bryozoan Bugula neritina. Certain antineoplastic agents, bryostatins 4 and 5, have been extracted from Aplidium californicum and are being...

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PPP2CA

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1998). "Reversible phosphorylation of Bcl2 following interleukin 3 or bryostatin 1 is mediated by direct interaction with protein phosphatase 2A". The...

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Gulf Specimen Marine Laboratory

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"Identifying bryostatins and potential precursors from the bryozoan 'Bugula neritina'", Natural Product Research 19.5 (2005) 467–1 Halford, B. "The Bryostatins' Tale"...

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Gary Keck

Last Update:

total synthesis of complex natural products, culminating in his work on bryostatins. Keck named several compounds after Merle Haggard. Gary Keck was a Fellow...

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