Tobramycin sulfate - 10mM in Water , CAS No.79645-27-5

CAS: 79645-27-5 Cat. No.: T580543 Formula: (C₁₈H₃₇N₅O₉)₂•5H₂SO₄ Peso molecolare: 1425.41 Numero EC: 616-717-2 PubChem CID: 54413

GRADE & PURITY 10mM in Water

Synonyms

1294492-03-7 | AKOS015895163 | BCP12890 | FT-0652844 | 4-AMINO-2-[4,6-DIAMINO-3-[3-AMINO-6-(AMINOMETHYL)-5-HYDROXYOXAN-2-YL]OXY-2-HYDROXYCYCLOHEXYL]OXY-6-(HYDROXYMETHYL)OXANE-3,5-DIOL SULFATE | HMS3371O08 | AC-4512 | 4-amino-2-[4,6-diamino-3-[3-amino-6-(a

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

product description：

Tobramycin Sulfate is a broad-spectrum antibiotic. It is effective against gram-negative bacteria. It especially potent against the Pseudomonas species.

Specifications

Sinonimi

1294492-03-7 | AKOS015895163 | BCP12890 | FT-0652844 | 4-AMINO-2-[4,6-DIAMINO-3-[3-AMINO-6-(AMINOMETHYL)-5-HYDROXYOXAN-2-YL]OXY-2-HYDROXYCYCLOHEXYL]OXY-6-(HYDROXYMETHYL)OXANE-3,5-DIOL SULFATE | HMS3371O08 | AC-4512 | 4-amino-2-[4,6-diamino-3-[3-amino-6-(a

Specifiche e purezza

10mM in Water

Condizioni di conservazione di stoccaggio

Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

Sorrisi canonici

C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N.OS(=O)(=O)O

IUPAC Name

4-amino-2-[4,6-diamino-3-[3-amino-6-(aminomethyl)-5-hydroxyoxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol;sulfuric acid

InChIKey

ZEUUPKVZFKBXPW-UHFFFAOYSA-N

INCHI

1S/C18H37N5O9.H2O4S/c19-3-9-8(25)2-7(22)17(29-9)31-15-5(20)1-6(21)16(14(15)28)32-18-13(27)11(23)12(26)10(4-24)30-18;1-5(2,3)4/h5-18,24-28H,1-4,19-23H2;(H2,1,2,3,4)

Isomeri SMILES

C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N.OS(=O)(=O)O

PubChem CID

54413

Peso molecolare

1425.41

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 Aminoglycosides
            • Level7 Aminocyclitol glycosides
              • Level8 2-deoxystreptamine aminoglycosides
                • Level9 4,6-disubstituted 2-deoxystreptamines

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides - Aminoglycosides - Aminocyclitol glycosides - 2-deoxystreptamine aminoglycosides
• Direct Parent: 4,6-disubstituted 2-deoxystreptamines
• Alternative Parents: O-glycosyl compounds Aminocyclitols and derivatives Cyclohexylamines Cyclohexanols Oxanes Organic sulfuric acids Monosaccharides 1,2-aminoalcohols Oxacyclic compounds Acetals Primary alcohols Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 4,6-disubstituted 2-deoxystreptamine - Glycosyl compound - O-glycosyl compound - Aminocyclitol or derivatives - Cyclohexanol - Cyclohexylamine - Sulfuric acid - Oxane - Cyclitol or derivatives - Monosaccharide - Organic sulfuric acid or derivatives - Cyclic alcohol - Secondary alcohol - 1,2-aminoalcohol - Oxacycle - Organoheterocyclic compound - Acetal - Primary amine - Organopnictogen compound - Primary aliphatic amine - Organic oxide - Alcohol - Organonitrogen compound - Organic nitrogen compound - Amine - Hydrocarbon derivative - Primary alcohol - Aliphatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 565.600 g/mol
• Hydrogen Bond Donor Count: 12
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 6
• Exact Mass: 565.227 Da
• Monoisotopic Mass: 565.227 Da
• Topological Polar Surface Area: 351.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 690.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 14
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

Application Protocols

The following non-validated, literature-based procedures are provided as general guidance for research use. Optimize for your system.

