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Palytoxin

Palytoxin
Names
Preferred IUPAC name
(2S,3R,5R,6E,8R,9S)-10-[(12R,13R,15S,41R,43R,45S,46R,6R,7R,8Z,102R,103S,104R,105R,106R,12R,13R,14R,15S,19Z,22R,23S,24R,26E,28Z,30S,322S,323R,324R,325S,326R,34R,35R,372R,373S,374R,376S,38R,39R,42S,43E,45S,46S,482S,483R,484R,485R,486R,50S,581S,583S,585R,586R,60S,66R,67S,68S,69R,70S,712R,713S,714R,715R,716R)-15-(Aminomethyl)-13,6,7,103,104,105,13,14,15,22,23,24,30,323,324,325,34,35,373,374,38,39,42,46,482,483,484,485,50,66,67,68,69,70,713,714,715-heptatriacontahydroxy-12,45,583,585,60-pentamethyl-18-methylidene-44,47,587,588-tetraoxa-10,32,37,48(2,6),71(2)-pentakis(oxana)-1(2)-oxolana-4(6,3),58(1,6)-bis(bicyclo[3.2.1]octana)henheptacontaphane-8,19,26,28,43-pentaen-716-yl]-N-{(1E)-3-[(3-hydroxypropyl)amino]-3-oxoprop-1-en-1-yl}-2,5,8,9-tetrahydroxy-3,7-dimethyldec-6-enamide
Identifiers
3D model (JSmol)
Abbreviations PTX
ChemSpider
ECHA InfoCard 100.162.538 Edit this at Wikidata
UNII
  • InChI=1S/C129H223N3O54/c1-62(29-33-81(143)108(158)103(153)68(7)47-93-111(161)117(167)110(160)91(180-93)36-35-76(138)82(144)51-73-50-74-53-92(178-73)90(177-74)38-37-89-85(147)52-75(61-130)179-89)23-20-28-78(140)105(155)77(139)26-18-13-16-25-70(135)48-94-112(162)118(168)113(163)97(181-94)55-84(146)83(145)54-95-107(157)87(149)57-96(182-95)106(156)80(142)34-32-69(134)31-30-65(4)88(150)60-129(176)125(174)123(173)115(165)99(184-129)49-71(136)24-15-10-9-11-19-40-128-59-64(3)58-127(8,186-128)100(185-128)44-63(2)22-14-12-17-27-79(141)109(159)116(166)120(170)122(172)124-121(171)119(169)114(164)98(183-124)56-86(148)102(152)66(5)45-72(137)46-67(6)104(154)126(175)132-42-39-101(151)131-41-21-43-133/h13,16,18,20,23,25,30-31,35-36,39,42,45,63-65,67-100,102-125,133-150,152-174,176H,1,9-12,14-15,17,19,21-22,24,26-29,32-34,37-38,40-41,43-44,46-61,130H2,2-8H3,(H,131,151)(H,132,175)/b18-13+,23-20-,25-16-,31-30+,36-35-,42-39+,66-45+/t63-,64-,65-,67+,68+,69+,70+,71-,72-,73-,74+,75-,76+,77+,78+,79+,80+,81-,82+,83+,84+,85+,86-,87+,88-,89+,90+,91+,92-,93+,94-,95+,96-,97+,98+,99+,100+,102+,103+,104-,105-,106+,107-,108+,109-,110+,111-,112-,113+,114-,115-,116-,117-,118+,119+,120+,121-,122-,123+,124-,125+,127+,128-,129-/m0/s1 checkY
    Key: CWODDUGJZSCNGB-HQNRRURTSA-N checkY
