2,3,10,11,12,13-ヘキサヒドロ-10α-メトキシ-9-メチル-11α-(メチルアミノ)-9β,13β-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン

スタウロスポリン · (9S,10α,11α,13β)-2,3,10,11,12,13-ヘキサヒドロ-10-メトキシ-9-メチル-11-(メチルアミノ)-9,13-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン · [9S,10α,11α,13β,(+)]-2,3,10,11,12,13-ヘキサヒドロ-10-メトキシ-9-メチル-11-(メチルアミノ)-9,13-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン · 2,3,10,11,12,13-ヘキサヒドロ-10α-メトキシ-9-メチル-11α-(メチルアミノ)-9β,13β-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン · スタウロスポリン放線菌由来 · (2S,3S,4S,6R)-3-メトキシ-2-メチル-4-(メチルアミノ)-29-オキサ-1,7,17-トリアザオクタシクロ[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]ノナコサ-8,10,12,14(28),15(19),20(27),21(26),22,24-ノナエン-16-オン · (9S,10α,11α,13β)-2,3,10,11,12,13-ヘキサヒドロ-10-メトキシ-9-メチル-11-(メチルアミノ)-9,13-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3′,2′,1′-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン · (9S,10R,11R,13R)-2,3,10,11,12,13-ヘキサヒドロ-10-メトキシ-9-メチル-11-(メチルアミノ)-9,13-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3′,2′,1′-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン

https://huagongshe.com/ja/chemical/44259

2,3,10,11,12,13-ヘキサヒドロ-10α-メトキシ-9-メチル-11α-(メチルアミノ)-9β,13β-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オンの分子構造式

識別子と物理属性

CAS No.	62996-74-1
分子式	C28H26N4O3
平均分子量	466.5 g/mol
単同位体質量	466.20049069 g/mol
SMILES	CN[C@@H]1C[C@H]2O[C@@](C)([C@@H]1OC)n1c3ccccc3c3c4c(c5c6ccccc6n2c5c31)C(=O)NC4
InChIKey	HKSZLNNOFSGOKW-FYTWVXJKSA-N
PubChem CID	44259
ChEMBL	CHEMBL388978
ChEBI	CHEBI:15738
EC No.	613-127-7
DTXSID	DTXSID6041131
現地名	2,3,10,11,12,13-ヘキサヒドロ-10α-メトキシ-9-メチル-11α-(メチルアミノ)-9β,13β-エポキシ-1H,9H-ジインドロ[1,2,3-gh:3',2',1'-lm]ピロロ[3,4-j][1,7]ベンゾジアゾニン-1-オン

化学・物理的性質

XLogP	3.2
極性表面積	69.5
水素結合供与体数	2
水素結合受容体数	4
回転可能結合数	2
重原子数	35
形式電荷	0
複雑度	901
医薬品	Pharmaceuticals -> AntibioticsPharmaceuticals -> Listed in ZINC15
融点	270°C
比旋光度	D25 +35.0° (c = 1 in methanol)D22 +56.1° (c = 0.14 in methanol)
沸点	677.5±55.0 °C(Predicted)
密度	1.56±0.1 g/cm3(Predicted)
貯蔵条件	2-8°C
溶解度	DMSO：可溶DMSOまたはエタノールに可溶。ジメチルスルホキシド、ジメチルホルムアミド、酢酸エチル、熱アセトン、エタノールに可溶。クロロホルム、メタノールに溶けにくい。水に溶けません。
外観・状態	白色～淡黄色の固体
pKa（酸解離定数）	14.25±0.70(Predicted)
色	オフホワイトから淡黄色
BRN	1060573
安定性	-20°C の DMSO 溶液で最大 4 か月間保存できます。
InChIKey	HKSZLNNOFSGOKW-WIFUGMKFSA-N
SMILES	CN[C@@H]1C[C@@H]2O[C@@](C)([C@@H]1OC)n3c4ccccc4c5c6CNC(=O)c6c7c8ccccc8n2c7c35
CAS データベース	62996-74-1

化学的特性

Light Yellow Solid

安全性と法規制

GHS 分類	DangerH302 (10%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 10 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報	9,13-Epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one, 2,3,10,11,12,13-hexahydro-10-methoxy-9-methyl-11-(methylamino)-, (9S,10R,11R,13R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories	Acute Tox. 4 (10%)
F	8-10
水環境危害等級（WGK）	2
輸送番号（UN）	UN 2811 6.1 / PGII
税関コード	29419090
危険文句（R）	40-45-36/37/38-46
危険表示	Xn,T,Xi
安全措置（S）	36/37-53-36-26-45
危険等級	3Aquatic Chronic 4Carc. 1BMuta. 1BRepr. 2
貯蔵分類	6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

用途

プロテインキナーゼC阻害剤。

説明

Staurosporine (Stsp) is potent inhibitor of protein kinase C (PKC) from rat brain, exhibiting an IC50 value of 2.7 nM. It inhibits rat recombinant PKC-α approximately 100- and 1,000-fold better than PKC-δ and PKC-ζ, respectively. However, Stsp is non-selective in that it also inhibits the activity of a variety of other protein kinases, not only PKC isoforms. The biological effects of Stsp include cytotoxicity, relaxation of smooth muscle, and regulation of eNOS gene expression.

天然物の起源

A complex alkaloid. staurosporine has been isolated from a strain of Streptomyces.

使用

Staurosporine is an unusual indolocarbazole alkaloid produced by a range of actinomycete species. It is a potent antitumour active, inducing apoptosis in a variety of cell lines. Staurosporine is a potent inhibitor of many kinases including protein kinase C, tyrosine kinase, CDK2/cyclin A and CDK4/cyclin D. At submicromolar concentrations, staurosporine inhibits both IKKalpha and IKKbeta.

一般的な説明

A potent, cell-permeable, reversible, ATP-competitive and broad spectrum inhibitor of protein kinases. Inhibits CaM kinase (IC50 = 20 nM), myosin light chain kinase (IC50 = 1.3 nM), protein kinase A (IC50 = 7 nM), protein kinase C (IC50 = 0.7 nM), and protein kinase G (IC50 = 8.5 nM). Also inhibits platelet aggregation induced by collagen or ADP but has no effect on thrombin-induced platelet aggregation. Induces apoptosis in human malignant glioma cell lines. Arrests normal cells at the G1 checkpoint.