• Preparation of sterile stock solutions:

  • Dissolve tobramycin sulfate in sterile water to prepare a convenient stock (e.g., 10–50 mg/mL; literature range). Mix gently until fully dissolved. Filter-sterilize through a 0.22 µm PES or PVDF membrane if sterility is required. Aliquot and store per Storage section.

• Use in microbial research assays (literature/general):

  • For antimicrobial susceptibility or mechanistic studies, prepare serial twofold dilutions in suitable broth. Include growth and solvent controls. Inoculate standardized cell densities and incubate per method (e.g., CLSI/ISO) to determine MIC.

• Biophysical binding studies:

  • For RNA-binding assays, prepare samples in buffered saline (e.g., 10–50 mM sodium phosphate, 50–150 mM NaCl). Titrate ligand into RNA and monitor by ITC, fluorescence, or NMR. Maintain pH ~7–7.5 to keep the compound polycationic and soluble.

• LC/LC-MS quantification (literature):

  • HILIC or ion-pair RP with aqueous-rich mobile phases. Detect by MS (positive ESI) or ELSD/charged aerosol; UV is weak at high wavelengths.

Note: Concentrations and conditions above are typical literature ranges and not specifications for this item.

Biological Roles

Literature/general overview of biological function (no clinical claims):

• Mechanism of action: Tobramycin is an aminoglycoside that binds to the bacterial 30S ribosomal subunit (A-site), perturbing decoding accuracy and inhibiting protein synthesis. Binding stabilizes mispaired tRNA–mRNA interactions, leading to translational errors and bactericidal effects in susceptible organisms.
• Physicochemical basis of binding: The polycationic amines engage negatively charged rRNA phosphates via electrostatic interactions and hydrogen bonding; hydroxyl groups further stabilize binding through specific H-bonds and solvent structuring.
• Spectrum context: Activity is typically stronger against aerobic Gram-negative species in vitro; uptake is facilitated by energy-dependent transport across the inner membrane.
• Resistance mechanisms (research context):
  • Aminoglycoside-modifying enzymes (acetyltransferases, nucleotidyltransferases, phosphotransferases) that chemically modify amine/hydroxyl groups.
  • Mutations/methylation in 16S rRNA A-site and changes in membrane permeability or efflux.
• Research uses:
  • Tool compound to interrogate ribosome function, decoding fidelity, and stress responses.
  • Selection/counterselection agent in microbial genetics when appropriate strains/vectors are used.

Note: The above roles describe biochemical mechanisms and laboratory research contexts and are not therapeutic claims. This product is supplied strictly for research use only.

Buffer Applications

This compound is not a buffering reagent and is not used to control pH. Consequently, classic buffer recipes and pKa-targeted buffer systems do not apply.

Practical notes for aqueous use (literature/general):

• Prepare solutions in water or physiological buffers (e.g., PBS, HEPES-buffered saline) appropriate for your biological assay; maintain ionic strength to ensure stability and minimize nonspecific adsorption.
• Avoid extreme pH (<4 or >9) that may promote degradation or alter activity; verify by assay-specific controls.

For detailed buffer composition and compatibility with your system, consult your assay protocol; this item does not serve as a buffer component.

Green Alternatives

This product is a bioactive aminoglycoside salt rather than a process solvent or reagent, so “green alternative solvent” frameworks do not directly apply. Environmental considerations focus on responsible use and disposal:

• Considerations (general):

  • Prepare only the quantities needed; minimize unused solutions to reduce pharmaceutical active residues.
  • Collect waste separately and dispose of as pharmaceutical/biologically active chemical waste per local regulations; avoid drain disposal.
  • For analytical workflows, select aqueous-rich mobile phases and volatile, lower-toxicity ion-pairing reagents when feasible.

• Comparison within class (literature/general):

  • Alternative selection agents (e.g., non-aminoglycoside antibiotics) may have different environmental persistence/toxicity profiles. Choice should be based on experimental need and institutional environmental health and safety guidance, not on generic “greenness.”

No direct greener substitute is recommended for this specific active; optimize protocols to use minimal effective concentrations and volumes.

