WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

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酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/02 11:57:29」(JST)

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δ-Aminolevulinic acid (dALA or δ-ALA or 5ala or 5-aminolevulinic acid ) is the first compound in the porphyrin synthesis pathway, the pathway that leads to heme in mammals and chlorophyll in plants.

In plants, production of δ-ALA is the step on which the speed of synthesis of chlorophyll is regulated. Plants that are fed by external δ-ALA accumulate toxic amounts of chlorophyll precursor, protochlorophyllide, indicating that the synthesis of this intermediate is not suppressed anywhere downwards in the chain of reaction. Protochlorophyllide is a strong photosensitizer in plants.

Production[edit]

In non-photosynthetic eukaryotes such as animals, insects, fungi, and protozoa, as well as the α-proteobacteria group of bacteria, it is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway.

In plants, algae, bacteria (except for the α-proteobacteria group) and archaea, it is produced from glutamic acid via glutamyl-tRNA and glutamate-1-semialdehyde. The enzymes involved in this pathway are glutamyl-tRNA synthetase, glutamyl-tRNA reductase, and glutamate-1-semialdehyde aminotransferase. This pathway is known as the C5 or Beale pathway.^[1]^[2]

Clinical significance[edit]

It elicits synthesis and accumulation of fluorescent porphyrins (protoporphyrin IX) in epithelia and neoplastic tissues, among them malignant gliomas. It is used to visualise tumorous tissue in neurosurgical procedures.^[3] Studies have shown that the intraoperative use of this guiding method may reduce the tumour residual volume and prolong progression-free survival in patients suffering from this disease.^[4]^[5]

Aminolevulinic acid is also a photosensitizer for photodynamic therapy.

Cancer diagnosis[edit]

Photodynamic detection is the use of photosensitive drugs with a light source of the right wavelength for the detection of cancer, using fluorescence of the drug.^{[citation needed]}

5-Aminolevulinic acid can be used to visualize bladder cancer.^[6]

Cancer treatment[edit]

Photodynamic therapy (PDT) treatment possibilities include those for cancer of the prostate, breast, giant BCC (skin), cervix, recurrent bladder, vulvar, brain (human glioblastoma cells), HPV, lung, stomach, head and neck, penis, and colon, as well as those for leukemia, Barrett's esophagus, squamous cell carcinoma (SCC), Bowen's disease, and other types of cancer.

References[edit]

^ Beale SI (August 1990). "Biosynthesis of the Tetrapyrrole Pigment Precursor, delta-Aminolevulinic Acid, from Glutamate". Plant Physiol. 93 (4): 1273–9. doi:10.1104/pp.93.4.1273. PMC 1062668. PMID 16667613.
^ Willows, R.D. (2004). "Chlorophylls". In Goodman, Robert M. Encyclopaedia of Plant and Crop Science. Marcel Dekker. pp. 258–262. ISBN 0-8247-4268-0.
^ Eyüpoglu, Ilker Y.; Buchfelder, Michael; Savaskan, Nic E. (2013). "Surgical resection of malignant gliomas—role in optimizing patient outcome". Nature Reviews Neurology 9 (3): 141–51. doi:10.1038/nrneurol.2012.279. PMID 23358480.
^ Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ (2006). "Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial". Lancet Oncol. 7 (5): 392–401. doi:10.1016/S1470-2045(06)70665-9. PMID 16648043.
^ Eyüpoglu, Ilker Y.; Hore, Nirjhar; Savaskan, Nic E.; Grummich, Peter; Roessler, Karl; Buchfelder, Michael; Ganslandt, Oliver (2012). "Improving the Extent of Malignant Glioma Resection by Dual Intraoperative Visualization Approach". In Berger, Mitch. PLoS ONE 7 (9): e44885. doi:10.1371/journal.pone.0044885. PMC 3458892. PMID 23049761.
^ "Bacillus Calmette-Guérin Immunotherapy for Bladder Cancer Overview of BCG Immunotherapy".

UpToDate Contents

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1. ポルフィリン症：概要 porphyrias an overview
2. ALA脱水酵素欠損性ポルフィリン症 ala dehydratase porphyria
3. 光線角化症の治療 treatment of actinic keratosis
4. Porphyria cutanea tarda and hepatoerythropoietic porphyria: Management and prognosis
5. 先天性および後天性鉄芽球性貧血の原因 causes of congenital and acquired sideroblastic anemias

English Journal

Physiological and molecular analyses of black and yellow seeded Brassica napus regulated by 5-aminolivulinic acid under chromium stress.

