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Merck
CN

S5822

Sigma-Aldrich

Spergualin trihydrochloride

>95% (HPLC and TLC), from Bacillus laterosporus

Synonym(s):

Antibiotic BMG 162aF2, Heptanamide,7-[(aminoiminomethyl)amino]-N-[(1S)-2-[[4-[(3-aminopropyl)amino]butyl]amino]-1-hydroxy-2-oxoethyl]-3-hydroxy-,3S)-trihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C17H40Cl3N7O4
CAS Number:
80952-47-2
Molecular Weight:
512.90
UNSPSC Code:
12352200

Key Documents

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biological source

Bacillus laterosporus

Assay

>95% (HPLC and TLC)

storage condition

desiccated

solubility

H2O: soluble
acetone: insoluble
ethanol: insoluble
ethyl acetate: insoluble
methanol: soluble

antibiotic activity spectrum

neoplastics

shipped in

wet ice

storage temp.

−20°C

InChI

1S/C17H37N7O4.3ClH/c18-7-5-9-21-8-3-4-10-22-15(27)16(28)24-14(26)12-13(25)6-1-2-11-23-17(19)20;;;/h13,16,21,25,28H,1-12,18H2,(H,22,27)(H,24,26)(H4,19,20,23);3*1H/t13-,16-;;;/m0.../s1

InChI key

XWNJZPKETIWTTF-RIHGSVRJSA-N

Application

Spergualin trihydrochloride was used to compare the 15-deoxyspergualin, a derivative of spergualin by thin layer chromatography.1

Biochem/physiol Actions

Spergualin is an antibiotic isolated from Bacillus laterosporus that has antibacterial, antitumor, and strong immunosuppressive properties. Spergualin exhibits antitumor activity against transplantable leukemias in mice such as lymphatic leukemia L1210, monocytic leukemia P388, mastocytoma P815, or thymoma EL-4. Spergualin was found effective in inhibiting skin graft rejection, preventing GVHD (Graft-Versus-Host-Disease) in mice recipients of allogeneic bone marrow and spleen cells, and modulating other immunologic diseases.
Spergualin is an antibiotic that posses antibacterial, antitumor, and strong immunosuppressive properties.

Preparation Note

Spergulain is very soluble in water and methanol. It is slighly or not soluble in ethanol, ethyl acetate, acetone cyclohexane, and other organic solvents. Spergualin solutions are unstable at acidic pH (pH <2) and at highly alkaline pH (pH >9). The powder is highly hygroscopic.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Christopher G Evans et al.
Bioorganic & medicinal chemistry letters, 21(9), 2587-2590 (2011-03-23)
Spergualin is a natural product that exhibits immunosuppressive, anti-tumor and anti-bacterial activities. Its derivatives, such as 15-deoxyspergualin (15-DSG), have been clinically approved for acute allograft rejection. However, the reported syntheses are cumbersome (>10 steps) and they suffer from low overall

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