21442-01-3

Basic information

• Product Name: N-(2-HYDROXYPROPYL)METHACRYLAMIDE
• Synonyms: N-(2-HYDROXYPROPYL)METHACRYLAMIDE;N-(2-Hydroxypropyl)-2-methyl-prop-2-enamide;N-(2-Hydroxypropyl)-2-methyl-prop-2-enamide AldrichCPR;2-Hydroxypropyl methacrylamide 99% (GC);2-Hydroxypropyl methacrylamide
• CAS NO: 21442-01-3
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18
• Product Categories: monomer
• Mol File: 21442-01-3.mol

Chemical Properties

• Melting Point: 67.92°C
• Boiling Point: 321.2 °C at 760 mmHg
• Flash Point: 148.1 °C
• Appearance: /
• Density: 1.002 g/mL ((predicted))
• Vapor Pressure: 2.43E-05mmHg at 25°C
• Refractive Index: 1.46
• Storage Temp.: 2-8°C
• PKA: 14.43±0.20(Predicted)
• CAS DataBase Reference: N-(2-HYDROXYPROPYL)METHACRYLAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-HYDROXYPROPYL)METHACRYLAMIDE(21442-01-3)
• EPA Substance Registry System: N-(2-HYDROXYPROPYL)METHACRYLAMIDE(21442-01-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 21442-01-3(Hazardous Substances Data)

Usage

Uses

Used in Biomedical Applications:
N-(2-HYDROXYPROPYL)METHACRYLAMIDE is used as a monomer for synthesizing biocompatible polymers and copolymers for various biomedical applications. The application reason is that these polymers can be tailored to have specific properties, such as biodegradability, biocompatibility, and controlled drug release, making them suitable for a range of medical applications.
Used in Drug Carriers:
In the pharmaceutical industry, N-(2-HYDROXYPROPYL)METHACRYLAMIDE is used as a monomer for creating drug carriers. The application reason is that the resulting polymers can be designed to encapsulate and release drugs in a controlled manner, improving the drug's efficacy and reducing side effects.
Used in Protein Conjugates:
In the field of biochemistry, N-(2-HYDROXYPROPYL)METHACRYLAMIDE is used as a monomer for the synthesis of protein conjugates. The application reason is that these conjugates can be used to improve the stability, solubility, and bioavailability of proteins, making them more effective for various therapeutic applications.
Used in Hydrogels:
In the material science and tissue engineering fields, N-(2-HYDROXYPROPYL)METHACRYLAMIDE is used as a monomer for the creation of hydrogels. The application reason is that these hydrogels can mimic the natural extracellular matrix, providing a supportive environment for cell growth and tissue regeneration.

InChI:InChI=1/C7H13NO2/c1-5(2)7(10)8-4-6(3)9/h6,9H,1,4H2,2-3H3,(H,8,10)

Upstream product

• 760-93-0 methacryloyl anhydride 
• 78-96-6 3-amino-2-propanol 
• 897017-30-0 (S)-2-Hydroxy-propionic acid 1-methyl-2-(2-methyl-acryloylamino)-ethyl ester 
• 920-46-7 Methacryloyl chloride 
• 675589-71-6 (S)-2-Hydroxy-propionic acid (S)-1-[1-methyl-2-(2-methyl-acryloylamino)-ethoxycarbonyl]-ethyl ester 

Downstream Products

• 288-32-4 1H-imidazole 
• 1434118-32-7 N-(2-benzoyloxypropyl)methacrylamide 
• 1450754-13-8 (Z)-N-[3-(2-hydroxypropylamino)-2-methyl-3-oxoprop-1-enyl]-4-nitrobenzamide 

Relevant articles and documents

RETRACTED ARTICLE: Folic acid mediated endocytosis enhanced by modified multi stimuli nanocontainers for cancer targeting and treatment: Synthesis, characterization, in-vitro and in-vivo evaluation of therapeutic efficacy

