Phenylboronic Acid Modified Hyaluronic Acid Methacryloyl (PBA-HA) — Research Grade Supplier
PBA-HA — a dual-functional, glucose-responsive HA derivative engineered with both photocrosslinkable methacrylate groups (40-60%) and glucose-sensitive phenylboronic acid moieties (15-30%). In hyperglycemic environments (>10 mM glucose, characteristic of diabetic wounds), boronic ester bonds with diol-containing therapeutics cleave to trigger on-demand drug release — creating a closed-loop smart hydrogel that automatically delivers more therapeutic when and where glucose levels are elevated. The definitive biomaterial for diabetic wound healing, stimuli-responsive drug delivery, and smart biomaterials research. ISO 9001:2015 and c-GMP manufactured with dual functionalization verified by ¹H-NMR. Research-grade PBA-HA supplier — UPOR Biotech.
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Phenylboronic Acid Modified Hyaluronic Acid Methacryloyl (PBA-HA) is a dual-functional, glucose-responsive hyaluronic acid derivative that integrates two orthogonal chemical functionalities onto the HA polysaccharide backbone: methacrylate (MA) groups (40-60% degree of methacrylation) for UV/visible light photocrosslinking, and phenylboronic acid (PBA) groups (15-30% degree of PBA functionalization) for glucose-sensitive dynamic covalent bonding. This unique molecular design creates a “smart” hydrogel that not only forms a stable primary crosslinked network through light-initiated free-radical polymerization, but also responds dynamically to its biochemical environment — specifically, to elevated glucose concentrations characteristic of diabetic wounds and hyperglycemic tissue. The mechanism of glucose responsiveness is based on the reversible boronic ester bond: PBA groups (pKa ~8.8 for phenylboronic acid; lowered to ~7.4 in the HA hydrogel microenvironment due to neighboring diol stabilization) form reversible cyclic boronic esters with molecules containing vicinal diol (1,2-diol or 1,3-diol) groups — such as catechins (EGCG from green tea), catechol-containing antioxidants (gallic acid, dopamine, norepinephrine), flavonoids (quercetin, myricetin), and polyphenols (tannic acid). Under normoglycemic conditions (3-7 mM glucose), these boronic ester bonds remain stable, retaining the therapeutic payload within the hydrogel matrix. In hyperglycemic environments (>10 mM glucose) — precisely the conditions found in diabetic wound exudate (interstitial glucose typically 2-4× blood glucose in diabetic ulcers) — glucose molecules competitively bind to PBA groups with higher affinity (formation constant Kf ~10-100 M⁻¹ for glucose-boronate vs ~5-50 M⁻¹ for catechol-boronate, glucose concentration advantage of 10-50 mM vs μM-nM drug concentrations drives equilibrium displacement), displacing the therapeutic diol bonds and triggering on-demand drug release. This creates a closed-loop feedback system: the higher the local glucose concentration, the faster the therapeutic release — delivering the right dose, at the right time, exactly where it is needed, without any external intervention.
As a specialized research-grade PBA-HA supplier, UPOR Biotech provides this advanced smart biomaterial to academic research laboratories, biomedical startups, and pharmaceutical R&D teams developing next-generation stimuli-responsive therapeutic systems. PBA-HA’s dual functionality — photocrosslinking for structural integrity + glucose-responsive dynamic bonding for smart release — makes it uniquely suited for diabetic wound healing where the wound’s own hyperglycemic condition serves as the endogenous trigger for therapeutic delivery. All products are labeled Research Use Only (RUO) — not for human diagnostic or therapeutic use. Free sample available for qualified academic and industry researchers.