  • InChI=1/C129H223N3O54/c1-62(29-33-81(143)108(158)103(153)68(7)47-93-111(161)117(167)110(160)91(180-93)36-35-76(138)82(144)51-73-50-74-53-92(178-73)90(177-74)38-37-89-85(147)52-75(61-130)179-89)23-20-28-78(140)105(155)77(139)26-18-13-16-25-70(135)48-94-112(162)118(168)113(163)97(181-94)55-84(146)83(145)54-95-107(157)87(149)57-96(182-95)106(156)80(142)34-32-69(134)31-30-65(4)88(150)60-129(176)125(174)123(173)115(165)99(184-129)49-71(136)24-15-10-9-11-19-40-128-59-64(3)58-127(8,186-128)100(185-128)44-63(2)22-14-12-17-27-79(141)109(159)116(166)120(170)122(172)124-121(171)119(169)114(164)98(183-124)56-86(148)102(152)66(5)45-72(137)46-67(6)104(154)126(175)132-42-39-101(151)131-41-21-43-133/h13,16,18,20,23,25,30-31,35-36,39,42,45,63-65,67-100,102-125,133-150,152-174,176H,1,9-12,14-15,17,19,21-22,24,26-29,32-34,37-38,40-41,43-44,46-61,130H2,2-8H3,(H,131,151)(H,132,175)/b18-13+,23-20-,25-16-,31-30+,36-35-,42-39+,66-45+/t63-,64-,65-,67+,68+,69+,70+,71-,72-,73-,74+,75-,76+,77+,78+,79+,80+,81-,82+,83+,84+,85+,86-,87+,88-,89+,90+,91+,92-,93+,94-,95+,96-,97+,98+,99+,100+,102+,103+,104-,105-,106+,107-,108+,109-,110+,111-,112-,113+,114-,115-,116-,117-,118+,119+,120+,121-,122-,123+,124-,125+,127+,128-,129-/m0/s1
    Key: CWODDUGJZSCNGB-HQNRRURTBU
  • NC[C@@H]1C[C@H]([C@H](O1)CC[C@H]1O[C@@H]2C[C@H](O[C@H]1C2)C[C@H]([C@@H](\C=C/[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)C[C@H]([C@H]([C@@H]([C@H](CCC(\C=C/C[C@H]([C@H]([C@@H](C/C=C/C=C\[C@H](C[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C[C@H]([C@@H](C[C@@H]2[C@H]([C@@H](C[C@H](O2)[C@@H]([C@@H](CC[C@@H](/C=C/[C@@H]([C@H](C[C@]2([C@@H]([C@@H]([C@H]([C@H](O2)C[C@H](CCCCCCC[C@]21C[C@H](C[C@]([C@H](O2)C[C@H](CCCCC[C@H]([C@@H]([C@@H]([C@H]([C@H](O)[C@@H]2[C@H]([C@@H]([C@H]([C@H](O2)C[C@@H]([C@@H](/C(=C/[C@@H](C[C@H]([C@@H](C(O)=N\C=C\C(=NCCCO)O)O)C)O)/C)O)O)O)O)O)O)O)O)O)C)(O1)C)C)O)O)O)O)O)O)C)O)O)O)O)O)O)O)O)O)O)O)O)O)O)=C)O)O)O)C)O)O)O)O)O)O
Properties
C129H223N3O54
Molar mass 2680.1386 grams/mol
Appearance white amorphous hygroscopic solid[1]
Melting point decomposes at 300 °C[1]
Solubility Very soluble in water, dimethyl sulfoxide, pyridine; slightly soluble in methanol and ethanol; insoluble in chloroform and diethyl ether[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Extremely toxic, symptoms of poisoning include: chest pains, breathing difficulties, tachycardia, unstable blood pressure and hemolysis.[2]
GHS labelling:
GHS06: Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Palytoxin, PTX[3] or PLTX[4] is an intense vasoconstrictor,[1] and is considered to be one of the most poisonous non-protein substances known, second only to maitotoxin in terms of toxicity in mice.[5]

