Pharmakologisch aktive polymere, 4. Monomere und polymere alkylsulfinyl‐alkylacrylate und ‐methacrylate als mögliche resorptionsvermittler

Batz, Hans‐Georg; Hofmann, Volker; Ringsdorf, Helmut

doi:10.1002/macp.1973.021690129

Cited by 42 publications

(13 citation statements)

References 7 publications

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“…The knowledge of the oxidized products is also important: sulfoxide‐containing polymers were initially studied by the group of Ringsdorf in the 1970s with very promising results in terms of extremely low in vivo toxicity 41, 42. On the other hand, low‐molecular‐weight depolymerization products and/or sulfone‐containing substrates may be considerably more toxic.…”

Section: Introductionmentioning

confidence: 99%

Oxidant‐Dependent REDOX Responsiveness of Polysulfides

Carampin

Lallana

Laliturai

et al. 2012

Macro Chemistry & Physics

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Poly(propylene sulfide) (PPS) is studied as an oxidation‐responsive macromolecular building block, in the perspective of anti‐inflammatory therapies. Here, we show that the nature of the oxidant has profound effects on the outcome of the oxidation process. PPS was exposed to hydrogen peroxide (H2O2) and hypochlorite (OCl−), which are oxidizing species commonly encountered during inflammatory processes. It was found that the oxidation with H2O2 converted thioethers into sulfoxides, producing water‐soluble macromolecular products with extremely low toxicity (L929 fibroblasts); on the contrary, the reaction with NaOCl produced sulfones in addition to sulfoxides, and this was accompanied by depolymerization, which appears to considerably affect the toxicity of the oxidation products.

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Section: Introductionmentioning

confidence: 99%

Oxidant‐Dependent REDOX Responsiveness of Polysulfides

Carampin

Lallana

Laliturai

et al. 2012

Macro Chemistry & Physics

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“…The comonomer units introduced to render the resulting polymer water soluble must satisfy some fundamental requirements, e.g., lack of toxicity and immunogenicity. For polyvinyl derivatives such nontoxic, water-solubilizing units have generally been introduced via vinylpyrrolidone [8], P-hydroxyethyl acrylates and acrylamides [ 181, vinylpyridine-N-oxides [ 191, and sulfoxide-containing acrylates [20]. Because of their pronounced lack of acute toxicity we have been especially interested in polymeric systems containing sulfoxide and N-oxide units [21].…”

Section: Discussion Of the Model For Pharmacologically Active Polymersmentioning

confidence: 99%

“…Transport systems which can act, according to Figure 11, as nonspecific resorption enhancers by inducing variation in the normal body distribution of polymers can be expected of surface-, membrane-and skinactive systems, e.g., sulfoxides and formamides. Based on studies of dimethyl sulfoxide as a carrier for drugs through the skin and various membranes [54], a series of sulfoxide-containing polymers was prepared [20,211 and their ability to enhance the uptake of certain drugs through the skin was successfully checked [21, 551. The body distribution of these water-soluble and very nontoxic polymers after i.v.…”

Section: N H -C H~mentioning

confidence: 99%

Structure and properties of pharmacologically active polymers

Ringsdorf

1975

J. polym. sci., C Polym. symp.

1,004

548

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SYNOPSISAlthough the concept of using pharmacologically active macromolecular compounds as drugs is still regarded with much skepticism for both theoretical and practical reasons, interest in this field has grown in recent years because of the opportunity to take advantage of the specific properties of polymeric materials. For low molecular weight drugs, changes in structure often lead to a loss of specific activity. On the other hand, the properties of macromolecular drugs depend on the structure of the polymer used and this can be varied over a wide range by the incorporation of comonomer units, by the application of polymer-analogous reactions, or by related structural changes. A new model is presented for pharmacologically active polymers which incorporates the possibility for continuous variation in ( a ) solubility and toxicity, ( b ) fixation and removal of active material, and (c) body distribution. Using the new model as a guide, examples of the synthesis and study of the biological activity of various macromolecular drugs are presented in order to emphasize the importance of this cooperative effort between polymer research and therapeutic problems. 135

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“…4 (268)(269)(270). Poly(sulfinyl acrylate)s exhibit some biological activity (271,272). Membranes bearing sulfoxide moieties are permeable, particularly to polar compounds (273,274).…”

