wikipedia: DCA – Deoxycholic acid

[Richard Moore]

http://en.wikipedia.org/wiki/Deoxycholic_acid

Deoxycholic acid From Wikipedia, the free encyclopedia Deoxycholic
acid, also known as deoxycholate, cholanoic acid, and
3N1,12N1-dihydroxy-5N2-cholanate, is a bile
acid<http://en.wikipedia.org/wiki/Bile_acid>. Deoxycholic acid is
one of the secondary bile acids, which are metabolic byproducts of
intestinal bacteria. The two primary bile acids secreted by the
liver are cholic acid<http://en.wikipedia.org/wiki/Cholic_acid> and
chenodeoxycholic acid<http://en.wikipedia.org/wiki/Chenodeoxycholic_acid>.
Bacteria metabolize chenodeoxycholic acid into the secondary bile
acid lithocholic acid<http://en.wikipedia.org/wiki/Lithocholic_acid>,
and they metabolize cholic acid into deoxycholic acid. There are
additional secondary bile acids, such asursodeoxycholic
acid<http://en.wikipedia.org/wiki/Ursodeoxycholic_acid>. Deoxycholic
acid is soluble in alcohol<http://en.wikipedia.org/wiki/Alcohol>
and acetic acid<http://en.wikipedia.org/wiki/Acetic_acid>. When
pure, it comes in a white to off-white crystalline powder form.

Deoxycholic acid has been used since its discovery in various fields
of human medicine. In the human
body<http://en.wikipedia.org/wiki/Human_body> deoxycholic acid is
used in the emulsification<http://en.wikipedia.org/wiki/Emulsification>
of fats<http://en.wikipedia.org/wiki/Fat> for the absorption in the
intestine<http://en.wikipedia.org/wiki/Intestine>. It has, in some
countries (including Switzerland) been licensed as an emulsifier
in food
industry[2]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-1>, but
it is no longer common. Outside the body it is used in experimental
basis of cholagogues<http://en.wikipedia.org/wiki/Cholagogue> and
is also in use to prevent and dissolve
gallstones<http://en.wikipedia.org/wiki/Gallstone>[3]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-2>[4]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-3>.[edit<http://en.wikipedia.org/w/index.php?title=Deoxycholic_acid&action=edit&section=1>]

Applications

Sodium deoxycholate, the sodium salt of deoxycholic acid, is
frequently used inmesotherapy<http://en.wikipedia.org/wiki/Mesotherapy>
injections, mixed with
phosphatidylcholine<http://en.wikipedia.org/wiki/Phosphatidylcholine>.[citation
needed<http://en.wikipedia.org/wiki/Wikipedia:Citation_needed>] In
research deoxycholic acid is used as a mild detergent for the
isolation of membrane associated proteins. The critical micelle
concentration<http://en.wikipedia.org/wiki/Critical_micelle_concentration>
for deoxycholic acid is approximately 2.4-4
mM.[5]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-4>
Sodium deoxycholate, the sodium salt of deoxycholic acid, is often
used as a biological detergent to lyse cells and solubilise cellular
and membrane
components.[6]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-5>
Deoxycholates and bile acid derivatives in general are actively
being studied as structures for incorporation in
nanotechnology.[7]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-6>
They also have found application in microlithography as photoresistant
components.[8]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-7>[9]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-8>
[edit<http://en.wikipedia.org/w/index.php?title=Deoxycholic_acid&action=edit&section=2>]Research
in immunology Many research reports consistently found that DCA was
concentrated in the vicinity of tumors<http://en.wikipedia.org/wiki/Tumor>
and inflammations<http://en.wikipedia.org/wiki/Inflammation>. In
conservative viewpoint, there was carcinogenicity suspected from
DCA, but causality has not been demonstrated. The opinion of
naturopaths and newer medical science is different.

In China, the traditional medicine "Niuhuang", which in Chinese
means "Oxen Yellow" and is actually bilestone of oxen, has been in
use for two millennia for the treatment of
inflammations<http://en.wikipedia.org/wiki/Inflammation> as well
as to enhance the immune
system[10]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-9>. One
of its main components is DCA.

Some european publications point towards the effect of DCA as an
immunostimulant<http://en.wikipedia.org/wiki/Immunostimulant>[11]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-10>[12]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-11>
of the unspecific immune
system<http://en.wikipedia.org/wiki/Immune_system>, activating its
main actors, the macrophages<http://en.wikipedia.org/wiki/Macrophage>.
According to these publications, a sufficient amount of DCA in the
human body would correspond with a good immune reaction of the
unspecific immune system. Clinical studies conducted in the 1970s
and 1980s confirm the expectation, that DCA is involved in the
natural healing prozesses of local
inflammations<http://en.wikipedia.org/wiki/Inflammation>[13]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-12>[14]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-13>,
different types of
herpes<http://en.wikipedia.org/wiki/Herpes>[15]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-14>[16]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-15>,
and possibly
cancer<http://en.wikipedia.org/wiki/Cancer>[17]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-16>[18]<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_note-17>.

