phorbol myristate acetate

ホルボールミリステートアセテート、酢酸ミリスチン酸ホルボール

関

phorbol 12-myristate 13-acetate、PMA、tetradecanoylphorbol acetate

WordNet

1. a salt or ester of acetic acid (同)ethanoate

PrepTutorEJDIC

1. 酢酸(さくさん)塩;アセテート(酢酸人造絹糸)

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/10/11 08:29:36」(JST)

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12-O-Tetradecanoylphorbol-13-acetate

Names
IUPAC name (1aR,1bS,4aR,7aS,7bS,8R,9R,9aS)-9a-(acetyloxy)-4a,7b-dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1a,1b,4,4a,5,7a,7b,8,9,9a-decahydro-H-cyclopropa[3,4]benzo[1,2-e]azulen-9-yl myristate
Other names TPA, PMA, Phorbol myristate acetate, Tetradecanoylphorbol acetate.
Identifiers
CAS Registry Number	16561-29-8 Y
ChEMBL	ChEMBL279115 N
ChemSpider	25977 N
InChI InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1 N Key: PHEDXBVPIONUQT-RGYGYFBISA-N N InChI=1/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1 Key: PHEDXBVPIONUQT-RGYGYFBIBK
IUPHAR/BPS	2341
Jmol-3D images	Image Image
KEGG	C05151 N
PubChem	27924
SMILES CCCCCCCCCCCCCC(=O)O[C@@H]1[C@H]([C@]2([C@@H](C=C(C[C@]3([C@H]2C=C(C3=O)C)O)CO)[C@H]4[C@@]1(C4(C)C)OC(=O)C)O)C CCCCCCCCCCCCCC(=O)O[C@@H]2C(C)[C@]1(O)C4/C=C(/C)C(=O)[C@@]4(O)CC(\CO)=C/[C@H]1[C@H]3[C@]2(OC(C)=O)C3(C)C
Properties
Chemical formula	C36H56O8
Molar mass	616.83 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is: Y/N?)
Infobox references

12-O-Tetradecanoylphorbol-13-acetate (TPA), also commonly known as tetradecanoylphorbol acetate, tetradecanoyl phorbol acetate, and phorbol 12-myristate 13-acetate (PMA), is a diester of phorbol and a potent tumor promoter often employed in biomedical research to activate the signal transduction enzyme protein kinase C (PKC). The effects of TPA on PKC result from its similarity to one of the natural activators of classic PKC isoforms, diacylglycerol. TPA is a small molecule drug.

In ROS biology, superoxide, but not hydrogen peroxide, hydroxyl radical, peroxynitrite, was identified as the major ROS species induced by TPA/PMA but not by ionomycin in mouse macrophages. Thus, TPA/PMA has been routinely used as an inducer for endogenous superoxide production.

TPA is also being studied as a drug in the treatment of hematologic cancer.

TPA has a specific use in cancer diagnostics as a B-cell specific mitogen in cytogenetic testing. To view the chromosomes, a cytogenetic test requires dividing cells. TPA is used to stimulate division of B-cells during cytogenetic diagnosis of B-cell cancers such as chronic lymphocytic leukemia.

TPA is also commonly used together with ionomycin to stimulate T-cell activation, proliferation, and cytokine production, and is used in protocols for intracellular staining of these cytokines.

TPA was first found in the croton plant, a shrub found in Southeast Asia, exposure to which provokes a poison ivy-like rash. It underwent a phase 1 clinical trial.

References

External links

• Tetradecanoylphorbol Acetate at the US National Library of Medicine Medical Subject Headings (MeSH)
• "NCI Dictionary Entry". Retrieved 2005-07-02. 
• "Phase 1 Clinical Trials". Retrieved 2005-07-02. 

UpToDate Contents

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English Journal

• Cycloartenyl trans-ferulate, a component of the bran byproduct of sake-brewing rice, inhibits mammalian DNA polymerase and suppresses inflammation.

• Mizushina Y, Kuriyama I, Yamazaki A, Akashi T, Yoshida H.SourceLaboratory of Food & Nutritional Sciences, Faculty of Nutrition, Kobe Gakuin University, Nishi-ku, Kobe, Hyogo 651-2180, Japan; Cooperative Research Center of Life Sciences, Kobe Gakuin University, Chuo-ku, Kobe, Hyogo 651-8586, Japan. Electronic address: mizushin@nutr.kobegakuin.ac.jp.
• Food chemistry.Food Chem.2013 Nov 15;141(2):1000-7. doi: 10.1016/j.foodchem.2013.04.048. Epub 2013 Apr 24.
• During the screening of selective DNA polymerase (pol) inhibitors, we isolated cycloartenyl trans-ferulate (CAF), which is a major component of γ-oryzanol, which is a byproduct formed during the production of Japanese rice wine "sake". CAF selectively inhibited the activity of mammalian A, B, and X
• PMID 23790879

• Knockdown of nucleophosmin by RNA interference reverses multidrug resistance in resistant leukemic HL-60 cells.