Polymeric materials are in the epicenter of scientific research the last decade and have been used in a range of pharmaceutical and biological applications. Multifunctional polymeric materials are capable targeting agents, which can be used as controlled drug release vehicles for the enhancement of therapeutic efficacy, as well as for diagnostic purposes. A newer generation of these smart polymeric entities constitutes of smart nanocontainers (NCs), which can navigate the drug to specific areas by avoiding random distribution, and thus resulting in drug toxicity reduction. The combination of pH, thermo and redox sensitivity of the multi stimuli NCs can help to achieve specific release of the drug in the tumor area, where these sensitivity parameters can be observed. Hollow polymeric multi stimuli fluorescent tNCs based on N-(2-Hydroxypropyl)methacrylamide (HPMA) were successfully functionalized with a specific targeting moiety; folic acid, and then characterized morphologically, by scanning electron and transmission electron microscopy, as well as structurally, by Fourier-transform infrared spectroscopy. Their targeting mechanism was investigated in vitro in cervical cancer cell lines and in vivo in tumor bearing mice. According to our results the folic acid functionalized NCs targeted HeLa cells’ surface within the first 30 min of treatment. Human tumor xenografted mice (nonobese diabetic/severe combined immunodeficient) were injected with folate functionalized NCs and their tumor uptake was estimated by γ-imaging at about 3.5%. The targeting efficiency of the folate functionalized NCs was investigated directly in vivo by γ-imaging and indirectly by a tumor efficacy protocol.

COMPOSITIONS AND METHODS OF MANUFACTURING STAR POLYMERS FOR LIGAND DISPLAY AND/OR DRUG DELIVERY

A star polymer of formula O[P1]-([X]-A[P2]-[Z]-[P3])n where O is a core; A is a polymer arm attached to the core; X is a linker molecule between the core and the polymer arm; Z is a linker molecule between the end of the polymer arm and P3; P1, P2 and P3 are each independently one or more pharmaceutically active compounds that act extracellularly or intracellularly, n is an integer number; [ ] denotes that the group is optional; and at least one of P1, P2 or P3 is present.

Overcoming resistance to rituximab in relapsed non-Hodgkin lymphomas by antibody-polymer drug conjugates actively targeted by anti-CD38 daratumumab

B-cell non-Hodgkin lymphomas (B-NHL) represent the most common type of hematologic malignancies in the Western hemisphere. The therapy of all B-NHL is based on the combination of different genotoxic cytostatics and anti-CD20 monoclonal antibody (mAb) rituximab. Unfortunately, many patients relapse after the mentioned front-line treatment approaches. The therapy of patients with relapsed/refractory (R/R) B-NHL represents an unmet medical need. We designed, developed and tested novel actively targeted hybrid mAb-polymer-drug conjugate (APDC) containing anti-CD20, anti-CD38 or anti-CD19 mAbs. Biocompatible copolymers based on N-(2-hydroxypropyl)methacrylamide (HPMA) with cytostatic agent doxorubicin attached via stimuli-sensitive hydrazone bond were employed for the mAb grafting. Anti-lymphoma efficacy of the APDC nanotherapeutics was evaluated in vivo on a panel of three patient-derived lymphoma xenografts derived from two patients with R/R B-NHL and one patient with so far untreated B-NHL. In both PDX models derived from patients with R/R B-NHL, the targeting with anti-CD38 antibody daratumumab demonstrated highly improved anti-lymphoma efficacy compared to the targeting with anti-CD20 rituximab, two experimental anti-CD19 antibodies and non-targeted controls. The results represent a proof-of-concept of a new algorithm of personalized anti-tumor therapy based on highly innovative APDC biomaterials.

