Calyculin

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Calyculins
Calyculin A and C Structure.svg
Calyculins A and C
Names
IUPAC name
((2R,3R,5R,7R,8S,9S)-2-((1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraenyl)-9-((E)-3-(2-((2S)-4-(((2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanoyl)amino)butan-2-yl)-1,3-oxazol-4-yl)prop-2-enyl)-7-hydroxy-4,4,8-trimethyl-1,10-dioxaspiro(4.5)decan-3-yl) dihydrogen phosphate (Calyculin A) [1]
Identifiers
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m1/s1 Yes check.svgY
    Key: FKAWLXNLHHIHLA-LIKMAGLISA-N Yes check.svgY
Properties
C51H83N4O15P (Calyculin C)
Molar mass 1023.2 g/mol (Calyculin C)
Properties
C50H81N4O15P (Calyculin A)
Molar mass 1009.17 g/mol (Calyculin A)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Calyculins are natural products originally isolated from the marine sponge Discodermia calyx. [2] Calyculins have proven to be strong serine/threonine protein phosphatase inhibitors and based on this property, calyculins might be potential tumor-promoting agents.

A laboratory synthesis of calyculin A has been reported. [3]

Related Research Articles

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Fostriecin is a type I polyketide synthase (PKS) derived natural product, originally isolated from the soil bacterium Streptomyces pulveraceus. It belongs to a class of natural products which characteristically contain a phosphate ester, an α,β-unsaturated lactam and a conjugated linear diene or triene chain produced by Streptomyces. This class includes structurally related compounds cytostatin and phoslactomycin. Fostriecin is a known potent and selective inhibitor of protein serine/threonine phosphatases, as well as DNA topoisomerase II. Due to its activity against protein phosphatases PP2A and PP4 which play a vital role in cell growth, cell division, and signal transduction, fostriecin was looked into for its antitumor activity in vivo and showed in vitro activity against leukemia, lung cancer, breast cancer, and ovarian cancer. This activity is thought to be due to PP2A's assumed role in regulating apoptosis of cells by activating cytotoxic T-lymphocytes and natural killer cells involved in tumor surveillance, along with human immunodeficiency virus-1 (HIV-1) transcription and replication.

References

  1. "Calyculin A" (PDF). Cell Signaling Technology. 2015-01-02.
  2. Suganuma M, Fujiki H, Furuya-Suguri H, Yoshizawa S, Yasumoto S, Kato Y, Fusetani N, Sugimura T (1990). "Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin". Cancer Res. 50 (12): 3521–3525. PMID   2160320.
  3. Tanimoto, Norihiko; Gerritz, Samuel W.; Sawabe, Akiyoshi; Noda, Takeshi; Filla, Sandra A.; Masamune, Satoru (1994-03-17). "Synthese von natürlich vorkommendem (−)‐Calyculin A". Angewandte Chemie. 106 (6): 674–677. doi:10.1002/ange.19941060611. ISSN   0044-8249.