Pharmaceutical Uses

Contextual, non-clinical information (literature/general):

• Role of the sulfate salt: Conversion of polycationic aminoglycosides to sulfate salts enhances aqueous solubility, facilitates sterile filtration, and provides robust solid-state stability suitable for manufacturing and formulation development.
• Typical formulation considerations (general):
  • Aqueous solutions at acidic to neutral pH with controlled ionic strength to maintain solubility and chemical integrity.
  • Compatibility with common excipients (e.g., sodium chloride for isotonicity) and process steps (sterile filtration, lyophilization) is often leveraged in development.
  • Analytical control includes assay on anhydrous basis, related substances profiling, water content (KF), and microbiological quality.
• Compendial status: Specific pharmacopeial monographs may exist for the active; consult the relevant pharmacopoeia. For this catalog item, no pharmacopeial grade is claimed unless stated on the CoA/Spec Sheet.

Important: This product is provided for research use only and is not intended for human or veterinary use, clinical applications, or diagnostic procedures.

Physical Properties

Item-specific physicochemical specifications are not provided for this catalog entry. The following are general literature descriptors for tobramycin and its sulfate salt; they are not product specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Typically decomposes on heating (literature, salt form); exact MP not reported here.
• Solubility (literature/general):
  • Water: Freely soluble due to multiple protonated amines and sulfate counterion(s).
  • Alcohols (MeOH, EtOH): Limited to moderate solubility; varies with water content.
  • Aprotic organics (DCM, EtOAc, hexanes, toluene): Practically insoluble.
• pKa/logP (literature/general): Multiple basic pKa values (primary/secondary amines) leading to a net polycation at neutral pH; effective logP is very low (high hydrophilicity).
• Hygroscopicity: Aminoglycoside sulfates can be hygroscopic; minimize moisture exposure.
• Density, refractive index, UV cutoff: Not applicable/not typically defined for this class in solid form.

Notes for practical handling (general):

• As a highly polar polyol/polyamine, tobramycin sulfate forms strong hydrogen-bonding networks; solution behavior is dominated by ionic strength and pH.
• In aqueous systems, ionic pairing with sulfate and protonation state influence apparent solubility and chromatographic mobility.

All numerical values and exact specifications for this item: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting typical grades for this compound class (general):

• Research-grade aminoglycoside sulfates are commonly supplied with high assay on anhydrous basis, but apparent purity can depend on the defined salt stoichiometry and water content (hydrates) and on related substances (e.g., closely related congeners or degradants).
• If a salt stoichiometry (e.g., mono-/di-/sesquisulfate) is declared on the CoA, assay calculations are typically reported either as free base or as salt; confirm which basis is used when preparing molar solutions.
• Microbial and endotoxin limits may be relevant for cell culture use; confirm on the CoA if your application is sensitive to bioburden or pyrogens.
• UV-Vis background is usually low above ~230 nm for this class, but for chromatographic assays, use ion-pairing or HILIC methods; do not assume “HPLC grade” unless explicitly stated on the CoA.
• Stabilizers: None are typically added to aminoglycoside sulfate solids; if any stabilizers or excipients are present, they will be listed on the CoA/Spec Sheet.

Recommendation:

• Verify identity (e.g., by HPLC, LC-MS, or NMR in D2O) and confirm water content (Karl Fischer) if exact stoichiometry impacts your assay. For any specification not listed here, consult the CoA/Spec Sheet.

Reaction and Applications

This compound is primarily used as a bioactive small molecule in research settings rather than as a synthetic reagent. Accordingly, “reaction applications” in an organic chemistry sense are limited. Relevant research applications (literature/general) include:

• Microbiology and cell culture research:
  • Employed as an aminoglycoside antibiotic standard in antimicrobial susceptibility testing and mechanistic studies of ribosomal inhibition.
  • Used to modulate bacterial contamination in specific experimental systems; selection pressure applications require organism-specific validation.
• Biophysical/biochemical studies:
  • Model ligand for studies of 16S rRNA A-site binding, decoding fidelity, and ribosome-target interactions.
  • Probe in spectroscopy/NMR to investigate aminoglycoside–RNA complexation; high aqueous solubility facilitates titration studies.
• Analytical chemistry:
  • Standard for developing/validating HPLC (ion-pair or HILIC) and LC-MS methods for aminoglycosides in matrices (literature).

