Valinomycin - ≥98%(TLC),≥93%(HPLC) , CAS No.2001-95-8

CAS: 2001-95-8 Cat. No.: V1522931 Fórmula: C₅₄H₉₀N₆O₁₈ Peso molecular: 1111.32 Beilstein Registry Number: 78657 Número CE: 217-896-6 PubChem CID: 3000706

GRADE & PURITY ≥98%(TLC),≥93%(HPLC)

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Especificações e pureza

≥98%(TLC),≥93%(HPLC)

Mecanismos bioquímicos e fisiológicos

K+-selective ionophoric cyclodepsipeptide; potassium ionophore which uncouples oxidative phosphorylation, induces apoptosis in murine thymocytes, inhibits NGF-induced neuronal differentiation and antagonizes ET-induced vasoconstriction.K + selective ionop

Condições de armazenamento de armazenamento

Protected from light,Store at -20°C

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one week. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%(TLC),≥93%(HPLC)

Nomes e identificadores

Sorrisos canónicos

CC1C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)OC(C(=O)NC(C(=O)O1)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C

IUPAC Name

(3S,6S,9R,12R,15S,18S,21R,24R,27S,30S,33R,36R)-6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nona(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone

InChIKey

FCFNRCROJUBPLU-DNDCDFAISA-N

INCHI

1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34+,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1

SMILES isoméricas

C[C@H]1C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O[C@H](C(=O)N[C@H](C(=O)O[C@@H](C(=O)N[C@@H](C(=O)O1)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C)C)C(C)C)C(C)C)C(C)C

WGK Alemanha

3

RTECS

YV9468000

PubChem CID

3000706

Número UN

2811

Grupo de embalagem

I

Peso molecular

1111.32

Beilstein

78657

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Peptidomimetics
      • Subclass Depsipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Peptidomimetics
• Subclass: Depsipeptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Cyclic depsipeptides
• Alternative Parents: Hexacarboxylic acids and derivatives Macrolide lactams Alpha amino acid esters Macrolactams Macrolides and analogues Lactones Lactams Secondary carboxylic acid amides Carboxylic acid esters Oxacyclic compounds Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Cyclic depsipeptide - Hexacarboxylic acid or derivatives - Macrolide lactam - Alpha-amino acid ester - Macrolactam - Macrolide - Alpha-amino acid or derivatives - Carboxamide group - Carboxylic acid ester - Lactam - Lactone - Secondary carboxylic acid amide - Oxacycle - Carboxylic acid derivative - Azacycle - Organoheterocyclic compound - Hydrocarbon derivative - Carbonyl group - Organic oxygen compound - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aliphatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
• External Descriptors: cyclodepsipeptide - macrocycle

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

Propriedades químicas e físicas

• Solubilidade: Soluble in ethanol (50 mg/ml), petroleum ether, ether, benzene, chloroform, glacial acetic, butyl acetate, and methanol (5 mg/ml). Soluble in DMSO at 10mg/ml. Insoluble in water
• Sensibilidade: Light & Moisture sensitive
• Ponto de fusão (°C): 190°C
• Peso molecular: 1111.300 g/mol
• XLogP3: 9.100
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 9
• Exact Mass: 1110.63 Da
• Monoisotopic Mass: 1110.63 Da
• Topological Polar Surface Area: 332.000 Ų
• Heavy Atom Count: 78
• Formal Charge: 0
• Complexity: 1910.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 12
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No manufacturer-validated protocols are provided for this SKU. The following are example literature-style procedures for common applications. Adapt to your system and consult primary sources.

1. Cell/mitochondrial membrane potential manipulation

• Stock: Prepare 10 mM valinomycin in DMSO; store at −20 °C, protected from light.
• Working solution: Dilute into pre-warmed buffer or medium to 10–100 nM (final DMSO ≤0.1%).
• Procedure: Add to cells or isolated mitochondria; incubate 5–15 min at 37 °C. Assess Δψ changes using potentiometric dyes (e.g., TMRE/TMRM) or electrodes. Include vehicle controls.

2. Liposome K+ flux assay

• Reconstitute liposomes with internal 100 mM KCl, external 100 mM NaCl (or K+-free buffer).
• Add valinomycin to 0.1–1 µM and monitor K+ efflux using PBFI fluorescence or 86Rb+ tracer. Perform at 20–25 °C with gentle mixing.

