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Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains

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Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains. / Xu, Jianfeng; Yang, Zhenjun; Dammermann, Werner; Zhang, Liangren; Guse, Andreas H; Zhang, Li-He.

In: J MED CHEM, Vol. 49, No. 18, 07.09.2006, p. 5501-12.

Research output: SCORING: Contribution to journal › SCORING: Journal article › Research › peer-review

Harvard

Xu, J, Yang, Z, Dammermann, W, Zhang, L, Guse, AH & Zhang, L-H 2006, 'Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains', J MED CHEM, vol. 49, no. 18, pp. 5501-12. https://doi.org/10.1021/jm060320e

APA

Xu, J., Yang, Z., Dammermann, W., Zhang, L., Guse, A. H., & Zhang, L-H. (2006). Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains. J MED CHEM, 49(18), 5501-12. https://doi.org/10.1021/jm060320e

Vancouver

Xu J, Yang Z, Dammermann W, Zhang L, Guse AH, Zhang L-H. Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains. J MED CHEM. 2006 Sep 7;49(18):5501-12. https://doi.org/10.1021/jm060320e

Bibtex

@article{7183db58fc124f87ab60f0f62684ac11,
title = "Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains",
abstract = "Novel analogues of cADPR with adenine as base and ether (10a) or different alkane chain (10b-d) substitutions of the northern ribose were synthesized from protected imidazole nucleoside 1 in good yields. The pharmacological activities of cyclic inosine diphosphoribose ether (cIDPRE) and the compounds (10a-d) were analyzed in intact human Jurkat T-lymphocytes. The results indicate that the analogues 10a-d permeate the plasma membrane and are weak agonists of the cADPR/ryanodine receptor signaling system in intact human Jurkat T cells. They are the first membrane-permeant and biologically active cADPR analogues that contain ether or alkane bridges instead of the northern ribose and retain adenine as its base.",
keywords = "Adenine, Alkanes, Calcium, Cell Membrane Permeability, Cyclic ADP-Ribose, Ethers, Humans, Jurkat Cells, Receptors, Cell Surface, Ryanodine Receptor Calcium Release Channel, Structure-Activity Relationship",
author = "Jianfeng Xu and Zhenjun Yang and Werner Dammermann and Liangren Zhang and Guse, {Andreas H} and Li-He Zhang",
year = "2006",
month = sep,
day = "7",
doi = "10.1021/jm060320e",
language = "English",
volume = "49",
pages = "5501--12",
journal = "J MED CHEM",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "18",

}

RIS

TY - JOUR

T1 - Synthesis and agonist activity of cyclic ADP-ribose analogues with substitution of the northern ribose by ether or alkane chains

AU - Xu, Jianfeng

AU - Yang, Zhenjun

AU - Dammermann, Werner

AU - Zhang, Liangren

AU - Guse, Andreas H

AU - Zhang, Li-He

PY - 2006/9/7

Y1 - 2006/9/7

N2 - Novel analogues of cADPR with adenine as base and ether (10a) or different alkane chain (10b-d) substitutions of the northern ribose were synthesized from protected imidazole nucleoside 1 in good yields. The pharmacological activities of cyclic inosine diphosphoribose ether (cIDPRE) and the compounds (10a-d) were analyzed in intact human Jurkat T-lymphocytes. The results indicate that the analogues 10a-d permeate the plasma membrane and are weak agonists of the cADPR/ryanodine receptor signaling system in intact human Jurkat T cells. They are the first membrane-permeant and biologically active cADPR analogues that contain ether or alkane bridges instead of the northern ribose and retain adenine as its base.

AB - Novel analogues of cADPR with adenine as base and ether (10a) or different alkane chain (10b-d) substitutions of the northern ribose were synthesized from protected imidazole nucleoside 1 in good yields. The pharmacological activities of cyclic inosine diphosphoribose ether (cIDPRE) and the compounds (10a-d) were analyzed in intact human Jurkat T-lymphocytes. The results indicate that the analogues 10a-d permeate the plasma membrane and are weak agonists of the cADPR/ryanodine receptor signaling system in intact human Jurkat T cells. They are the first membrane-permeant and biologically active cADPR analogues that contain ether or alkane bridges instead of the northern ribose and retain adenine as its base.

KW - Adenine

KW - Alkanes

KW - Calcium

KW - Cell Membrane Permeability

KW - Cyclic ADP-Ribose

KW - Ethers

KW - Humans

KW - Jurkat Cells

KW - Receptors, Cell Surface

KW - Ryanodine Receptor Calcium Release Channel

KW - Structure-Activity Relationship

U2 - 10.1021/jm060320e

DO - 10.1021/jm060320e

M3 - SCORING: Journal article

C2 - 16942023

VL - 49

SP - 5501

EP - 5512

JO - J MED CHEM

JF - J MED CHEM

SN - 0022-2623

IS - 18

ER -