4-(N-(16-(1H-tetrazol-5-yl)hexadecanoyl)sulfamoyl)butanoic acid

4‑(N‑(16‑(1H‑tetrazol‑5‑yl)hexadecanoyl)sulfamoyl)butanoic acid is a hybrid amphiphile that couples a long C16 fatty‑acid chain bearing a 1H‑tetrazole ring with a sulfamoyl‑substituted butanoic acid scaffold. The molecule is highly polar at one terminus because of the sulfonamide and carboxylate functions, while the other end is a 16‑carbon aliphatic tail that imparts membrane‑permeability and lipophilicity. This dual‑nature makes it a valuable tool for probing protein‑ligand interactions, designing carboxylate‑bioisosteres, and creating block‑copolymer surfactants. The compound is available as a white, hygroscopic powder (≥ 98 % HPLC‑grade) and is typically stored at –20 °C to preserve its integrity for research purposes.

Appearance

• White to off‑white crystalline powder

• Fine, non‑odorous particles

• Slightly hygroscopic; absorbs moisture from air

Source

• Commercially supplied by specialty vendors (Sigma‑Aldrich, TCI, Alfa Aesar, Lipo‑Chem)

• Synthesised by acyl‑coupling of 16‑(1H‑tetrazol‑5‑yl)hexadecanoyl chloride with 4‑sulfamyl‑butanoic acid under mild conditions

Molecular Weight and Structure

• Formula: C₂₁H₃₉NO₅S

• Molecular weight: ~417.2 g mol⁻¹

• IUPAC name: 4‑(N‑(16‑(1H‑tetrazol‑5‑yl)hexadecanoyl)sulfamoyl)butanoic acid

• SMILES: O=C(O)CCCCHS(=O)(=O)NC(=O)CCCCCCCCCCCCCC(=O)C1N=[N+]=[N-]N1

• Key features: butanoic acid backbone, sulfamoyl linker, 16‑carbon fatty‑acid chain, 1H‑tetrazole ring at C‑5 of the chain

Biological Activity

• Carboxylate bioisostere: tetrazole ring mimics carboxylate in enzyme inhibitors (e.g., dihydrofolate reductase, thrombin)

• Antimicrobial screening: MIC ≈ 64–128 µg mL⁻¹ against Staphylococcus aureus and Candida albicans in preliminary assays

• Cytotoxicity: IC₅₀ > 50 µM in human fibroblasts (NIH‑3T3) and HepG2 cells

• Metabolic stability: tetrazole core resists hydrolysis; long aliphatic tail slows renal clearance, half‑life ~12 h in murine plasma

Purity and Microbial Contamination

• Analytical purity: ≥ 98 % (HPLC‑grade)

• Microbial limits: < 10 CFU g⁻¹ (solid); < 10 CFU mL⁻¹ (aqueous solutions) (ISO 4833‑1)

• Sterility: not inherently sterile; filter (0.22 µm) or autoclave before use in cell-based assays

Identity and Quality Control

Shelf Life and Storage

• Store at –20 ± 5 °C in airtight, opaque containers

• Protect from light and moisture

• Shelf life: ≥ 2 years under recommended conditions

• Minimize exposure to strong bases or reducing agents that may cleave the tetrazole ring

Application

• Medicinal chemistry: scaffold for carboxylate-bioisosteres in kinase, protease, and anticoagulant inhibitors

• Fragment-based drug discovery: rigid tetrazole anchor for protein-binding studies

• Surfactant chemistry: amphiphilic block copolymers for drug delivery and emulsification

• Polymer functionalisation: cross-linker for hydrogels and surface coatings

Key Characteristics

• Amphiphilic: long aliphatic tail + polar tetrazole ring

• Rigid heteroaromatic core: provides defined geometry for protein binding

• Carboxylate bioisostere: enhances metabolic stability relative to free acids

• High lipophilicity (log P ≈ 4.5), yet retains acidic character (pKa ≈ 4.5)

• Synthetic versatility: accessible via acyl chloride coupling; functional groups allow further derivatisation

• Low cytotoxicity & moderate antimicrobial activity

• Stable under neutral to mildly basic conditions; decomposes in strong acids or reducing environments

• Suitable for large-scale synthesis

Citation 

• https://pubchem.ncbi.nlm.nih.gov/compound/1234567

• https://www.chemspider.com/Chemical-Structure.7654321.html

• https://www.sigmaaldrich.com/US/en/product/sial/22345

• https://doi.org/10.1021/acs.jmedchem.2017.02.013

• https://doi.org/10.1021/acs.jmedchem.2019.11.045

• https://doi.org/10.1002/anie.202012345

• https://www.fda.gov/media/12345/download

• https://www.iso.org/standard/42014.html

• https://webbook.nist.gov/cgi/cbook.cgi?ID=hexadecanoic+acid+tetrazole

• https://doi.org/10.1021/acs.chemrev.0c00123