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Cyclic di-GMP disodium Sale

(Synonyms: c-di-GMP, Cyclic diguanylate, 3',5'-Cyclic diguanylic acid) 目录号 : GC19526

Cyclic di-GMP disodium是一种由细菌合成的环二核苷酸信号分子,是STING激动剂。

Cyclic di-GMP disodium Chemical Structure

Cas No.:2222132-40-1

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1mg
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Sample solution is provided at 25 µL, 10mM.

Description

Cyclic di-GMP disodium is a cyclic dinucleotide signaling molecule synthesized by bacteria and is a STING agonist [1]. Cyclic di-GMP disodium induces increased CD4 receptor expression and causes cell cycle arrest [2-3]. Cyclic di-GMP disodium is often used in cancer research [4].

In Escherichia coli, Cyclic di-GMP disodium (7.5μM; 18-24h) rescues rLCN2-mediated inhibition of Escherichia coli growth [5]. In H508 cells, Cyclic di-GMP disodium (2-400μM; 72h) inhibits basal and growth factor-induced proliferation of human colon cancer [1]. In CD4+ T cells, Cyclic di-GMP disodium (3μg/mL, 10μg/mL; 24h) treatment of anti-CD3/CD28 stimulated wild-type T cells resulted in significant inhibition of proliferation and upregulation of CD80 expression [6]. In myeloid-derived suppressor cells (MDSCs), low doses of Cyclic di-GMP disodium (0.2μM; 24h) significantly increased IL12 production [7].

In mouse mastitis model, prophylactic pretreatment of mice with Cyclic di-GMP disodium (1mg/kg, 4.1mg/kg; sc; injected every 6 hours, twice in total) inhibits infection [8]. In a mouse bacterial pneumonia model, pretreatment of mice with Cyclic di-GMP disodium (2.5mg/kg; sc; injected every 12 hours, twice in total) induced a significant protective immune response against challenge with a virulent strain of Klebsiella pneumoniae [9]. In pertussis mouse model, injection of Cyclic di-GMP disodium (2.5mg/kg; nasal; single administration) can induce protective immune responses against Bordetella pertussis bacterial challenge [10].

References:
[1]. Karaolis DK, Cheng K, Lipsky M, et al. 3′, 5′-Cyclic diguanylic acid (c-di-GMP) inhibits basal and growth factor-stimulated human colon cancer cell proliferation. Biochemical and biophysical research communications. 2005 Apr 1; 329(1): 40-45.
[2]. Wang Z, Celis E. STING activator c-di-GMP enhances the anti-tumor effects of peptide vaccines in melanoma-bearing mice. Cancer Immunology, Immunotherapy. 2015 Aug; 64: 1057-1066.
[3]. JSteinberger O, Lapidot Z, Ben-Ishai Z, et al. Elevated expression of the CD4 receptor and cell cycle arrest are induced in Jurkat cells by treatment with the novel cyclic dinucleotide 3′, 5′-cyclic diguanylic acid. FEBS letters. 1999 Feb 5; 444(1): 125-129.
[4]. Jenal U, Reinders A, Lori C. Cyclic di-GMP: second messenger extraordinaire. Nature Reviews Microbiology. 2017 May; 15(5): 271-284.
[5]. Li W, Cui T, Hu L, et al. Cyclic diguanylate monophosphate directly binds to human siderocalin and inhibits its antibacterial activity. Nature Communications. 2015 Sep 22; 6(1): 8330.
[6]. Concepcion AR, Wagner LE, Zhu J, et al. The volume-regulated anion channel LRRC8C suppresses T cell function by regulating cyclic dinucleotide transport and STING–p53 signaling. Nature immunology. 2022 Feb; 23(2): 287-302.
[7]. Chandra D, Quispe-Tintaya W, Jahangir A, et al. STING ligand c-di-GMP improves cancer vaccination against metastatic breast cancer. Cancer immunology research. 2014 Sep 1; 2(9): 901-910.
[8]. Karaolis DK, Means TK, Yang D, et al. Bacterial c-di-GMP is an immunostimulatory molecule. The Journal of Immunology. 2007 Feb 15; 178(4): 2171-2181.
[9]. Karaolis DK, Newstead MW, Zeng X, et al. Cyclic di-GMP stimulates protective innate immunity in bacterial pneumonia. Infection and immunity. 2007 Oct; 75(10): 4942-4950.
[10]. Elahi S, Van Kessel J, Kiros TG, et al. c-di-GMP enhances protective innate immunity in a murine model of pertussis. PloS one. 2014 Oct 15; 9(10): e109778.

