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PREPARATION OF NEW BIOCOMPATIBLE COMPOUNDS FROM FLUORINATED PRECURSORS |
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Staff: |
Vladimír Církva |
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External co-workers: |
Oldřich Paleta, Jaroslav Kvíčala (Institute of Chemical Technology (ICT) Prague, Department of organic chemistry); Jiří Michálek (Institute of Macromolecular Chemistry AS CR, Prague); Kamil Wichterle, Jana Wichterlová (VŠB-Technical University of Ostrava, FMME, Department of Chemistry) |
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Financing, funding: |
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What is the biocompatible compound?
It is compound with biological inertness which is compatible in contact with live matter.
What kind of fluorinated precursors we are using?
- perfluoroalkyl iodides, RFI (RF = C4F9, C6F13, C8F17)
- fluorinated olefins, CX2=CX-RF (X = F, H)
- fluorinated epoxides and diepoxides, (RF = C4F9, C6F13, C8F17; QF = C4F8, C6F12)
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Solved problems:
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Preparation of new biocompatible monomers for contact lenses
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Synthesis of new co-emulsifiers for fluorinated blood substitutes
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Study of effect of perfluoroalkylated chain on the physico-chemical properties of bio-compounds
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Publications:
[1] Paleta, O.; Církva, V.; Kvíčala, J.: Macromol. Symp. 82 (1994) 111-114. Photoaddition reactions of fluoroolefins with diols and cyclic ethers.
[2] Církva, V.; Ameduri, B.; Boutevin, B.; Kvíčala, J.; Paleta, O.: J. Fluorine Chem. 74 (1995) 97-105. Radical-induced reaction of monoiodo-perfluoroalkanes and diiodo-perfluoroalkanes with allyl acetate-telomer and rearranged products, mass-spectral distinguishing of regioisomers.
[3] Církva, V.; Paleta, O.; Ameduri, B.; Boutevin, B.: J. Fluorine Chem. 75 (1995) 87-92. Radical additions to fluoroolefins. Thermal reaction of perfluoroallyl chloride with perfluoroalkyl iodides as a selective synthesis of terminal perfluoroolefins.
[4] Paleta, O.; Církva, V.; Kvíčala, J.: J. Fluorine Chem. 80 (1996) 125-134. Radical additions to fluoro-olefins. Photochemical mono-fluoroalkylation and sequential bis-fluoro-alkylation of oxolane.
[5]
Církva, V.; Polák, R.; Paleta, O.:
J. Fluorine Chem.
80 (1996) 135-144.
Radical additions to fluoro-olefins. Photochemical
fluoroalkylation of alkanols and alkane diols with perfluoro vinyl
ethers; Photo-supported O-alkylation of butane-1,4-diol with
hexafluoropropene.
[6] Církva, V.; Ameduri, B.; Boutevin, B.; Paleta, O.:
J. Fluorine Chem.
83 (1997) 151-158.
Highly selective synthesis of
[(perfluoroalkyl)methyl]oxiranes (by the addition of
iodoperfluoroalkanes to allyl acetate).
[7] Církva, V.; Ameduri, B.; Boutevin,
B.; Paleta, O.: J.
Fluorine Chem. 84 (1997) 53-61.
Chemistry of [(perfluoroalkyl)methyl]
oxiranes. Regioselectivity of ring opening with O-nucleophiles and the
preparation of amphiphilic monomers.
[8] Paleta, O.; Církva, V.; Budková, Z.; Böhm, S.:
J. Fluorine Chem.
86 (1997) 155-171.
Radical addition reactions of fluorinated species - Part
6. Regioselectivity of the addition of nucleophilic radicals to
halogenopropenes and evidence for a steric effect of the chlorine
substituent.
[9] Paleta, O.; Církva, V.; Kvíčala, J.:
Czech Rep. 1997, 7
pp. CZ 282756 B6, Application: CZ 9301427, 19930716.
[CAN 131: 44830]. Způsob přípravy fluoralkylderivátů cyklických etherů.
(Process for preparing fluoroalkyl derivatives of cyclic ethers).
[10] Církva,V: Fluoroalkylderivatives of hydroxycompounds and ethers. Ph.D. Thesis. Praha: VŠCHT, ÚOCH, 1997. 145 p.
[11] Církva, V.; Paleta, O.:
J. Fluorine Chem. 94 (1999) 141-156.
Radical addition reactions of fluorinated species. Part
7. Highly selective two-step synthesis of
1-(polyfluoroalkyl)ethane-1,2-diols; regioselectivity of the additions
of methylated 1,3-dioxolanes to perfluoroolefins.
[12] Církva, V.; Hájek, M.:
J. Photochem.
Photobiol. A 123 (1999) 21-23.
Microwave photochemistry. Photoinitiated radical addition of
tetrahydrofuran to perfluorohexylethene under microwave irradiation.
[13] Církva, V.; Gaboyard, M.; Paleta,
O.:
J. Fluorine Chem.
102 (2000) 349-361.
Fluorinated epoxides 5. Highly selective
synthesis of diepoxides from α,ω-diiodoperfluoroalkanes.
Regioselectivity of nucleophilic epoxide-ring opening and new
amphiphilic compounds and monomers.
[14] Církva, V.; Böhm, S.; Paleta, O.:
J. Fluorine Chem.
102 (2000) 159-168. Radical
addition reactions of fluorinated species. Part 8. Regioselectivity of
radical additions to perfluoroalkylethylenes and quantum chemical
calculations. Highly selective two-step synthesis of
4-(perfluoroalkyl)butane-1,2-diols.
[15] Církva, V.: Chem. Listy 94 (2000) 1031. Od radikálových a fotochemických reakcí k biokompatibilním látkám. (From radical and photochemical reactions to biocompatible compounds)
[16] Církva, V.; Kaplánek, R.; Paleta, O.; Kodíček, K.: Collect. Czech. Chem. Commun. 67 (2002) 1436-1448. Amphiphilic perfluoroalkylated derivatives of aliphatic triols: Hemocompatibility and effect on perfluorocarbon emulsion.
[17] Církva, V.; Duchek, J.; Paleta, O.: J. Fluorine Chem. 121 (2003) 101-104. Fluorinated epoxides: 6. Chemoselectivity in the preparation of 2-[(heptafluoroisopropyl)methyl]-oxirane from iodoacetate and iodohydrin precursors.
[18] Církva, V.; Polák, R.; Paleta, O.; Kefurt, K.; Moravcová, J.; Kodíček, M.; Forman, S.: Carbohydr. Res. 339 (2004) 2177-2185. Novel perfluoroalkylated derivatives of D-galacto-pyranose and xylitol for biomedical uses. Hemocompatibility and effect on perfluorocarbon emulsions.
[19] Paleta, O.; Církva, V.; Kodíček, M.; Michálek, J.: Chem. Listy 98 (2004) 1046-1047. Přenašeče kyslíku a příbuzné medicinální aplikace. (Oxygen carriers and related medical applications).
[20] Církva, V.; Duchek, J.; Kaplánek, R.; Paleta, O.; Michálek, J.; Přádný, M.; Chmelíková, D.; Wichterlová, J.: Eur. J. Med. Chem. (2006) in print. New perfluoroalkylated amphiphilic methacrylates bearing sulfinyl group as monomers for biomedical applications: water content and oxygen permeability of their copolymers with DEGMA.
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