Teleocidin A1

Names

[ Name ]:
Teleocidin A1

[Synonym ]:
lyngbyatoxin
3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one,9-(1-ethenyl-1,5-dimethyl-4-hexenyl)-1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)
(2S,5S)-9-[(R)-1-Ethenyl-1,5-dimethyl-4-hexenyl]-1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one
3h-pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one,1,2,4,5,6,8-hexahydro-9-(1-etheny
teleocidina
Teleocicin A-1
lyngbyatoxin A (teleocidin A-1)
3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one,1,2,4,5,6,8-hexahydro-9-(1-ethenyl-1,5-dimethyl-4-hexenyl)-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)
5-dimethyl-4-hexenyl)-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-l
teleocidin A1

Biological Activity

[Description]:

Teleocidin A1 (Lyngbyatoxin A), a highly toxic skin irritant, is a potent activator of protein kinase C (PKC). Teleocidin A1 shows antiproliferative activity against HeLa cancer cells (IC50=9.2 nM)[1][2].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> PKC

Research Areas >> Cancer

Signaling Pathways >> TGF-beta/Smad >> PKC

[References]

[1]. Stafford RG, et al. Comparison of the partition coefficient and skin penetration of a marine algal toxin (lyngbyatoxin A). Food Chem Toxicol. 1992;30(9):795-801.

[2]. Youssef DT, Shaala LA, Mohamed GA, et al. 2,3-seco-2,3-dioxo-lyngbyatoxin A from a Red Sea strain of the marine cyanobacterium Moorea producens. Nat Prod Res. 2015;29(8):703-709.

Chemical & Physical Properties

[ Density]:
1.06 g/cm3

[ Boiling Point ]:
665.1ºC at 760 mmHg

[ Molecular Formula ]:
C₂₇H₃₉N₃O₂

[ Molecular Weight ]:
437.61700

[ Flash Point ]:
356ºC

[ Exact Mass ]:
437.30400

[ PSA ]:
68.36000

[ LogP ]:
5.24580

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WY1981000

CHEMICAL NAME :: 3H-Pyrrolo(4,3,2-gh)-1,4-benzodiazonin-3-one, 1,2,4,5,6,8-hexahydro-9-(1-ethenyl-1,5- dimethyl-4-hexenyl)-5-(hydroxymethyl)-1-methyl-2-(1-m ethylethyl)-

CAS REGISTRY NUMBER :: 70497-14-2

LAST UPDATED :: 199012

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C27-H39-N3-O2

MOLECULAR WEIGHT :: 437.69

WISWESSER LINE NOTATION :: T569 1A O DM JN LVM&&TJ FX1&1U1&3UY1&1 J1 KY1&1 N1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85FZAT "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967 Volume(issue)/page/year: -,636,1967

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 204,193,1979

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ABCHA6 Agricultural and Biological Chemistry. (Maruzen Co. Ltd., POB 5050, Tokyo International, Tokyo 100-31, Japan) V.25- 1961- Volume(issue)/page/year: 26,660,1962