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Chemical Compound Review

Carbomer     prop-2-enoic acid

Synonyms: Carbopol, Carbomere, Carbomero, enoates, Carbomerum, ...
 
 
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Disease relevance of acrylic acid

  • An enema that contained a complex of bismuth citrate and polyacrylate was compared with 5-aminosalicylic acid (5-ASA) enemas for treatment of distal ulcerative colitis [1].
  • The use of pAA also increased the levels of lung expression in mice in vivo substantially above the levels achieved with just binary complexes of DNA and linear PEI (lPEI) or CL and reduced their toxicity [2].
  • Bismuth carbomer foam enemas for active chronic pouchitis: a randomized, double-blind, placebo-controlled trial [3].
  • Efficacy and safety of 0.3% carbomer gel compared to placebo in patients with moderate-to-severe dry eye syndrome [4].
  • RESULTS: All primary subjective symptoms decreased significantly in the carbomer gel-treated group compared to the placebo group (i.e., dryness, discomfort, and foreign body sensation) [4].
 

High impact information on acrylic acid

  • The SFR of patients who preferred polyacrylic acid-based saliva substitutes was lower than that in patients who preferred the porcine mucin-based substitute (P < 0.05) [5].
  • After a final step of hydrolysis of the tert-butyl ester groups, double, hydrophilic, dendrimer-like PEOs comprising 21 internal junction-attached poly(acrylic acid) (PAA) blocks could be obtained [6].
  • In both nanotube synthesis processes, PEI (polyethylenimine), PAA (poly(acrylic acid)), and Au nanoparticles served as the building blocks on the Na(2)SO(4) templates, which were then rinsed with water to remove the core templates [7].
  • This article reports on the preparation of environmentally responsive "hairy" nanoparticles by growth of mixed poly(tert-butyl acrylate) (PtBA)/polystyrene (PS) brushes from silica particles using living radical polymerization techniques and subsequent hydrolysis of PtBA to produce amphiphilic mixed poly(acrylic acid) (PAA)/PS brushes [8].
  • Polyelectrolyte multilayers of poly(acrylic acid) (PAA) and polyacrylamide (PAAm) were prepared via hydrogen-bonding interactions [9].
 

Chemical compound and disease context of acrylic acid

 

Biological context of acrylic acid

  • Aromatic amino acid ammonia-lyases catalyze the deamination of L-His, L-Phe, and L-Tyr, yielding ammonia plus aryl acids bearing an alpha,beta-unsaturated propenoic acid [15].
  • The present study found that the inclusion of polyacrylic acid (pAA) with DNA/polycation and DNA/CL complexes prevented the serum inhibition of the transfection complexes in cultured cells [2].
  • Also, the use of a "chaser" injection of pAA 30 min after injection of the ternary DNA/lPEI/pAA complexes further aided this effort to reduce toxicity while not affecting foreign gene expression [2].
  • These compounds are comprised of a peptidomimetic binding determinant and an ethyl propenoate Michael acceptor moiety which forms an irreversible covalent adduct with the active site cysteine residue of the 3C enzyme [16].
  • A decrease in cell viability with chromatin condensation appeared with 0.3% preserved carbomer 934P at the two times tested [17].
 

Anatomical context of acrylic acid

 

Associations of acrylic acid with other chemical compounds

 

Gene context of acrylic acid

  • Acrylic acid analogs with a C-2 4-hydoxyphenyl (9d, IC(50)=0.56muM), or 4-acetamidophenyl (9g, IC(50)=0.11muM), substituent were particularly potent 5-LOX inhibitors that may participate in an additional specific hydrogen-bonding interaction [27].
  • Complexation of bFGF with acidic gelatin was slower than that with poly(acrylic acid) probably because of the lower density of gelatin negative charge than that of poly(acrylic acid) [28].
  • The tert-butyl groups of these appended polymers could also be removed to produce nanotubes functionalized with poly(acrylic acid), resulting in structures that are soluble in aqueous solutions [29].
  • Compound 40, (E)-3-[2-butyl-1- [(2-chlorophenyl)methyl]imidazol-5-yl]-2-[(2-thienyl)methyl]-2- propenoic acid, has been shown to be a potent, competitive, and orally active small molecule AT-1 receptor antagonist [30].
  • Substitution of propanoic or propenoic acid moieties for the acidic heterocyclic units of these compounds gave the monocyclic amino acids 15-18, which have very little or no affinity for GABAA receptor sites [31].
 

