Influence of the backbone structure on the release of bioactive volatiles from maleic acid-based polymer conjugates

Bioconjugate Chemistry

Volumn 21, Issue 11, 2010, Pages 2000-2012

  Berthier, Damien L ^a   Paret, Nicolas ^a   Trachsel, Alain ^a   Herrmann, Andreas ^a  

^a Email:   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

1 OCTADECENE; 3 (2 HYDROXYETHYLSULFANYL) 1 (2,6,6 TRIMETHYLCYCLOHEX 3 ENYL) BUTAN 1 ONE; COPOLYMER; DAMASCONE; ETHER DERIVATIVE; ETHYLENE; ISOBUTYLENE; KETONE DERIVATIVE; MALEIC ACID; MALEIC ANHYDRIDE; METHYL VINYL ETHER; UNCLASSIFIED DRUG; VOLATILE AGENT;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATE; FLUORESCENCE SPECTROSCOPY; HYDROPHILICITY; HYDROPHOBICITY; ONE POT SYNTHESIS; PH; RING OPENING;

GOSSYPIUM HIRSUTUM;

EID: 78649263640     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100223s     Document Type: Article

References (68)

1. Pichersky, E., Noel, J. P., and Dudareva, N. (2006) Biosynthesis of plant volatiles: nature's diversity and ingenuity Science 311, 808-811
2. Baldwin, I. T., Halitschke, R., Paschold, A., von Dahl, C. C., and Preston, C. A. (2006) Volatile signaling in plant-plant interactions: "talking trees" in the genomics era Science 311, 812-815
3. Bergström, L. G. W. (2008) Chemical communication by behaviour-guiding olfactory signals Chem. Commun. 3959-3979
4. Arctander, S. (1969) Perfume and Flavor Chemicals, Vol. 1 (A-J) and 2 (K-Z), published by the author, Montclair, NJ.
5. Surburg, H. and Panten, J. (2006) Common Fragrance and Flavor Materials, 5 th ed. (Surburg, H. and Panten, J., Eds.) pp 1 - 318, Wiley-VCH, Weinheim.
6. Kraft, P., Bajgrowicz, J. A., Denis, C., and Fráter, G. (2000) Odds and trends: recent developments in the chemistry of odorants Angew. Chem., Int. Ed. 39, 2980-3010
7. Brenna, E. (2003) Enzyme-mediated syntheses of chiral communication substances: fragrances for perfumery applications Curr. Org. Chem. 7, 1347-1367
8. Chapuis, C. and Jacoby, D. (2001) Catalysis in the preparation of fragrances and flavours Appl. Catal., A 221, 93-117
9. Saudan, L. (2007) Hydrogenation processes in the synthesis of perfumery ingredients Acc. Chem. Res. 40, 1309-1319
10. Friberg, S. E. (1998) Fragrance compounds and amphiphilic association structures Adv. Colloid Interface Sci. 75, 181-214
11. Zhang, Z., Friberg, S. E., and Aikens, P. A. (2000) Change of amphiphilic association structures during evaporation from emulsions in surfactant-fragrance-water systems Int. J. Cosmet. Sci. 22, 181-199
12. Milotic, D. (2003) The impact of fragrance on consumer choice J. Consum. Behav. 3, 179-191
13. Ness, J., Simonsen, O., and Symes, K. (2003) Microcapsules for household products Microspheres, Microcapsules Liposomes 6, 199-234
14. Park, S.-J. and Arshady, R. (2003) Microcapsules for fragrances and cosmetics Microspheres, Microcapsules Liposomes 6, 157-198
15. Herrmann, A. (2007) Controlled release of volatiles under mild reaction conditions: from nature to everyday products Angew. Chem., Int. Ed. 46, 5836-5863
16. ® P-85 J. Dispersion Sci. Technol. 17, 567-576
17. Suzuki, K., Saito, Y., Tokuoka, Y., Abe, M., and Sato, T. (1997) Poly(ethylene oxide)/poly(propylene oxide)/poly(ethylene oxide) triblock copolymer as a sustained-release carrier for perfume compounds J. Am. Oil Chem. Soc. 74, 55-59