• Lin M, Hu J, Liu T, Li J, Chen B, Chen X.SourceFujian Institute of Hematology, Fujian Medical University Union Hospital, 29 Xinquan Road, Fuzhou 350001, Fujian, China.
• Immunobiology.Immunobiology.2013 Sep;218(9):1147-54. doi: 10.1016/j.imbio.2013.04.001. Epub 2013 Apr 10.
• Nucleophosmin, a multifunctional nucleolar phosphoprotein, is involved in many cellular activities. However, the role of NPM in drug-resistance of leukemia has not yet been explored. We designed and selected one shRNA targeting on NPM gene transduction into HL-60 and HL-60/ADR cell lines (an adriamy
• PMID 23669237

• Vigna angularis inhibits mast cell-mediated allergic inflammation.

• Kim HH, Kim SW, Kim DS, Oh HM, Rho MC, Kim SH.SourceKorean Traditional Medicine Agency, Korea Promotion Institute for Traditional Medicine Industry, Gyeongsan 712‑210, Republic of Korea.
• International journal of molecular medicine.Int J Mol Med.2013 Sep;32(3):736-42. doi: 10.3892/ijmm.2013.1430. Epub 2013 Jul 4.
• The aim of the present study was to elucidate whether extracts of Vigna angularis (EVA) inhibit allergic inflammatory reactions and to elucidate the possible mechanisms of action. For the assessment of allergic inflammatory response, histamine release and the expression of pro-inflammatory cytokines
• PMID 23828310

Japanese Journal

• Interferon regulatory factor-4 activates IL-2 and IL-4 promoters in cooperation with c-Rel.

• Shindo Hisakazu,Yasui Kiyoshi,Yamamoto Kazuo,Honma Kiri,Yui Katsuyuki,Kohno Tomoko,Ma Yuhua,Chua Koon Jiew,Kubo Yoshinao,Aihara Hitoshi,Ito Takashi,Nagayasu Takeshi,Matsuyama Toshifumi,Hayashi Hideki
• Cytokine 56(3), 564-572, 2011-12
• … In T-cells, IRF-4 expression is induced by T-cell receptor (TCR) cross-linking or treatment with phorbol-12-myristate-13-acetate (PMA)/Ionomycin, and IRF-4 is thought to be a critical factor for various functions of T-cells. …
• NAID 120003659758

• 2,3,7,8-Tetrachlorodibenzo-p-dioxin potentially attenuates the gene expression of pituitary gonadotropin β-subunits in a fetal age-specific fashion : a comparative study using cultured pituitaries

• TAKEDA Tomoki,YAMAMOTO Midori,HIMENO Masaru,TAKECHI Shinji,YAMAGUCHI Tadatoshi,ISHIDA Takumi,ISHII Yuji,YAMADA Hideyuki
• Journal of toxicological sciences 36(2), 221-229, 2011-04-01
• … A protein kinase C (PKC) activator (phorbol 12-myristate 13-acetate) and a PKA activator (8-bromoadenosine-3’ 5’-cyclic monophosphate) induced the expression of gonadotropin mRNAs in the fetal pituitary. …
• NAID 10028101312

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★リンクテーブル★

リンク元	「酢酸ミリスチン酸ホルボール」「PMA」「phorbol 12-myristate 13-acetate」「ホルボールミリステートアセテート」「tetradecanoylphorbol acetate」
関連記事	「myristate」「phorbol」

「酢酸ミリスチン酸ホルボール」

　　[★]

英

phorbol 12-myristate 13-acetate、phorbol myristate acetate

関

ホルボールミリステートアセテート、テトラデカノイルホルボールアセテート

「PMA」

　　[★]

• ホルボールミリステートアセテート phorbol 12-myristate 13-acetate、phorbol myristate acetate
• 進行性筋萎縮症 progressive muscular atrophy

「phorbol 12-myristate 13-acetate」

　　[★]

ホルボールミリステートアセテート、酢酸ミリスチン酸ホルボール

関

phorbol myristate acetate、PMA

「ホルボールミリステートアセテート」

　　[★]

英

phorbol 12-myristate 13-acetate、phorbol myristate acetate、PMA

関

酢酸ミリスチン酸ホルボール

「tetradecanoylphorbol acetate」

　　[★]

テトラデカノイルホルボールアセテート

関

phorbol myristate acetate

「myristate」

　　[★]

ミリスチン酸、ミリスチン酸エステル

関

myristic acid

• myristic acid

「phorbol」

　　[★]

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