Analytical, diagnostic and therapeutic context of acrylic acid

  • Coating of substrates with polyelectrolyte multilayers terminated with poly(acrylic acid) (PAA) followed by activation of the free -COOH groups of PAA provides a surface that readily reacts with amine groups to allow covalent immobilization of antibodies [32].
  • FTIR has been used to examine the cements as they set, and has confirmed previous results that (+)-tartaric acid reacts more readily with the glass than does poly(acrylic acid), thereby delaying the setting of the cement [33].
  • Circulating half-lives were found to be less than 12 min for amphiphilic poly(acrylic acid), short-chain (750 Da) methoxy-PEG or long-chain (3400 Da) carboxy-PEG quantum dots, but approximately 70 min for long-chain (5000 Da) methoxy-PEG quantum dots [34].
  • Conductometric titration of aqueous solutions of polyacrylic acid and its copolymers [35].
  • A clinical trial for the final cementation of crowns and bridges with a reinforced zinc oxide and eugenol cement, a polyacrylic acid cement and a zinc phosphate cement was made over a 3-year period [36].

References

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  2. Recharging cationic DNA complexes with highly charged polyanions for in vitro and in vivo gene delivery. Trubetskoy, V.S., Wong, S.C., Subbotin, V., Budker, V.G., Loomis, A., Hagstrom, J.E., Wolff, J.A. Gene Ther. (2003) [Pubmed]
  3. Bismuth carbomer foam enemas for active chronic pouchitis: a randomized, double-blind, placebo-controlled trial. Tremaine, W.J., Sandborn, W.J., Wolff, B.G., Carpenter, H.A., Zinsmeister, A.R., Metzger, P.P. Aliment. Pharmacol. Ther. (1997) [Pubmed]
  4. Efficacy and safety of 0.3% carbomer gel compared to placebo in patients with moderate-to-severe dry eye syndrome. Sullivan, L.J., McCurrach, F., Lee, S., Taylor, H.R., Rolando, M., Marechal-Courtois, C., Creuzot-Garcher, C., Easty, D.L., Karabatsas, C., Bingh Hoh, M., Faschinger, C., Laroche, L. Ophthalmology (1997) [Pubmed]
  5. Treatment of xerostomia with polymer-based saliva substitutes in patients with Sjögren's syndrome. van der Reijden, W.A., van der Kwaak, H., Vissink, A., Veerman, E.C., Amerongen, A.V. Arthritis Rheum. (1996) [Pubmed]
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  7. Water-dissolvable sodium sulfate nanowires as a versatile template for the fabrication of polyelectrolyte- and metal-based nanotubes. Pu, Y.C., Hwu, J.R., Su, W.C., Shieh, D.B., Tzeng, Y., Yeh, C.S. J. Am. Chem. Soc. (2006) [Pubmed]
  8. Environmentally responsive "hairy" nanoparticles: mixed homopolymer brushes on silica nanoparticles synthesized by living radical polymerization techniques. Li, D., Sheng, X., Zhao, B. J. Am. Chem. Soc. (2005) [Pubmed]
  9. Micropatterning of polymer thin films with pH-sensitive and cross-linkable hydrogen-bonded polyelectrolyte multilayers. Yang, S.Y., Rubner, M.F. J. Am. Chem. Soc. (2002) [Pubmed]
  10. Pharmacokinetics of nicotine carbomer enemas: a new treatment modality for ulcerative colitis. Green, J.T., Thomas, G.A., Rhodes, J., Evans, B.K., Russell, M.A., Feyerabend, C., Fuller, G.S., Newcombe, R.G., Sandborn, W.J. Clin. Pharmacol. Ther. (1997) [Pubmed]
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  12. Effects of penetration enhancers on the in-vitro percutaneous absorption of progesterone. Valenta, C., Wedenig, S. J. Pharm. Pharmacol. (1997) [Pubmed]
  13. Study of interaction effects of polyacrylic acid polymers (carbopol 940) on antimicrobial activity of methyl parahydroxybenzoate against some gram-negative, gram-positive bacteria and yeast. Scalzo, M., Orlandi, C., Simonetti, N., Cerreto, F. J. Pharm. Pharmacol. (1996) [Pubmed]
  14. Whole blood selective LDL-apheresis: a comparison of two different adsorbers. Poli, L., Busnach, G. The International journal of artificial organs. (2006) [Pubmed]
  15. Structural determinants and modulation of substrate specificity in phenylalanine-tyrosine ammonia-lyases. Louie, G.V., Bowman, M.E., Moffitt, M.C., Baiga, T.J., Moore, B.S., Noel, J.P. Chem. Biol. (2006) [Pubmed]
