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NorrChemica™
VI116 | Diazaborine 1 | Free-Acid Parent | ≥95%
VI116 | Diazaborine 1 | Free-Acid Parent | ≥95%
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€65,00 EUR (incl. VAT)
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€65,00 EUR
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Technical Specifications
| SMILES | B1(C2=CC=CC=C2C=NN1S(=O)(=O)C3=CC=C(C=C3)[N+](=O)[O-])O |
| InChI | InChI=1S/C13H10BN3O5S/c18-14-13-4-2-1-3-10(13)9-15-17(14)23(21,22)12-7-5-11(6-8-12)16(19)20/h1-9,18H |
| InChIKey | OMIOMDKFWXJETP-UHFFFAOYSA-N |
| PubChem CID | 177864762 |
| Molecular Formula | C13H10BN3O5S |
| Molecular Weight | 331.11 g/mol |
| Solubility | Soluble in DMSO, methanol, slightly soluble in chloroform. |
| Purity | ≥95% |
| Physical Form | White to yellow solid |
| HS Code | 2934.99 |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Store in a cool, dry place in a tightly sealed container |
Product Description & Scientific Applications
- Identity: 4-nitrophenylsulfonyl benzodiazaborine, the free-acid parent compound (Diazaborine 1) of the series reported in Ilina et al., J. Med. Chem. 2026, 69, 3796–3810. The benzodiazaborine ring system fuses a benzene ring to a six-membered ring containing the B–N–N sequence, with an exocyclic B–OH and a 4-nitrobenzenesulfonyl group on the N2 nitrogen.
- Position in the SAR series: VI116 is the simplest phenyl-series member: R¹ = H on the benzodiazaborine ring and R² = 4-nitrophenyl on the sulfonyl side chain. It is the structural reference for the SAR optimisation reported in the paper.
- Relationship to the optimised lead: The most active compound in the paper (compound 11) differs from VI116 in two positions: a 3-methyl on the benzodiazaborine ring and a 3-aminophenyl on the sulfonyl side chain. Compound 11 shows MIC 6.25 μM against E. coli ATCC 25922, low cytotoxicity (HepG2 IC₅₀ 106 μM), synergy with colistin (FICI 0.25), and rescued Galleria mellonella larvae infected with E. coli at therapeutic doses of 1.13 and 2.81 mg/kg; the 2.81 mg/kg dose matched ciprofloxacin at 20 mg/kg.
- Aqueous handling: The free-acid parent diazaborines in this series are barely soluble in water. The water and human-plasma stability experiments at 37 °C were therefore performed on the corresponding water-soluble salt forms; salt forms of compound 11 retained the same MIC as the parent. For aqueous-handling research applications, NorrChemica supplies VI706 (Diazaborine 62, sodium salt of compound 11) and VI880 (Diazaborine 64, sodium salt of compound 13) as separate catalogue items.
- Mechanism of action of the diazaborine class: Diazaborines inhibit enoyl-acyl carrier protein reductase (FabI) by forming a covalent adduct between the boron atom and the 2′-hydroxyl of the ribose in the enzyme-bound NAD⁺ cofactor, evidenced by E. coli FabI crystal structures (PDB 5CG1, 5CG2; 2.07–2.2 Å). A disordered loop (Leu195–Met206 in E. coli) folds to cover the inhibitor site.
- Reported profile of VI116: Compound 1 did not reach ≥50% growth inhibition of E. coli ATCC 25922 at 50 μM in the primary screening assay and was not included in the FabI inhibition subset. Its value as a catalogue item is as the parent SAR scaffold, not as a bioactive compound.
- Research applications: Parent reference for SAR comparison within the benzodiazaborine scaffold; scaffold characterisation, biophysical, and computational studies; ¹¹B NMR reference for the benzodiazaborine ring system.
- Class context: The benzodiazaborine ring is mechanistically distinct from cyclic boronate β-lactamase inhibitors approved or in clinical development (vaborbactam, FDA-approved 2017; taniborbactam and xeruborbactam in clinical development). Different target (FabI vs β-lactamases), different binding partner (NAD⁺ ribose vs active-site serine), different ring geometry. The original Sandoz diazaborine programme (Grassberger 1984, J. Med. Chem. 27, 947) was halted on intrinsic-toxicity concerns about boron, a position the modern boron-drug regulatory record reopens.
- Documentation: ≥95% purity by ¹H NMR. CoA and SDS provided with each shipment. DDP shipping to EU, UK, EFTA, and worldwide locations.
- Further reading: Scientific background on diazaborine FabI inhibitors and the water-soluble sodium-salt derivatives in NorrChemica's Lab Journal: Water-Soluble Diazaborines: Selective Gram-Negative Antibiotic Candidates for Synergy Studies and R&D.
Shipping Destinations
- EU & UK: Priority delivery, 2–5 business days.
- United States (DDP): 3–7 business days, duties and taxes prepaid.
- EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
- Worldwide: 7–14 business days, selected locations.
The NorrChemica™ Standard
Identity Verified — Batch-verified via analytical QC; documentation available on request.
Direct EU Distribution — Dispatched from Finland for fast delivery to EU-based laboratories.
Professional Logistics — Tracked courier shipping via UPS / Matkahuolto / Posti.
Packaging & Storage
- Supplied in tightly sealed containers suitable for laboratory handling.
- Store under recommended conditions as specified on the product label and SDS.
- Retest period per lot-specific CoA / label under recommended conditions.
Technical Documentation
- Batch-specific Certificate of Analysis (CoA) included with every order.
- GHS-compliant Safety Data Sheet (SDS) provided with every shipment.
- Batch documentation available for institutional procurement.
| Payment: Wise (Bank Transfer) or Manual Invoice. |
| Disclaimer: Research Use Only (RUO) — not for human or veterinary use. Sold strictly for laboratory research and technical applications. By purchasing this item, the buyer confirms professional intent and compliance with applicable regulations. |
Safety Information
| Hazard Class | None — not subject to transport regulations |
| Transport Category | Not classified as dangerous goods for transport (ADR/IATA/IMDG) |
NorrChemica™ is a Finnish supplier of niche research reagents — focused on reliable EU distribution, transparent analytical documentation, and specialist technical support.
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