3. K+-selective electrode membrane casting (research)

• Dissolve PVC (330 mg), plasticizer (e.g., DOS, 660 mg), valinomycin (10 mg), and lipophilic salt (e.g., KTFPB, 5 mg) in 10–15 mL THF.
• Cast onto electrode body or glass plate; allow solvent to evaporate in a fume hood. Condition membrane overnight in 1 mM KCl.

4. Aqueous dosing tips

• To minimize adsorption, deliver from glass syringes into vigorously stirred buffer with 0.1% BSA when compatible. Prepare fresh working solutions immediately before use.

All concentrations/times are general literature guidance and are not product specifications.

Biological Roles

General/literature overview (no medical claims):

• Origin: Valinomycin is a natural cyclodepsipeptide produced by certain Streptomyces species. It functions ecologically as an ionophoric antibiotic by disrupting ion gradients in susceptible organisms.
• Mechanism: Exhibits exceptional selectivity for K+ over Na+ and other cations. The macrocycle binds K+ via coordination of six carbonyl oxygens, forming a neutral, lipophilic complex that diffuses across lipid bilayers. Release occurs on the opposite side, enabling electroneutral transport of K+ and collapse of K+ gradients.
• Selectivity/affinity: Selectivity for K+ over Na+ can exceed 10^4 (literature), driven by optimal ionic radius matching and coordination geometry within the macrocyclic cavity. Binding affinity depends on solvent polarity and membrane environment.
• Cellular/organellar effects: In mitochondria and bacteria, valinomycin can dissipate membrane potential (Δψ), uncouple ion homeostasis, and modulate processes dependent on K+ gradients. It is a standard tool to probe the role of K+ in signaling, volume regulation, and transport.
• Analytical role: Incorporated in K+-selective electrodes and optical sensors as the recognition element, enabling sensitive and selective measurement of K+ in complex matrices.

Use considerations:

• Because of its potency and lipophilicity, even nanomolar to low micromolar concentrations can have pronounced biological effects; dose carefully and include appropriate vehicle controls.
• Effects are context-dependent (ionic strength, membrane composition, temperature); calibrate under assay-relevant conditions.

Buffer Applications

Valinomycin is not a buffering agent and is not used to control solution pH. However, it is often employed in buffered systems for biological assays.

Practical notes (literature/general):

• Vehicle in buffers: Prepare a concentrated stock in DMSO or ethanol, then add to the desired buffer (e.g., HBSS, PBS, respiration buffer) to the final concentration, keeping the final organic co-solvent typically ≤0.1–0.5% v/v to minimize solvent effects on cells or membranes.
• Compatibility: Works across a wide pH range typical of biological buffers (pH ~6.8–8.0), but prolonged exposure to alkaline pH can promote slow ester hydrolysis. Prepare working solutions immediately before use.
• Additives: To reduce nonspecific adsorption and improve delivery, consider 0.1% BSA or a mild nonionic surfactant when compatible with the assay.
• Ion considerations: Since valinomycin complexes K+, buffer composition (K+ vs Na+ salts) directly influences activity. For experiments requiring rapid equilibration of K+ across membranes, use buffers with defined K+ concentrations and ionic strength. For K+-free controls, use buffers formulated with Na+ salts only.

Summary: While not a buffering reagent, valinomycin is routinely dosed into buffered media to manipulate K+ gradients and membrane potentials. Optimize solvent percentage and K+ content of the buffer according to the experimental objective.

Green Alternatives

Because valinomycin is a specific bioactive macrocycle rather than a general solvent or reagent, “green alternatives” focus on reducing environmental/health impacts of its use and the auxiliary materials required for its applications.

Strategies (general/literature):

• Prefer greener solvents for stock preparation when compatible:
  • Ethanol and isopropanol are generally regarded as greener than chlorinated solvents and DMF. They can replace chloroform/DCM for some membrane preparations or cleaning steps, though solubility and film-forming behavior must be verified.
  • DMSO has favorable safety/environmental profiles relative to DMF/CHCl3 but should be minimized in biological assays.
• Minimize waste:
  • Prepare small aliquots to avoid repeated freeze–thaw and disposal of degraded material.
  • Use microscale sensor casting or liposome prep protocols to reduce solvent volumes.
• Safer functional substitutes (application-dependent):
  • For generating K+ equilibrium or collapsing Δψ in mitochondria/cells, combinations of valinomycin with lower solvent levels or the use of genetic/optogenetic tools may reduce reliance on chemical ionophores; however, these are not direct drop-in chemical replacements.
  • For K+-selective electrodes, alternative ionophores (e.g., nonactin derivatives, crown ethers) exist but generally provide inferior selectivity vs Na+ or different response characteristics; selection should be performance-driven rather than purely “green.”

