Copyright © 1996, 1997, 2001
by Galen Daryl Knight and VitaleTherapeutics, Inc.
VitaleTheine Modulators
The vitaletheine modulators provide an interesting array of stabilities
and biological activities. Generally, the oxidized versions, such as the
disulfide, vitalethine, and its benzyl derivative (the
bis-benzyl derivative of a sulfenic acid dimer) have tumor-negating
activities at relatively low concentrations. In non-oxidizing environments,
vitaletheine and its polymerized tetramer are thought to have primarily
proliferative activities. Theoretically this system can result in proliferation
through at least two possible scenarios:
-
Direct activation of HMG-CoA reductase by thiols
(including vitaletheine or glutathione); or
-
When the monooxygenase is compromised, diverted
by other substrates, or in an inactivating aggregation
with the tetramer, vitaletheine V4.
Treatment with the tetramer increases melanoma growth
in the allogeneic model and enhances red blood cell formation from erythroid
progenitors, indicating that this type of regulation is important in
the control of both normal and cancer cells.
The stability of these compounds from the most chemically dynamic to
the most stable are as follows: vitaletheine, vitaletheine V4, vitalethine,
and the sulfenate-linked benzyl derivative of vitalethine. For example,
vitaletheine is almost too reactive to chemically analyze in an environment
not stabilized by proteinaceous receptors, yet the sulfenate-linked benzyl
derivative of vitalethine shows no signs of thermal decomposition or melting
until well over 300 degrees (Centigrade).
VitaleThine
Although vitalethine appears stable for years when frozen as a powder,
its synthesis is not trivial. In the approximately five years that it took
to perfect the reported synthesis, many solvent
systems and strategies for producing free carbamic acid or imidocarbonate
moieties were attempted. None of the other procedures tested to date have
produced the pristine material obtained using
the reported procedure and additional tips on synthesis
included in this Web Page.
Bis-Benzyl Sulfenate-Linked Dimer
Anyone want to have a stab at chemical nomenclature for this beast? A comparison
of the infrared spectra for this benzyl derivative with the spectra of
vitalethine and of bis-CBZ-ß-alethine are very enlightening, particularly
around the C-O stretch regions.
VitaleTheine V4
The tetramer may slowly rearrange when not stored under anhydrous conditions,
but storage of the zinc salt of this compound under anhydous conditions
and/or reduced pressures can also lead to dehydration through
sublimation
of ZnO and rehydration to a different product.
GO TO: