n-alkyl-glucosides as detergents for the preparation of highly homogeneous bilayer liposomes of variable sizes (60–240 nm φ) applying defined rates of detergent removal by dialysis

Schwendener, R.A.; Asanger, M.; Weder, H. G.

doi:10.1016/0006-291x(81)91930-6

Cited by 81 publications

(35 citation statements)

References 12 publications

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“…The assignment of an a or /3 configuration to compounds 1-10 was straightforward. All these molecules adopted essentially the 4C 1 conformation, thus allowing an easy distinction between the /3 (J1,2 [7][8] and the a anomers (J1, [2][3][4].…”

Section: Resultsmentioning

confidence: 99%

“…All hyperfine coupling constants were checked by simulating the corresponding EPR spectra using a PC program developed in this laboratory [22]. Allyl 2,3,4,.--To a suspension of D-glucose (2 g, 11 mmol) in anhydrous allyl alcohol (40 mL) was added BF 3 etherate (0.2 mL, 1.63 mmol), and the mixture was heated under reflux for 2 h. The clear solution was cooled, concentrated to a syrup, then, to remove some minor impurities, submitted to column chromatography (9:1 CH2C12-MeOH) which yielded 1.7 g (69.5%) of an 8:1 a/[3 syrupy mixture. This mixture was peracetylated with AC20 (20 mL) in pyridine (50 mL).…”

Section: Methodsmentioning

confidence: 99%

“…After the usual work-up, the residue was subjected to column chromatography (3:2 hexane-acetone) to give a-5 (0.19 g, 79%) as a syrup; Rf 0.11 (3:2 hexane-acetone); [a] 2,3, 4,6-tetra-O-acetyl-fl-o-glucopyranoside (/3-5).-- -7-(cholest-5-en-3 fl-yloxy)hept-3-enyl 2,3, 4,6-tetra-O-acetyl-a-D-glucopyranoside N-oxide (a-7).--To a solution of or-5 (0.6 g, 1.47 mmol) in CHEC12 (20 mL) was added 6 (0.8 g, 1.75 mmol), and the mixture was stirred 2 h at room temperature. The concentrated mixture was then subjected to column chromatography to give oe-7 (0.85 g, 68%); Rf 0.13 ( , 1 H, H-2), 4.33-3.68 (ms, 7 H, H-6a,b, H-5, H-l'a,b, H-7'a,b), 3.50 (dt, 2 H, H-2'a,b), 3.13 (tt,1 H,JCholZa,3 =ffCholaa,[3][4][5][6][7][8][9][10][11] Hz,ffChol2b,3 ~" JCholab,3 = 4.5 HZ, H-3 chol), 2.66-0.54 (m, chol skeleton), 2.57 (q, 2 H, H-5'a,b), 2.08, 2.06, 2.03, and 2.00 (4 s,each 3 H,40Ac). ELMS: m/z (%) 829 (1, M'+), 770 (2.5), 531 (4.5), 462 (20,386 (40,Ochol),368 (90),353 (38),247 (40),213 (38),169 (82),145 (76),115 (80),95 (78), and 55 (72).…”

Section: -( N-acetoxyacetamido)ethyl 23 46-tetra-o-acetyl-a-d-glumentioning

confidence: 99%

“…Found: C,66.44;H,8.88; N, 1.66. 3,4,.--Treatment of fl-5 and 6 as described for the preparation of or-7 gave /3-7 (64%) as a white foam; R I 0.09 ; [a] 25 -26.1 ° (c 0.77, CHCI3); ,Emt aCxn 233 nm (E 8472); /.' mahtlx r 2936 (CH), 2867 (CH), and 1757 cm -1 (C=O).…”

Section: -( N-acetoxyacetamido)ethyl 23 46-tetra-o-acetyl-a-d-glumentioning

confidence: 99%

“…Artificial glycolipids exhibit a large spectrum of useful properties: liquid crystals [1], specific detergents [2,3], immunomodulators [4], recognition markers for targeting drug delivery systems [5], or antiviral agents [6,7]. In most of these applications, the usefulness of neoglycolipids should be further increased by spin-labelling which would allow the monitoring of the interaction of these compounds with neighbouring molecules.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Spin-labelled glycolipid analogues: d-glucose series

Tronchet

Zsely

Geoffroy

1995

Carbohydrate Research

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Neoglycolipids bearing a paramagnetic probe in their lipophilic aglycon have been prepared. All belong to the D-glucose series, both anomers for the glucoside representatives, respectively /3 and t~ anomers in the S-and C-glucosyl series. Two different types of radical sites have been used, a relatively short-lived imino N-oxyl group for glucosides and a more stable N-acylamino N-oxyl moiety in the other cases. EPR spectra of these radical species afforded information on the conformation of the lipophilic chain in the vicinity of the paramagnetic probe.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: -( N-acetoxyacetamido)ethyl 23 46-tetra-o-acetyl-a-d-glumentioning

confidence: 99%

Section: -( N-acetoxyacetamido)ethyl 23 46-tetra-o-acetyl-a-d-glumentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Spin-labelled glycolipid analogues: d-glucose series

Tronchet

Zsely

Geoffroy

1995

Carbohydrate Research

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Liposomes: Preparation, Characterization, and Preservation

Lichtenberg

Barenholz

1988

Methods of Biochemical Analysis

240

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Discrepancy in the abilities of lymphokines and bacteria to mediate tumor protection in vivo and/or tumoricidal activity by macrophages in vitro

Keller

Keist

Schwendener

1989

Intl Journal of Cancer

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In the present study, the ability of lymphokines (MAF and IFN gamma) and microbial agents (CP and LM) to induce and maintain tumoricidal activity in BMMP in vitro and to enhance local resistance to the DA rat D-12 ascites tumor in vivo was assessed comparatively. Under standard conditions in vitro, i.e., when present during the 24-hr induction and the 36-hr effector phase, both lymphokines and microbes were similarly potent for eliciting tumoricidal activity in BMMP. When the activating agents were present only during the induction phase, and effector cells were interacted with tumor targets after a 24-hr interval, clear differences were observed: BMMP which had been incubated with lymphokines had largely if not completely lost their tumoricidal activity; in contrast, BMMP which had been incubated with microbes still manifested considerable tumoricidal activity. Experiments performed to assess the in vivo significance of the discrepancy established in vitro have shown that resistance to the D-12 ascites tumor was markedly enhanced after local inoculation of microbes but was affected very little or not at all by soluble lymphokines. The causes responsible for the discrepancy in the antitumor potential of lymphokines vs. microbes are probably manifold. Extensive attempts to improve the efficacy of lymphokines by repeated administration or by incorporation into liposomes were not successful.

show abstract

n-alkyl-glucosides as detergents for the preparation of highly homogeneous bilayer liposomes of variable sizes (60–240 nm φ) applying defined rates of detergent removal by dialysis

Cited by 81 publications

References 12 publications

Spin-labelled glycolipid analogues: d-glucose series

Spin-labelled glycolipid analogues: d-glucose series

Liposomes: Preparation, Characterization, and Preservation

Discrepancy in the abilities of lymphokines and bacteria to mediate tumor protection in vivo and/or tumoricidal activity by macrophages in vitro

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