18. Kayali, I. (2003) Solubilization of fragrance compounds in block copolymer/water system Jordan. J. Appl. Sci. 5, 42-49
19. Berthier, D. L., Schmidt, I., Fieber, W., Schatz, C., Furrer, A., Wong, K., and Lecommandoux, S. (2010) Controlled release of volatile fragrance molecules from PEO- b -PPO- b -PEO block copolymer micelles in ethanol-water mixtures Langmuir 26, 7953-7961
20. Ternat, C., Ouali, L., Sommer, H., Fieber, W., Velazco, M. I., Plummer, C. J. G., Kreutzer, G., Klok, H.-A., Månson, J.-A. E., and Herrmann, A. (2008) Investigation of the release of bioactive volatiles from amphiphilic multiarm star-block copolymers by thermogravimetry and dynamic headspace analysis Macromolecules 41, 7079-7089
21. Perry, R. J. (2005) "Pro-fragrant" silicone delivery polymers. Delivery System Handbook for Personal Care and Cosmetic Products: Technology, Applications, and Formulations (Rosen, M. R., Ed.) pp 667 - 682, William Andrew Publishing, Norwich.
22. Kamogawa, H., Okabe, S., and Nanasawa, M. (1976) Synthesis of polymerizable acetals. I. Vinylbenzaldehyde acetals with perfume alcohols Bull. Chem. Soc. Jpn. 49, 1917-1919
23. Kamogawa, H., Haramoto, Y., and Nanasawa, M. (1979) Synthesis of polymerizable acetals. II. Readily hydrolyzable acetals from citronellol and vitamins Bull. Chem. Soc. Jpn. 52, 846-848
24. Kamogawa, H., Mukai, H., Nakajima, Y., and Nanasawa, M. (1982) Chemical release control-Schiff bases of perfume aldehydes and aminostyrenes J. Polym. Sci., Polym. Chem. Ed. 20, 3121-3129
25. Kamogawa, H., Haramoto, Y., Misaka, Y., Asada, Y., Ohno, Y., and Nanasawa, M. (1985) Chemical release control: sulfonate esters from perfume and herbicide alcohols and p-styrenesulfonyl chloride J. Polym. Sci., Polym. Chem. Ed. 23, 1517-1526
26. Galioǧlu, O. and Akar, A. (1988) Perfume alcohols supported to sulfochlorinated poly(styrene-co-divinyl benzene) beads J. Polym. Sci., Part A: Polym. Chem. 26, 2355-2357
27. Kamogawa, H., Kohno, H., and Kitagawa, R. (1989) Chemical release control: carbamates of 3-vinylphenyl and 2-methacryloyloxyethyl isocyanates and perfume and herbicide alcohols J. Polym. Sci., Part A: Polym. Chem. 27, 487-495
28. Berthier, D., Trachsel, A., Fehr, C., Ouali, L., and Herrmann, A. (2005) Amphiphilic polymethacrylate- and polystyrene-based chemical delivery systems for damascones Helv. Chim. Acta 88, 3089-3108
29. Trachsel, A., de Saint Laumer, J.-Y., Haefliger, O. P., and Herrmann, A. (2009) Parameters influencing the release of tertiary alcohols from the surface of "spherical" dendrimers and "linear" stylomers by neighbouring-group-assisted hydrolysis of 2-carbamoylbenzoates Chem.-Eur. J. 15, 2846-2860
30. Morinaga, H., Morikawa, H., Wang, Y., Sudo, A., and Endo, T. (2009) Amphiphilic copolymer having acid-labeile acetal in the side chain as a hydrotrope: controlled release of aldehyde by thermoresponsive aggregation-dissociation of polymer micelles Macromolecules 42, 2229-2235
31. Fehr, C. and Galindo, J. (2005) Aldols by Michael addition: application of the retro-Michael addition to the slow release of enones Helv. Chim. Acta 88, 3128-3136
32. Kastner, D. (1994) 25 Jahre Rosenketone-Thema mit Variationen Parfuem. Kosmet. 75 (3) 170-81
