Name: 2',3'-cGAMP-C2-PPA
Brand: BOC Sciences
Rating: 5 (1 reviews)

IUPAC Name

4-[2-[(1R,6R,8R,9R,10S,15S,17R,18R)-17-(2-amino-6-oxo-1H-purin-9-yl)-8-(6-aminopurin-9-yl)-3,9,12-trihydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.2.1.06,10]octadecan-18-yl]ethyldisulfanyl]pentanoic acid

Canonical SMILES

CC(CCC(=O)O)SSCCC1C2COP(=O)(OC3C(COP(=O)(OC1C(O2)N4C=NC5=C4N=C(NC5=O)N)O)OC(C3O)N6C=NC7=C(N=CN=C76)N)O

InChI

InChI=1S/C27H36N10O14P2S2/c1-11(2-3-15(38)39)55-54-5-4-12-13-6-46-53(44,45)51-20-14(49-25(18(20)40)36-9-32-16-21(28)30-8-31-22(16)36)7-47-52(42,43)50-19(12)26(48-13)37-10-33-17-23(37)34-27(29)35-24(17)41/h8-14,18-20,25-26,40H,2-7H2,1H3,(H,38,39)(H,42,43)(H,44,45)(H2,28,30,31)(H3,29,34,35,41)/t11?,12-,13-,14-,18-,19-,20-,25-,26-/m1/s1

InChIKey

IBPLNKRENHFZJM-AYPAWVCOSA-N

Storage

Store at 2-8°C

2,'3'-cGAMP-C2-PPA is a synthetic analog of cyclic GMP-AMP (cGAMP), an important molecule in the study of immune response and cellular signaling. Here are some key applications of 2',3'-cGAMP-C2-PPA:

Immunotherapy Research: 2',3'-cGAMP-C2-PPA is used to activate the STING (Stimulator of Interferon Genes) pathway, which plays a critical role in innate immunity. By stimulating this pathway, researchers can explore new strategies for cancer immunotherapy, infectious disease treatments, and autoimmune disorders. This molecule helps in understanding how to modulate immune responses to enhance therapeutic outcomes.

Vaccine Development: In vaccine research, 2',3'-cGAMP-C2-PPA serves as an adjuvant to enhance the efficacy of vaccines. By promoting a stronger and more durable immune activation, it can improve the body's defense against various pathogens. This application is particularly valuable in developing vaccines for hard-to-target diseases like HIV and emerging infectious agents.

Antiviral Research: 2',3'-cGAMP-C2-PPA is studied for its potential to boost antiviral defenses by stimulating interferon production. This can inhibit the replication of viruses such as influenza, herpes simplex virus, and others. Researchers use this compound to identify new antiviral strategies and develop treatments that can effectively control viral infections.

Cellular Signaling Studies: 2',3'-cGAMP-C2-PPA is an important tool in the study of cGAMP-mediated signaling pathways. By elucidating how these pathways regulate immune responses and other cellular processes, scientists can uncover new therapeutic targets. This knowledge is essential for developing drugs that can precisely manipulate cellular signaling for therapeutic benefit.

1. 2,5-Bis(1,3-dithiol-2-yl-idene)-1,3-dithiol-ane-4-thione

Kazumasa Ueda, Kenta Suzuki, Kei Kunimoto, Kenji Yoza Acta Crystallogr Sect E Struct Rep Online . 2012 Jan;68(Pt 1):o52. doi: 10.1107/S1600536811051518.

The asymmetric unit of the title compound, C(9)H(4)S(7), contains two independent mol-ecules, in one of which the central five-membered ring is disordered over two orientations in a 0.924 (3):0.076 (3) ratio. The mol-ecular skeleton is almost planar: the average distance of the atoms from their mean plane is 0.128 (7) Å in the ordered mol-ecule, and 0.088 (5) and 0.123 (2) Å in the major and minor disorder components, respectively. The ordered and disordered mol-ecules form separate columns by stacking along the b axis. Adjacent columns inter-act via short S⋯S [3.33 (2), 3.434 (3), 3.444 (2), 3.503 (2), 3.519 (3) and 3.53 (4) Å] and S⋯H [2.814 (2), 2.87 (7), 2.92 (2), 2.9269 (18), 2.93 (2), 2.94 (2), 2.939 (2), 2.967 (2) and 2.974 (1) Å] contacts.

