neamine

Names

[ Name ]:
neamine

[Synonym ]:
(1R,2R,3S,4R,6S)-4,6-Diamino-2,3-dihydroxycyclohexyl 2,6-diamino-2,6-dideoxy-α-D-glucopyranoside
2-Deoxy-4-O-(2,6-diamine-2,6-dideoxy-α-D-glucopyranosyl)-D-streptamine
U-5214
α-D-Glucopyranoside, (1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl 2,6-diamino-2,6-dideoxy-
Neomycin A
Negamicin
dekamycinv
Neamine
neomycina
(2R,3S,4R,5R,6R)-6-((1R,2R,3S,4R,6S)-4,6-DIAMINO-2,3-DIHYDROXYCYCLOHEXYLOXY)-5-AMINO-2-(AMINOMETHYL)-TETRAHYDRO-2H-PYRAN-3,4-DIOL
2-Deoxy-4-O-(2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl)-D-streptamine
neamin
(1'R,3'S,3S,5R,6R)-5-AMINO-2-AMINOMETHYL-6-(4,6-DIAMINO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL
nebramycinx

Biological Activity

[Description]:

Neamine is a non-toxic derivative derivative of Neomycin and is a broad-spectrum aminoglycoside antibiotic. Neamine is an anti-angiogenesis agent targeting angiogenin. Neamine has potent antibacterial, antitumor and neuroprotective activities[1][2].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Research Areas >> Infection

Research Areas >> Neurological Disease

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Neamine (0.625-25 μM; 48 hours; AsPC-1 cells) treatment inhibits ANG-mediated AsPC-1 cell proliferation in a dose-dependent manner in the range of 0.625-25 μM[1]. Neamine (100 μM) also blocks the nuclear translocation of ANG effectively[1]. Cell Proliferation Assay[1] Cell Line: AsPC-1 cells Concentration: 0.625 µM, 1.25 µM, 2.5 µM, 5 µM, 10 µM, 25 µM Incubation Time: 48 hours Result: Inhibited angiogenin (ANG)-induced AsPC-1 cells proliferation.

[In Vivo]

Neamine (30-60 mg/kg; subcutaneous injection; daily; for 14 days; male Balb/c nude mice) has anti-tumor effects on AsPC-1 xenograft models. Neamine reduces the expression levels of ANG, Ki-67 and CD31 in tumor xenografts[1]. Animal Model: Male Balb/c nude mice (4 weeks old) injected with AsPC-1 cells[1] Dosage: 30 mg/kg, 60 mg/kg Administration: Subcutaneous injection; daily; for 14 days Result: Had anti-tumor effects on AsPC-1 xenograft models.

[References]

[1]. Ya-Ping Liu, et al. Neamine Inhibits Growth of Pancreatic Cancer Cells in Vitro and in Vivo. J Huazhong Univ Sci Technolog Med Sci. 2016 Feb;36(1):82-87.

[2]. R Ning, et al. Neamine Induces Neuroprotection After Acute Ischemic Stroke in Type One Diabetic Rats. Neuroscience. 2014 Jan 17;257:76-85.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
577.9±50.0 °C at 760 mmHg

[ Melting Point ]:
225.5°C (rough estimate)

[ Molecular Formula ]:
C₁₂H₂₆N₄O₆

[ Molecular Weight ]:
322.358

[ Flash Point ]:
303.3±30.1 °C

[ Exact Mass ]:
322.185242

[ PSA ]:
203.46000

[ LogP ]:
-2.78

[ Vapour Pressure ]:
0.0±3.6 mmHg at 25°C

[ Index of Refraction ]:
1.649

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QP3860000

CHEMICAL NAME :: Neomycin A

CAS REGISTRY NUMBER :: 3947-65-7

BEILSTEIN REFERENCE NO. :: 0026714

LAST UPDATED :: 199712

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H26-N4-O6

MOLECULAR WEIGHT :: 322.42

WISWESSER LINE NOTATION :: T6OTJ B1Z CQ DQ EZ FO- BL6TJ AZ CQ DQ EZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 1,664,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 125 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 27,677,1974

Safety Information

[ Hazard Codes ]:
T

Articles

CuAAC-mediated diversification of aminoglycoside-arginine conjugate mimics by non-reducing di- and trisaccharides.

Carbohydr. Res. 371 , 61-7, (2013)

Di- and triguanidinylation of trehalose, sucrose, and melizitose has been achieved via a Huisgen-cycloaddition approach. They can serve as aminoglycoside-arginine conjugate mimics, which has been demo...

Kaposi's sarcoma-associated herpesvirus-positive primary effusion lymphoma tumor formation in NOD/SCID mice is inhibited by neomycin and neamine blocking angiogenin's nuclear translocation.

J. Virol. 87(21) , 11806-20, (2013)

Angiogenin (ANG) is a 14-kDa multifunctional proangiogenic secreted protein whose expression level correlates with the aggressiveness of several tumors. We observed increased ANG expression and secret...

Investigation of RNA-ligand interactions by 19F NMR spectroscopy using fluorinated probes.

Angew. Chem. Int. Ed. Engl. 51(38) , 9530-4, (2012)