PBA-HA vs Standard MA-HA — From Passive Scaffold to Smart Biomaterial
Standard methacrylated HA (MA-HA) provides photocrosslinking only — a passive hydrogel scaffold with no environmental responsiveness. PBA-HA adds a second, orthogonal chemical functionality: glucose-sensitive phenylboronic acid groups (15-30%) that form reversible boronic ester bonds with diol-containing therapeutics. In hyperglycemic environments (diabetic wounds, >10 mM glucose), glucose competitively displaces the therapeutic-diol bond, triggering automatic, on-demand drug release without external intervention. The two functionalization parameters — MA (40-60%) and PBA (15-30%) — are independently tunable, allowing researchers to separately program the hydrogel’s structural integrity (via MA photocrosslink density) and its responsive release profile (via PBA content and glucose affinity). This transforms the hydrogel from a passive structural support into an active, environment-sensing biomaterial — the critical technological leap for diabetic wound healing where the wound’s own hyperglycemic condition becomes the therapeutic trigger.
Technical Specifications
| Property | Specification |
|---|---|
| Product Name | Phenylboronic Acid Modified Hyaluronic Acid Methacryloyl (PBA-HA) — Research Grade |
| Common Name / Abbreviations | PBA-HA; Glucose-Responsive HA; PBA-Modified Methacrylated HA; Dual-Functional HA; Phenylboronic Acid HA Methacryloyl; Smart Hydrogel HA |
| Parent HA CAS Number | 9004-61-9 (Sodium Hyaluronate); PBA-HA — CAS not assigned (custom-synthesized dual-functional polymer derivative) |
| PBA Precursor CAS | 98-80-6 (Phenylboronic Acid); 3-Aminophenylboronic Acid / 4-Carboxyphenylboronic Acid (functionalized PBA linkers used in HA conjugation) |
| Chemical Description | HA backbone co-functionalized with: (1) Methacrylate ester groups (-O-CO-C(CH₃)=CH₂) at C6 of GlcNAc — photocrosslinkable, (2) Phenylboronic acid groups (-C₆H₄-B(OH)₂) via amide/ester linker — glucose-sensitive dynamic covalent bonding |
| Key Advantage | Glucose-responsive smart hydrogel — dual orthogonal functionality. Hyperglycemic environments (>10 mM) trigger on-demand therapeutic release. Independently tunable MA (40-60%) and PBA (15-30%) parameters. |
| Appearance | White to off-white lyophilized powder |
| Parent HA Molecular Weight | 100-400 kDa (custom MW ranges available) |
| Degree of Methacrylation (MA) | 40-60% (verified by ¹H-NMR — characteristic methacrylate vinyl protons at δ 5.6 and 6.0 ppm, methyl at δ 1.8 ppm) |
| PBA Functionalization Degree | 15-30% (verified by ¹H-NMR — characteristic aromatic PBA protons at δ 7.2-7.8 ppm, broad B(OH)₂ signal at δ 8.0-8.5 ppm) |
| Glucose Responsiveness — Critical Quality Attribute | Boronic ester bonds with diol-containing drugs cleave at glucose concentrations >10 mM (hyperglycemic range); release rate proportional to glucose concentration; verified by in vitro glucose-triggered release assay using EGCG as model drug |
| pH-Dependent PBA Activity | Optimal boronic ester formation at pH 7.4-8.5; PBA pKa ~8.8 (free) lowered to ~7.4 in hydrogel microenvironment due to B-N dative bond stabilization from neighboring amide linker |
| Solubility | Soluble in water, PBS (pH 7.4), DPBS, and alkaline buffers (pH >7); limited solubility at pH <5 due to PBA protonation and HA acid precipitation |
| pH (1% Aqueous Solution, 25°C) | 6.0-7.5 |
| Working Concentration | 2-10% (w/v) in PBS or alkaline buffer; dissolution 2-24h with gentle agitation |
| Photoinitiator Compatibility | LAP (405 nm visible light, 0.05-0.5% w/v — recommended for cell applications); Irgacure 2959 (365 nm UV, 0.05-0.5% w/v — acellular scaffolds); Ruthenium/SPS (visible 400-450 nm) |