Comparison snapshot (conceptual):

• Valinomycin in CHCl3: Excellent solubility/membrane casting; higher environmental and worker hazards.
• Valinomycin in EtOH: Good solubility for many tasks; better EHS profile; verify performance in final device/assay.

Pharmaceutical Uses

No therapeutic or clinical uses are claimed or supported for this catalog item. The following discusses formulation/manufacturing-adjacent contexts in research and analytical technology (literature/general):

• Analytical devices: Valinomycin is the archetypal ionophore for potassium-selective electrodes (ISEs) and optical sensors. In PVC-based membranes plasticized with phthalates or adipates, valinomycin provides high K+/Na+ selectivity. It is used as a performance benchmark and in research prototypes and quality control references for ISE membranes.
• Reference material: Due to its well-characterized selectivity, valinomycin can serve as a methodological standard for validating K+ measurement systems and sensor fabrication workflows in non-clinical settings.
• Excipients: Valinomycin is not an excipient; its potent bioactivity and lipophilicity preclude use as a general-purpose formulation aid.
• Process considerations: For sensor membrane casting, CHCl3, THF, or cyclohexanone are often used as solvents (literature). Where possible, greener solvents (e.g., ethanol/ethyl acetate mixtures) can be explored, but membrane performance must be validated.

Important: This product is for research use only. Do not use for diagnosis, treatment, or in any application involving human or veterinary administration.

Physical Properties

Item-specific specifications (this listing):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

General/literature and computed values (for reference only; not item specifications):

• Typical molecular formula (literature): C54H90N6O18
• Typical molecular weight (literature): ~1111.34 g/mol
• Physical state/appearance (literature): White to off-white amorphous solid; crystalline when purified.
• Melting behavior (literature): Reported to soften and decompose >190–200 °C (decomp.; exact MP can vary with sample history).
• Solubility (literature):
  • Highly soluble in organic solvents such as methanol, ethanol, isopropanol, acetone, acetonitrile, chloroform, dichloromethane, ethyl acetate, DMSO, and DMF.
  • Practically insoluble in water and aqueous buffers; stock solutions are typically prepared in DMSO or ethanol and then diluted into aqueous media with carrier proteins or surfactants if needed.
• LogP (literature/estimated): High hydrophobicity; reported values ~5–6 depending on method.
• UV characteristics (literature): Lacks strong UV chromophores >220–230 nm; may be monitored at low UV or via derivatization/complexation; no item-specific UV cutoff available here.
• Optical rotation (literature): Specific rotation reported but varies by solvent and supplier; consult primary literature or CoA for exact values.

Note: Values above are provided as general literature guidance for planning purposes and should not be construed as specifications for this SKU.

Quality and Grades

Item-specific grade/purity and appearance are not provided in the Product Data for this SKU.

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

Context and guidance (general):

• Research-grade ionophores like valinomycin are typically supplied at high purity to ensure reproducible bioactivity (e.g., K+ selectivity and transport rate). When grade is unspecified, consult the CoA for assay purity (HPLC/LC–MS), water content (Karl Fischer), and residual solvent data.
• Identity confirmation: For macrocycles, LC–MS (observed [M+H]+ ~1112; literature) and HRMS, plus 1H/13C NMR in CDCl3/CD3OD are commonly reported. Optical rotation may also be provided.
• Stabilizers: This item lists no stabilizer. If stabilizers are absent, handle under dry, light-protected conditions to minimize hydrolysis and photodegradation.
• Use implications:
  • Electrode/sensor applications are sensitive to lipophilic impurities that alter membrane properties—seek specifications for UV absorbance and impurity profile if using in analytical devices.
  • Biological assays (cells/mitochondria) require endotoxin control and solvent-quality considerations (e.g., DMSO grade) to avoid confounding toxicity.

Recommendations:

• Verify the batch-specific CoA before critical work.
• For trace-analysis or sensor fabrication, consider requesting additional data (e.g., HPLC chromatogram, residual metal analysis) as required by your quality system.

Reaction and Applications

This product is not a typical small-molecule reagent for synthetic transformations; its primary value lies in its function as a K+-selective ionophore.

Key application areas (literature/general):

• Membrane transport studies: Valinomycin shuttles K+ across lipid bilayers, collapsing K+ gradients without directly exchanging protons. It is widely used to manipulate or clamp membrane potentials in cells, organelles (e.g., mitochondria), liposomes, and synthetic membranes.
• Electrophysiology and bioenergetics: Employed to dissipate membrane potential (Δψ) while maintaining ΔpH, or in combination with protonophores (e.g., CCCP, FCCP) to dissect contributions of Δψ vs ΔpH.
• Calibration standard: Integral component in K+-selective electrodes (ISEs) and optodes, providing high selectivity for K+ over Na+ (often >10^4-fold; literature). Used to benchmark sensor response functions and selectivity coefficients.
• Transport kinetics: Enables quantitative assays of K+ flux using fluorescent indicators (e.g., PBFI) or radioisotopes (86Rb+ as K+ surrogate).
• Microbiology/toxicology research: As a membrane-active compound, valinomycin is used to probe ion homeostasis and stress responses in microbes and mammalian cells.

Practical tips:

• Ensure accurate dosing via concentrated stock solutions in DMSO/EtOH; pre-wet plasticware with solvent or use glass to minimize adsorption losses.
• Protect from light and moisture; prepare fresh aqueous working solutions immediately before use.
• Combine thoughtfully with other ionophores (e.g., nigericin) to control transmembrane electrochemical gradients in a defined way.

Note: No manufacturer applications were provided beyond research-use context; the above summarizes common literature uses.

Reaction Conditions

This section summarizes typical experimental conditions for common research uses of valinomycin (literature/general guidance only; adjust to your system):

Biological assays:

• Stock preparation: 1–10 mM in DMSO or ethanol. Filter if needed through PTFE; avoid aqueous filtration.
• Cell/mitochondrial studies: 10–100 nM often sufficient to modulate membrane potential (Δψ); up to 1–2 µM for robust K+ equilibration. Incubation times: 5–30 min at 25–37 °C. Maintain vehicle ≤0.1–0.2% v/v.
• Liposome transport assays: 0.05–5 µM valinomycin in reconstituted vesicles with defined K+ gradients. Monitor flux via fluorescent indicators (e.g., PBFI) or 86Rb+. Temperature 20–30 °C; time scale seconds to minutes.

Ion-selective electrode (ISE) membranes:

• Composition (one example, literature): PVC (33 wt%), plasticizer (e.g., DOS or NPOE, 66 wt%), valinomycin (1 wt%) plus lipophilic salt (e.g., KTFPB ~0.5 wt%). Dissolve in THF or CHCl3, cast on electrode body, and allow solvent to evaporate in a dust-free environment.
• Conditioning: Soak membranes in 10−3–10−2 M KCl prior to use; store in dilute KCl when idle.

Chemical stability:

• Avoid strong base and prolonged aqueous exposure to limit ester hydrolysis. Protect from light.

Expected outcomes:

• High K+/Na+ selectivity; near-Nernstian electrode slopes (~55–60 mV/decade for K+ at 25 °C; literature). In bioassays, rapid dissipation of K+ gradients and effects on Δψ at low nanomolar to micromolar concentrations.

These ranges are typical literature values and not product specifications.

Safety and Handling

Authoritative safety information must be taken from the product SDS. Where Product Data fields are blank below, consult the SDS.

