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Zetekitoxin AB Zetekitoxin AB Kate Wilkin Laura Graham Background of Zetekitoxin AB Potent water-soluble guanidinium toxin extracted from the skin of the Panamanian golden frog, Atelopus zeteki. Identified by Harry S. Mosher and colleagues at Stanford University, 1969. Originally named 1,2- atelopidtoxin. Progression 1975 – found chiriquitoxin in a Costa Rican Atelopus frog. 1977 – Mosher isolated 2 components of 1,2-atelopidtoxin. AB major component, more toxic C minor component, less toxic 1986 – purified from skin extracts by Daly and Kim. 1990 – the major component was renamed after the frog species zeteki. Classification Structural Identification Structural Identification - IR -1 Cm Functional Groups 1268 OSO3H 1700 Carbamate 1051 – 1022 C – N Structural Identification – MS Structural Identification – 13C Carbon Number Ppm Assignment 2 ~ 159 C = NH 4 ~ 85 Quaternary Carbon 5 ~ 59 Tertiary Carbon 6 ~ 54 Tertiary Carbon 8 ~ 158 C = NH Structural Identification – 13C Carbon Number Ppm Assignment 10 55 / 43 C H2 - more subst. on ZTX 11 89 / 33 Ring and OSO3H on ZTX 12 ~ 98 Carbon attached to 2 OH groups 19 / 13 70 / 64 ZTX: C – N STX: C – C 20 / 14 ~ 157 Carbamate Structural Identification – 13C Carbon Number Ppm Assignment 13 156 Amide 14 34 CH2 15 54 C – N 16 47 Tertiary Carbon 17 69 C – O – N 18 62 C – OH Structural Identification - 1H Synthesis Synthesis O. Iwamoto and Dr. K. Nagasawa Tokyo University of Agriculture and Technology. October 10th, 2007 “Further work to synthesize natural STXs and various derivatives is in progress with the aim of developing isoform-selective sodium-channel inhibitors” Therapeutic Applications Possible anesthetic, but has poor therapeutic index. Toxicity occurs before therapeutic effects. Possible combinations with other drugs to create a larger window between toxic and effect doses. Research done on STXs effect on the sciatic nerves in rats. Research done on ZTXs effect on the brain cells. Structure and Toxicity Guanidinium groups essential for binding and must be in charged state. Carbamoyl chain Zetekitoxin AB has highest affinity for sodium channels. Research and the Environment Other sources of the toxin? Absorbed from algal blooms? Produced internally? How to improve detection methods? Spread awareness. Sensitivity to toxin varies, why? Biosynthetic profits? Obviously a defense. Other reasons? The End.. almost http://www.youtube.com/watch ?v=ZOp3rFQvgPI Citations 1) Iwamoto, O., Koshino, H. Hashizume., D., Nagasawa, K. (2007). Total synthesis of (-)-decarbamoyloxysaxitoxin. Angew. Chem. Int. Ed. 46, 8625-8628. 2) Llewellyn, L.E. (2006). Saxitoxin, a toxic marine natural product that targets a multitude of receptors. Nat. Prod. Rep. 23, 200-222. 3) Mosher, H.S., Fuhrman, F.A., Buchwald, H.D., Fischer, H.G. (1964). Tarichatoxin- tetrodotoxin: a potent neurotoxin. Science. 144, 1100-1110. 4) Yang, L., Kao, C.Y. (1992). Actions of chiriquitoxin on frog skeletal muscle fibers and implications for the tetrodotoxin/saxitoxin receptor. J. Gen. Physiol. 100, 609-622. 5) Yotsu-Yamashita, M., Kim, Y.H., Dudley, S. C. Jr., Choudhary, G., Pfahnl, A., Oshima, Y., Daly, J.W. (2004). The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: a potent sodium-channel blocker. PNAS. 101, 4346-4351. 6) Yotsu-Yamashita, M. (2006). Spectroscopic study of the structure zetekitoxin AB. Top Heterocycl. Chem. 5, 53-63. .
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