[edit<http://en.wikipedia.org/w/index.php?title=Deoxycholic_acid&action=edit&section=3>]See
also

* Ursodiol<http://en.wikipedia.org/wiki/Ursodiol> (ursodeoxycholic
acid) * Bile acids<http://en.wikipedia.org/wiki/Bile_acids>

[edit<http://en.wikipedia.org/w/index.php?title=Deoxycholic_acid&action=edit&section=4>]References

1. ^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-hand_0-0>
Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.),
Boca Raton, FL: CRC Press, pp. 1287,
ISBN<http://en.wikipedia.org/wiki/International_Standard_Book_Number>
0849305942<http://en.wikipedia.org/wiki/Special:BookSources/0849305942> 2.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-1> Streuli,
H. et. al.: SLMB - Schweizer Lebensmittelbuch, 1992, chapter 58,
4/3 3. ^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-2>
Combichole, Trout Medical Inc., Houston, US 4.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-3>
Cholecysmon, Riemser Arzneimittel AG, Riems, Germany 5.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-4> J.M.
Neugebauer, Detergents: An Overview, in: M.P. Deutscher, Guide to
Protein Purification (Methods in Enzymology Vol. 182), Academic
Press, San Diego 1990 6.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-5> Sodium
deoxycholate<http://www.nzp.co.nz/products.php?cid=2&pid=251> 7.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-6> Molecules,
2001, 6, 21.

8. ^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-7>
Polym. Mat. Sci. Eng., 1997, 77, 445.

9. ^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-8>
Chemistry Letters, 2000, 414.

10. ^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-9>
Chen X, Mellon RD, Yang L, Dong H, Oppenheim JJ, Howard OM. (The
Laboratory of Molecular Immunoregulation, Center for Cancer Research,
National Cancer Institute-Frederick, Bldg. 560, Rm. 31-19, Frederick,
MD 21702-1201, USA): Regulatory effects of deoxycholic acid, a
component of the anti-inflammatory traditional Chinese medicine
Niuhuang, on human leukocyte response to chemoattractants. Biochemical
Pharmacology 2002, 63(3), 533-541.

11. ^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-10>
VlDek B.: Potentiation of the immune response with DCA (czech),
Prakt.Lekar 52, 326-330 (1972) 12.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-11> Chyle
M., Chyle P.: Regulation of the immune response with DCA (czech,
engl. summary), Sbornik lek. 84, 212-218 (1982) 13.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-12> VlDek
B.: Deoxycholic acid as a potential cancerostatic and antiviral
factor, Advances in Antimicrobial and Antineoplastic Chemotherapy,
Vol. II/1, p.145-147 (Urban & Schwarzenberg, MC<nchen 1972 14.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-13> Chyle
M., Chyle P., Dolezal V. (Inst. f. hygiene and epidemiology, Prag):
Deoxycholic acid b Therapy of viral infections and a toxicological
inquiry 2nd Symp. on Prevention and Treatment of Viral Infections,
Bechyne Castle 1988, p. 56f.

15. ^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-14>
Chyle M. (UniversitC$t Prag), Chyle P.: Deoxycholic acid in therapy
of herpes labialis (czech, engl. summary), Cas. Lek. ces. 114,
1226b1229 (1975) 16.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-15> Bradna
J. (Poliklinik, Kutna Hora): Treatment of herpes zoster with
deoxycholic acid (czech, engl. summary), Rehabilitacia (Bratislava)
16, 77-86 (1983) 17.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-16> VlDek
B., Reif A., Budsky F. (Inst. f. Strahlenhygiene, Prag): Toxicity
of deoxycholate at pH below 7,3 as a potential cancerostatic property,
Experientia 26, 776-778 (1970) 18.
^<http://en.wikipedia.org/wiki/Deoxycholic_acid#cite_ref-17> VlDek
B., Reif A., Seidlova B.: Evidence of the participation of deoxycholate
in cancer immunity, Z.Naturforsch. 26 b, 419-424 (1971)

[edit<http://en.wikipedia.org/w/index.php?title=Deoxycholic_acid&action=edit&section=5>]Weblinks

* www.dca-immunity.com: Information about the use of DCA in human
medicine<http://www.dca-immunity.com/>

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