메뉴 건너뛰기




Volumn 11, Issue 8, 2013, Pages 2799-2813

First identification of 5,11-dideoxytetrodotoxin in marine animals, and characterization of major fragment ions of tetrodotoxin and its analogs by high resolution ESI-MS/MS

Author keywords

5,11 dideoxytetrodotoxin; Biosynthesis; LC MS MS; Tetrodotoxin

Indexed keywords

11 DEOXYTETRODOTOXIN; 11 NORTETRODOTOXIN 6 OL; 11 OXOTETRODOTOXIN; 4 EPITETRODOTOXIN; 4,9 ANHYDROTETRODOTOXIN; 5 DEOXYTETRODOTOXIN; 5,11 DIDEOXYTETRODOTOXIN; 5,6,11 TRIDEOXYTETRODOTOXIN; 6,11 DIDEOXYTETRODOTOXIN; TETRODOTOXIN; UNCLASSIFIED DRUG;

EID: 84883779786     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11082799     Document Type: Article
Times cited : (96)

References (50)
  • 2
    • 84931650591 scopus 로고
    • The structure of tetrodotoxin
    • Woodward, R.B. The structure of tetrodotoxin. Pure Appl. Chem. 1964, 9, 49-74.
    • (1964) Pure Appl. Chem. , vol.9 , pp. 49-74
    • Woodward, R.B.1
  • 4
    • 0000433667 scopus 로고
    • Stabilization and rectification of muscle fiber membrane by tetrodotoxin
    • Narahashi, T.; Deguchi, T.; Urakawa, N.; Ohkubo, Y. Stabilization and rectification of muscle fiber membrane by tetrodotoxin. Am. J. Physiol. 1960, 198, 934-938.
    • (1960) Am. J. Physiol. , vol.198 , pp. 934-938
    • Narahashi, T.1    Deguchi, T.2    Urakawa, N.3    Ohkubo, Y.4
  • 5
    • 0023032629 scopus 로고
    • Tetrodotoxin saxitoxin, and the molecular biology of the sodium channel
    • Kao, C.Y. Tetrodotoxin, saxitoxin, and the molecular biology of the sodium channel. Ann. N. Y. Acad. Sci. 1986, 479, 1-14.
    • (1986) Ann. N. Y. Acad. Sci. , vol.479 , pp. 1-14
    • Kao, C.Y.1
  • 6
    • 0001027002 scopus 로고
    • Chemical studies on tetrodotoxin Rept. III. Isolation of spheroidine
    • Yokoo, A. Chemical studies on tetrodotoxin Rept. III. Isolation of spheroidine. J. Chem. Soc. Japan 1950, 71, 591-592.
    • (1950) J. Chem. Soc. Japan , vol.71 , pp. 591-592
    • Yokoo, A.1
  • 7
    • 85008119150 scopus 로고
    • Occurrence of tetrodotoxin as the major toxin in xanthid crab Atergatis floridus
    • Noguchi, T.; Uzu, A.; Koyama, K.; Hashimoto, K. Occurrence of tetrodotoxin as the major toxin in xanthid crab Atergatis floridus. Bull. Jpn. Soc. Sci. Fish. 1983, 49, 1887-1892.
    • (1983) Bull. Jpn. Soc. Sci. Fish. , vol.49 , pp. 1887-1892
    • Noguchi, T.1    Uzu, A.2    Koyama, K.3    Hashimoto, K.4
  • 9
    • 0023023518 scopus 로고
    • Occurrence of tetrodotoxin in the flatworm Planocera multitentaculata
    • Miyazawa, K.; Jeon, J.K.; Maruyama, J.; Noguchi, T.; Ito, K.; Hashimoto, K. Occurrence of tetrodotoxin in the flatworm Planocera multitentaculata. Toxicon 1986, 24, 645-650.
    • (1986) Toxicon , vol.24 , pp. 645-650
    • Miyazawa, K.1    Jeon, J.K.2    Maruyama, J.3    Noguchi, T.4    Ito, K.5    Hashimoto, K.6
  • 13
    • 0017870726 scopus 로고
    • Maculotoxin: A Neurotoxin from the venom glands of the octopus Hapalochlaena maculosa identified as tetrodotoxin
    • Sheumack, D.D.; Howden, M.E.H.; Spence, I.; Quinn, R.J. Maculotoxin: A Neurotoxin from the venom glands of the octopus Hapalochlaena maculosa identified as tetrodotoxin. Science 1978, 199, 188-189.
    • (1978) Science , vol.199 , pp. 188-189
    • Sheumack, D.D.1    Howden, M.E.H.2    Spence, I.3    Quinn, R.J.4
  • 14
    • 77954144509 scopus 로고    scopus 로고
    • Detection of tetrodotoxin from the grey sided-gilled sea slug-Pleurobranchaea maculata, and associated dog neurotoxicosis on beaches adjacent to the Hauraki Gulf, Auckland, New Zealand
    • McNabb, P.; Selwood, A.I.; Munday, R.; Wood, S.A.; Taylor, D.I.; MacKenzie, A.L.; van Ginkel, R.; Rhodes, L.L.; Cornelisen, C.; Heasman, K.; Patrick, T.; Holland, C.K. Detection of tetrodotoxin from the grey sided-gilled sea slug-Pleurobranchaea maculata, and associated dog neurotoxicosis on beaches adjacent to the Hauraki Gulf, Auckland, New Zealand. Toxicon 2010, 56, 466-473.
    • (2010) Toxicon , vol.56 , pp. 466-473
    • McNabb, P.1    Selwood, A.I.2    Munday, R.3    Wood, S.A.4    Taylor, D.I.5    Mackenzie, A.L.6    Van Ginkel, R.7    Rhodes, L.L.8    Cornelisen, C.9    Heasman, K.10    Patrick, T.11    Holland, C.K.12
  • 15
    • 0014692071 scopus 로고
    • Toxin from skin of frogs of the genus Atelopus: Differentiation from Dendrobatid toxins
    • Fuhrman, F.A.; Fuhrman, G.J.; Mosher, H.S. Toxin from skin of frogs of the genus Atelopus: differentiation from Dendrobatid toxins. Science 1969, 165, 1376-1379.
    • (1969) Science , vol.165 , pp. 1376-1379
    • Fuhrman, F.A.1    Fuhrman, G.J.2    Mosher, H.S.3
  • 18
    • 0022658561 scopus 로고
    • Occurrence of tetrodotoxin and anhydrotetrodotoxin in vibrio Sp isolated from the intestines of a xanthid crab atergatis floridus
    • Noguchi, T.; Jeo, J.; Arakawa, O.; Sugita, H.; Deguchi, Y.; Shida, Y.; Hashimoto, K. Occurrence of tetrodotoxin and anhydrotetrodotoxin in Vibrio sp. isolated from the intestines of a xanthid crab, Atergatis floridus. J. Biochem. 1986, 99, 311-314.
    • (1986) J. Biochem. , vol.99 , pp. 311-314
    • Noguchi, T.1    Jeo, J.2    Arakawa, O.3    Sugita, H.4    Deguchi, Y.5    Shida, Y.6    Hashimoto, K.7
  • 19
    • 43649086171 scopus 로고    scopus 로고
    • Accumulation of tetrodotoxin and 4,9-anhydrotetrodotoxin in cultured juvenile kusafugu Fugu niphobles by dietary administration of natural toxic komonfugu Fugu poecilonotus liver
    • Kono, M.; Matsui, T.; Furukaw, K.; Yotsu-Yamashita, M.; Yamamori, K. Accumulation of tetrodotoxin and 4,9-anhydrotetrodotoxin in cultured juvenile kusafugu Fugu niphobles by dietary administration of natural toxic komonfugu Fugu poecilonotus liver. Toxicon 2008, 51, 1269-1273.
    • (2008) Toxicon , vol.51 , pp. 1269-1273
    • Kono, M.1    Matsui, T.2    Furukaw, K.3    Yotsu-Yamashita, M.4    Yamamori, K.5
  • 20
    • 84874417210 scopus 로고    scopus 로고
    • Change in the transfer profile of orally administered tetrodotoxin to non-toxic cultured pufferfish Takifugu rubripes depending of its development stage
    • Tatsuno, R.; Shikina, M.; Shirai, Y.; Wang, J.; Soyano, K.; Nishihara, J.N.; Takatani, T.; Arakawa, O. Change in the transfer profile of orally administered tetrodotoxin to non-toxic cultured pufferfish Takifugu rubripes depending of its development stage. Toxicon 2013, 65, 76-80.