Gill RA1, Ali B1, Islam F1, Farooq MA1, Gill MB1, Mwamba TM1, Zhou W2.
Plant physiology and biochemistry : PPB / Société française de physiologie végétale.Plant Physiol Biochem.2015 Sep;94:130-43. doi: 10.1016/j.plaphy.2015.06.001. Epub 2015 Jun 3.
Brassica napus L. is a promising oilseed crop among the oil producing species. So, it is prime concern to screen the metal tolerant genotypes in order to increase the oilseed rape production through the utilization of pollutant soil regimes. Nowadays, use of plant growth regulators against abiotic s
PMID 26079286

5-Aminolevulinic acid-mediated sonodynamic therapy induces anti-tumor effects in malignant melanoma via p53-miR-34a-Sirt1 axis.

Hu Z1, Fan H2, Lv G3, Zhou Q1, Yang B1, Zheng J4, Cao W5.
Journal of dermatological science.J Dermatol Sci.2015 Aug;79(2):155-62. doi: 10.1016/j.jdermsci.2015.04.010. Epub 2015 May 1.
BACKGROUD: Malignant melanoma is a very refractory skin tumor due to its high metastasis, poor prognosis, and insensitivity to chemotherapy. Sonodynamic therapy has recently evolved as a potential method to treat cancers. In this study, 5-aminolevulinic acid-mediated sonodynamic therapy (ALA-SDT) wa
PMID 25982144

Ambient light Promotes Selective Subcellular Proteotoxicity after Endogenous and Exogenous Porphyrinogenic Stress.

Maitra D1, Elenbaas JS2, Whitesall SE2, Basrur V2, D' Alecy LG2, Omary MB2.
The Journal of biological chemistry.J Biol Chem.2015 Jul 23. pii: jbc.M114.636001. [Epub ahead of print]
Hepatic accumulation of protoporphyrin-IX (PP-IX) in erythropoietic protoporphyria (EPP) or X-linked-dominant protoporphyria (XLP) cause liver damage. Hepatocyte nuclear lamin aggregation is a sensitive marker for PP-IX-mediated liver injury. We tested the hypothesis that extracellular or intracellu
PMID 26205816

Japanese Journal

Application of 5-aminolevulinic Acid for the in vitro Micropropagation of Cymbidium as a Potential Novel Plant Regulator

NAHAR Syeda Jabun,SHIMASAKI Kazuhiko
Environment control in biology 52(3), 117-121, 2014-09
NAID 40020189334

Molecular Mechanism for Heme-Mediated Inhibition of 5-Aminolevulinic Acid Synthase 1

Kitatsuji Chihiro,Ogura Mariko,Uchida Takeshi [他]
Bulletin of the Chemical Society of Japan 87(9), 997-1004, 2014-09
NAID 40020189317

Reactive oxygen species involved cancer cellular specific 5-aminolevulinic acid uptake in gastric epithelial cells

Ito Hiromu,Tamura Masato,Matsui Hirofumi,Majima Hideyuki J.,Indo Hiroko P.,Hyodo Ichinosuke
Journal of clinical biochemistry and nutrition 54(2), 81-85, 2014-03
… Photodynamic therapy and photodynamic diagnosis using 5-aminolevulinic acid (ALA) are clinically useful for cancer treatments. … Cancer cells have been reported that 5-aminolevulinic acid is incorporated via peptide transporter 1, which is one of the membrane transport proteins, and has been reported to be significantly expressed in various gastrointestinal cancer cells such as Caco-2. …
NAID 120005447548

Related Pictures

★リンクテーブル★

リンク元	「ヘム」「5-アミノレブリン酸」「アミノレブリン酸」
拡張検索	「aminolevulinic acid dehydratase」

「ヘム」

δ-Aminolevulinic acid
Systematic (IUPAC) name
	5-amino-4-oxo-pentanoic acid
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	106-60-5
ATC code	L01XD04
PubChem	CID 137
DrugBank	DB00855
ChemSpider	134
UNII	88755TAZ87
KEGG	D07567
ChEBI	CHEBI:356416
ChEMBL	CHEMBL601
Chemical data
Formula	C5H9NO3
Mol. mass	131.13 g/mol
	SMILES O=C(CN)CCC(=O)O;
	InChI InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9) ; Key:ZGXJTSGNIOSYLO-UHFFFAOYSA-N ;
(what is this?) (verify);

　　[★]

