Synthesis and anti-shock activity of divalent β-D-galactopyranosyl-(1→4)-β-D-glucopyranosides

Abstract

Abstract: Three divalent β-D-galactopyranosyl-(1→ 4)-β-D-glucopyranosides were synthesized using acetylated lactosyl bromide as donor and polyethylene glycols with different polymeric degree (n = 4, 5, 6) as linker, and evaluated for in vivo inhibitory activity to leukocyte-endothelial cell adhesion on severe burn-shock rats. The result showed that the length of linkers had apparent influence on anti cell adhesion activity.

Key words: Divalent lactosides, Divalent lactosides, Leukocyte-endothelial cell, Leukocyte-endothelial cell, Anti-shock, Anti-shock

CLC Number:

R916

Supporting:

Wan Zhang, Qing Li, Xiang-Bao Meng, Zhi-Hui Zhao, Zhong-Jun Li^*. Synthesis and anti-shock activity of divalent β-D-galactopyranosyl-(1→4)-β-D-glucopyranosides[J]. .

References

[1] Nakae H, Endo S, Yamada Y, et al. Bound and soluble adhesion molecule and cytokine levels in patients with severe burns [J]. Burns, 2000, 26: 139–144.
[2] Pu FR, Williams RL, Markkula TK, et al. Expression of leukocyte-endothelial cell adhesion molecules on monocyte adhesion to human endothelial cells on plasma treated PET and PTFE in vitro [J]. Biomaterials, 2002, 23: 4705–7418.
[3] Gahmberg CG, Tolvanen M, Kotovuori P. Leukocyte adhesion structure and function of human leukocyte β2- integrins and their cellular ligands [J]. Eur J Biochem, 1997, 245: 215–232.
[4] Tees David FJ, Waugh RE, Hammer DA. A microcantilever device to assess the effect of force on the lifetime of selectin-carbohydrate bonds [J]. Biophys J, 2001, 80 (2): 668–682.
[5] Wu XB, Zhao KS, Huang XL. Changes in adhesion features of leukocytes in rats with severe burns [J]. Natl Med J China, 1994, 74 (5): 312–314.
[6] Stoll Mark S, Feizi T, Loveless RW, et al. Fluorescent neoglycolipids improved probes for oligosaccharides ligand discovery [J]. Eur J Biochem, 2000, 267: 1795–1804.
[7] Zhao KS, Wu QY, Zhu ZJ, et al. Effect of leukocytes on microcirculation of rats during burn shock [J]. Natl Med J China, 1986, 66: 722.
[8] Li Q, Li H, Cai MS, et al. Studies on carbohydrates. part 33: Synthesis of spacer-armed 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-α-D-mannosides and their dimmers [J]. Tetrahedron Asymmetry, 1999, 10 (14): 2675–2683.
[9] Zhao ZH, Zhang MH, Chen Y, et al. Study on the expression of L-selectin at transcription level in severe burn shock rat [J]. Chin J Pathophysiol, 2000, 16 (2): 169–171.
[10 Li Q, Cai MS, Li ZJ. Study on carbohydrates (XXXI): Synthesis of spacer-armed lactoses and their dimers [J]. Chem J Chin Univ, 2000, 21: 70–73.
[11] Meng XB,Yang LD, Li ZJ, et al. Facile synthesis of 1-thio-β-lactoside clusters scaffolded onto p-methoxyphenyl, β-D-galactopyranoside, β-D-glucopyranoside, and lactoside [J]. Carbohydr Res, 2002, 337: 977–981.
[12] Zhao ZH, Zhu J, Chen Y, et al., New applications of lactoside derivates [P]. ZL: 03112879.3 (China Patent).
[13] Zanini D, Roy R. Practical synthesis of starburst PAMAM α-thiosialodendrimers for probing multivalent carbohydrate-lectin binding properties [J]. J Org Chem, 1998, 63: 3486–3491.
[14] Lindhorst TK, Kieburg C. Glycocoating of oligovalent amines: Synthesis of thiourea-bridged cluster glycosides from glycosyl isothiocyanates [J]. Angew Chem (Int Ed Engl), 1996, 35: 1953–1956.
[15] Zhao KS, Zhu ZJ, Wu KY, et al. Importance of enhancing cardiac function in the treatment of burn shock-effect of crystal No 4 of polygonum caspidatum [A]. Sheng CY et al. Advances in Burns [M]. Beijing: International Academic Publishers, 1992. 31–38.