    • (2013) Toxicon , vol.65 , pp. 76-80
    • Tatsuno, R.1    Shikina, M.2    Shirai, Y.3    Wang, J.4    Soyano, K.5    Nishihara, J.N.6    Takatani, T.7    Arakawa, O.8
  • 21
    • 53449096903 scopus 로고    scopus 로고
    • Examination of transformation among tetrodotoxin and its analogs in the living cultured juvenile puffer fish, kusafugu, Fugu niphobles by intramuscular administration
    • Kono, M.; Matsui, T.; Furukawa, K.; Takase, T.; Yamamori, K.; Kaneda, H.; Aoki, D.; Jang, J.H.; Yotsu-Yamashita, M. Examination of transformation among tetrodotoxin and its analogs in the living cultured juvenile puffer fish, kusafugu, Fugu niphobles by intramuscular administration. Toxicon 2008, 52, 714-720.
    • (2008) Toxicon , vol.52 , pp. 714-720
    • Kono, M.1    Matsui, T.2    Furukawa, K.3    Takase, T.4    Yamamori, K.5    Kaneda, H.6    Aoki, D.7    Jang, J.H.8    Yotsu-Yamashita, M.9
  • 22
    • 57749086851 scopus 로고    scopus 로고
    • Transfer profile of intramuscularly administered tetrodotoxin to non-toxic cultured specimens of the pufferfish Takifugu rubripes
    • Ikeda, K.; Murakami, Y.; Emoto, Y.; Ngy, L.; Taniyama, S.; Yagi, M.; Takatani, T.; Arakawa, O. Transfer profile of intramuscularly administered tetrodotoxin to non-toxic cultured specimens of the pufferfish Takifugu rubripes. Toxicon 2009, 53, 99-103.
    • (2009) Toxicon , vol.53 , pp. 99-103
    • Ikeda, K.1    Murakami, Y.2    Emoto, Y.3    Ngy, L.4    Taniyama, S.5    Yagi, M.6    Takatani, T.7    Arakawa, O.8
  • 23
    • 82555197960 scopus 로고    scopus 로고
    • Transfer profile of intramuscularly administered tetrodotoxin to artificial hybrid specimens of pufferfish, Takifugu rubripes and Takifugu niphobles
    • Wang, J.; Araki, T.; Tatsuno, R.; Nina, S.; Ikeda, K.; Hamasaki, M.; Sakakura, Y.; Takatani, T.; Arakawa, O. Transfer profile of intramuscularly administered tetrodotoxin to artificial hybrid specimens of pufferfish, Takifugu rubripes and Takifugu niphobles. Toxicon 2011, 58, 565-569.
    • (2011) Toxicon , vol.58 , pp. 565-569
    • Wang, J.1    Araki, T.2    Tatsuno, R.3    Nina, S.4    Ikeda, K.5    Hamasaki, M.6    Sakakura, Y.7    Takatani, T.8    Arakawa, O.9
  • 24
    • 77952520268 scopus 로고    scopus 로고
    • The chemical and evolutionary ecology of tetrodotoxin (TTX) toxicity in terrestrial vertebrates
    • Hanifin, C.T. The chemical and evolutionary ecology of tetrodotoxin (TTX) toxicity in terrestrial vertebrates. Mar. Drugs 2010, 8, 577-593.
    • (2010) Mar. Drugs , vol.8 , pp. 577-593
    • Hanifin, C.T.1
  • 25
    • 0029978602 scopus 로고    scopus 로고
    • Chemical and etiological studies on tetrodotoxin and its analogs
    • Yasumoto, T.; Yotsu-Yamashita, M. Chemical and etiological studies on tetrodotoxin and its analogs. J. Toxicol. Toxin Rev. 1996, 15, 81-90.
    • (1996) J. Toxicol. Toxin Rev. , vol.15 , pp. 81-90
    • Yasumoto, T.1    Yotsu-Yamashita, M.2
  • 27
    • 0022260928 scopus 로고
    • Tetrodotoxin derivatives in puffer fish
    • Nakamura, M.; Yasumoto, T. Tetrodotoxin derivatives in puffer fish. Toxicon 1985, 23, 271-276.
    • (1985) Toxicon , vol.23 , pp. 271-276
    • Nakamura, M.1    Yasumoto, T.2
  • 28
    • 0033127752 scopus 로고    scopus 로고
    • Isolation and structural assignment of 5-deoxytetrodotoxin from the puffer fish Fugu poecilonotus
    • Yotsu-Yamashita, M.; Schimmele, B.; Yasumoto, T. Isolation and structural assignment of 5-deoxytetrodotoxin from the puffer fish Fugu poecilonotus. Biosci. Biotechnol. Biochem. 1999, 63, 961-963.