2. Dichloralphenazone

Short-term or occasional use of dichloralphenazone during breastfeeding is unlikely to adversely affect the breastfed infant, especially if the infant is older than 2 months. Because the active metabolite, trichloroethanol, has a long half-life, long-term use of repeated doses during breastfeeding could result in infant sedation, especially while nursing a neonate or preterm infant. The low doses of dichloralphenazone found in combination migraine products (e.g., Midrin) are less likely to cause drowsiness in the infant unless doses are repeated several times daily. The antipyrine component of dichloralphenazone is considered unlikely to harm the infant.[1,2] Monitor the infant for excessive drowsiness during use.

3. Tetrakis(mu-2,3-dimethoxybenzoato)bis[(2,2'-bipyridine)(2,3-dimethoxybenzoato)lanthanum(III)]

Y Li, Y Q Zou, H M Hu, X Li Acta Crystallogr C . 2001 Sep;57(Pt 9):1048-50. doi: 10.1107/s0108270101009337.

The title compound, tetrakis(mu-2,3-dimethoxybenzoato)-kappa(4)O:O';kappa(6)O,O':O'-bis[(2,2'-bipyridine-N,N')(2,3-dimethoxybenzoato-O,O')lanthanum(III)], [La(2)(2,3-DMOBA)(6)(2,2'-bpy)(2)], where 2,3-DMOBA is 2,3-dimethoxybenzoate (C(9)H(9)O(4)) and 2,2'-bpy is 2,2'-bipyridine (C(10)H(8)N(2)), is a dimer with a centre of inversion between the La atoms bridged by four carboxylate ligands. The central La atom is ennea-coordinated and has a distorted monocapped square-antiprism geometry.

What is 2',3'-cGAMP-C2-PPA?

2',3'-cGAMP-C2-PPA is a chemically modified cyclic GMP-AMP (cGAMP) derivative designed to enhance cellular uptake and stability. It serves as a tool for activating the STING pathway in immuno-oncology research.

15/7/2019

Dear BOC Sciences, could you explain how 2',3'-cGAMP-C2-PPA enhances STING activation?

The C2-PPA modification improves membrane permeability and bioavailability of 2',3'-cGAMP, facilitating efficient delivery to cytosolic STING receptors and promoting robust type I interferon signaling.

5/10/2017

Dear BOC Sciences, could you please advise what research applications are suitable for 2',3'-cGAMP-C2-PPA?

2',3'-cGAMP-C2-PPA is commonly used in studies of innate immunity, antiviral responses, and cancer immunotherapy, particularly in preclinical models exploring STING pathway activation.

14/5/2020

Could you kindly confirm if 2',3'-cGAMP-C2-PPA is compatible with both in vitro and in vivo studies?

Yes, 2',3'-cGAMP-C2-PPA can be applied in both in vitro cell-based assays and in vivo models, offering flexibility for mechanistic studies and translational research in immune modulation.

7/12/2017

Good afternoon! What handling considerations are necessary for 2',3'-cGAMP-C2-PPA?

2',3'-cGAMP-C2-PPA should be handled using standard laboratory precautions for nucleotide derivatives, including storage at low temperature, protection from moisture, and use of personal protective equipment.

15/8/2017

— Dr. Peter Hall, Senior Scientist (USA)

2',3'-cGAMP-C2-PPA arrived with exceptional purity, enabling reliable payload conjugation.

14/5/2020

— Dr. Sophia Wright, ADC Chemist (UK)

Batch-to-batch consistency of 2',3'-cGAMP-C2-PPA minimized variability in signaling assays.

15/8/2017

— Dr. Thomas Weber, Medicinal Chemist (Germany)

Fast delivery and clear QC documentation for 2',3'-cGAMP-C2-PPA improved experimental workflow.

7/12/2017

— Dr. Emily Scott, Biochemist (Canada)

Reliable 2',3'-cGAMP-C2-PPA quality allowed reproducible in vitro experiments.