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Swainsonine

Swainsonine structure

Swainsonine 

structure
  • CAS No:

    72741-87-8

  • Formula:

    C8H15NO3

  • Chemical Name:

    Swainsonine

  • Synonyms:

    1,2,8-Indolizinetriol,octahydro-,(1S,2R,8R,8aR)-;1,2,8-Indolizinetriol,octahydro-,[1S-(1α,2α,8β,8aβ)]-;(1S,2R,8R,8aR)-Octahydro-1,2,8-indolizinetriol;Swainsonine;(-)-Swainsonine;Tridolgosir;D-Swainsonine

  • Categories:

    Natural Products  >  Alkaloids

Description

Swainsonine is an alkaloid isolated from Astragalus, acts as an inhibitor of α-mannosidase, with anti-tumor activity[1].


Swainsonine is an indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8. It has a role as an antineoplastic agent, an immunological adjuvant, an EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor and a plant metabolite.|An indolizidine alkaloid from the plant Swainsona canescens that is a potent alpha-mannosidase inhibitor. Swainsonine also exhibits antimetastatic, antiproliferative, and immunomodulatory activity.

Swainsonine Basic Attributes

173.21

173.21

615-797-6

RSY4RK37KQ

614553

DTXSID5046356

29339900

Characteristics

63.9

-0.79

white to faint yellow lyophilized powder

1.38±0.1 g/cm3

138-142 °C

353.3±21.0 °C at 760 mmHg

209.7±20.7 °C

1.609

H2O: Freely soluble (170 g/L) (25 ºC)

2-8°C

Safety Information

NONH for all modes of transport

3

20/21/22

36

NM2408666

Xn

P280

H302-H312-H332

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)|Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Tridolgosir competitively inhibits the alpha manosidase II (alphaMII), which processes N linked carbohydrates of newly synthesized glycoproteins passing through the Golgi apparatus to the cell surface. Highly branched carbohydrate structures are created which bind to Lectin-phytohemagglutinin (L-PHA) and are subsequently expressed in different tumor types which results in metastatic phenotype, which is correlated with an increased aggressiveness in animals and causes other human malignancies. Inhibition of alphaMII reduces carbohydrates that bind to L-PHA, reducing aggressiveness, metastatic phenotype cells, slows tumor growth, and increases“hybrid type” carbohydrates on the cell surface. Hybrid type carbohydrates may increase cytokine activation of lymphocytes, increasing tumor susceptibility to lymphokine activated and natural killer cells.

Swainsonine

Swainsonine Use and Manufacturing

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.

Computed Properties

Molecular Weight:173.21
XLogP3:-1.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Exact Mass:173.10519334
Monoisotopic Mass:173.10519334
Topological Polar Surface Area:63.9
Heavy Atom Count:12
Complexity:176
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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