    • (1999) Biosci. Biotechnol. Biochem. , vol.63 , pp. 961-963
    • Yotsu-Yamashita, M.1    Schimmele, B.2    Yasumoto, T.3
  • 29
    • 33750931583 scopus 로고    scopus 로고
    • Distribution of tetrodotoxin, saxitoxin, and their analogs among tissues of the puffer fish Fugu pardalis
    • Jang, J.; Yotsu-Yamashita, M. Distribution of tetrodotoxin, saxitoxin, and their analogs among tissues of the puffer fish Fugu pardalis. Toxicon 2006, 48, 980-987.
    • (2006) Toxicon , vol.48 , pp. 980-987
    • Jang, J.1    Yotsu-Yamashita, M.2
  • 30
    • 33845280591 scopus 로고
    • New tetrodotoxin analogue from the newt Cynops ensicauda
    • Yasumoto, T.; Yotsu, M.; Murata, M.; Naoki, H. New tetrodotoxin analogue from the newt Cynops ensicauda. J. Am. Chem. Soc. 1988, 110, 2344-2345.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 2344-2345
    • Yasumoto, T.1    Yotsu, M.2    Murata, M.3    Naoki, H.4
  • 31
    • 35649001902 scopus 로고    scopus 로고
    • 6,11-DideoxyTTX from the puffer fish, Fugu pardalis
    • Jang, J.H.; Yotsu-Yamashita, M. 6,11-DideoxyTTX from the puffer fish, Fugu pardalis. Toxicon 2007, 50, 947-951.
    • (2007) Toxicon , vol.50 , pp. 947-951
    • Jang, J.H.1    Yotsu-Yamashita, M.2
  • 32
    • 0028841233 scopus 로고
    • 5,611-Trideoxytetrodotoxin from the puffer fish Fugu poecilonotus
    • Yotsu-Yamashita, M.; Yamagishi, Y.; Yasumoto, T. 5,6,11- Trideoxytetrodotoxin from the puffer fish, Fugu poecilonotus. Tetrahedron Lett. 1995, 36, 9329-9332.
    • (1995) Tetrahedron Lett , vol.36 , pp. 9329-9332
    • Yotsu-Yamashita, M.1    Yamagishi, Y.2    Yasumoto, T.3
  • 33
    • 0001454350 scopus 로고
    • Isolation of 11-oxotetrodotoxin from the puffer Arothron nigropunctatus
    • Khora, S.S.; Yasumoto, T. Isolation of 11-oxotetrodotoxin from the puffer Arothron nigropunctatus. Tetrahedron Lett. 1989, 30, 4393-4394.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4393-4394
    • Khora, S.S.1    Yasumoto, T.2
  • 34
    • 0000404977 scopus 로고
    • Isolation and structural assignment of 11-nortetrodotoxin-6(S)-ol from the puffer Arothron nigropunctatus
    • Yotsu-Yamashita, M.; Hayashi, Y.; Khora, S.S.; Sato, S.; Yasumoto, T. Isolation and structural assignment of 11-nortetrodotoxin-6(S)-ol from the puffer Arothron nigropunctatus. Biosci. Biotechnol. Biochem. 1992, 56, 370-371.
    • (1992) Biosci. Biotechnol. Biochem. , vol.56 , pp. 370-371
    • Yotsu-Yamashita, M.1    Hayashi, Y.2    Khora, S.S.3    Sato, S.4    Yasumoto, T.5
  • 35
    • 0000893969 scopus 로고
    • Isolation of 11-nortetrodotoxin-6(R)-ol and other tetrodotoxin derivatives from the puffer Fugu niphobles
    • Endo, A.; Khora, S.S.; Murata, M.; Yasumoto, T. Isolation of 11-nortetrodotoxin-6(R)-ol and other tetrodotoxin derivatives from the puffer Fugu niphobles. Tetrahedron Lett. 1988, 29, 4127-4128.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4127-4128
    • Endo, A.1    Khora, S.S.2    Murata, M.3    Yasumoto, T.4
  • 36
    • 0025368753 scopus 로고
    • The structure of chiriquitoxin from the Costa Rican frog Atelopus chiriquiensis
    • Yotsu, M.; Yasumoto, T.; Kim, Y.H.; Kao, C.Y. The structure of chiriquitoxin from the Costa Rican frog Atelopus chiriquiensis. Tetrahedron Lett. 1990, 31, 3187-3190.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 3187-3190
    • Yotsu, M.1    Yasumoto, T.2    Kim, Y.H.3    Kao, C.Y.4
  • 37
    • 70649101317 scopus 로고    scopus 로고
    • First report on toxins in the Panamanian toads Atelopus limosus, A glyphus and A certus
    • Yotsu-Yamashita, M.; Tateki, E. First report on toxins in the Panamanian toads Atelopus limosus, A. glyphus and A. certus. Toxicon 2010, 55, 153-156.
