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MedKoo product information:
Docosahexaenoic acid
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MedKoo Code#: 201060
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Name: Docosahexaenoic acid
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CAS#: 6217-54-5
Synonym:
DHA; Doconexent; cervonic acid,;
IUPAC/Chemical name:
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid;
all-cis-docosa-4,7,10,13,16,19-hexa-enoic acid.
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Chemical structure |
Theoretical analysis
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Chemical Formula: C22H32O2
Exact Mass: 328.24023
Molecular Weight: 328.49
m/z: 328.24023 (100.0%), 329.24359 (23.8%),
330.24694 (2.7%)
Elemental Analysis: C, 80.44; H, 9.82; O,
9.74
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Availability and price:
This product is available. To inquire quotation, please send email to
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Information about this agent
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Docosahexaenoic acid (DHA) is an omega-3 fatty acid.
In chemical structure, DHA is a carboxylic acid with a 22-carbon chain
and six cis double bonds; the first double bond is located at the third
carbon from the omega end. Its trivial name is cervonic acid, its
systematic name is all-cis-docosa-4,7,10,13,16,19-hexa-enoic acid, and
its shorthand name is 22:6(n-3) in the nomenclature of fatty acids. Fish
oils are rich in DHA. Most of the DHA in fish and more complex organisms
originates in photosynthetic and heterotrophic microalgae, and becomes
increasingly concentrated in organisms as it moves up the food chain.
DHA is also commercially manufactured from microalgae; Crypthecodinium
cohnii and another of the genus Schizochytrium. DHA manufactured using
microalgae is vegetarian. Most animals make very little DHA through
metabolism; however small amounts are manufactured internally through
the consumption of α-linolenic acid, an omega-3 fatty acid found in
plants, animals, and milk. DHA is metabolized to form the docosanoids,
which comprise several families of potent hormones. DHA is a major fatty
acid in sperm and brain phospholipids, particularly in the retina.
Dietary DHA may reduce the risk of heart disease by reducing the level
of blood triglycerides in humans. Low levels of DHA have been associated
with Alzheimer's disease.
DHA was found to inhibit growth of human colon
carcinoma cells, more than other omega-3 PUFAs. The cytotoxic effect of
DHA wasn't caused by increased lipid peroxidation or any other oxidative
damage, but rather decrease in cell growth regulators. However,
different cancer lines handle PUFAs differently and display different
sensitivities towards them. Such preliminary findings point to the need
for further research and are not proof that DHA does or does not provide
any benefit for intended treatment, cure, or mitigation of cancer.
However, in 2008, DHA was shown to increase the efficacy of chemotherapy
in prostate cancer cells, and in 2009, a chemoprotective effect in
a mouse model was reported. See:
http://en.wikipedia.org/wiki/Docosahexaenoic_acid.
Current developer:
1: Puskás LG, Fehér LZ, Vizler C, Ayaydin F, Rásó E,
Molnár E, Magyary I, Kanizsai I, Gyuris M, Madácsi R, Fábián G, Farkas
K, Hegyi P, Baska F, Ozsvári B, Kitajka K. Polyunsaturated fatty acids
synergize with lipid droplet binding thalidomide analogs to induce
oxidative stress in cancer cells. Lipids Health Dis. 2010 Jun 2;9:56.
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JI, Kogner P. Omega-3 fatty acid supplementation delays the progression
of neuroblastoma in vivo. Int J Cancer. 2010 May 24. [Epub ahead of
print] PubMed PMID: 20499314.
3: Kang KS, Wang P, Yamabe N, Fukui M, Jay T, Zhu BT. Docosahexaenoic
acid induces apoptosis in MCF-7 cells in vitro and in vivo via reactive
oxygen species formation and caspase 8 activation. PLoS One. 2010 Apr
22;5(4):e10296. PubMed PMID: 20421971; PubMed Central PMCID: PMC2858652.
