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SWAINSONINE

SWAINSONINE 구조식 이미지
카스 번호:
72741-87-8
상품명:
SWAINSONINE
동의어(영문):
8AR)-1;SwainMoia;Tridolgosir;SWAINSONINE;D-Swainsonine;SWAINSONINE 98+%;(-)-D-Swainsonine;Swainsonine min. 99%;swainsonine synthetic;swainsonine from locoweed
CBNumber:
CB0484750
분자식:
C8H15NO3
포뮬러 무게:
173.21
MOL 파일:
72741-87-8.mol

SWAINSONINE 속성

녹는점
148-149°C
끓는 점
353.3±21.0 °C(Predicted)
밀도
1.38±0.1 g/cm3 (20 ºC 760 Torr)
저장 조건
-20°C
용해도
H2O: soluble1mg/mL
산도 계수 (pKa)
14.01±0.60(Predicted)
물리적 상태
lyophilized powder
색상
white to faint yellow
BRN
4175740
CAS 데이터베이스
72741-87-8

안전

위험품 표기 Xn
위험 카페고리 넘버 20/21/22
안전지침서 36
WGK 독일 3
RTECS 번호 NM2408666
HS 번호 29339900

SWAINSONINE C화학적 특성, 용도, 생산

화학적 성질

White Crystalline Solid

출처

Swainsonia canescens yields this simple alkaloid.

용도

Swainsonine is an indolizidine alkaloid naturally found in certain plants including locoweed that inhibits N-linked glycoside hydrolases, preventing the processing of asparagine-linked glycoproteins. It reversibly inhibits lysosomal α-mannosidase and Golgi α-mannosidase II (IC50 = 0.2 μM). Swainsonine is used to study the role of N-linked glycosylation in cellular processes and has been shown to have antiproliferative and antimetastatic effects of cancer cells in culture and in mice. The inhibition of α-mannosidase activity in lysosomes produces an accumulation of partially-processed oligosaccharides and glycoproteins, giving rise to lysosomal storage disease. Swainsonine toxicity in herbivores results in a condition known as locoism, characterized by hyperactivity, aggression, stiff and clumsy gait, low head carriage, salivation, seizures, and apparent blindness, culminating in increased miscoordination, weakness and death.

용도

Swainsonine is a plant alkaloid derived from Swainsona canescens (a leguminous plant). It is a reversible, active-site directed inhibitor of a-mannosidase at concentrations of 5-10mM. At acid pH, swainsonine resembles an intermediate in the hydrolysis of mannosidases. Swainsonine completely inhibits mammalian Golgi a-mannosidase II (a-3/6-mannosidase in the glycoprotein processing pathway) and mammalian lysosomal a-mannosidase (acid mannosidase). At higher concentrations, swainsonine also inhibits mammalian cytosolic a-mannosidase. It has been shown to inhibit growth of transformed fibroblasts in soft agar and to enhance the antiproliferative effects of INF on murine lymphoreticular tumor cells in vitro. It also blocks the expression of b1-6 branched complex-type oligosaccharides and shunts the pathway towards hybrid-type oligosaccharides. Swainsonine does not appear to inhibit secretion or expression of glycoproteins at the cell surface. Swainsonine is stable for at least 24 h at 37oC in culture media at physiological pH. Working concentration range is 17-1700 ng/ml (0.1-10mM). Swainsonine (at 1 mg/ml) is not cytotoxic and does not inhibit the growth of a variety of mammalian cell lines. Concentrations required to inhibit Golgi a-mannosidase II in vivo may be somewhat higher, as swainsonine tends to concentrate in the acid environment of cell lysosomes, where it exists as a charged cation and does not permeate through membranes readily. Swainsonine blocks the processing of high-mannose oligosaccharides to complex oligosaccharides. Glycoproteins synthesized in the presence of swainsonine tend to carry mostly high-mannose and hybrid oligosaccharide chains. With short treatments (<24 h) with the inhibitor, cells may retain some complex glycoproteins due to asynchronous cell growth and glycoprotein synthesis.

정의

ChEBI: An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.

생물학적 활성

Inhibitor of α -mannosidase II which inhibits glycoprotein processing. Displays anticancer and immune modulatory properties.

SWAINSONINE 준비 용품 및 원자재

원자재

준비 용품


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