GHS fields for this item:

• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• GHS Classification: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety considerations for valinomycin (literature/good laboratory practice):

• Toxicity: Valinomycin is a potent potassium ionophore that can disrupt cellular membrane potential; handle as a toxic compound. Avoid inhalation, ingestion, and skin/eye contact.
• PPE: Wear lab coat, nitrile gloves (double-glove for extended handling), and safety glasses or face shield. Work in a certified chemical fume hood or biosafety cabinet to minimize aerosol exposure.
• Handling: Prepare stocks in closed containers; avoid generating dust. Use light-protective containers or foil wrapping due to light sensitivity.
• Incompatibilities: Strong oxidizers; aqueous solutions can promote hydrolysis of ester linkages at elevated pH or temperature. Avoid prolonged exposure to basic conditions.
• Special risks: Highly lipophilic; may adsorb to plastics and labware. Use low-binding tubes or glass when possible. Solutions in DMSO/ethanol readily penetrate gloves—change gloves frequently and clean spills promptly.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention.
  • Skin/eye contact: Rinse with copious water for ≥15 min; remove contaminated clothing; seek medical attention.
  • Ingestion: Rinse mouth; do not induce vomiting; get medical assistance immediately.
• Waste: Collect as hazardous organic waste; do not discharge to drains. Decontaminate surfaces with appropriate organic solvent followed by detergent wash.

Solvent Selection

Valinomycin is highly hydrophobic and essentially insoluble in water. Selecting an appropriate organic solvent is key to reliable handling and dosing.

Polarity/miscibility profile (literature/general):

• Readily soluble: DMSO, DMF, acetone, acetonitrile, methanol, ethanol, isopropanol, chloroform, dichloromethane, ethyl acetate, toluene.
• Practically insoluble: Water, aqueous buffers, saline.

Practical guidance:

• Stock solutions:
  • DMSO: Common for bioassays; prepare 1–10 mM stocks; aliquot and store frozen to minimize freeze–thaw.
  • Ethanol or methanol: Useful when DMSO must be minimized; final aqueous dilutions often require ≤0.1–0.5% v/v solvent.
  • Chlorinated solvents (CHCl3, DCM): Excellent solubility for materials prep (e.g., ion-selective membranes) but less desirable for biological work.
• Adsorption/carrier considerations: Due to lipophilicity, valinomycin may adsorb to plastics. Use glass vials and low-bind tips/tubes. For aqueous dosing, include a carrier protein (e.g., 0.1% BSA) or non-ionic surfactant when compatible with the assay.
• pH stability: Avoid prolonged exposure to basic aqueous media which can promote ester hydrolysis; prepare fresh working dilutions immediately before use.

Comparison (when to choose each; literature):

• DMSO: Best for small aliquots and accurate micromolar dosing in cells; watch for DMSO toxicity.
• Ethanol: Good compromise for biological compatibility and volatility; ensure consistent evaporation control.
• CHCl3/DCM: Preferred for sensor membrane casting and extractions; not suitable for live-cell dosing.

Always verify solvent compatibility with your biological system or device materials.

Storage and Reconstitution

Item-specific instructions (from Product Data):

• Storage Conditions: Protected from light, Store at −20 °C.
• Shipped In: Ice chest + Ice pads.

General best practices (supplemental, literature/good practice):

• Container: Store in tightly sealed, light-protective (amber) vials. Include desiccant to minimize moisture exposure.
• Stability: Avoid repeated freeze–thaw cycles. Aliquot upon first opening into single-use portions.
• Reconstitution:
  • Solvents: DMSO, ethanol, or methanol are recommended for preparing concentrated stock solutions (e.g., 1–10 mM). Use anhydrous solvent to limit hydrolysis.
  • Procedure: Allow container to equilibrate to room temperature in the dark before opening to prevent condensation. Weigh rapidly, dissolve in chosen solvent with gentle vortexing/sonication.
  • Filtration: If particulate is present, filter through a PTFE syringe filter. Avoid aqueous filtration to prevent loss and hydrolysis.
• Working solutions:
  • Prepare immediately before use by diluting the organic stock into buffer or medium with vigorous mixing. Keep final organic solvent typically ≤0.1–0.5% v/v in biological systems.
  • Use glass or low-binding plasticware to minimize adsorption. Protect from light during experiments.
• Short-term storage of stocks: Maintain at −20 °C (as above); for extended storage, consider −80 °C if compatible with your workflow. Always protect from light.

Note: For batch-specific stability and any additional handling precautions, consult the CoA and SDS. This product is for research use only.

Structure and Identity

Brief: Valinomycin is a classic macrocyclic ionophore (cyclodepsipeptide) with exceptional selectivity for K+ over Na+, widely used as a biochemical tool and in ion-selective sensors.