Cyclic di-GMP disodium是一种由细菌合成的环二核苷酸信号分子,是STING激动剂 [1]。Cyclic di-GMP disodium可诱导CD4受体表达增加,并导致细胞周期停滞 [2-3]。Cyclic di-GMP disodium常用于癌症研究 [4]

在大肠杆菌中,Cyclic di-GMP disodium(7.5μM;18-24h)可挽救rLCN2介导的大肠杆菌生长抑制 [5]。在H508细胞中,Cyclic di-GMP disodium(2-400μM;72h)可抑制人结肠癌的基底细胞癌和生长因子诱导的增殖 [1]。在CD4+T细胞中,Cyclic di-GMP disodium(3μg/mL、10μg/mL;24h)处理抗CD3/CD28刺激的野生型T细胞,可显著抑制其增殖并上调CD80表达 [6]。在髓系抑制细胞(MDSC)中,低剂量Cyclic di-GMP disodium(0.2μM;24小时)可显著增加IL12的产生 [7]

在小鼠乳腺炎模型中,用Cyclic di-GMP disodium(1mg/kg,4.1mg/kg;sc;每6小时注射一次,共两次)对小鼠进行预防性预处理可抑制感染 [8]。在小鼠细菌性肺炎模型中,预先用Cyclic di-GMP disodium(2.5mg/kg;sc;每12小时注射一次,共两次)对小鼠进行治疗,可诱导对肺炎克雷伯菌强毒株攻击的保护性免疫反应 [9]。在小鼠百日咳模型中,注射Cyclic di-GMP disodium(2.5mg/kg;鼻腔给药;单次给药)可诱导对百日咳博德特氏菌攻击的保护性免疫反应 [10]

实验参考方法

Antibacterial experiment [1]:

Bacterial

Escherichia coli

Preparation Method

To evaluate whether Cyclic di-GMP disodium could alleviate the inhibitory effect of rLCN2 on bacterial growth, Escherichia coli (E. coli) was cultured in standard 7H9-OADC and M9 medium, respectively, and treated with 0.15μM rLCN2 at 37℃, and Cyclic di-GMP disodium (7.5μM) was added. The colony forming units (CFU) were measured at different time points (18-24h).

Reaction Conditions

7.5μM; 18-24h

Applications

Cyclic di-GMP disodium rescues rLCN2-mediated inhibition of E. coli growth.
Animal experiment [2]:

Animal models

Mouse mastitis model

Preparation Method

12 and 6h before bacterial inoculation, saline or 50 or 200nmol of Cyclic di-GMP disodium was administered into the fourth pair of abdominal mammary glands of lactating CD-1 mice. Administration of 50 and 200nmol of Cyclic di-GMP disodium corresponded to a dose of 1.0 and 4.1mg of compound per kg of body weight, respectively, considering an average weight of 35g for a mouse. For inoculation, 100 CFU of S. aureus Newbould 305 (ATCC 29740) were injected into each gland and the colonization was allowed for 10h. Raw bacterial CFU counts obtained after plating serial logarithmic dilutions of mammary gland homogenates were transformed in base 10 logarithm values.

Dosage form

1mg/kg, 4.1mg/kg; sc; injected every 6 hours, twice in total

Applications

Prophylactic pretreatment of mice with Cyclic di-GMP disodium inhibits infection in vivo.

References:
[1]. Li W, Cui T, Hu L, et al. Cyclic diguanylate monophosphate directly binds to human siderocalin and inhibits its antibacterial activity. Nature Communications. 2015 Sep 22; 6(1): 8330.
[2]. Karaolis DK, Means TK, Yang D, et al. Bacterial c-di-GMP is an immunostimulatory molecule. The Journal of Immunology. 2007 Feb 15; 178(4): 2171-2181.

化学性质

Cas No. 2222132-40-1 SDF
别名 c-di-GMP, Cyclic diguanylate, 3',5'-Cyclic diguanylic acid
化学名 guanylyl-(3'→5')-3'-guanylic acid, cyclic nucleotide, disodium salt
Canonical SMILES O=C1NC(N)=NC2=C1N=CN2[C@@H]([C@@H]3O)O[C@@]([H])([C@]3(OP([O-])(OC[C@]([H])([C@]4(O5)[H])O[C@H]([C@@H]4O)N6C(N=C(N7)N)=C(N=C6)C7=O)=O)[H])COP5([O-])=O.[Na+].[Na+]
分子式 C20H22N10O14P2Na2 分子量 734.4
溶解度 1mg/mL in water 储存条件 Store at -80°C, protect from light, stored under nitrogen
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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1 mg 5 mg 10 mg
1 mM 1.3617 mL 6.8083 mL 13.6166 mL
5 mM 0.2723 mL 1.3617 mL 2.7233 mL
10 mM 0.1362 mL 0.6808 mL 1.3617 mL
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