NEAMINE SULFATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H26N4O6.H2O4S
Molecular Weight	420.437
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.[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=UPUAISIJDDQCRN-SQAHNGQVSA-N

InChI=1S/C12H26N4O6.H2O4S/c13-2-5-8(18)9(19)6(16)12(21-5)22-11-4(15)1-3(14)7(17)10(11)20;1-5(2,3)4/h3-12,17-20H,1-2,13-16H2;(H2,1,2,3,4)/t3-,4+,5-,6-,7+,8-,9-,10-,11-,12-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C12H26N4O6
Molecular Weight	322.358
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Synthesis of biomimetic analogs of neomycin B: potential inhibitors of the HIV RNA Rev response element.	2000 Jan-Feb	10772716
Study of aminoglycoside-nucleic acid interactions by an HPLC method.	2001 Apr 23	11327578
Aminoglycoside antibiotics, neamine and its derivatives as potent inhibitors for the RNA-protein interactions derived from HIV-1 activators.	2001 Feb 26	11229778
An efficient synthesis of mimetics of neamine for RNA recognition.	2001 May 31	11405670
Design of novel antibiotics that bind to the ribosomal acyltransfer site.	2002 Apr 3	11916405
Crystal structure of geneticin bound to a bacterial 16S ribosomal RNA A site oligonucleotide.	2003 Feb 28	12589761
Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step.	2003 Nov	14638394
Regioselective glycosylation of neamine core: a facile entry to kanamycin B related analogues.	2004 Feb 19	14961629
Fluorinated aminoglycosides and their mechanistic implication for aminoglycoside 3'-phosphotransferases from Gram-negative bacteria.	2004 Mar 9	14992574
Voltage-dependent inhibition of rat skeletal muscle sodium channels by aminoglycoside antibiotics.	2004 May	14963710
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
A peptide nucleic acid-neamine conjugate that targets and cleaves HIV-1 TAR RNA inhibits viral replication.	2004 Sep 23	15369382
Disaccharide mimetics of the aminoglycoside antibiotic neamine.	2004 Sep 6	15368574
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
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
Mechanism of RNA cleavage catalyzed by sequence specific polyamide nucleic acid-neamine conjugate.	2007 Fall	17854270
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
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
Fluorescence correlation spectroscopy at single molecule level on the Tat-TAR complex and its inhibitors.	2008 Jan	17764074
Studies on the synthesis of neamine-dinucleosides and neamine-PNA conjugates and their interaction with RNA.	2008 Oct 15	18829307
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
Chiral ligand-exchange chromatography of amino acids using porous graphitic carbon coated with a dinaphthyl derivative of neamine.	2009 Jan	18998115
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 21:28:07 GMT 2023` Edited by `admin` on `Fri Dec 15 21:28:07 GMT 2023`
Record UNII	XYP2JD4C64
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NEAMINE SULFATE

Common Name

English

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

Common Name

English

NEOMYCIN A SULFATE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID50188726