Neomycin Sulfate EP Impurity A (Neamine)
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| Category | Antibiotics |
| Catalog number | BBF-02599 |
| CAS | 3947-65-7 |
| Molecular Weight | 322.36 |
| Molecular Formula | C12H26N4O6 |
| Purity | >95% |
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Description
Also known as neamine; a highly purified neomycin compound found in standard grade neomycin; has the lowest antibacterial activity; about 10% of the activity of neomycin B; resistant to bacteria and mycobacteria.
Specification
| Synonyms | Negamicin; Dekamycin V; Neomycin A; 4-O-(2,6-Diamino-2,6-dideoxy-alpha-D-glucopyranosyl)-2-deoxy-D-streptamine; 2-Desoxy-4-O-(2,6-diamino-2,6-didesoxy-alpha-D-glucopyranosyl)-D-streptamin; BRN 0026714 |
| Storage | Store at -20°C |
| IUPAC Name | (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxyoxane-3,4-diol |
| Canonical SMILES | C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)O)O)N |
| InChI | InChI=1S/C12H26N4O6/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20/h3-12,17-20H,1-2,13-16H2/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-/m1/s1 |
| InChI Key | SYJXFKPQNSDJLI-HKEUSBCWSA-N |
Properties
| Appearance | Off-White to Pale Yellow Solid |
| Antibiotic Activity Spectrum | mycobacteria |
| Boiling Point | 577.9±50.0°C at 760 mmHg |
| Melting Point | 250-256°C |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Aqueous Acid (Slightly), Methanol (Slightly), Water (Slightly) |
Reference Reading
1.Nucleobase modified neamines with a lysine as a linker, their inhibition specificity for TAR-Tat derived from HIV-1.
Inoue R1, Watanabe K1, Katou T1, Ikezawa Y1, Hamasaki K2. Bioorg Med Chem. 2015 May 1;23(9):2139-47. doi: 10.1016/j.bmc.2015.03.001. Epub 2015 Mar 7.
Nucleobase modified neamines with a lysine as the linker (NbK-neamines) were synthesized and their binding toward hairpin RNAs derived from HIV-1 activator region were studied. NbK-neamines were bind those RNAs with micro molar level of binding affinities and compete with corresponding activator peptide for TAR RNA, but not for RRE RNA. GbK-neamine denotes the highest binding affinity with TAR RNA, three to five times higher than other three NbK-neamines. GbK-neamine could be a candidate of potential inhibitor for TAR-Tat.
2.Neamine is preferential as an anti-prostate cancer reagent by inhibiting cell proliferation and angiogenesis, with lower toxicity than cis-platinum.
Liu YP1, Hu GF2, Wu YX1. Oncol Lett. 2015 Jul;10(1):137-142. Epub 2015 May 19.
Hormone therapy is the most commonly used treatment for prostate cancer, but for androgen-independent cancer, few effective treatment methods are available. Therefore, the requirement to develop novel and effective anti-prostate cancer drugs is extremely urgent. Angiogenin has been suggested as a molecular target for prostate cancer treatment; its overexpression contributes to androgen-dependent prostate cancer growth and castration-resistant growth of androgen-independent prostate cancer. The aim of the present study was to investigate whether neamine, a low toxicity angiogenin nuclear translocation inhibitor, has preferential anti-prostate cancer activity compared with cis-platinum (DDP) and the mechanisms involved. Immunofluorescence and MTT assays were used to observe the effect of neamine on the nuclear translocation of angiogenin and cell proliferation, and a PC-3 cell transplanted tumor model was used to investigate the in vivo activity of neamine and DDP.
3.Pharmacokinetics of neamine in rats and anti-cervical cancer activity in vitro and in vivo.
Liu Y1, Zhang X, An S, Wu Y, Hu G, Wu Y. Cancer Chemother Pharmacol. 2015 Mar;75(3):465-74. doi: 10.1007/s00280-014-2658-7. Epub 2015 Jan 1.
OBJECTIVE: To study the pharmacokinetics of neamine in rats and to evaluate its anti-cervical cancer activity.
4.Chemically related 4,5-linked aminoglycoside antibiotics drive subunit rotation in opposite directions.
Wasserman MR1, Pulk A2, Zhou Z1, Altman RB1, Zinder JC3, Green KD4, Garneau-Tsodikova S4, Doudna Cate JH2, Blanchard SC5. Nat Commun. 2015 Jul 30;6:7896. doi: 10.1038/ncomms8896.
Dynamic remodelling of intersubunit bridge B2, a conserved RNA domain of the bacterial ribosome connecting helices 44 (h44) and 69 (H69) of the small and large subunit, respectively, impacts translation by controlling intersubunit rotation. Here we show that aminoglycosides chemically related to neomycin-paromomycin, ribostamycin and neamine-each bind to sites within h44 and H69 to perturb bridge B2 and affect subunit rotation. Neomycin and paromomycin, which only differ by their ring-I 6'-polar group, drive subunit rotation in opposite directions. This suggests that their distinct actions hinge on the 6'-substituent and the drug's net positive charge. By solving the crystal structure of the paromomycin-ribosome complex, we observe specific contacts between the apical tip of H69 and the 6'-hydroxyl on paromomycin from within the drug's canonical h44-binding site. These results indicate that aminoglycoside actions must be framed in the context of bridge B2 and their regulation of subunit rotation.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
