cyclic adenosine monophosphate

環状アデノシン一リン酸

WordNet

1. of a compound having atoms arranged in a ring structure
2. recurring in cycles (同)cyclical
3. conforming to the Carnot cycle
4. forming a whorl or having parts arranged in a whorl; "cyclic petals"; "cyclic flowers"
5. marked by repeated cycles
6. (biochemistry) a nucleoside that is a structural component of nucleic acids; it is present in all living cells in a combined form as a constituent of DNA and RNA and ADP and ATP and AMP

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/22 10:36:07」(JST)

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Cyclic adenosine monophosphate

Identifiers
CAS Number	60-92-4 Y
ChEBI	CHEBI:17489 Y
ChEMBL	ChEMBL316966 Y
ChemSpider	5851 Y
DrugBank	DB02527 Y
IUPHAR/BPS	2352
Jmol interactive 3D	Image
KEGG	C00575 Y
MeSH	Cyclic+AMP
PubChem	6076
UNII	E0399OZS9N Y
InChI InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 Y Key: IVOMOUWHDPKRLL-KQYNXXCUSA-N Y InChI=1/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1 Key: IVOMOUWHDPKRLL-KQYNXXCUBU
SMILES c1nc(c2c(n1)n(cn2)[C@H]3[C@@H]([C@H]4[C@H](O3)COP(=O)(O4)O)O)N
Properties
Chemical formula	C10H12N5O6P
Molar mass	329.206 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Cyclic adenosine monophosphate (cAMP, cyclic AMP, or 3',5'-cyclic adenosine monophosphate) is a second messenger important in many biological processes. cAMP is a derivative of adenosine triphosphate (ATP) and used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway.

History

Earl Sutherland of Case Western Reserve University won a Nobel Prize in Physiology or Medicine in 1971 "for his discoveries concerning the mechanisms of the action of hormones," especially epinephrine, via second messengers (such as cyclic adenosine monophosphate, cyclic AMP).

Synthesis and decomposition

Cyclic AMP is synthesized from ATP by adenylate cyclase located on the inner side of the plasma membrane and anchored at various locations in the interior of the cell. Adenylate cyclase is activated by a range of signaling molecules through the activation of adenylate cyclase stimulatory G (G_s)-protein-coupled receptors. Adenylate cyclase is inhibited by agonists of adenylate cyclase inhibitory G (G_i)-protein-coupled receptors. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline.

cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase.

Functions

cAMP is a second messenger, used for intracellular signal transduction, such as transferring into cells the effects of hormones like glucagon and adrenaline, which cannot pass through the plasma membrane. It is involved in the activation of protein kinases and regulates the effects of adrenaline and glucagon. cAMP also binds to and regulates the function of ion channels such as the HCN channels and a few other cyclic nucleotide-binding proteins such as Epac1 and RAPGEF2.

Role of cAMP in eukaryotic cells

Main article: function of cAMP-dependent protein kinase

cAMP and its associated kinases function in several biochemical processes, including the regulation of glycogen, sugar, and lipid metabolism.

In eukaryotes, cyclic AMP works by activating protein kinase A (PKA, or cAMP-dependent protein kinase). PKA is normally inactive as a tetrameric holoenzyme, consisting of two catalytic and two regulatory units (C₂R₂), with the regulatory units blocking the catalytic centers of the catalytic units.

Cyclic AMP binds to specific locations on the regulatory units of the protein kinase, and causes dissociation between the regulatory and catalytic subunits, thus enabling those catalytic units to phosphorylate substrate proteins.

The active subunits catalyze the transfer of phosphate from ATP to specific serine or threonine residues of protein substrates. The phosphorylated proteins may act directly on the cell's ion channels, or may become activated or inhibited enzymes. Protein kinase A can also phosphorylate specific proteins that bind to promoter regions of DNA, causing increased expression of specific genes. Not all protein kinases respond to cAMP. Several classes of protein kinases, including protein kinase C, are not cAMP-dependent.

Further effects mainly depend on cAMP-dependent protein kinase, which vary based on the type of cell.

Still, there are some minor PKA-independent functions of cAMP, e.g., activation of calcium channels, providing a minor pathway by which growth hormone-releasing hormone causes a release of growth hormone.

However, the view that the majority of the effects of cAMP are controlled by PKA is an outdated one. In 1998 a family of cAMP-sensitive proteins with guanine nucleotide exchange factor (GEF) activity was discovered. These are termed Exchange proteins activated by cAMP (Epac) and the family comprises Epac1 and Epac2. The mechanism of activation is similar to that of PKA: the GEF domain is usually masked by the N-terminal region containing the cAMP binding domain. When cAMP binds, the domain dissociates and exposes the now-active GEF domain, allowing Epac to activate small Ras-like GTPase proteins, such as Rap1.

Additional role of secreted cAMP in social amoebas

See also: Fungal behavior

In the species Dictyostelium discoideum, cAMP acts outside the cell as a secreted signal. The chemotactic aggregation of cells is organized by periodic waves of cAMP that propagate between cells over distances as large as several centimetres. The waves are the result of a regulated production and secretion of extracellular cAMP and a spontaneous biological oscillator that initiates the waves at centers of territories.