33. Williams, A. (2002) Rose ketones: celebrating 30 years of success Perfum. Flavor. 27 (2) 18-32
34. Shulkin, A. and Stöver, H. D. H. (2002) Polymer microcapsules by interfacial polyaddition between styrene-maleic anhydride copolymers and amines J. Membr. Sci. 209, 421-432
35. Donati, I., Gamini, A., Vetere, A., Campa, C., and Paoletti, S. (2002) Synthesis, characterization, and preliminary biological study of glyconjugates of poly(styrene-co-maleic acid) Biomacromolecules 3, 805-812
36. Boztuǧ, A. and Basan, S. (2003) Synthesis and characterization of maleic anhydride-styrene-allyl propionate terpolymer ester derivatives J. Appl. Polym. Sci. 89, 296-299
37. Xi, F., Basset, Jr, W., and Vogl, O. (1983) Esters of alternating copolymers of maleic or 2,3-dimethylmaleic anhydride with alkyl vinyl ethers J. Polym. Sci., Part A: Polym. Chem. 21, 891-911
38. Chiellini, E. M., Leonardi, G., Giannasi, D., and Solaro, R. (1992) Partial esters of alternating copolymers of maleic anhydride and alkyl vinyl ethers for pharmaceutical applications J. Bioact. Compat. Polym. 7, 161-174
39. Zatz, J. L., Weiner, N. D., and Gibaldi, M. (1968) Monomolecular film properties of protective and enteric film formers I. Effect of polymer side chain on surface pressure-area isotherms J. Pharm. Sci. 57, 1440-1442
40. Zatz, J. L., Weiner, N. D., and Gibaldi, M. (1970) Orientation of monolayers of half-esters of poly(methyl vinyl ether maleic anhydride) J. Colloid Interface Sci. 33, 1-7
41. Finne, U., Kyyrönen, K., and Urtti, A. (1989) Drug release from monoisopropyl ester of poly(vinyl methyl ether-maleic anhydride) can be modified by basic salts in the polymer matrix J. Controlled Release 10, 189-194
42. Uglea, C. V., Panaitescu, L., Spridon, D., Ursu, D., Popa, I., and Ottenbrite, M. (1996) Biological activity of maleic anhydride copolymers. I. Biocompatibility and antitumoural effects of maleic anhydride-vinyl acetate, maleic anhydride-methyl methacrylate and maleic anhydride-styrene copolymers J. Biomater. Sci., Polym. Ed. 8, 269-280
43. Plochocka, K. (2001) Polymeric delivery and release systems for oral care actives (to ISP Investments Inc.), US Patent 6,315,987, Chem. Abstract 135, 362395.
44. Winnik, F. M. and Regismond, S. T. A. (1996) Fluorescence methods in the study of the interactions of surfactants with polymers Colloids Surf., A 118, 1-39
45. Vitenberg, A. G. (2003) Equilibrium model in the description of gas extraction and headspace analysis J. Anal. Chem. 58, 2-15
46. Snow, N. H. and Slack, G. C. (2002) Head-space analysis in modern gas chromatography Trends Anal. Chem. 21, 608-617
47. Penton, Z. E. (2002) Headspace gas chromatography Compr. Anal. Chem. 37, 279-296
48. Levrand, B., Fieber, W., Lehn, J.-M., and Herrmann, A. (2007) Controlled release of volatile aldehydes and ketones from dynamic mixtures generated by reversible hydrazone formation Helv. Chim. Acta 90, 2281-2314
49. Nyqvist, H. (1983) Saturated salt solutions for maintaining specified relative humidities Int. J. Pharm. Technol. Prod. Manuf. 4, 47-48
50. Davaran, S., Rashidi, M. R., and Hashemi, M. (2003) Synthesis and hydrolytic behaviour of 2-mercaptoethyl ibuprofenate-polyethylene glycol conjugate as a novel transdermal prodrug J. Pharm. Pharmacol. 55, 513-517