Biotinylated HPMA centered polymeric nanoparticles for Bortezomib delivery

Bortezomib (BTZ) is a proteasome inhibitor as approved by US FDA for the treatment of multiple myeloma. It exhibits significant anti-cancer properties, against solid tumors; but lacks aqueous solubility, chemical stability which hinders its successful formulation development. The present study is an attempt to deliver BTZ using N-(2-hydroxypropyl) methacrylamide (HPMA) based copolymeric conjugates and biotinylated PNPs in an effective manner. Study describes a systematic synthetic pathway to synthesize functional polymeric conjugates such as HPMA-Biotin (HP-BT) HPMA-Polylactic acid (HPLA) and HPMA-PLA-Biotin (HPLA-BT) followed by exhaustive characterization both spectroscopically and microscopically. Our strategy yielded polymeric nanoparticles (PNPs) of narrow size range of 199.7 ± 1.32 nm. Release studies were performed at pH 7.4 and 5.6. PNPs were 2-folds less hemolytic (p 50 value of these PNPs was 56.06 ± 0.12 nM, which was approximately two folds less than BTZ (p 0 t-∞) of DL-HPLA-BT PNPs (drug loaded) than BTZ with an improved half-life. Overall the developed PNPs led to the improved and effective BTZ delivery.

Polyvalent Diazonium Polymers Provide Efficient Protection of Oncolytic Adenovirus Enadenotucirev from Neutralizing Antibodies while Maintaining Biological Activity in Vitro and in Vivo

Oncolytic viruses offer many advantages for cancer therapy when administered directly to confined solid tumors. However, the systemic delivery of these viruses is problematic because of the host immune response, undesired interactions with blood components, and inherent targeting to the liver. Efficacy of systemically administered viruses has been improved by masking viral surface proteins with polymeric materials resulting in modulation of viral pharmacokinetic profile and accumulation in tumors in vivo. Here we describe a new class of polyvalent reactive polymer based on poly(N-(2-hydroxypropyl)methacrylamide) (polyHPMA) with diazonium reactive groups and their application in the modification of the chimeric group B oncolytic virus enadenotucirev (EnAd). A series of six copolymers with different chain lengths and density of reactive groups was synthesized and used to coat EnAd. Polymer coating was found to be extremely efficient with concentrations as low as 1 mg/mL resulting in complete (>99%) ablation of neutralizing antibody binding. Coating efficiency was found to be dependent on both chain length and reactive group density. Coated viruses were found to have reduced transfection activity both in vitro and in vivo, with greater protection against neutralizing antibodies resulting in lower transgene production. However, in the presence of neutralizing antibodies, some in vivo transgene expression was maintained for coated virus compared to the uncoated control. The decrease in transgene expression was found not to be solely due to lower cellular uptake but due to reduced unpackaging of the virus within the cells and reduced replication, indicating that the polymer coating does not cause permanent inactivation of the virus. These data suggest that virus activity may be modulated by the appropriate design of coating polymers while retaining protection against neutralizing antibodies.

Impact of Polymer-TLR-7/8 Agonist (Adjuvant) Morphology on the Potency and Mechanism of CD8 T Cell Induction

Small molecule Toll-like receptor-7 and -8 agonists (TLR-7/8a) can be used as vaccine adjuvants to induce CD8 T cell immunity but require formulations that prevent systemic toxicity and focus adjuvant activity in lymphoid tissues. Here, we covalently attached TLR-7/8a to polymers of varying composition, chain architecture and hydrodynamic behavior (～300 nm submicrometer particles, ～10 nm micelles and ～4 nm flexible random coils) and evaluated how these parameters of polymer-TLR-7/8a conjugates impact adjuvant activity in vivo. Attachment of TLR-7/8a to any of the polymer compositions resulted in a nearly 10-fold reduction in systemic cytokines (toxicity). Moreover, both lymph node cytokine production and the magnitude of CD8 T cells induced against protein antigen increased with increasing polymer-TLR-7/8a hydrodynamic radius, with the submicrometer particle inducing the highest magnitude responses. Notably, CD8 T cell responses induced by polymer-TLR-7/8a were dependent on CCR2+ monocytes and IL-12, whereas responses by a small molecule TLR-7/8a that unexpectedly persisted in vaccine-site draining lymph nodes (T1/2 = 15 h) had less dependence on monocytes and IL-12 but required Type I IFNs. This study shows how modular properties of synthetic adjuvants can be chemically programmed to alter immunity in vivo through distinct immunological mechanisms.