    • (2010) Toxicon , vol.55 , pp. 153-156
    • Yotsu-Yamashita, M.1    Tateki, E.2
  • 38
    • 0343905314 scopus 로고
    • 1-Hydroxy-5,11-dideoxytetrodotoxin, the first N-hydroxy and ringdeoxy derivative of tetrodotoxin found in the newt Taricha granulosa
    • Kotaki, Y.; Shimizu, Y. 1-Hydroxy-5,11-dideoxytetrodotoxin, the first N-hydroxy and ringdeoxy derivative of tetrodotoxin found in the newt Taricha granulosa. J. Am. Chem. Soc. 1993, 115, 827-830.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 827-830
    • Kotaki, Y.1    Shimizu, Y.2
  • 39
    • 84859614907 scopus 로고    scopus 로고
    • Isolation and structural determination of the first 8-epi-type tetrodotoxin analogs from the newt, Cynops ensicauda popei, and comparison of tetrodotoxin analogs profiles of this newt and the puffer fish, Fugu poecilonotus
    • Kudo, Y.; Yasumoto, T.; Konoki, K.; Cho, Y.; Yotsu-Yamashita, M. Isolation and structural determination of the first 8-epi-type tetrodotoxin analogs from the newt, Cynops ensicauda popei, and comparison of tetrodotoxin analogs profiles of this newt and the puffer fish, Fugu poecilonotus. Mar. Drugs 2012, 10, 655-667.
    • (2012) Mar. Drugs , vol.10 , pp. 655-667
    • Kudo, Y.1    Yasumoto, T.2    Konoki, K.3    Cho, Y.4    Yotsu-Yamashita, M.5
  • 40
    • 84870291037 scopus 로고    scopus 로고
    • Comparison of sample preparation methods, validation of an UPLC-MS/MS procedure for the quantification of tetrodotoxin present in marine gastropods and analysis of pufferfish
    • Nzoughet, J.K.; Campbell, K.; Barnes, P.; Cooper, K.M.; Chevallier, O.P.; Elliott, C.T. Comparison of sample preparation methods, validation of an UPLC-MS/MS procedure for the quantification of tetrodotoxin present in marine gastropods and analysis of pufferfish. Food Chem. 2013, 136, 1584-1589.
    • (2013) Food Chem. , vol.136 , pp. 1584-1589
    • Nzoughet, J.K.1    Campbell, K.2    Barnes, P.3    Cooper, K.M.4    Chevallier, O.P.5    Elliott, C.T.6
  • 41
    • 33646021320 scopus 로고    scopus 로고
    • Hydrophilic interaction liquid chromatography-electrospray ionization mass spectrometry of tetrodotoxin and its analogs
    • Nakagawa, T.; Jang, J.; Yotsu-Yamashita, M. Hydrophilic interaction liquid chromatography-electrospray ionization mass spectrometry of tetrodotoxin and its analogs. Anal. Biochem. 2006, 352, 142-144.
    • (2006) Anal. Biochem. , vol.352 , pp. 142-144
    • Nakagawa, T.1    Jang, J.2    Yotsu-Yamashita, M.3
  • 42
    • 0035282987 scopus 로고    scopus 로고
    • Electrospray ionization mass spectrometry of tetrodotoxin and its analogs: Liquid mass spectrometry, and liquid chromatography/tandem mass spectrometry
    • Shoji, Y.; Yotsu-Yamashita, M.; Miyazawa, T.; Yasumoto, T. Electrospray ionization mass spectrometry of tetrodotoxin and its analogs: Liquid mass spectrometry, and liquid chromatography/tandem mass spectrometry. Anal. Biochem. 2001, 290, 10-17.
