Preparation of photoreactive 12-[(4-azidosalicyl)amino] dodecanoic acid acylated derivatives of gangliosides radioioiodinated to high specific radioactivity

Abstract

We describe the preparation of 125I labeled 12[(4‐azidosalicyl)amino]dodecanoic acid (ASD) acylated derivatives of GM3, GD3, GM1 and SPG gangliosides. Gangliosides isolated from natural sources were deacylated, reacylated with ASD and radioiodinated with 125I and chloramine T as an oxidant. During purification by HPLC each radioiodinated ganglioside derivative emerged from the column as two peaks differing in the substitution of 4‐azidosalicylic acid residue. Radioiodinated gangliosides‐ASD were of over 95% purity and about 2200 Ci/mmole specific activity. They were used for photolabeling of erythrocyte membrane proteins. Copyright © 2000 John Wiley & Sons, Ltd.

Untitled

“…The labelling with iodine-125 of pindol, 132 a-methyl-L-tyrosine, 133 lanreotide 134 and ganglioside derivatives 135 has been reported. The standard Chloramine-T or iodogen procedure was used in all cases.…”

“…A mixture of isotopes also results from the bombardment of antimony oxide with 78 MeV 16 O 6+ ions. First 133 & 135 Pr are formed 35 but these rapidly decay to 133 Ce (t 1/2 = 4.9 h) and 135 Ce (t 1/2 = 17.7 h). If 90 MeV 19 F 7+ ions are used neodymium isotopes are first formed which decay via praseodymium to [135][136][137][138] Ce.…”

“…First 133 & 135 Pr are formed 35 but these rapidly decay to 133 Ce (t 1/2 = 4.9 h) and 135 Ce (t 1/2 = 17.7 h). If 90 MeV 19 F 7+ ions are used neodymium isotopes are first formed which decay via praseodymium to [135][136][137][138] Ce. Cerium-135 can also be made 35 by irradiating caesium (nitrate) with a beam of 44 MeV 7 Li 3+ ions.…”

Untitled

“…The labelling with iodine-125 of pindol, 132 a-methyl-L-tyrosine, 133 lanreotide 134 and ganglioside derivatives 135 has been reported. The standard Chloramine-T or iodogen procedure was used in all cases.…”

“…A mixture of isotopes also results from the bombardment of antimony oxide with 78 MeV 16 O 6+ ions. First 133 & 135 Pr are formed 35 but these rapidly decay to 133 Ce (t 1/2 = 4.9 h) and 135 Ce (t 1/2 = 17.7 h). If 90 MeV 19 F 7+ ions are used neodymium isotopes are first formed which decay via praseodymium to [135][136][137][138] Ce.…”

“…First 133 & 135 Pr are formed 35 but these rapidly decay to 133 Ce (t 1/2 = 4.9 h) and 135 Ce (t 1/2 = 17.7 h). If 90 MeV 19 F 7+ ions are used neodymium isotopes are first formed which decay via praseodymium to [135][136][137][138] Ce. Cerium-135 can also be made 35 by irradiating caesium (nitrate) with a beam of 44 MeV 7 Li 3+ ions.…”

Enhanced transient recombinant protein production in CHO cells through the co‐transfection of the product gene with Bcl‐xL

“…This work builds on the group's previous studies of the synthesis of GM1 derivatives bearing Dcp groups;83 the use of the 125 I‐Dcp photoactive group has subsequently been extended to the synthesis of photoaffinity neoglycoconjugates containing the oligosaccharides SLe X and Le A trisaccharide 84. Other gangliosides, such as 125 I‐labelled 12[(4‐azidosalicyl)amino]dodecanoic acid acylated derivatives of GM3, GD3 and GM1 gangliosides such as 38 and sialyl paragloboside (SPG) have also been prepared by Pacuszka and Panasiewicz and used for the photolabelling of erythrocyte membrane proteins,85 whereas Hatanaka and Yasumaru prepared biotinylated diazirinyl ceramide GM1 derivative 39 86 and determined that it was a substrate for Pseudomonas sp. sphingolipid ceramide N ‐deacylase.…”

Regioselective iodination of chlorinated aromatic compounds using silver salts

“…thyroid hormone) and a synthetic intermediate for a variety of fine chemistry products (e.g. isovanillyl sweeteners 1 ), radiopharmaceuticals, 2 environmental contaminants 3,4 and numerous bioactive compounds, such as camptothecin, 5 cephalosporin derivatives, 6 dehydrotubifoline, 7 morphine, 8 sangliferine A, 9 ecteinascidine, 10 and berkelic acid methyl ester. 11 One example of a prescription drug synthesized from an iodoarene intermediate is galanthamine, an acetylcholinesterase inhibitor for the symptomatic treatment of senile dementia of Alzheimer patients.…”

Untitled

“…The labelling with iodine-125 of pindol, 132 a-methyl-L-tyrosine, 133 lanreotide 134 and ganglioside derivatives 135 has been reported. The standard Chloramine-T or iodogen procedure was used in all cases.…”