英: heme
同: プロトヘム protoheme、フェロプロトポルフィリンIX ferroprotoporphyrin IX
関: ヘマチン hematin

ポルフィリンと鉄イオンの錯体

生合成

→ポルフィリン

反応場所						酵素	補酵素	酵素阻害物質	酵素の障害による疾患
ミトコンドリア	サクシニルCoA succinyl-CoA	グリシン glycine	5-アミノレブリン酸 aminolevulinic acid aminolevulinate ALA	CoA	CO2	5-アミノレブリン酸シンターゼ ALA synthase	ビタミンB6
細胞質	5-アミノレブリン酸 aminolevulinic acid aminolevulinate ALA	←2分子	ポルホビリノゲン porphobilinogen PBG	2H2O		ALA dehydratase		Pb
細胞質	ポルホビリノゲン porphobilinogen PBG		ヒドロキシメチルビラン	4NH3		ウロポルフィリゲノンIシンターゼ uroporphyrinogen I synthase			急性間欠性ポルフィリン症 acute intermittent porphyria
細胞質	ヒドロキシメチルビラン		ウロポルフィリノゲンIII			ウロポルフィリゲノンIIIシンターゼ uroporphyrinogen III synthase
細胞質	ウロポルフィリノゲンIII		コプロポルフィリノゲンIII	4CO2		ウロポルフィリノゲンデカルボキシラーゼ			晩発性皮膚ポルフィリン症 porphyria cutanea tarda
ミトコンドリア	コプロポルフィリノゲンIII		プロトポルフィリノゲンIX	2CO2		コプロポルフィリノゲンオキシダーゼ
ミトコンドリア	プロトポルフィリノゲンIX		プロトポルフィリンIX			プロトポルフィリノゲンオキシダーゼ
ミトコンドリア	プロトポルフィリンIX	Fe2+	ヘム			フェロケラターゼ		Pb

生合成の場所

哺乳類細胞では、赤血球以外は何処でも行われる(ミトコンドリアを有するなら)
実際には、赤血球前駆細胞(erythroid precursor cell)で85%行われており、残りは肝細胞で行われている。

「5-アミノレブリン酸」

　　[★]

英: 5-aminolevulinate 5-aminolevulinic acid , δ-aminolevulinate δ-aminolevulinic acid δ-ALA, aminolevulinate aminolevulinic acid ALA
同: δ-アミノレブリン酸
関: ALA synthase、レブリン酸

構造式：H₂NCH₂COCH₂CH₂COOH

レブリン酸のδ酸素にアミノ基がついた形

概念

ヘム合成の中間体
ミトコンドリアでサクシニルCoAとグリシンからALA synthaseにより5-アミノレブリン酸が生成する。
ミトコンドリアで作成された5-アミノレブリン酸は細胞質に移動
細胞質の2分子の5-アミノレブリン酸はポルホビリノゲンシンターゼによりポルホビリノゲンを生成する。

「アミノレブリン酸」

　　[★]

英: aminolevulinic acid
同: 5-アミノレブリン酸
商: アラベル、アラグリオ

「aminolevulinic acid dehydratase」

　　[★] アミノレブリン酸脱水酵素

[1] Beale SI (August 1990). "Biosynthesis of the Tetrapyrrole Pigment Precursor, delta-Aminolevulinic Acid, from Glutamate". Plant Physiol. 93 (4): 1273–9. doi:10.1104/pp.93.4.1273. PMC 1062668. PMID 16667613.

[2] Willows, R.D. (2004). "Chlorophylls". In Goodman, Robert M. Encyclopaedia of Plant and Crop Science. Marcel Dekker. pp. 258–262. ISBN 0-8247-4268-0.

[3] Eyüpoglu, Ilker Y.; Buchfelder, Michael; Savaskan, Nic E. (2013). "Surgical resection of malignant gliomas—role in optimizing patient outcome". Nature Reviews Neurology 9 (3): 141–51. doi:10.1038/nrneurol.2012.279. PMID 23358480.

[4] Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ (2006). "Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial". Lancet Oncol. 7 (5): 392–401. doi:10.1016/S1470-2045(06)70665-9. PMID 16648043.

[5] Eyüpoglu, Ilker Y.; Hore, Nirjhar; Savaskan, Nic E.; Grummich, Peter; Roessler, Karl; Buchfelder, Michael; Ganslandt, Oliver (2012). "Improving the Extent of Malignant Glioma Resection by Dual Intraoperative Visualization Approach". In Berger, Mitch. PLoS ONE 7 (9): e44885. doi:10.1371/journal.pone.0044885. PMC 3458892. PMID 23049761.

[6] "Bacillus Calmette-Guérin Immunotherapy for Bladder Cancer Overview of BCG Immunotherapy".

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案内

案内

aminolevulinic acid