  16. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics. Dragovich, P.S., Prins, T.J., Zhou, R., Fuhrman, S.A., Patick, A.K., Matthews, D.A., Ford, C.E., Meador, J.W., Ferre, R.A., Worland, S.T. J. Med. Chem. (1999) [Pubmed]
  17. Cytoprotective effects of hyaluronic acid and Carbomer 934P in ocular surface epithelial cells. Debbasch, C., De La Salle, S.B., Brignole, F., Rat, P., Warnet, J.M., Baudouin, C. Invest. Ophthalmol. Vis. Sci. (2002) [Pubmed]
  18. Solid-phase microextraction in combination with GC/MS for quantification of the major volatile free fatty acids in ewe cheese. Pinho, O., Ferreira, I.M., Ferreira, M.A. Anal. Chem. (2002) [Pubmed]
  19. Protective and inhibitory effects of various types of amphipols on the Ca2+-ATPase from sarcoplasmic reticulum: a comparative study. Picard, M., Dahmane, T., Garrigos, M., Gauron, C., Giusti, F., le Maire, M., Popot, J.L., Champeil, P. Biochemistry (2006) [Pubmed]
  20. The effects of the solubility of artificial fissures on plaque pH. Zaura, E., Buijs, M.J., ten Cate, J.M. J. Dent. Res. (2002) [Pubmed]
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  23. Assembly of nanotubes of poly(4-vinylpyridine) and poly(acrylic acid) through hydrogen bonding. Tian, Y., He, Q., Cui, Y., Tao, C., Li, J. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  24. Structure-activity relationships of (E)-3-(1,4-benzoquinonyl)-2-[(3-pyridyl)-alkyl]-2-propenoic acid derivatives that inhibit both 5-lipoxygenase and thromboxane A2 synthetase. Hibi, S., Okamoto, Y., Tagami, K., Numata, H., Kobayashi, N., Shinoda, M., Kawahara, T., Harada, K., Miyamoto, K., Yamatsu, I. J. Med. Chem. (1996) [Pubmed]
  25. Fiber-optic pH-sensors in long-period fiber gratings using electrostatic self-assembly. Corres, J.M., Del Villar, I., Matias, I.R., Arregui, F.J. Optics letters (2007) [Pubmed]
  26. The influence of high- and low-molecular-weight inhibitors on dissolution kinetics of hydroxyapatite and human enamel in lactate buffers: a constant composition study. Budz, J.A., Lo Re, M., Nancollas, G.H. J. Dent. Res. (1988) [Pubmed]
  27. Design, synthesis, and biological evaluation of (E)-3-(4-methanesulfonylphenyl)-2-(aryl)acrylic acids as dual inhibitors of cyclooxygenases and lipoxygenases. Moreau, A., Chen, Q.H., Praveen Rao, P.N., Knaus, E.E. Bioorg. Med. Chem. (2006) [Pubmed]
  28. Complexation of basic fibroblast growth factor with gelatin. Muniruzzaman, n.u.l.l., Tabata, Y., Ikada, Y. Journal of biomaterials science. Polymer edition. (1998) [Pubmed]
  29. Polymerization from the surface of single-walled carbon nanotubes - preparation and characterization of nanocomposites. Yao, Z., Braidy, N., Botton, G.A., Adronov, A. J. Am. Chem. Soc. (2003) [Pubmed]
  30. Imidazole-5-acrylic acids: potent nonpeptide angiotensin II receptor antagonists designed using a novel peptide pharmacophore model. Keenan, R.M., Weinstock, J., Finkelstein, J.A., Franz, R.G., Gaitanopoulos, D.E., Girard, G.R., Hill, D.T., Morgan, T.M., Samanen, J.M., Hempel, J. J. Med. Chem. (1992) [Pubmed]
  31. Partial GABAA receptor agonists. Synthesis and in vitro pharmacology of a series of nonannulated analogs of 4,5,6,7-tetrahydroisoxazolo[5,4-c]pyridin-3-ol. Frølund, B., Kristiansen, U., Brehm, L., Hansen, A.B., Krogsgaard-Larsen, P., Falch, E. J. Med. Chem. (1995) [Pubmed]
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  33. Fourier transform infrared spectroscopic study of the role of tartaric acid in glass-ionomer dental cements. Nicholson, J.W., Brookman, P.J., Lacy, O.M., Wilson, A.D. J. Dent. Res. (1988) [Pubmed]
  34. Noninvasive imaging of quantum dots in mice. Ballou, B., Lagerholm, B.C., Ernst, L.A., Bruchez, M.P., Waggoner, A.S. Bioconjug. Chem. (2004) [Pubmed]
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  36. Clinical study of dental cements. VI. A study of zinc phosphate, EBA-reinforced zinc oxide eugenol and polyacrylic acid cements as luting agents in fixed prostheses. Silvey, R.G., Myers, G.E. J. Dent. Res. (1977) [Pubmed]
 
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