“…A mixture of isotopes also results from the bombardment of antimony oxide with 78 MeV 16 O 6+ ions. First 133 & 135 Pr are formed 35 but these rapidly decay to 133 Ce (t 1/2 = 4.9 h) and 135 Ce (t 1/2 = 17.7 h). If 90 MeV 19 F 7+ ions are used neodymium isotopes are first formed which decay via praseodymium to [135][136][137][138] Ce.…”

“…First 133 & 135 Pr are formed 35 but these rapidly decay to 133 Ce (t 1/2 = 4.9 h) and 135 Ce (t 1/2 = 17.7 h). If 90 MeV 19 F 7+ ions are used neodymium isotopes are first formed which decay via praseodymium to [135][136][137][138] Ce. Cerium-135 can also be made 35 by irradiating caesium (nitrate) with a beam of 44 MeV 7 Li 3+ ions.…”

Enhanced transient recombinant protein production in CHO cells through the co‐transfection of the product gene with Bcl‐xL

“…This work builds on the group's previous studies of the synthesis of GM1 derivatives bearing Dcp groups;83 the use of the 125 I‐Dcp photoactive group has subsequently been extended to the synthesis of photoaffinity neoglycoconjugates containing the oligosaccharides SLe X and Le A trisaccharide 84. Other gangliosides, such as 125 I‐labelled 12[(4‐azidosalicyl)amino]dodecanoic acid acylated derivatives of GM3, GD3 and GM1 gangliosides such as 38 and sialyl paragloboside (SPG) have also been prepared by Pacuszka and Panasiewicz and used for the photolabelling of erythrocyte membrane proteins,85 whereas Hatanaka and Yasumaru prepared biotinylated diazirinyl ceramide GM1 derivative 39 86 and determined that it was a substrate for Pseudomonas sp. sphingolipid ceramide N ‐deacylase.…”

Regioselective iodination of chlorinated aromatic compounds using silver salts

“…thyroid hormone) and a synthetic intermediate for a variety of fine chemistry products (e.g. isovanillyl sweeteners 1 ), radiopharmaceuticals, 2 environmental contaminants 3,4 and numerous bioactive compounds, such as camptothecin, 5 cephalosporin derivatives, 6 dehydrotubifoline, 7 morphine, 8 sangliferine A, 9 ecteinascidine, 10 and berkelic acid methyl ester. 11 One example of a prescription drug synthesized from an iodoarene intermediate is galanthamine, an acetylcholinesterase inhibitor for the symptomatic treatment of senile dementia of Alzheimer patients.…”

Untitled

“…The labelling with iodine-125 of pindol, 132 a-methyl-L-tyrosine, 133 lanreotide 134 and ganglioside derivatives 135 has been reported. The standard Chloramine-T or iodogen procedure was used in all cases.…”

“…A mixture of isotopes also results from the bombardment of antimony oxide with 78 MeV 16 O 6+ ions. First 133 & 135 Pr are formed 35 but these rapidly decay to 133 Ce (t 1/2 = 4.9 h) and 135 Ce (t 1/2 = 17.7 h). If 90 MeV 19 F 7+ ions are used neodymium isotopes are first formed which decay via praseodymium to [135][136][137][138] Ce.…”

“…First 133 & 135 Pr are formed 35 but these rapidly decay to 133 Ce (t 1/2 = 4.9 h) and 135 Ce (t 1/2 = 17.7 h). If 90 MeV 19 F 7+ ions are used neodymium isotopes are first formed which decay via praseodymium to [135][136][137][138] Ce. Cerium-135 can also be made 35 by irradiating caesium (nitrate) with a beam of 44 MeV 7 Li 3+ ions.…”

Enhanced transient recombinant protein production in CHO cells through the co‐transfection of the product gene with Bcl‐xL

“…This work builds on the group's previous studies of the synthesis of GM1 derivatives bearing Dcp groups;83 the use of the 125 I‐Dcp photoactive group has subsequently been extended to the synthesis of photoaffinity neoglycoconjugates containing the oligosaccharides SLe X and Le A trisaccharide 84. Other gangliosides, such as 125 I‐labelled 12[(4‐azidosalicyl)amino]dodecanoic acid acylated derivatives of GM3, GD3 and GM1 gangliosides such as 38 and sialyl paragloboside (SPG) have also been prepared by Pacuszka and Panasiewicz and used for the photolabelling of erythrocyte membrane proteins,85 whereas Hatanaka and Yasumaru prepared biotinylated diazirinyl ceramide GM1 derivative 39 86 and determined that it was a substrate for Pseudomonas sp. sphingolipid ceramide N ‐deacylase.…”

Regioselective iodination of chlorinated aromatic compounds using silver salts

“…thyroid hormone) and a synthetic intermediate for a variety of fine chemistry products (e.g. isovanillyl sweeteners 1 ), radiopharmaceuticals, 2 environmental contaminants 3,4 and numerous bioactive compounds, such as camptothecin, 5 cephalosporin derivatives, 6 dehydrotubifoline, 7 morphine, 8 sangliferine A, 9 ecteinascidine, 10 and berkelic acid methyl ester. 11 One example of a prescription drug synthesized from an iodoarene intermediate is galanthamine, an acetylcholinesterase inhibitor for the symptomatic treatment of senile dementia of Alzheimer patients.…”