[1]	Meng Wang, Lei Xing, Shifang Lu, Zhu Guan^*, Zhenjun Yang, Lihe Zhang. Synthesis and the anti-HIV activity of novel dinucleotides containing L-isonucleosides [J]. , 2013, 22(4): 314-318.
[2]	Andreas H. Guse^*. Structure-activity relationship of cyclic ADP-ribose, an update [J]. , 2013, 22(2): 127-136.
[3]	Long Ren, Ning Jiao^*. A perspective on picornavirus inhibitors and concrete evolution of WIN compounds [J]. , 2012, 21(6): 509-525.
[4]	Hongrui Liu^¶, Guangzhi Bao^¶, Suna Yang, Lixin Wu, Xianfeng Gu^, Yizhun Zhu^. Synthesis and evaluation of tetrahydro β-carboline derivatives as anticancer agents [J]. , 2012, 21(5): 416-420.
[5]	Jing Deng, Fei Zhao, Jian Li, Hong Liu, Hualiang Jiang^* . Discovery and early evaluation of new chemical entities [J]. , 2012, 21(5): 369-387.
[6]	Mengzhu Xue, Jun Yuan, Bin Wu, Xue Zhao, Xiaofeng Liu, Jin Huang, Zhenjiang Zhao^, Honglin Li^, Yufang Xu. Novel inhibitors for p90 ribosomal S6 protein kinase 2: design, synthesis and SAR [J]. , 2012, 21(5): 401-408.
[7]	Xin Zhang^¶, Xueling Hou^¶, Fangbin Han, Zemei Ge^, Tieming Cheng, Runtao Li^. Oxidative coupling of α–bromoarylacetonitriles and oxidative decyanation of diarylacetonitriles catalyzed by solid-liquid phase transfer [J]. , 2012, 21(5): 409-415.
[8]	Yue Zhou, Pei-Lin Yu, Zhen-Jun Yang, Liang-Ren Zhang^*, Li-He Zhang. Design and synthesis of cADPR analogues with simplified ribose and nucleobase [J]. , 2012, 21(4): 287-291.
[9]	Shan-Shan Luo, Xian-Feng Gu^, Yi-Zhun Zhu^. Improved synthesis of leonurine as cardioprotective agent [J]. , 2012, 21(4): 292-295.
[10]	Xing-Yue Ji⁺, Si-Yang Li⁺, Shuai Meng, Chun-Ling Xiao, Xue-Fu You, Zhuo-Rong Li^*. Synthesis and antimycobacterial activity of ternatolide [J]. , 2012, 21(3): 265-268.
[11]	Gang Li, Yu-Peng Liu, Meng Lei, Xin Wang^, Tie-Ming Cheng, Run-Tao Li^. Efficient synthesis of thiohydantoin derivatives from amino acid esters and isothiocyanates in alkaline Al₂O₃ [J]. , 2012, 21(2): 136-141.
[12]	Chun-Ling Hu, Yin-Ping Tang, Yan-Wen Liu^*. Synthesis of an active peptide from Carapax Trionycis and its inhibitory effect on the proliferation of hepatic stellate cells [J]. , 2012, 21(2): 132-135.
[13]	Hai-Fei Gao, Yan Niu^, Feng-Rong Xu, Lei Liang, Bo Zhou, Yong-Jian Li, Chao Wang, Peng Liu, Ping Xu^ . Design and synthesis of benzimidamides as potential BACE1 inhibitors [J]. , 2012, 21(2): 124-131.
[14]	Liang Zhang, Xiao-Wei Wang, Jun-Yi Liu^* . Synthesis and biological evaluation of novel 2-arylalkylthio-5-iodo-6-benzyl S-DABOs as potent non-nucleoside HIV-1 reverse transcriptase inhibitors [J]. , 2012, 21(1): 28-32.
[15]	A-Min Li, Xiang-Yi Liu, Xiao-Wei Wang^, Jun-Yi Liu^. Design, synthesis and anti-HIV-1 activity of 4,6-dibenzyl-2-oxo-1,2-dihydropyridine-3-carbonitrile [J]. , 2011, 20(5): 447-453.