4: Harvey KA, Xu Z, Whitley P, Davisson VJ, Siddiqui RA.
Characterization of anticancer properties of
2,6-diisopropylphenol-docosahexaenoate and analogues in breast cancer
cells. Bioorg Med Chem. 2010 Mar 1;18(5):1866-74. Epub 2010 Jan 25.
PubMed PMID: 20153203.
5: Gleissman H, Yang R, Martinod K, Lindskog M, Serhan CN, Johnsen JI,
Kogner P. Docosahexaenoic acid metabolome in neural tumors:
identification of cytotoxic intermediates. FASEB J. 2010
Mar;24(3):906-15. Epub 2009 Nov 4. PubMed PMID: 19890019; PubMed Central
PMCID: PMC2830131.
6: Yu JH, Kang SG, Jung UY, Jun CH, Kim H. Effects of omega-3 fatty
acids on apoptosis of human gastric epithelial cells exposed to
silica-immobilized glucose oxidase. Ann N Y Acad Sci. 2009
Aug;1171:359-64. PubMed PMID: 19723076.
7: Lee SE, Lim JW, Kim H. Activator protein-1 mediates docosahexaenoic
acid-induced apoptosis of human gastric cancer cells. Ann N Y Acad Sci.
2009 Aug;1171:163-9. PubMed PMID: 19723051.
8: Giros A, Grzybowski M, Sohn VR, Pons E, Fernandez-Morales J, Xicola
RM, Sethi P, Grzybowski J, Goel A, Boland CR, Gassull MA, Llor X.
Regulation of colorectal cancer cell apoptosis by the n-3
polyunsaturated fatty acids Docosahexaenoic and Eicosapentaenoic. Cancer
Prev Res (Phila Pa). 2009 Aug;2(8):732-42. Epub 2009 Jul 28. PubMed
PMID: 19638488.
9: Tuller ER, Beavers CT, Lou JR, Ihnat MA, Benbrook DM, Ding WQ.
Docosahexaenoic acid inhibits superoxide dismutase 1 gene transcription
in human cancer cells: the involvement of peroxisome proliferator-activated
receptor alpha and hypoxia-inducible factor-2alpha signaling. Mol
Pharmacol. 2009 Sep;76(3):588-95. Epub 2009 Jun 15. PubMed PMID:
19528198.
10: Wendel M, Heller AR. Anticancer actions of omega-3 fatty
acids--current state and future perspectives. Anticancer Agents Med
Chem. 2009 May;9(4):457-70. Review. PubMed PMID: 19442044.
11: Tuller ER, Brock AL, Yu H, Lou JR, Benbrook DM, Ding WQ. PPARalpha
signaling mediates the synergistic cytotoxicity of clioquinol and
docosahexaenoic acid in human cancer cells. Biochem Pharmacol. 2009 May
1;77(9):1480-6. Epub 2009 Feb 13. PubMed PMID: 19426685.
12: Zhuo Z, Zhang L, Mu Q, Lou Y, Gong Z, Shi Y, Ouyang G, Zhang Y. The
effect of combination treatment with docosahexaenoic acid and
5-fluorouracil on the mRNA expression of apoptosis-related genes,
including the novel gene BCL2L12, in gastric cancer cells. In Vitro Cell
Dev Biol Anim. 2009 Jan-Feb;45(1-2):69-74. Epub 2008 Nov 18. PubMed
PMID: 19015929.
13: Gani OA. Are fish oil omega-3 long-chain fatty acids and their
derivatives peroxisome proliferator-activated receptor agonists?
Cardiovasc Diabetol. 2008 Mar 20;7:6. PubMed PMID: 18355413; PubMed
Central PMCID: PMC2322958.
14: Siddiqui RA, Harvey K, Stillwell W. Anticancer properties of
oxidation products of docosahexaenoic acid. Chem Phys Lipids. 2008
May;153(1):47-56. Epub 2008 Feb 23. Review. PubMed PMID: 18343223.