If you intend to derivatize or immobilize the molecule (e.g., for probe development), the multiple primary amines can undergo acylation, alkylation, or carbamate formation under mild aqueous-compatible conditions; however, such transformations are outside typical use and must be optimized to preserve the polyol/glycosidic integrity.

For classical named organic reactions or catalytic applications, this compound is not commonly utilized.

Reaction Conditions

Classical reaction condition guidance is not directly applicable since this compound is not typically used as a reagent. For chemical modifications or conjugations (literature/general):

• Medium: Aqueous buffers (e.g., bicarbonate or phosphate) at pH 7.5–8.5 are commonly used for NHS-ester acylations of primary amines; maintain ionic strength to ensure solubility.
• Temperature: 0–25°C for most conjugation steps to minimize degradation; avoid prolonged heating.
• Time: Minutes to a few hours depending on reagent excess and sterics; monitor by LC-MS/HPLC.
• Stoichiometry: Use modest excess of activated ester (1.5–5 eq per targeted amine); control degree of substitution by limiting equivalents and reaction time.
• Quenching/purification: Quench unreacted NHS-esters with Tris or ethanolamine; purify by desalting (SEC), ion-exchange, or HILIC.
• Stability cautions: Avoid strong bases/acids and high temperatures that can cleave glycosidic linkages or induce amine oxidation.

These are general literature guidelines for conjugation chemistry on aminoglycosides and are not specifications or validated procedures for this catalog item.

Safety and Handling

Authoritative safety information should be taken from the product SDS. The following are general laboratory precautions for aminoglycoside sulfate salts.

• GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
• Hazard considerations (general):
  • May cause irritation to eyes/skin/respiratory tract upon contact with powders or aerosols.
  • Sensitization/allergic responses are possible with aminoglycosides in sensitized individuals; avoid inhalation and skin contact.
• PPE: Wear lab coat, safety glasses, and suitable gloves (e.g., nitrile). Handle powders in a fume hood or ventilated enclosure to prevent aerosolization.
• Handling practices:
  • Avoid generating dust; open vials carefully.
  • Use dedicated tools/spatulas to prevent cross-contamination.
  • For sterile applications, prepare solutions with sterile water and use sterile filtration (0.22 µm) when appropriate.
• Incompatibilities (general): Strong oxidizers; bases/acids can alter protonation state and solubility. Avoid reactive acylating/alkylating agents that can modify amines if chemical integrity must be preserved.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with plenty of water for several minutes; remove contaminated clothing; seek medical advice if irritation continues.
  • Ingestion: Rinse mouth with water; do not induce vomiting; seek medical advice.
• Waste: Dispose of according to institutional and local regulations for pharmaceutical/biologically active chemicals.

Solvent Selection

Tobramycin sulfate is a highly polar, polycationic small molecule salt. Solvent choice is therefore driven by ionic strength and hydrogen-bonding capability rather than by classical organic polarity scales.

• Polarity/miscibility (literature/general):

  • Water: Preferred; freely soluble at typical laboratory concentrations.
  • Aqueous buffers: Compatible over pH ~4–8; maintain ionic strength to control activity; avoid extreme pH that may promote degradation.
  • Alcohols (MeOH/EtOH): Limited solubility unless significant water present; often used in mixed aqueous-organic mobile phases.
  • Aprotic organics (MeCN with water, DMSO): DMSO can dissolve at moderate levels; MeCN requires water co-solvent. Pure aprotic solvents without hydrogen-bonding are generally unsuitable.

• Practical selection guidance:

  • For stock solutions for bioassays or microbiology, use water (sterile) or PBS. Filter-sterilize (0.22 µm) if sterility is required.
  • For analytical LC, use HILIC or ion-pair RP with aqueous-rich mobile phases; ensure compatibility with detection (UV ~ weak above 260 nm; consider ELSD/MS).
  • Avoid nonpolar solvents; precipitation or strong adsorption to glass/plastics may occur when ionic strength is low.

• Comparison (general):

  • Tobramycin sulfate vs base: Salt form offers markedly higher water solubility and easier handling; the free base is less soluble and not typically supplied for aqueous work.

Storage and Reconstitution

• Storage conditions (from Product Data):

  • Store at −80°C.
  • Shipped on dry ice packs + cold packs.