| Endotoxin Level | ≤100 EU/g (LAL kinetic chromogenic method) |
| Sterility | Sterile or no growth (USP <71> tested) |
| Protein Content | ≤0.1% |
| Loss on Drying | ≤10.0% (105°C, 2h) |
| Heavy Metals (Total) | ≤20 ppm (as Pb) |
| Elemental Impurities | Pb ≤5 ppm; As ≤2 ppm; Hg ≤1 ppm; Cd ≤1 ppm (ICH Q3D) |
| Microbial Limits | TAMC ≤100 CFU/g; TYMC ≤50 CFU/g (USP <61>); Pathogens — Negative (USP <62>) |
| Residual PBA Precursor | Not detected (¹H-NMR; residual phenylboronic acid and coupling reagents removed by dialysis and ethanol precipitation) |
| Grade / Intended Use | Research Grade (RUO — Research Use Only; not for human diagnostic, therapeutic, or clinical applications) |
| Certifications | ISO 9001:2015, c-GMP (ICH Q7), FDA Facility Registration |
| Storage — Lyophilized Powder | -20°C to 4°C; dry, light-protected (both MA and PBA groups are light- and moisture-sensitive); minimum 6 months shelf life under recommended conditions |
| Packaging | 100 mg / 500 mg / 1 g amber glass vials with PTFE-lined cap, nitrogen-flushed; custom packaging available |
| Shelf Life | Minimum 6 months from receipt in lyophilized form under recommended storage; MA and PBA functionalization stability verified at 0/3/6 months by ¹H-NMR |
Key Benefits — PBA-HA
Glucose-Responsive On-Demand Drug Release
PBA groups form reversible boronic ester bonds with diol-containing drugs (catechins, catechols, flavonoids, polyphenols). In hyperglycemic conditions (>10 mM glucose — diabetic wound environment), glucose competitively displaces these bonds, triggering automatic therapeutic release without external intervention.
Smart ReleaseDual Orthogonal Crosslinking — Photocuring + Dynamic Covalent
Combines two independent curing modes: (1) Photocrosslinking via methacrylate groups for primary hydrogel network and structural integrity; (2) Boronic ester-diol dynamic crosslinks via PBA groups for glucose-responsive, reversible secondary network — stable structure with stimuli-responsive behavior.
Dual-CureDiabetic Wound Healing Optimized — Endogenous Glucose as Trigger
Specifically engineered for the hyperglycemic wound microenvironment. Glucose-triggered release of antioxidants (EGCG, gallic acid) neutralizes excessive ROS, reduces chronic inflammation (IL-6, TNF-α), and promotes angiogenesis (VEGF) — addressing the core pathological features of diabetic non-healing wounds.
Wound HealingIndependently Tunable — MA and PBA Parameters Programmable
Degree of methacrylation (40-60%) and PBA functionalization (15-30%) are independently tunable — allowing researchers to separately program the hydrogel’s mechanical properties (via MA crosslink density) and its glucose-responsive release kinetics (via PBA content).
TunableApplications
Diabetic Wound Healing — Glucose-Responsive Antioxidant Release
Primary application. PBA-HA + EGCG/catechin hydrogel: glucose-triggered antioxidant release neutralizes chronic wound ROS and inflammation. Use at 2-5% w/v with LAP photoinitiator for in-situ photocuring over irregular wound geometries.
Stimuli-Responsive Drug Delivery — On-Demand Release
Glucose-triggered release of catechins, polyphenols, and diol-containing therapeutics. Release rate proportional to glucose concentration — enabling closed-loop delivery without external pumps or sensors.
Glucose-Responsive 3D Cell Culture Platforms
Create 3D microenvironments that change mechanical and biochemical properties in response to cellular metabolic activity (glucose consumption). Study cell-matrix interactions under dynamic, pathophysiologically relevant conditions.
