MedKoo Cat#: 207033 | Name: Ulevostinag

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ulevostinag, also known as MK-1454 is a STING agonist with potential immunoactivating and antineoplastic activities. MK-1454 binds to STING and activates the STING pathway, which promotes IKK-related kinase TANK-binding kinase 1 (TBK1) signaling and activates nuclear factor-kappa B (NF-kB) and interferon regulatory factor 3 (IRF3) in immune cells in the tumor microenvironment; this leads to the production of pro-inflammatory cytokines, including interferons (IFNs). Specifically, expression of IFN-beta (IFNb) enhances the cross-presentation of tumor-associated antigens by CD8alpha-positive and CD103-positive dendritic cells (DCs) to cytotoxic T lymphocytes (CTLs). This results in a CTL-mediated immune response against tumor cells and causes tumor cell lysis.

Chemical Structure

Ulevostinag
Ulevostinag
CAS#2082743-99-3

Theoretical Analysis

MedKoo Cat#: 207033

Name: Ulevostinag

CAS#: 2082743-99-3

Chemical Formula: C20H22F2N10O9P2S2

Exact Mass: 710.0456

Molecular Weight: 710.52

Elemental Analysis: C, 33.81; H, 3.12; F, 5.35; N, 19.71; O, 20.27; P, 8.72; S, 9.02

Price and Availability

Related CAS #
No Data
Synonym
MK-1454; MK 1454; MK1454; Ulevostinag;
IUPAC/Chemical Name
(2R,5R,7R,8S,10R,12aR,14R,15S,15aR,16R)-7- (2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-14-(6-amino-9Hpurin- 9-yl)-15,16-difluoro-2,10-bis(sulfanyl)octahydro- 2H,10H,12H-2λ5,10λ5-5,8-methanofuro[3,2-l][1,3,6,9,11,2,10]- pentaoxadiphosphacyclotetradecine-2,10-dione
InChi Key
YSUIQYOGTINQIN-KZNNIMRESA-N
InChi Code
InChI=1S/C20H22F2N10O9P2S2/c21-8-6-1-36-42(34,44)40-12-7(39-18(9(12)22)31-4-27-10-14(23)25-3-26-15(10)31)2-37-43(35,45)41-13(8)19(38-6)32-5-28-11-16(32)29-20(24)30-17(11)33/h3-9,12-13,18-19H,1-2H2,(H,34,44)(H,35,45)(H2,23,25,26)(H3,24,29,30,33)/t6-,7-,8-,9+,12-,13-,18-,19-,42-,43+/m1/s1
SMILES Code
S[P@@](OC[C@H]([C@H]1O[P@@](OC[C@H]2O[C@H]([C@H]3[C@@H]2F)N4C5=C(N=C4)C(NC(N)=N5)=O)(S)=O)O[C@H]([C@H]1F)N6C=NC7=C(N=CN=C67)N)(O3)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 710.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Benkovics T, Peng F, Phillips EM, An C, Bade RS, Chung CK, Dance ZEX, Fier PS, Forstater JH, Liu Z, Liu Z, Maligres PE, Marshall NM, Salehi Marzijarani N, McIntosh JA, Miller SP, Moore JC, Neel AJ, Obligacion JV, Pan W, Pirnot MT, Poirier M, Reibarkh M, Sherry BD, Song ZJ, Tan L, Turnbull BWH, Verma D, Waldman JH, Wang L, Wang T, Winston MS, Xu F. Diverse Catalytic Reactions for the Stereoselective Synthesis of Cyclic Dinucleotide MK-1454. J Am Chem Soc. 2022 Apr 6;144(13):5855-5863. doi: 10.1021/jacs.1c12106. Epub 2022 Mar 25. PMID: 35333525. 2: Chang W, Altman MD, Lesburg CA, Perera SA, Piesvaux JA, Schroeder GK, Wyss DF, Cemerski S, Chen Y, DiNunzio E, Haidle AM, Ho T, Kariv I, Knemeyer I, Kopinja JE, Lacey BM, Laskey J, Lim J, Long BJ, Ma Y, Maddess ML, Pan BS, Presland JP, Spooner E, Steinhuebel D, Truong Q, Zhang Z, Fu J, Addona GH, Northrup AB, Parmee E, Tata JR, Bennett DJ, Cumming JN, Siu T, Trotter BW. Discovery of MK-1454: A Potent Cyclic Dinucleotide Stimulator of Interferon Genes Agonist for the Treatment of Cancer. J Med Chem. 2022 Mar 25. doi: 10.1021/acs.jmedchem.1c02197. Epub ahead of print. PMID: 35332774. 3: McIntosh JA, Liu Z, Andresen BM, Marzijarani NS, Moore JC, Marshall NM, Borra-Garske M, Obligacion JV, Fier PS, Peng F, Forstater JH, Winston MS, An C, Chang W, Lim J, Huffman MA, Miller SP, Tsay FR, Altman MD, Lesburg CA, Steinhuebel D, Trotter BW, Cumming JN, Northrup A, Bu X, Mann BF, Biba M, Hiraga K, Murphy GS, Kolev JN, Makarewicz A, Pan W, Farasat I, Bade RS, Stone K, Duan D, Alvizo O, Adpressa D, Guetschow E, Hoyt E, Regalado EL, Castro S, Rivera N, Smith JP, Wang F, Crespo A, Verma D, Axnanda S, Dance ZEX, Devine PN, Tschaen D, Canada KA, Bulger PG, Sherry BD, Truppo MD, Ruck RT, Campeau LC, Bennett DJ, Humphrey GR, Campos KR, Maddess ML. A kinase-cGAS cascade to synthesize a therapeutic STING activator. Nature. 2022 Mar;603(7901):439-444. doi: 10.1038/s41586-022-04422-9. Epub 2022 Mar 16. PMID: 35296845. 4: Zawit M, Swami U, Awada H, Arnouk J, Milhem M, Zakharia Y. Current status of intralesional agents in treatment of malignant melanoma. Ann Transl Med. 2021 Jun;9(12):1038. doi: 10.21037/atm-21-491. PMID: 34277838; PMCID: PMC8267328. 5: Gogoi H, Mansouri S, Jin L. The Age of Cyclic Dinucleotide Vaccine Adjuvants. Vaccines (Basel). 2020 Aug 13;8(3):453. doi: 10.3390/vaccines8030453. PMID: 32823563; PMCID: PMC7563944.