Role of cAMP in bacteria

In bacteria, the level of cAMP varies depending on the medium used for growth. In particular, cAMP is low when glucose is the carbon source. This occurs through inhibition of the cAMP-producing enzyme, adenylate cyclase, as a side-effect of glucose transport into the cell. The transcription factor cAMP receptor protein (CRP) also called CAP (catabolite gene activator protein) forms a complex with cAMP and thereby is activated to bind to DNA. CRP-cAMP increases expression of a large number of genes, including some encoding enzymes that can supply energy independent of glucose.

cAMP, for example, is involved in the positive regulation of the lac operon. In an environment of a low glucose concentration, cAMP accumulates and binds to the allosteric site on CRP (cAMP receptor protein), a transcription activator protein. The protein assumes its active shape and binds to a specific site upstream of the lac promoter, making it easier for RNA polymerase to bind to the adjacent promoter to start transcription of the lac operon, increasing the rate of lac operon transcription. With a high glucose concentration, the cAMP concentration decreases, and the CRP disengages from the lac operon.

Pathology

Role of cAMP in human carcinoma

Some research has suggested that a deregulation of cAMP pathways and an aberrant activation of cAMP-controlled genes is linked to the growth of some cancers.

Role of cAMP in prefrontal cortex disorders

Recent research suggests that cAMP affects the function of higher-order thinking in the prefrontal cortex through its regulation of ion channels called hyperpolarization-activated cyclic nucleotide-gated channels (HCN). When cAMP stimulates the HCN, the channels open, closing the brain cell to communication and thus interfering with the function of the prefrontal cortex. This research, especially the cognitive deficits in age-related illnesses and ADHD, is of interest to researchers studying the brain.

See also

• Cyclic guanosine monophosphate (cGMP)
• 8-Bromoadenosine 3',5'-cyclic monophosphate (8-Br-cAMP)
• Acrasin specific to chemotactic use in Dictyostelium discoideum.
• phosphodiesterase 4 (PDE 4) which degrades cAMP

References

Additional images

• cAMP represented in three ways

• Adenosine triphosphate

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• Sex Steroids Influence Brain-Derived Neurotropic Factor Secretion From Human Airway Smooth Muscle Cells.

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• Calmodulin kinase II inhibition limits the pro-arrhythmic Ca2+ waves induced by cAMP-phosphodiesterase inhibitors.

• Bobin P1, Varin A1, Lefebvre F1, Fischmeister R1, Vandecasteele G1, Leroy J2.
• Cardiovascular research.Cardiovasc Res.2016 May 1;110(1):151-61. doi: 10.1093/cvr/cvw027. Epub 2016 Feb 4.
• AIMS: A major concern of using phosphodiesterase (PDE) inhibitors in heart failure is their potential to increase mortality by inducing arrhythmias. By diminishing cyclic adenosine monophosphate (cAMP) hydrolysis, they promote protein kinase A (PKA) activity under β-adrenergic receptor (β-AR) stim
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Japanese Journal

• Theobromine up-regulates cerebral brain-derived neurotrophic factor and facilitates motor learning in mice

• Journal of Nutritional Biochemistry 39, 110-116, 2017-01-01
• NAID 120005895700

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• Toho journal of medicine 2(3), 95-105, 2016-09
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• Suppressive Effects of Glucose-Dependent Insulinotropic Polypeptide on Cardiac Hypertrophy and Fibrosis in Angiotensin II-Infused Mouse Models

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cyclic adenosine monophosphate a cyclic nucleotide, adenosine 3′,5′-cyclic monophosphate, involved in the action of many hormones, including catecholamines, ACTH, and vasopressin. The hormone binds to a specific receptor on ...

Related Pictures

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★リンクテーブル★

リンク元	「環状アデノシン一リン酸」「CAMP receptors」
拡張検索	「8-bromo cyclic adenosine monophosphate」
関連記事	「cyclic」「monophosphate」「adenosine monophosphate」

「環状アデノシン一リン酸」

　　[★]

英

cyclic adenosine monophosphate、cyclic AMP、cAMP

同

環状アデノシン3'、5'-一リン酸 サイクリックアデノシン3',5'一リン酸 cyclic adenosine 3',5'-monophosphate。環状AMP、サイクリックAMP

関

副甲状腺機能亢進症、副甲状腺機能低下症。環状ヌクレオチド

概念

• アデノシン一リン酸(AMP)のリン酸が同一分子内リボースの3位水酸基とさらにエステル結合をつくったもの。
• セカンドメッセンジャーとして働くことが知られている。

臨床検査

• 血漿のサイクリックAMPは細胞内のサイクリックAMP濃度を反映している。肝硬変の重症度判定に用いられている。
• 尿中のサイクリックAMPは副甲状腺疾患の病型の鑑別に用いられている。

• Ellsworth-Howard試験(PTH負荷試験)による副腎甲状腺機能低下症の病型鑑別

血漿

• 高値：

• 肝；肝硬変、閉塞性黄疸
• 心；心筋梗塞、心不全
• 腎；腎不全、

尿

• 高値：甲状腺機能亢進症、副甲状腺機能亢進症
• 低値：

• アルコール常飲者
• 内分泌；偽性副甲状腺機能低下症、甲状腺機能低下症
• 腎；腎不全

「CAMP receptors」

　　[★]

同

cyclic adenosine monophosphate

「8-bromo cyclic adenosine monophosphate」

　　[★]

8-ブロモサイクリックアデノシン一リン酸

関

8-bromo cyclic AMP、8-bromo-cAMP

「cyclic」

　　[★]

• adj.

• 環状の、環式の、周期性の、サイクリック

関

annular、circular、cyclical、cyclicity、cyclo、periodic、periodicity

　 　 　 　 　

「monophosphate」

　　[★]

• n.

• 一リン酸塩、一リン酸エステル、一リン酸

「adenosine monophosphate」

　　[★] アデノシン一リン酸