15: Vibet S, Goupille C, Bougnoux P, Steghens JP, Goré J, Mahéo K.
Sensitization by docosahexaenoic acid (DHA) of breast cancer cells to
anthracyclines through loss of glutathione peroxidase (GPx1) response.
Free Radic Biol Med. 2008 Apr 1;44(7):1483-91. Epub 2008 Jan 26. PubMed
PMID: 18267129.
16: Dupertuis YM, Meguid MM, Pichard C. Colon cancer therapy: new
perspectives of nutritional manipulations using polyunsaturated fatty
acids. Curr Opin Clin Nutr Metab Care. 2007 Jul;10(4):427-32. Review.
PubMed PMID: 17563460.
17: Vibet S, Mahéo K, Goré J, Dubois P, Bougnoux P, Chourpa I.
Differential subcellular distribution of mitoxantrone in relation to
chemosensitization in two human breast cancer cell lines. Drug Metab
Dispos. 2007 May;35(5):822-8. Epub 2007 Feb 12. PubMed PMID: 17296624.
18: Narayanan BA. Chemopreventive agents alters global gene expression
pattern: predicting their mode of action and targets. Curr Cancer Drug
Targets. 2006 Dec;6(8):711-27. Review. PubMed PMID: 17168675.
19: Butovich IA, Lukyanova SM, Bachmann C. Dihydroxydocosahexaenoic
acids of the neuroprotectin D family: synthesis, structure, and
inhibition of human 5-lipoxygenase. J Lipid Res. 2006
Nov;47(11):2462-74. Epub 2006 Aug 9. PubMed PMID: 16899822.
20: Chiu LC, Tong KF, Ooi VE. Cytostatic and cytotoxic effects of
cyclooxygenase inhibitors and their synergy with docosahexaenoic acid on
the growth of human skin melanoma A-375 cells. Biomed Pharmacother. 2005
Oct;59 Suppl 2:S293-7. PubMed PMID: 16507396.
21: Kuznetsova L, Chen J, Sun L, Wu X, Pepe A, Veith JM, Pera P,
Bernacki RJ, Ojima I. Syntheses and evaluation of novel fatty
acid-second-generation taxoid conjugates as promising anticancer agents.
Bioorg Med Chem Lett. 2006 Feb 15;16(4):974-7. Epub 2005 Nov 18. PubMed
PMID: 16298526.
22: Siddiqui RA, Zerouga M, Wu M, Castillo A, Harvey K, Zaloga GP,
Stillwell W. Anticancer properties of propofol-docosahexaenoate and
propofol-eicosapentaenoate on breast cancer cells. Breast Cancer Res.
2005;7(5):R645-54. Epub 2005 Jun 7. PubMed PMID: 16168109; PubMed
Central PMCID: PMC1242121.
23: Mahéo K, Vibet S, Steghens JP, Dartigeas C, Lehman M, Bougnoux P,
Goré J. Differential sensitization of cancer cells to doxorubicin by
DHA: a role for lipoperoxidation. Free Radic Biol Med. 2005 Sep
15;39(6):742-51. PubMed PMID: 16109304.
24: Menendez JA, Lupu R, Colomer R. Exogenous supplementation with
omega-3 polyunsaturated fatty acid docosahexaenoic acid (DHA; 22:6n-3)
synergistically enhances taxane cytotoxicity and downregulates Her-2/neu
(c-erbB-2) oncogene expression in human breast cancer cells. Eur J
Cancer Prev. 2005 Jun;14(3):263-70. PubMed PMID: 15901996.
25: Baumgartner M, Sturlan S, Roth E, Wessner B, Bachleitner-Hofmann T.
Enhancement of arsenic trioxide-mediated apoptosis using docosahexaenoic
acid in arsenic trioxide-resistant solid tumor cells. Int J Cancer. 2004
Nov 20;112(4):707-12. PubMed PMID: 15382055.