• Stability notes (general/literature, not product-specific):

  • Solid aminoglycoside sulfates are generally stable when kept dry, protected from light, and tightly capped. Minimize freeze–thaw and moisture exposure (use desiccant).
  • After reconstitution in water or buffer, prepare single-use aliquots to avoid repeated freeze–thaw. For sterile applications, filter through 0.22 µm.
  • Aqueous stocks are commonly stored at −20°C to −80°C for extended periods and at 2–8°C for short-term use; verify suitability in your assay.

• Reconstitution (general guidance):

  • Use water or physiological buffer. Gently swirl; avoid vigorous vortexing that may cause foaming/aerosolization. Confirm complete dissolution visually.
  • If exact concentration on a free-base basis is required, confirm the salt stoichiometry and water content from the CoA and adjust calculations accordingly.

• Packaging/containers:

  • Use polypropylene tubes for frozen aliquots. For analytical work, low-bind plastics or glass may reduce adsorption at very low concentrations.

For any specification not listed here (appearance, assay basis, salt stoichiometry, hydration), consult the CoA/Spec Sheet. Research use only.

Structure and Identity

Tobramycin sulfate is the sulfate salt of the aminoglycoside antibiotic tobramycin, supplied for research use only.

• Item-specific identifiers (from Product Data):

  • SKU: T580543
  • Product Name: Tobramycin sulfate
  • CAS: 79645-27-5 (tobramycin sulfate)
  • PubChem CID: 54413 (tobramycin base; literature reference)
  • InChIKey: 455021 (as provided; not a full-length InChIKey string)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (literature/general):

  • Chemotype: Aminoglycoside; 2-deoxystreptamine core glycosidically linked to amino sugars.
  • Functional groups: Multiple primary and secondary amines (polycationic at physiological pH), numerous hydroxyls (polyol), glycosidic linkages (O-glycosides).
  • Salt form: Sulfate counterion(s) to the protonated amines; exact stoichiometry/hydration can vary by manufacturer and is not specified for this item.
  • 2D description: Central 1,3-diaminocyclohexane (2-deoxystreptamine) ring bearing two glycosidic substituents; each substituent contains sugar-like rings richly decorated with –OH and –NH2 groups, giving a compact, highly polar scaffold capable of dense hydrogen bonding and electrostatic interactions.

• Molecular formula and molecular weight:

  • Tobramycin base (literature): MF ~ C18H37N5O9; MW ~ 467.5 g/mol.
  • Tobramycin sulfate (this item): Not specified for this item; refer to CoA/Spec Sheet (salt stoichiometry/hydration dependent).

Synthetic Utility

As a densely functionalized polyol/polyamine, tobramycin sulfate is generally not employed as a building block in routine organic synthesis. However, in specialized research contexts (literature/general):

• Functional handle chemistry:
  • Primary amines permit selective acylation (e.g., NHS-esters) to generate conjugates or immobilized ligands for ribosomal RNA-binding studies.
  • Hydroxyl groups can be derivatized (e.g., silylation, carbonate formation) for analytical derivatization prior to GC or to modulate chromatographic properties, though LC-MS methods usually obviate this.
• Affinity probes:
  • Attachment of fluorophores or biotin via linkers on nonessential amines has been reported for imaging or pull-down of RNA targets.
• SAR/semisynthesis:
  • Site-selective protection–deprotection strategies on aminoglycosides enable preparation of analogs for structure–activity studies, often using orthogonal protecting groups under aqueous-compatible conditions.

Because the molecule contains multiple basic centers and glycosidic bonds, harsh basic or acidic conditions can cause degradation (deamination, glycosidic cleavage). Any synthetic manipulation should be performed under carefully controlled, mild conditions, and analytical verification (LC-MS, NMR in D2O) is recommended after each step.

Target Specificity

This section typically applies to biological macromolecules such as antibodies or ligand-targeted probes with defined specificity. For a small-molecule aminoglycoside like tobramycin sulfate, target specificity data (clone, isotype, antigen, species reactivity) are not applicable.

General literature note: Tobramycin interacts with the bacterial ribosomal 30S A-site RNA; however, no antibody-style specificity parameters are defined for this product.