NEAMINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H26N4O6
Molecular Weight	322.358
Optical Activity	( + )
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]2(O[C@@H]1[C@@H](N)C[C@@H](N)[C@H](O)[C@H]1O)O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2N

InChI

InChIKey=SYJXFKPQNSDJLI-HKEUSBCWSA-N

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

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993 Sep 24	8402886
Structure-activity relationships of aminoglycoside-arginine conjugates that bind HIV-1 RNAs as determined by fluorescence and NMR spectroscopy.	2004 Nov 19	15556620
Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands.	2004 Oct 6	15453764
Structure-activity relationships of bivalent aminoglycosides and evaluation of their microbiological activities.	2005 Apr 15	15808482
Neamine inhibits xenografic human tumor growth and angiogenesis in athymic mice.	2005 Dec 15	16361562
The RNA-bound conformation of neamine as determined by transferred NOE experiments.	2005 Jul	15937986
Neamine dimers targeting the HIV-1 TAR RNA.	2005 Nov 1	16153833
Neamine derivatives having a nucleobase with a lysine or an arginine as a linker, their synthesis and evaluation as potential inhibitors for HIV TAR-Tat.	2006 Apr 15	16413787
A molecular dynamics simulation study of an aminoglycoside/A-site RNA complex: conformational and hydration patterns.	2006 Aug	16824662
Synthesis and antibacterial activity of novel neamine derivatives.	2006 Dec 15	16997557
Interactions of designer antibiotics and the bacterial ribosomal aminoacyl-tRNA site.	2006 Feb	16492561
Mixed-type noncompetitive inhibition of anthrax lethal factor protease by aminoglycosides.	2006 Jul	16817854
Cationic polyamines inhibit anthrax lethal factor protease.	2006 Jun 8	16762077
Determination of tobramycin and impurities using high-performance anion exchange chromatography with integrated pulsed amperometric detection.	2006 Mar 3	16243470
Selectively guanidinylated derivatives of neamine. Syntheses and inhibition of anthrax lethal factor protease.	2006 Oct 1	16870442
Nucleobase modified neamines, their synthesis and binding specificity for HIV TAR RNA.	2007	18029660
Structure-function relationship of novel X4 HIV-1 entry inhibitors - L- and D-arginine peptide-aminoglycoside conjugates.	2007 Dec	18028446
Mechanism of RNA cleavage catalyzed by sequence specific polyamide nucleic acid-neamine conjugate.	2007 Fall	17854270
Elaboration of neosamine rings in the biosynthesis of neomycin and butirosin.	2007 Feb 12	17206729
Determination of neomycin sulfate and impurities using high-performance anion-exchange chromatography with integrated pulsed amperometric detection.	2007 Jan 4	16860963
Unique O-ribosylation in the biosynthesis of butirosin.	2007 Jul 1	17482823
Design and synthesis of a structurally constrained aminoglycoside.	2007 Jul 6	17579461
Aminoglycoside antibiotic derivatives: preparation and evaluation of toxicity on cochlea and vestibular tissues and antimicrobial activity.	2007 Jun 1	17416529
Monitoring aminoglycoside-induced conformational changes in 16S rRNA through acrylamide quenching.	2007 Jun 1	17399988
Fluorescent HIV-1 Dimerization Initiation Site: design, properties, and use for ligand discovery.	2007 Mar 21	17319662
Synthesis of a neamine dimer targeting the dimerization initiation site of HIV-1 RNA.	2007 Oct 25	17915882
Two-dimensional combinatorial screening identifies specific aminoglycoside-RNA internal loop partners.	2008 Aug 20	18652457
Identification of tobramycin impurities for quality control process monitoring using high-performance anion-exchange chromatography with integrated pulsed amperometric detection.	2008 Aug 5	18486398
Two-dimensional combinatorial screening identifies specific 6'-acylated kanamycin A- and 6'-acylated neamine-RNA hairpin interactions.	2008 Dec 2	18991404
Biosynthesis of 3'-deoxy-carbamoylkanamycin C in a Streptomyces tenebrarius mutant strain by tacB gene disruption.	2008 Feb	18408324
Fluorescence correlation spectroscopy at single molecule level on the Tat-TAR complex and its inhibitors.	2008 Jan	17764074
Copper(II) complexes of lipophilic aminoglycoside derivatives for the amino acid enantiomeric separation by ligand-exchange liquid chromatography.	2008 Mar 28	18295773
Studies on the synthesis of neamine-dinucleosides and neamine-PNA conjugates and their interaction with RNA.	2008 Oct 15	18829307
Synthesis of a phosphonate-linked aminoglycoside-coenzyme a bisubstrate and use in mechanistic studies of an enzyme involved in aminoglycoside resistance.	2009	19152351
Synthesis and evaluation of novel neamine derivatives effectively targeting to RNA.	2009 Apr 15	19327991
Aminoglycosides: molecular insights on the recognition of RNA and aminoglycoside mimics.	2009 Apr 28	19812740
Enantioseparation by MEKC using a ligand exchange-based chiral pseudostationary phase.	2009 Aug	19637217
Search for novel aminoglycosides by combining fragment-based virtual screening and 3D-QSAR scoring.	2009 Feb	19434840
Chiral ligand-exchange chromatography of amino acids using porous graphitic carbon coated with a dinaphthyl derivative of neamine.	2009 Jan	18998115
Neamine inhibits prostate cancer growth by suppressing angiogenin-mediated rRNA transcription.	2009 Mar 15	19276260
Synthesis and transfection properties of a series of lipidic neamine derivatives.	2009 Nov	19848402
Synthesis of neamine-derived pseudodisaccharides by stereo- and regio-selective functional group transformations.	2009 Oct 21	19795065
Mutation K42R in ribosomal protein S12 does not affect susceptibility of Mycobacterium smegmatis 16S rRNA A-site mutants to 2-deoxystreptamines.	2010 Aug 5	20700526
Neamine inhibits cell proliferation, migration, and invasion in H7402 human hepatoma cells.	2010 Dec	21135992
The nebramycin aminoglycoside profiles of Streptomyces tenebrarius and their characterization using an integrated liquid chromatography-electrospray ionization-tandem mass spectrometric analysis.	2010 Feb 19	20113718
Synthesis and antimicrobial evaluation of amphiphilic neamine derivatives.	2010 Jan 14	20000576
Two-dimensional combinatorial screening of a bacterial rRNA A-site-like motif library: defining privileged asymmetric internal loops that bind aminoglycosides.	2010 Mar 9	20108982
Antibacterial activities of aminoglycoside antibiotics-derived cationic amphiphiles. Polyol-modified neomycin B-, kanamycin A-, amikacin-, and neamine-based amphiphiles with potent broad spectrum antibacterial activity.	2010 May 13	20373816
Aminoglycoside binding to Oxytricha nova telomeric DNA.	2010 Nov 16	20886815

Patents

Name

Type

Language

NEAMINE

Common Name

English

NEBRAMYCIN X

Common Name

English

O-2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-1,3-DIAMINO-1,2,3-TRIDEOXY-D-MYO-INOSITOL

Common Name

English

D-STREPTAMINE, 2-DEOXY-4-O-(2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL)-

Common Name

English

TOBRAMYCIN IMPURITY C [EP IMPURITY]

Common Name

English

NEOMYCIN SULFATE IMPURITY A [EP IMPURITY]

Common Name

English

(+)-NEAMINE

Common Name

English

DEKAMYCIN V

Common Name

English

NEAMINE [MI]

Common Name

English

ST 7

Code

English

NEGAMICIN

Common Name

English

NEAMIN

Common Name

English

NEOMYCIN A

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2363