HPMA-PLGA Based Nanoparticles for Effective In Vitro Delivery of Rifampicin

Purpose: Tuberculosis (TB) chemotherapy witnesses some major challenges such as poor water-solubility and bioavailability of drugs that frequently delay the treatment. In the present study, an attempt to enhance the aqueous solubility of rifampicin (RMP) was made via co-polymeric nanoparticles approach. HPMA (N-2-hydroxypropylmethacrylamide)-PLGA based polymeric nanoparticulate system were prepared and evaluated against Mycobacterium tuberculosis (MTB) for sustained release and bioavailability of RMP to achieve better delivery. Methodology: HPMA-PLGA nanoparticles (HP-NPs) were prepared by modified nanoprecipitation technique, RMP was loaded in the prepared NPs. Characterization for particle size, zeta potential, and drug-loading capacity was performed. Release was studied using membrane dialysis method. Results: The average particles size, zeta potential, polydispersity index of RMP loaded HPMA-PLGA-NPs (HPR-NPs) were 260.3 ± 2.21?nm, ?6.63 ± 1.28?mV, and 0.303 ± 0.22, respectively. TEM images showed spherical shaped NPs with uniform distribution without any cluster formation. Entrapment efficiency and drug loading efficiency of HPR-NPs were found to be 76.25 ± 1.28%, and 26.19 ± 2.24%, respectively. Kinetic models of drug release including Higuchi and Korsmeyer-peppas demonstrated sustained release pattern. Interaction studies with human RBCs confirmed that RMP loaded HP-NPs are less toxic in this model than pure RMP with (p 0.05). Conclusions: The pathogen inhibition studies revealed that developed HPR-NPs were approximately four times more effective with (p 0.05) than pure drug against sensitive Mycobacterium tuberculosis (MTB) stain. It may be concluded that HPR-NPs holds promising potential for increasing solubility and bioavailability of RMP.

Polymer Cancerostatics Targeted by Recombinant Antibody Fragments to GD2-Positive Tumor Cells

A water-soluble polymer cancerostatic actively targeted against cancer cells expressing a disialoganglioside antigen GD2 was designed, synthesized and characterized. A polymer conjugate of an antitumor drug doxorubicin with a N-(2-hydroxypropyl)methacrylamide-based copolymer was specifically targeted against GD2 antigen-positive tumor cells using a recombinant single chain fragment (scFv) of an anti-GD2 monoclonal antibody. The targeting protein ligand was attached to the polymer-drug conjugate either via a covalent bond between the amino groups of the protein using a traditional nonspecific aminolytic reaction with a reactive polymer precursor or via a noncovalent but highly specific interaction between bungarotoxin covalently linked to the polymer and the recombinant scFv modified with a C-terminal bungarotoxin-binding peptide. The GD2 antigen binding activity and GD2-specific cytotoxicity of the targeted noncovalent polymer-scFv complex proved to be superior to the covalent polymer-scFv conjugate.

Based on N - (2 - hydroxypropyl) methacrylamide polymer nanometer grain and its preparation method

The invention discloses an N-(2-hydroxypropyl) methacrylamide polymer based nanoparticles capable of overcoming a mucus barrier and a preparation method thereof. The nanoparticles consist of nucleuses and shells, wherein the kernels are a nanometer compound prepared from a biocompatible carrier material and active ingredients, and the shells are an HPMA polymer and its derivatives.

Cyclic Peptide-Polymer Nanotubes as Efficient and Highly Potent Drug Delivery Systems for Organometallic Anticancer Complexes

Functional drug carrier systems have potential for increasing solubility and potency of drugs while reducing side effects. Complex polymeric materials, particularly anisotropic structures, are especially attractive due to their long circulation times. Here, we have conjugated cyclic peptides to the biocompatible polymer poly(2-hydroxypropyl methacrylamide) (pHPMA). The resulting conjugates were functionalized with organoiridium anticancer complexes. Small angle neutron scattering and static light scattering confirmed their self-assembly and elongated cylindrical shape. Drug-loaded nanotubes exhibited more potent antiproliferative activity toward human cancer cells than either free drug or the drug-loaded polymers, while the nanotubes themselves were nontoxic. Cellular accumulation studies revealed that the increased potency of the conjugate appears to be related to a more efficient mode of action rather than a higher cellular accumulation of iridium.