Section: Polysulfoxidesmentioning

confidence: 99%

“…Polysulfoxides with sulfoxide group in the side chain are obtained by polymerization of monomers containing a sulfoxide group linked to the unsaturated carbon-carbon bond via aromatic or aliphatic units (107) (268,269,271,272,277). They are also synthesized by a Michael-type addition of dithiols to diolefins with a double bond activated by an adjacent sulfoxide group (274,278).…”

Section: Polysulfoxidesmentioning

confidence: 99%

Sulfur‐Containing Polymers

Kultys¹

2001

Encyclopedia of Polymer Science and Technology

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Vol. 4 SULFUR-CONTAINING POLYMERS 337Nevertheless, the only commercial poly(monosulfide) is Ryton [Philips Petroleum Co., poly(thio-1,4-phenylene) more frequently referred to as poly(p-phenylene sulfide) or poly(phenylene sulfide) (PPS)]. Much effort has been devoted to preparing aromatic compounds in view of their significance as reactive intermediates for the synthesis of high performance linear aromatic polymers by ring-opening polymerization (ROP) (5). In an attempt to develop a novel synthetic method for the preparation of high molecular weight poly(thioarylene)s, macrocyclic aromatic sulfides and disulfides have been intensively prepared (6-14). The coordination chemistry of macrocyclic polysulfides has also received considerable attention during the past years. The thiacrown ether polymer ligands can be used as ion-exchange resins, metal ion adsorbents, and polymeric phase-transfer catalysts (15,16). Molecular systems in which tetrathiafulvalene is incorporated into macrocycles with supplementary donor atoms are potential electroactive cation sensors (17). The π -conjugated polymers have been extensively studied because of their attractive electronic properties. SULFUR-CONTAINING POLYMERSVol. 4The novel partially crystalline polymer (3) with number-average molecular weight (M n ) of up to 5700 was prepared under various conditions by catalyzed self-condensation of 3-hydroxypropyl methoxycarbonylethyl sulfide (4) or 3-hydroxypropyl carboxyethyl sulfide (5) (22). The degree of crystallinity, melting temperature (T m ), T g , and temperature of initial decomposition (T d ) were 36-46%, 37-47 • C, −61 to −70 • C, and 164-260 • C, respectively. The monomers (4) and (5) were prepared by an addition of methyl 3-mercaptopropionate and 3-mercaptopropionic acid with allyl alcohol [107-18-6] catalyzed by AIBN [2,2 -azobis(2-methylpropionitrile), azobisisobutyronitrile, azodiisobutyrodinitrile, 2,2 -azobis(2-methylpropanenitrile), α,α -azodiisobutyronitrile, 2,2 -azobis(isobutyronitrile), 2,2 -dicyano-2,2 -azopropane, Porofor-57, 2,2 -dimethyl-2,2azodipropionitrile, 2,2(-azobis(2-methylpropionitrile))] [78-67-1].An addition of conjugate 1,4-benzenedithiol (A) to 1,4-divinylbenzene (1,4diethenylbenzene, p-divinylbenzene) (B) [105-06-6] was investigated in detail in the presence of the AIBN initiator in toluene at 75 • C (23). It was found that the polymerization proceeded without an induction period, to give a white polymer with a high molecular weight [weight-average molecular weight (M w ) = 110,000] in ∼90% yield for 2 h. In addition, it was confirmed by 1 H nmr, ir, and the sulfur contents that the polymer had an alternating structure of A and B units.The synthesis and radical addition behavior of optically active cysteinebased monomers with mercapto and olefin groups have also been studied (24). N-4-vinylbenzoyl-L-cysteine methyl ester polymerized satisfactorily to afford the corresponding polysulfide (with M n in the range of 7000-23,000) in good yields.A novel one-pot synthesis of sulfur-containing polymers incl...

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Pharmakologisch aktive polymere, 4. Monomere und polymere alkylsulfinyl‐alkylacrylate und ‐methacrylate als mögliche resorptionsvermittler

Cited by 42 publications

References 7 publications

Oxidant‐Dependent REDOX Responsiveness of Polysulfides

Oxidant‐Dependent REDOX Responsiveness of Polysulfides

Structure and properties of pharmacologically active polymers

Sulfur‐Containing Polymers

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