Glucose Biosensors — PBA-Glucose Binding Transduction
PBA-glucose binding changes hydrogel swelling, refractive index, and fluorescence (when coupled with fluorophore). Enables hydrogel-based continuous glucose monitoring platforms without enzymatic (GOx) components.
Smart Tissue Engineering Scaffolds — Multi-Stimuli Responsive
Responsive to glucose, pH, and light. Scaffolds that release pro-angiogenic factors (VEGF, deferoxamine) in response to local ischemic/hyperglycemic conditions — programmable multi-stimuli biomaterial behavior.
3D Bioprinting — Dual-Cure Smart Bioink
Rapid photocrosslinking (MA groups) for print fidelity + dynamic boronic ester bonds (PBA groups) for post-printing stimuli-responsive behavior. Compatible with extrusion-based and DLP bioprinting platforms.
Molecular Weight Comparison — HA Grades
| Grade | Molecular Weight / Structure | Primary Function | Skin Penetration / Application |
|---|---|---|---|
| High MW | 1,500-2,000 kDa | Film-forming, thickening, surface hydration | Surface only (stratum corneum) |
| Medium MW | 1,000-1,500 kDa | Moisturizing, moderate thickening | Upper epidermis |
| Low MW | 400-1,000 kDa | Deep hydration, anti-wrinkle | Deeper epidermis |
| Extra Low MW | 100-400 kDa | Deep skin penetration, firming | Epidermis-dermis junction |
| Super Low MW | 20-50 kDa | Transdermal delivery, plumping | Dermis |
| Oligo HA | 7-10 kDa | Cellular signaling, wound healing | Deep dermis |
| Cationic HA | >1,000 kDa + cationic charge (quaternized) | Electrostatic adhesion, rinse-resistant moisturization, hair conditioning | Surface-adherent film (electrostatic bonding) |
| Acetylated HA (AcHA) | ~20-100 kDa + acetyl groups (23-29%) | Amphiphilic, 2× moisture retention, barrier repair, antioxidant | Stratum corneum (lipid-anchored) |
| Crosspolymer HA | Cross-linked 3D network | Long-lasting hydration, anti-pollution, 5× moisture retention | Surface film + sustained release |
| PBA-HA — Glucose-Responsive (this product) | 100-400 kDa + MA (40-60%) + PBA (15-30%) | Glucose-responsive smart hydrogel, diabetic wound healing, stimuli-responsive drug delivery, biosensors | Not applicable — designed as smart biomaterial with environment-sensing dual functionality |
| HA Low pH (<50 kDa) | <50 kDa | Acidic delivery, exfoliation-compatible hydration | Epidermis-Dermis |
| Zinc Hyaluronate | 10-50 kDa (hydrolyzed) | Anti-acne, sebum regulation, wound healing | Epidermis-Dermis |
Frequently Asked Questions
PBA-HA is a dual-functional HA derivative combining methacrylate groups (photocrosslinkable) with phenylboronic acid groups (glucose-sensitive). PBA groups (pKa ~8.8 free; lowered to ~7.4 in hydrogel) form reversible cyclic boronic ester bonds with molecules containing vicinal diol (1,2-diol or 1,3-diol) groups — catechins (EGCG), catechol-containing antioxidants (gallic acid, dopamine), flavonoids, and polyphenols. In hyperglycemic environments (>10 mM glucose) — typical of diabetic wound exudate where interstitial glucose is 2-4× blood levels — glucose molecules competitively bind to PBA groups, displacing the therapeutic diol bonds and triggering on-demand drug release. This creates a closed-loop smart hydrogel: the higher the local glucose concentration, the faster the therapeutic release — delivering treatment automatically in response to the wound’s own hyperglycemic condition without external pumps, sensors, or intervention.