Palytoxin is a polyhydroxylated and partially unsaturated compound (8 double bonds) with a long carbon chain. It has water-soluble and fat-soluble parts, 40 hydroxy groups and 64 chiral centers. Due to chirality and possible double bond cis-trans isomerism, it has over 1021 alternative stereoisomers. It is thermostable, and treatment with boiling water does not remove its toxicity. It remains stable in aqueous solutions for prolonged periods but rapidly decomposes and loses its toxicity in acidic or alkaline solutions. It has multiple analogues with a similar structure like ostreocin-D, mascarenotoxin-A and -B.[3]

Palytoxin occurs at least in tropics and subtropics where it is made by Palythoa corals and Ostreopsis dinoflagellates, or possibly by bacteria occurring in these organisms. It can be found in many more species like fish and crabs due to the process of biomagnification. It can also be found in organisms living close to palytoxin producing organisms like sponges, mussels, starfish and cnidaria.[3]

People are rarely exposed to palytoxin. Exposures have happened in people who have eaten sea animals like fish and crabs, but also in aquarium hobbyists who have handled Palythoa corals incorrectly and in those who have been exposed to certain algal blooms.[2]

Palytoxin targets the sodium-potassium pump protein by locking it into a position where it allows passive transport of both sodium and potassium ions, thereby destroying the ion gradient that is essential for life.[6] Because palytoxin can affect every type of cell in the body, the symptoms can be very different for the various routes of exposure.[2]

Palytoxin's planar chemical structure was solved in 1981 by two research groups independently from each other.[3] Stereochemistry was solved in 1982.[7][8][9] Palytoxin carboxylic acid was synthesized by Yoshito Kishi and colleagues in 1989[10] and actual palytoxin in 1994 by Kishi and Suh.[11]

  1. ^ a b c d Budavari, Susan, ed. (2001), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.), Merck, ISBN 0911910131
  2. ^ a b c Cite error: The named reference deeds was invoked but never defined (see the help page).
  3. ^ a b c d Ramos V, Vasconcelos V (June 2010). "Palytoxin and analogs: biological and ecological effects". Marine Drugs. 8 (7): 2021–37. doi:10.3390/md8072021. PMC 2920541. PMID 20714422.
  4. ^ Pelin M, Brovedani V, Sosa S, Tubaro A (February 2016). "Palytoxin-Containing Aquarium Soft Corals as an Emerging Sanitary Problem". Marine Drugs. 14 (2): 33. doi:10.3390/md14020033. PMC 4771986. PMID 26861356.
  5. ^ Sud P, Su MK, Greller HA, Majlesi N, Gupta A (September 2013). "Case series: inhaled coral vapor--toxicity in a tank". Journal of Medical Toxicology. 9 (3): 282–6. doi:10.1007/s13181-013-0307-x (inactive 3 May 2024). PMC 3770997. PMID 23702624.{{cite journal}}: CS1 maint: DOI inactive as of May 2024 (link)
  6. ^ Cite error: The named reference gadsby was invoked but never defined (see the help page).
  7. ^ Moore RE, Bartolini G, et al. (June 1982). "Absolute Stereochemistry of Palytoxin". Journal of the American Chemical Society. 104 (13): 3776–3779. doi:10.1021/ja00377a064.
  8. ^ Klein LL, McWhorter WW, Ko SS, Pfaff KP, KishiB Y, Uemura D, Hirata Y (December 1982). "Stereochemistry of palytoxin. Part 1. C85-C115 segment". Journal of the American Chemical Society. 104 (25): 7362–7364. doi:10.1021/ja00389a098.
  9. ^ Cha JK, Christ WJ, Finan JM, Fujioka H, Kishi Y, Klein LL, et al. (December 1982). "Stereochemistry of palytoxin. Part 4. Complete structure". Journal of the American Chemical Society. 104 (25): 7369–7371. doi:10.1021/ja00389a101. ISSN 0002-7863.
  10. ^ Armstrong RW, Beau JM, Cheon SH, Christ WJ, Fujioka H, Ham WH, et al. (1989). "Total Synthesis of Palytoxin Carboxylic Acid and Palytoxin Amide". J. Am. Chem. Soc. 111 (19): 7530. doi:10.1021/ja00201a038.
  11. ^ Suh EM, Kishi Y (1994). "Synthesis of Palytoxin from Palytoxin Carboxylic Acid". J. Am. Chem. Soc. 116 (24): 11205. doi:10.1021/ja00103a065.

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