    • (2001) Anal. Biochem. , vol.290 , pp. 10-17
    • Shoji, Y.1    Yotsu-Yamashita, M.2    Miyazawa, T.3    Yasumoto, T.4
  • 43
    • 77952580254 scopus 로고    scopus 로고
    • LC/MS analysis of tetrodotoxin and its deoxy analogs in the marine puffer fish Fugu niphobles from the southern coast of Korea, and in the brackishwater puffer fishes Tetraodon nigroviridis and Tetraodon biocellatus from Southeast Asia
    • Jang, J.; Lee, J.S.; Yotsu-Yamashita, M. LC/MS analysis of tetrodotoxin and its deoxy analogs in the marine puffer fish Fugu niphobles from the southern coast of Korea, and in the brackishwater puffer fishes Tetraodon nigroviridis and Tetraodon biocellatus from Southeast Asia. Mar. Drugs 2010, 8, 1049-1058.
    • (2010) Mar. Drugs , vol.8 , pp. 1049-1058
    • Jang, J.1    Lee, J.S.2    Yotsu-Yamashita, M.3
  • 44
    • 79251625665 scopus 로고    scopus 로고
    • Optimization of simultaneous analysis of tetrodotoxin, 4-epitetrodotoxin, 4,9-anhydrotetrodotoxin, and 5,6,11-trideoxytetrodotoxin by hydrophilic interaction liquid chromatography-tandem mass spectrometry
    • Yotsu-Yamashita, M.; Jang, J.H.; Cho, Y.; Konoki, K. Optimization of simultaneous analysis of tetrodotoxin, 4-epitetrodotoxin, 4,9- anhydrotetrodotoxin, and 5,6,11-trideoxytetrodotoxin by hydrophilic interaction liquid chromatography-tandem mass spectrometry. Forensic Toxicol. 2011, 29, 61-64.
    • (2011) Forensic Toxicol. , vol.29 , pp. 61-64
    • Yotsu-Yamashita, M.1    Jang, J.H.2    Cho, Y.3    Konoki, K.4
  • 46
    • 0035927211 scopus 로고    scopus 로고
    • Stereocontrolled Synthesis of (-)-5,11-Dideoxytetrodotoxin
    • Asai, M.; Nishikawa, T.; Ohyabu, N.; Yamamoto, N.; Isobe, M. Stereocontrolled Synthesis of (-)-5,11-Dideoxytetrodotoxin. Tetrahedron 2001, 57, 4543-4558.
    • (2001) Tetrahedron , vol.57 , pp. 4543-4558
    • Asai, M.1    Nishikawa, T.2    Ohyabu, N.3    Yamamoto, N.4    Isobe, M.5
  • 47
    • 84879148880 scopus 로고    scopus 로고
    • Synthesis of tetrodotoxin, a classic but still fascinating natural product
    • Nishikawa, T.; Isobe, M. Synthesis of tetrodotoxin, a classic but still fascinating natural product. Chem. Rec. 2013, 13, 286-302.
    • (2013) Chem. Rec. , vol.13 , pp. 286-302
    • Nishikawa, T.1    Isobe, M.2
  • 48
    • 84883817806 scopus 로고    scopus 로고
    • Recent progress in ultramicroanalysis by LC-Q-TOF
    • Isobe, M.; Suwan, S.; Franz, T. Recent progress in ultramicroanalysis by LC-Q-TOF. JASCO Report 2000, 42, 1-18.
    • (2000) JASCO Report , vol.42 , pp. 1-18
    • Isobe, M.1    Suwan, S.2    Franz, T.3
  • 49
    • 84873958745 scopus 로고    scopus 로고
    • An improved synthesis of (-)-5, 11-dideoxytetrodotoxin
    • Adachi, M.; Imazu, T.; Isobe, M.; Nishikawa, T. An improved synthesis of (-)-5, 11-dideoxytetrodotoxin. J. Org. Chem. 2013, 78, 1699-1705.
    • (2013) J. Org. Chem. , vol.78 , pp. 1699-1705
    • Adachi, M.1    Imazu, T.2    Isobe, M.3    Nishikawa, T.4
  • 50
    • 0033061210 scopus 로고    scopus 로고
    • Effects of specific modifications of several hydroxyls of tetrodotoxin on its affinity to rat brain membrane
    • Yotsu-Yamashita, M.; Sugimoto, A.; Takai, A.; Yasumoto, T. Effects of specific modifications of several hydroxyls of tetrodotoxin on its affinity to rat brain membrane. J. Pharmacol. Exp. Ther. 1999, 289, 1688-1696.
    • (1999) J. Pharmacol. Exp. Ther. , vol.289 , pp. 1688-1696
    • Yotsu-Yamashita, M.1    Sugimoto, A.2    Takai, A.3    Yasumoto, T.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.