Standard MA-HA provides photocrosslinking only — a passive hydrogel scaffold with no environmental responsiveness. PBA-HA adds a second, orthogonal chemical functionality: glucose-responsive dynamic covalent crosslinks via PBA groups (15-30%). The two functionalization parameters — degree of methacrylation (40-60%) and degree of PBA functionalization (15-30%) — are independently tunable, allowing researchers to separately program the hydrogel’s structural integrity (via MA crosslink density → stiffness, swelling, degradation rate) and its responsive release profile (via PBA content → glucose affinity, release kinetics, dynamic bond density). This transforms the hydrogel from passive structural support into an active, environment-sensing biomaterial. For diabetic wound healing applications, this glucose-responsiveness is the critical differentiator — enabling automatic therapeutic release triggered by the wound’s endogenous hyperglycemic condition, creating a self-regulating delivery system.
Any molecule containing vicinal diol (1,2-diol or 1,3-diol) groups can form reversible boronic ester bonds with PBA. Common compatible therapeutics include: Catechins — EGCG (epigallocatechin gallate from green tea, potent antioxidant with demonstrated diabetic wound healing efficacy via Nrf2/HO-1 pathway activation), ECG, EGC; Catechol-containing antioxidants — gallic acid, dopamine, norepinephrine, L-DOPA; Flavonoids — quercetin, myricetin, luteolin, fisetin, kaempferol; Polyphenols — tannic acid, proanthocyanidins, resveratrol. Therapeutic release is triggered when glucose competitively displaces the drug-diol bond at concentrations >10 mM (glucose-boronate Kf ~10-100 M⁻¹ with mM concentration advantage over μM-nM drug levels). For molecules without natural diol groups, chemical derivatization strategies (e.g., conjugating a glycerol, catechol, or sugar linker) can expand the range of compatible payloads.
Yes. PBA-HA retains full photocrosslinking capability via its methacrylate groups (40-60% DoM). Compatible photoinitiators: LAP (lithium phenyl-2,4,6-trimethylbenzoylphosphinate, 405 nm visible light, 0.05-0.5% w/v — recommended for cell-containing applications due to low cytotoxicity and compatibility with standard bioprinter LED sources), Irgacure 2959 (2-hydroxy-4′-(2-hydroxyethoxy)-2-methylpropiophenone, 365 nm UV, 0.05-0.5% w/v — for acellular scaffolds), and Ruthenium/SPS (Ru(II)bpy₃²⁺/S₂O₈²⁻, visible 400-450 nm, 1/10 mM — highest cytocompatibility, slower gelation). The photocrosslinking forms the primary hydrogel network providing structural integrity and shape fidelity; the PBA-diol bonds provide the secondary, glucose-responsive dynamic network enabling stimuli-responsive behavior. Both mechanisms operate orthogonally — light initiates methacrylate polymerization to set the hydrogel, while glucose concentration modulates boronic ester bond stability to control drug release — enabling independent optimization of mechanical and responsive properties.
Every shipment includes: COA (¹H-NMR spectrum confirming both MA functionalization — vinyl protons δ 5.6/6.0 ppm, methyl δ 1.8 ppm — and PBA functionalization — aromatic protons δ 7.2-7.8 ppm, integration ratio vs HA N-acetyl methyl δ 2.0 ppm; degree of methacrylation 40-60%; PBA functionalization 15-30%; endotoxin ≤100 EU/g LAL; sterility USP <71>; parent HA MW by GPC-MALLS; solubility verification; heavy metals; microbial panel USP <61>/<62>; residual PBA precursor — not detected by ¹H-NMR), MSDS, ¹H-NMR Spectral Report (full peak assignments and integration for MA and PBA degree of substitution calculation — signed and dated), Stability Data (MA and PBA functionalization re-verified at 0/3/6 months by ¹H-NMR), and Complete Lot Traceability. ISO 9001:2015 and c-GMP (ICH Q7) manufacturing ensures batch-to-batch consistency in both methacrylation and PBA functionalization degrees. All products labeled Research Use Only (RUO). Free sample available for qualified researchers.
