Cylindrospermopsin

For other uses, see CYL.
"CYN" redirects here. For the prefix "cyn-", see List of commonly used taxonomic affixes.
Cylindrospermopsin
Names
IUPAC name
2,4(1H,3H)-Pyrimidinedione, 6-[(R)-hydroxy[(2aS,3R,4S,5aS,7R) -2,2a,3,4,5,5a,6,7-octahydro-3-methyl-4-(sulfooxy) -1H-1,8,8b-triazaacenaphthylen-7-yl]methyl]-
Other names
Cylindrospermopsine[citation needed]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.229.780 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/p+1/t6-,7+,8-,10?,11+,13+/m1/s1 checkY
    Key: LHJPHMKIGRLKDR-NPSYHWQSSA-O checkY
  • InChI=1/C15H21N5O7S/c1-6-10-5-16-14-17-8(13(22)9-4-12(21)19-15(23)18-9)2-7(20(10)14)3-11(6)27-28(24,25)26/h4,6-8,10-11,13,22H,2-3,5H2,1H3,(H,16,17)(H,24,25,26)(H2,18,19,21,23)/p+1/t6-,7+,8-,10?,11+,13+/m1/s1
    Key: LHJPHMKIGRLKDR-FGVRTCLEBA
  • O=C1/C=C(\N=C(\O)N1)[C@@H](O)[C@H]2C[C@H]4C[C@H](OS(O)(=O)=O)[C@H](C)C3C\[NH+]=C(\N2)N34
Properties
C15H21N5O7S
Molar mass 415.43
Appearance White solid
High
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazard
Danger
H300, H341, H370
P201, P202, P260, P264, P270, P281, P301+P310, P307+P311, P308+P313, P321, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Cylindrospermopsin (abbreviated to CYN, or CYL) is a cyanotoxin produced by a variety of freshwater cyanobacteria.[1] CYN is a polycyclic uracil derivative containing guanidino and sulfate groups. It is also zwitterionic, making it highly water soluble. CYN is toxic to liver and kidney tissue and is thought to inhibit protein synthesis and to covalently modify DNA and/or RNA. It is not known whether cylindrospermopsin is a carcinogen, but it appears to have no tumour initiating activity in mice.[2]

CYN was first discovered after an outbreak of a mystery disease on Palm Island, Queensland, Australia. The outbreak was traced back to a bloom of Cylindrospermopsis raciborskii in the local drinking water supply, and the toxin was subsequently identified. Analysis of the toxin led to a proposed chemical structure in 1992, which was revised after synthesis was achieved in 2000. Several analogues of CYN, both toxic and non-toxic, have been isolated or synthesised.

C. raciborskii has been observed mainly in tropical areas, however has also recently been discovered in temperate regions of Australia, North, South America, New Zealand and Europe.[3] However, CYN-producing strain of C. raciborskii has not been identified in Europe, several other cyanobacteria species occurring across the continent are able to synthesize it.[3]

  1. ^ Fastner J, Heinze R, Humpage AR, Mischke U, Eaglesham GK, Chorus I (September 2003). "Cylindrospermopsin occurrence in two German lakes and preliminary assessment of toxicity and toxin production of Cylindrospermopsis raciborskii (Cyanobacteria) isolates". Toxicon. 42 (3): 313–21. doi:10.1016/S0041-0101(03)00150-8. PMID 14559084.
  2. ^ Falconer IR, Humpage AR (2001). "Preliminary evidence for in vivo tumour initiation by oral administration of extracts of the blue-green alga cylindrospermopsis raciborskii containing the toxin cylindrospermopsin". Environmental Toxicology. 16 (2): 192–5. Bibcode:2001EnTox..16..192F. doi:10.1002/tox.1024. PMID 11339720. S2CID 36541311.
  3. ^ a b Poniedziałek B, Rzymski P, Kokociński M (2012). "Cylindrospermopsin: Water-linked potential threat to human health in Europe". Environmental Toxicology and Pharmacology. 34 (3): 651–60. doi:10.1016/j.etap.2012.08.005. PMID 22986102.