51. Burattini, S., Colquhoun, H. M., Greenland, B. W., Hayes, W., and Wade, M. (2009) Pyrene-functionalised, alternating copolymimide for sensing nitroaromatic compounds Macromol. Rapid Commun. 30, 459-463
52. Yamamoto, H., Mizusaki, M., Yoda, K., and Morishima, Y. (1998) Fluorescence studies of hydrophobic association of random copolymers of sodium 2-(acrylamido)-2-methylpropanesulfonate and N -dodecylmethacrylamide in water Macromolecules 31, 3588-3594
53. Zhu, L.-P., Yi, Z., Liu, F., Wei, X.-Z., Zhu, B.-K., and Xu, Y.-Y. (2008) Amphiphilic graft copolymers based on ultrahigh molecular weight poly(styrene-alt-maleic anhydride) with poly(ethylene glycol) side chains for surface modification of polyethersulfone membranes Eur. Polym. J. 44, 1907-1914
54. Mazi, H., Kibarer, G., Emregül, E., and Rzaev, Z. M. O. (2006) Bioengineering functional copolymers. IX. Poly[(maleic anhydride-co-hexene-1)- g -poly(ethylene glycol)] Macromol. Biosci. 6, 311-321
55. Ding, L. M., Shi, J., and Yang, C. Z. (1997) Ion-conducting polymers based on modified alternating maleic anhydride copolymer with oligo(oxyethylene) side chains Synth. Met. 87, 157-163 (Pubitemid 127438513)
56. 1 methyl esters with thiols J. Am. Chem. Soc. 119, 2376-2385
57. Ladavière, C., Delair, T., Domard, A., Pichot, C., and Mandrand, B. (1999) Studies of the thermal stability of maleic anhydride co-polymers in aqueous solution Polym. Degrad. Stab. 65, 231-241
58. Levinson, M. I. (1999) Rinse-added fabric softener technology at the close of the twentieth century J. Surfactants Deterg. 2, 223-235
59. Mishra, S. and Tyagi, V. K. (2007) Esterquats: the novel class of cationic fabric softeners J. Oleo Sci. 56, 269-276
60. Berg, J. C. (1985) The role of surfactants. Absorbency (Chatterjee, P. K., Ed.) pp 149 - 195, Elsevier, New York.
61. Laughlin, R. G. (1991) Fabric softening. Cationic Surfactants-Physical Chemistry, Surfactant Sci. Ser., Vol. 37 (Rubingh, D. N. and Holland, P. M., Eds.), pp 449 - 467, Dekker, New York.
62. Escher, S. and Oliveros, E. (1994) A quantitative study of factors that influence the substantivity of fragrance chemicals on laundered and dried fabrics J. Am. Oil Chem. Soc. 71, 31-40
63. Stora, T., Escher, S., and Morris, A. (2001) The physicochemical basis of perfume performance in consumer products Chimia 55, 406-412
64. Liu, H., Obendorf, S. K., Leonard, M. J., Young, T. J., and Incorvia, M. J. (2005) Adsorption of aroma chemicals on cotton fabric from aqueous systems J. Surfactants Deterg. 8, 311-317
65. Obendorf, S. K., Liu, H., Tan, K., Leonard, M. J., Young, T. J., and Incorvia, M. J. (2009) Adsorption of aroma chemicals on cotton fabric in different aqueous environments J. Surfactants Deterg. 12, 43-58
66. Schoenmakers, R. G., van de Wetering, P., Elbert, D. L., and Hubbell, J. A. (2004) The effect of the linker on the hydrolysis rate of drug-linked ester bonds J. Controlled Release 95, 291-300
67. Delben, F., Paoletti, S., Porasso, R. D., and Benegas, J. C. (2006) Potentiometric titrations of maleic acid copolymers in dilute aqueous solution: experimental results and theoretical interpretation Macromol. Chem. Phys. 207, 2299-2310
68. Berthier, D. and Herrmann, A. (2008) Polymer conjugates for a controlled release of active molecules (to Firmenich SA), WO 2008/044178, Chem. Abstract 148, 472574.