26: Field CJ, Schley PD. Evidence for potential mechanisms for the
effect of conjugated linoleic acid on tumor metabolism and immune
function: lessons from n-3 fatty acids. Am J Clin Nutr. 2004 Jun;79(6
Suppl):1190S-1198S. Review. PubMed PMID: 15159256.
27: Sturlan S, Baumgartner M, Roth E, Bachleitner-Hofmann T.
Docosahexaenoic acid enhances arsenic trioxide-mediated apoptosis in
arsenic trioxide-resistant HL-60 cells. Blood. 2003 Jun
15;101(12):4990-7. Epub 2003 Feb 27. PubMed PMID: 12609832.
28: Germain E, Bonnet P, Aubourg L, Grangeponte MC, Chajčs V, Bougnoux
P. Anthracycline-induced cardiac toxicity is not increased by dietary
omega-3 fatty acids. Pharmacol Res. 2003 Feb;47(2):111-7. PubMed PMID:
12543058.
29: Baker SD, Verweij J, Rowinsky EK, Donehower RC, Schellens JH,
Grochow LB, Sparreboom A. Role of body surface area in dosing of
investigational anticancer agents in adults, 1991-2001. J Natl Cancer
Inst. 2002 Dec 18;94(24):1883-8. PubMed PMID: 12488482.
30: Zerouga M, Stillwell W, Jenski LJ. Synthesis of a novel
phosphatidylcholine conjugated to docosahexaenoic acid and methotrexate
that inhibits cell proliferation. Anticancer Drugs. 2002
Mar;13(3):301-11. PubMed PMID: 11984074.
31: Bradley MO, Webb NL, Anthony FH, Devanesan P, Witman PA, Hemamalini
S, Chander MC, Baker SD, He L, Horwitz SB, Swindell CS. Tumor targeting
by covalent conjugation of a natural fatty acid to paclitaxel. Clin
Cancer Res. 2001 Oct;7(10):3229-38. PubMed PMID: 11595719.
32: Kageyama K, Yamada R, Otani S, Onoyama Y, Yano I, Yamaguchi W,
Yamaguchi Y, Kogawa H, Nagao N, Miwa N. Cytotoxicity of docosahexaenoic
acid and eicosapentaenoic acid in tumor cells and the dependence on
binding to serum proteins and incorporation into intracellular lipids.
Oncol Rep. 2000 Jan-Feb;7(1):79-83. PubMed PMID: 10601596.
33: Madhavi N, Das UN. Effect of n-6 and n-3 fatty acids on the survival
of vincristine sensitive and resistant human cervical carcinoma cells in
vitro. Cancer Lett. 1994 Aug 29;84(1):31-41. PubMed PMID: 8076361.
34: Wagner BA, Buettner GR, Burns CP. Increased generation of
lipid-derived and ascorbate free radicals by L1210 cells exposed to the
ether lipid edelfosine. Cancer Res. 1993 Feb 15;53(4):711-3. PubMed
PMID: 8428351.
35: Petersen ES, Kelley EE, Modest EJ, Burns CP. Membrane lipid
modification and sensitivity of leukemic cells to the thioether lipid
analogue BM 41.440. Cancer Res. 1992 Nov 15;52(22):6263-9. PubMed PMID:
1423272.
36: Burns CP, North JA, Petersen ES, Ingraham LM. Subcellular
distribution of doxorubicin: comparison of fatty acid-modified and
unmodified cells. Proc Soc Exp Biol Med. 1988 Sep;188(4):455-60. PubMed
PMID: 3420109.
37: Burns CP, Haugstad BN, Mossman CJ, North JA, Ingraham LM. Membrane
lipid alteration: effect on cellular uptake of mitoxantrone. Lipids.
1988 May;23(5):393-7. PubMed PMID: 3412115.
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