Teleocidin A1
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04107 |
| CAS | 70497-14-2 |
| Molecular Weight | 437.62 |
| Molecular Formula | C27H39N3O2 |
| Purity | >98% by HPLC |
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Description
Teleocidin A1 is a powerful nematicide and acaricide produced by Streptomyces, which acts as an effective activator of protein kinase C, a tumor promoter, an inducer of colony stimulating factors, and regulator of expression of several genes.
Specification
| Synonyms | Lyngbyatoxin; Lyngbyatoxin-A |
| Storage | Store at -20°C |
| IUPAC Name | (10S,13S)-5-[(3R)-3,7-dimethylocta-1,6-dien-3-yl]-13-(hydroxymethyl)-9-methyl-10-propan-2-yl-3,9,12-triazatricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-11-one |
| Canonical SMILES | CC(C)C1C(=O)NC(CC2=CNC3=C(C=CC(=C23)N1C)C(C)(CCC=C(C)C)C=C)CO |
| InChI | InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25-,27-/m0/s1 |
| InChI Key | KISDGNGREAJPQR-OICBGKIFSA-N |
| Source | Lyngbyatoxin A is a cyanotoxin produced by certain cyanobacteria species, notably Moorea producens (formerly classified as Lyngbya majuscula). |
Properties
| Appearance | White to Light Tan Solid |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 665.1°C at 760 mmHg |
| Density | 1.06 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Toxicity
| Carcinogenicity | Not listed by IARC. |
| Mechanism Of Toxicity | Lyngbyatoxin A is a tumor promoter. Lyngbyatoxin A and related compounds bind to the cysteine-rich C1 domains (C1A and C1B) of protein kinase C (PKC) isozymes to activate them, possibly leading to tumor formation. In cancer cells, PKC isozymes are involved in cell proliferation, survival, invasion, migration, apoptosis, angiogenesis, and anticancer drug resistance through their increased or decreased participation in various cellular signaling pathways. Lyngbyatoxin A also induces ornithine decarboxylase. The ornithine decarboxylation reaction catalyzed by ornithine decarboxylase (ODC) is the first and committed step in the synthesis of polyamines, particularly putrescine, spermidine and spermine. ODC is upregulated in a wide variety of cancers. The mechanism by which ODC promotes carcinogenesis is complex and not entirely known. Along with their direct effect on DNA stability, polyamines also upregulate gap junction genes and downregulate tight junction genes. Gap junction genes are involved in communication between carcinogenic cells and tight junction genes act as tumor suppressors. |
Reference Reading
1. A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens
Ryuichi Watanabe, Bryan Sakamoto, Weina Jiang, Michiya Kamio, Masayuki Kikumori, Kazuhiro Irie, Wei Zhou, Hajime Uchida, Toshiyuki Suzuki, Hiroshi Nagai Mar Drugs . 2014 May 12;12(5):2748-59. doi: 10.3390/md12052748.
Lyngbyatoxin A from the marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) is known as the causative agent of "swimmer's itch" with its highly inflammatory effect. A new toxic compound was isolated along with lyngbyatoxin A from an ethyl acetate extract of M. producens collected from Hawaii. Analyses of HR-ESI-MS and NMR spectroscopies revealed the isolated compound had the same planar structure with that of lyngbyatoxin A. The results of optical rotation and CD spectra indicated that the compound was a new lyngbyatoxin A derivative, 12-epi-lyngbyatoxin A (1). While 12-epi-lyngbyatoxin A showed comparable toxicities with lyngbyatoxin A in cytotoxicity and crustacean lethality tests, it showed more than 100 times lower affinity for protein kinase Cδ (PKCδ) using the PKCδ-C1B peptide when compared to lyngbyatoxin A.
2. Pendolmycin, a new tumor promoter of the teleocidin A class on skin of CD-1 mice
K Okabe, S Okabe, H Furuya-Suguri, H Fujiki, S Nishiwaki, H Muratake, M Nakayasu, M Suganuma, S Yoshizawa, M Natsume Jpn J Cancer Res . 1991 Jul;82(7):779-83. doi: 10.1111/j.1349-7006.1991.tb02702.x.
Pendolmycin, isolated from Nocardiopsis, is a compound structurally similar to teleocidin A, one of the 12-O-tetradecanoylphorbol-13-acetate (TPA)-type tumor promoters. Pendolmycin has a C5 dimethyl allyl group attached to C-7 of (-)-indolactam-V, whereas teleocidin A has a C10 linalyl group attached to the molecule. The structure-activity relationships of a hydrophobic moiety attached to (-)-indolactam-V were studied in four compounds, (-)-indolactam-V, pendolmycin, teleocidin A and newly synthesized 7-(nerolidyl)-(-)-indolactam-V in tests on inhibition of the specific [3H]TPA binding to a particulate fraction of mouse skin, activation of protein kinase C and induction of both adhesion of HL-60 cells and ornithine decarboxylase in mouse skin. The potencies of the compounds for these activities increased mainly depending on the length of the hydrophobic group. Pendolmycin had a tumor-promoting activity on mouse skin initiated with a single application of 7,12-dimethyl-benz[a]anthracene, and its potency was just between those of (-)-indolactam-V and teleocidin A. The role of the hydrophobic moiety is discussed with particular emphasis on the results obtained with 7-(nerolidyl)-(-)-indolactam-V.
3. The toxins of Lyngbya majuscula and their human and ecological health effects
G R Shaw, N J Osborne, P M Webb Environ Int . 2001 Nov;27(5):381-92. doi: 10.1016/s0160-4120(01)00098-8.
Lyngbya majuscula is a benthic filamentous marine cyanobacterium, which in recent years appears to have been increasing in frequency and size of blooms in Moreton Bay, Queensland. It has a worldwide distribution throughout the tropics and subtropics in water to 30m. It has been found to contain a variety of chemicals that exert a range of biological effects, including skin, eye and respiratory irritation. The toxins lyngbyatoxin A and debromoaplysiatoxin appear to give the most widely witnessed biological effects in relation to humans, and experiments involving these two toxins show the formation of acute dermal lesions. Studies into the epidemiology of the dermatitic, respiratory and eye effects of the toxins of this organism are reviewed and show that Lyngbya induced dermatitis has occurred in a number of locations. The effects of aerosolised Lyngbya in relation to health outcomes were also reported. Differential effects of bathing behaviour after Lyngbya exposure were examined in relation to the severity of health outcomes. The potential for Lyngbya to exhibit differential toxicologies due to the presence of varying proportions of a range of toxins is also examined. This paper reviews the present state of knowledge on the effects of Lyngbya majuscula on human health, ecosystems and human populations during a toxic cyanobacterial bloom. The potential exists for toxins from Lyngbya majuscula affecting ecological health and in particular marine reptiles.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
