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I-1711 (-)-Indolactam V, >99%

M.W. 301.38

C17H23N3O2

[90365-57-4]

RTECS:  UY8547000

SPECIAL HAZARD:  Weak tumor promoter.  Gloves and mask should be worn when using this compound.  Care must be taken to avoid contact via all routes of exposure.

Storage:  Store at or below -20 ºC.  Solubility:  Soluble in DMSO or ethanol.  Disposal:  A

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• Moderately potent indolactam activator of protein kinase C; Kd for binding at the PDBu site is in the micromolar range.  Weak tumor promoter.  Fujiki, H., et al.  "Structure-activity studies on synthetic analogues (indolactams) of the tumor promoter teleocidin."  Gann 75:  866-870 (1984).  Heikkila, J. and Akerman, K.E.O.  "(-)-Indolactam V activates protein kinase C and induces changes in muscarinic receptor functions in SH-SY5Y human neuroblastoma cells."  Biochem. Biophys. Res. Comm. 162:  1207-1213 (1989).

• Differentiation of human embryonic stem cells to pancreatic cells.  Recently, the Melton group found that (-)-ILV is capable of inducing differentiation of human and mouse embryonic stem cells (ESCs) to pancreatic cells, identified by their expresstion of Pdx-1 and their further differentiation to exocrine, endocrine and duct cells in response to nicotinamide and bovine FGF.  Chen, S., et al.  "A small molecule that directs differentiation of human ESCs into the pancreatic lineage."  Nature Chemical Biology 5:  258-265 (2009).

  The Melton paper also showed that phorbol 12-myristate 13-acetate (PMA), the widely used standard protein kinase C (PKC) activator, produced effects essentially equivalent to those of (-)-ILV, but PMA was far more potent than (-)-ILV.  Also, PKC inhibitors blocked the effects of (-)-ILV.  Thus, (-)-ILV appears to be acting as an ordinary PKC activator in inducing differentation of the ESCs.

  Since PMA is about 100-fold more potent than (-)-ILV for differentiating ESCs and about 10-fold cheaper, PMA would be far preferable to (-)-ILV from a cost point of view, assuming the further testing does not reveal any major differences between the two compounds in the ESC system.

  Moreover, PMA is the most popular choice by far of researchers wishing to use a standard PKC activator.  Researchers use thousands of vials of PMA every year from our LC Labs division, directly and through distributors like Sigma, Biomol, Cell Signaling Technolgies, Promega, Tocris, Wako and others.  In contrast, (-)-ILV is rarely used, because it does not appear to have any significantly different properties from PMA, is much less potent, and is far more expensive. Thus, PMA has long been the standard PKC activator used in biological research -- its biological properties are very well known, and there is a huge existing literature on its effects in hundreds of cell types.

  Nonetheless, some researchers may prefer to use (-)-ILV because it and its effects were extensively highlighted and characterized in the Melton paper, in contrast to the limited experiments with PMA.

  Both PMA and (-)-ILV are potent skin inflammatory agents and skin tumor promoters in mice (but are not carcinogens, an important distinction).  The same is true of (-)-7-octyl-ILV, which is a more hydrophobic analog of (-)-ILV having potency about the same as PMA.

  For researchers who wish to avoid using even small quantities of a tumor promoter, we recommend a similar phorbol-type compound known as prostratin.  Prostratin has reduced skin inflammatory activity compared to PMA and is definitely not a skin tumor promoter in mice, but it faithfully mimics the effects of PMA in a wide variety of in vitro assays.  [The quantities of these compounds being used in typical lab studies are so small, however, that there are probably no real safety differences among the four -- PMA, (-)-ILV, (-)-7-octyl-ILV and prostratin].

• Please request Technical Note #3 for additional information.

• Sold for laboratory or manufacturing purposes only; not for human, veterinary, food, or household use.