Palytoxin
Title: Palytoxin
CAS Registry Number: 77734-91-9
CAS Name: Palytoxin (C51-55 hemiacetal)
Additional Names: PTX
Molecular Formula: C129H223N3O54
Molecular Weight: 2680.14
Percent Composition: C 57.81%, H 8.39%, N 1.57%, O 32.24%
Literature References: Potent toxin isolated from zoanthid coral of the genus Palythoa that is the most poisonous non-proteinaceous substance known. Isoln from "Limu-make-o-Hana", the Hawaiian name for the highly toxic coelenterate Palythoa toxica: R. E. Moore, P. J. Scheuer, Science 172, 495 (1971). Structure: R. E. Moore, G. Bartolini, J. Am. Chem. Soc. 103, 2491 (1981). Structure of palytoxin from P. tuberculosa of Okinawa (differs from palytoxin from P. toxica at two positions): D. Uemura et al., Tetrahedron Lett. 22, 2781 (1981). Proposed absolute configuration of 60 of the 64 chiral centers: R. E. Moore et al., J. Am. Chem. Soc. 104, 3776 (1982). Structure and stereochemistry: J. K. Cha et al., ibid. 7369. Discussion of the structural elucidation, see Y. Shimizu, Nature 302, 212 (1983); review: R. E. Moore, Prog. Chem. Org. Nat. Prod. 48, 82-202 (1985). Synthetic studies: Y. Kishi, Chem. Scr. 27, 573 (1987). Pharmacological study: P. N. Kaul et al., Proc. West. Pharmacol. Soc. 17, 294 (1974). Mechanism of action and treatment of palytoxin poisoning: J. A. Vick et al., Toxicol. Appl. Pharmacol. 34, 214 (1975). Mode of contractile action on vascular smooth muscle: K. Ito et al., Eur. J. Pharmacol. 46, 9 (1977). Depolarizing action on frog spinal cord: Y. Kudo, S. Shibata, Br. J. Pharmacol. 71, 575 (1980). Toxicology and toxicity studies: J. S. Wiles et al., Toxicon 12, 427 (1974); K. Ito et al., Arch. Int. Pharmacodyn. Ther. 258, 146 (1982). Brief review of biology: P. J. Scheuer, Acc. Chem. Res. 10, 33-39 (1977). Review of synthetic studies and conformational analysis: Y. Kishi, Pure Appl. Chem. 61, 313-324 (1989).
Properties: White amorphous hygroscopic solid. No definite mp; chars when heated to 300°. [a]D25 +26° (water). Insol in chloroform, ether, acetone. Sparingly sol in methanol, ethanol. Sol in pyridine, DMSO, water. LD50 in mice: 0.45 mg/kg i.v. (Wiles); 50-100 ng/kg i.p. (Kaul).
Optical Rotation: [a]D25 +26° (water)
Toxicity data: LD50 in mice: 0.45 mg/kg i.v. (Wiles); 50-100 ng/kg i.p. (Kaul)
CAUTION: Palytoxin is an intense vasoconstrictor. In intact dogs, doses of >0.06 mg/kg i.v. caused a transient rise in arterial pressure followed by rapid hypotension and resulted in death within 5 minutes (Ito, 1982).
Use: As a physiological tool to evaluate anti-anginal chemotherapeutic agents.

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