• SKU: V1522931
• Product Name: Valinomycin
• CAS: 2001-95-8
• PubChem CID: 3000706 (literature)
• InChIKey: 78961 (as provided in Product Data)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet. • Typical literature: C54H90N6O18
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet. • Typical literature: ~1111.34 g/mol

Structural features (general/literature):

• Macrocycle: A large ring (36-membered) cyclodepsipeptide built from alternating amino acid (valine) and hydroxy acid residues, yielding six amide and six ester linkages around the ring.
• Functional groups: Multiple carbonyls (amides and esters) arranged to create a polar interior cavity for cation binding and a hydrophobic exterior that promotes membrane solubility.
• Stereochemistry: Precisely defined alternating L/D centers (including L-valine, D-valine, L-lactic acid, and D-α-hydroxyisovaleric acid residues; literature) create a preorganized binding pocket for K+.
• Binding mode: K+ is coordinated by six carbonyl oxygens in an approximately octahedral arrangement; the exterior methyl-rich surface shields the complex, facilitating diffusion through lipid bilayers.

2D description in words (general): The ring is composed of repeating –(Val–hydroxy acid)– units, with each peptide carbonyl alternating with an ester carbonyl. Side chains (predominantly isopropyl and methyl groups) project outward, while carbonyl oxygens face inward to form the K+-selective cavity.

Synthetic Utility

As a complex natural macrocycle, valinomycin is typically a target of synthesis rather than a building block. Nevertheless, it has instructive roles in synthetic methodology and analysis (literature/general):

• Benchmark macrocyclization target: Total syntheses of valinomycin have informed strategies for macrolactonization/macrolactamization, chemoselective ester–amide formation, and control of stereochemistry across multiple chiral centers.
• Conformational studies: Its well-defined cation-binding conformations provide a platform for studying macrocycle preorganization, intramolecular H-bonding, and the enthalpy/entropy balance of ion complexation.
• Analytical standard: In MS method development, valinomycin’s high mass and distinctive isotopic pattern can serve as a reference for tuning and calibration (research-only context).
• Derivatization chemistry: Semi-synthetic analogs (e.g., labeled or photoactivatable derivatives) are prepared via selective modification of hydroxyl groups or amide N-acylation to probe transport mechanisms and sensor performance.

Practical notes:

• Stability: Multiple ester linkages are susceptible to base-catalyzed hydrolysis; use neutral to mildly acidic conditions for manipulations.
• Solubility: Favor anhydrous organic solvents (e.g., CHCl3, MeOH, EtOH, DMSO) for reactions and purifications; avoid prolonged aqueous exposure.
• Purification: Silica gel chromatography with nonpolar to moderately polar eluents (hexanes/EtOAc, CHCl3/MeOH) is common; monitor by LC–MS due to weak UV chromophores.

Summary: While not a general reagent, valinomycin remains a valuable didactic target and probe for macrocyclic synthesis and ion-binding studies.

Target Specificity

This item is not an antibody or affinity reagent; there are no antigen/epitope specifications. Instead, valinomycin’s “specificity” refers to ion recognition (literature/general):

• Primary target: Potassium ion (K+).
• Selectivity: Very high selectivity for K+ over Na+, Li+, and larger alkaline-earth cations. Reported selectivity coefficients often correspond to >10^4 preference for K+ over Na+ in membrane environments (exact values depend on membrane composition and test method).
• Mechanistic basis: Size/coordination match between K+ (ionic radius ~1.38 Å in 8-coordinate; ~1.33 Å in 6-coordinate, literature) and the macrocyclic cavity created by six carbonyl oxygens. Na+ is too small to achieve optimal coordination without incurring a high energetic penalty.
• Environmental modulation: Selectivity and binding affinity vary with solvent polarity, membrane plasticizer, and presence of competing complexing agents. In highly polar media, complex stability is reduced; in hydrophobic membranes, selectivity is maximized.

Implications for use:

• For electrophysiology and organelle assays, ensure extracellular and intracellular K+ levels are defined; the presence of Na+ typically does not significantly interfere at equal molarity, but high Na+ activity can reduce effective selectivity depending on conditions.
• For sensors, choose membrane composition (PVC/plasticizer/lipophilic salt) to optimize K+ activity coefficients and minimize interference from ammonium and other cations.