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MedKoo Cat#: 526783 | Name: UK-5099
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Description:

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

UK-5099 is a specific and potent mitochondrial pyruvate carrier blocker (MCK blocker). The UK5099 treated cells showed significantly higher proportion of side population (SP) fraction and expressed higher levels of stemness markers Oct3/4 and Nanog. Chemosensitivity examinations revealed that the UK5099 treated cells became more resistant to chemotherapy compared to the non-treated cells. MPC blocker (UK5099) application may be an ideal model for Warburg effect studies

Chemical Structure

UK-5099
UK-5099
CAS#56396-35-1

Theoretical Analysis

MedKoo Cat#: 526783

Name: UK-5099

CAS#: 56396-35-1

Chemical Formula: C18H12N2O2

Exact Mass: 288.0899

Molecular Weight: 288.31

Elemental Analysis: C, 74.99; H, 4.20; N, 9.72; O, 11.10

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
100mg USD 650.00
200mg USD 950.00
500mg USD 1,950.00
1g USD 3,250.00
2g USD 5,450.00
5g USD 7,950.00
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Related CAS #
No Data
Synonym
UK-5099, UK 5099, UK5099
IUPAC/Chemical Name
2-cyano-3-(1-phenyl-1H-indol-3-yl)-2-propenoic acid
InChi Key
BIZNHCWFGNKBBZ-JLHYYAGUSA-N
InChi Code
InChI=1S/C18H12N2O2/c19-11-13(18(21)22)10-14-12-20(15-6-2-1-3-7-15)17-9-5-4-8-16(14)17/h1-10,12H,(H,21,22)/b13-10+
SMILES Code
O=C(O)/C(C#N)=C/C1=CN(C2=CC=CC=C2)C3=C1C=CC=C3
Appearance
Yellow to light brown 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
>2 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 288.31 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: Pozzo E, Yedigaryan L, Giarratana N, Wang CC, Garrido GM, Degreef E, Marini V, Rinaldi G, van der Veer BK, Sassi G, Eelen G, Planque M, Fanzani A, Koh KP, Carmeliet P, Yustein JT, Fendt SM, Uyttebroeck A, Sampaolesi M. miR-449a/miR-340 reprogram cell identity and metabolism in fusion-negative rhabdomyosarcoma. Cell Rep. 2025 Jan 11;44(1):115171. doi: 10.1016/j.celrep.2024.115171. Epub ahead of print. PMID: 39799567. 2: Ali HA, Karasinska JM, Topham JT, Johal D, Kalloger S, Metcalfe A, Warren CS, Miyagi A, Tao LV, Kevorkova M, Chafe SC, McDonald PC, Dedhar S, Parker SJ, Renouf DJ, Schaeffer DF. Pancreatic cancer tumor organoids exhibit subtype- specific differences in metabolic profiles. Cancer Metab. 2024 Oct 3;12(1):28. doi: 10.1186/s40170-024-00357-z. PMID: 39363341; PMCID: PMC11448267. 3: Huang Y, Peng X, Zhang H, Pan M, Su X, Li G, Zhang Q. Design, synthesis and biological evaluation of novel cyano-cinnamate derivatives as mitochondrial pyruvate carrier inhibitors. Bioorg Med Chem Lett. 2024 Nov 1;112:129923. doi: 10.1016/j.bmcl.2024.129923. Epub 2024 Aug 10. PMID: 39134097. 4: Hadfield CM, Walker JK, Arnatt C, McCommis KS. Computational structural prediction and chemical inhibition of the human mitochondrial pyruvate carrier protein heterodimer complex. bioRxiv [Preprint]. 2024 Aug 10:2024.05.16.594520. doi: 10.1101/2024.05.16.594520. PMID: 39071381; PMCID: PMC11275797. 5: Pye D, Scholey R, Ung S, Dawson M, Shahmalak A, Purba TS. Activation of the integrated stress response in human hair follicles. PLoS One. 2024 Jun 20;19(6):e0303742. doi: 10.1371/journal.pone.0303742. PMID: 38900734; PMCID: PMC11189182. 6: Li Y, Song Y, Shi Z, Hou H, Yu Y, Pan F, Ji J, Chen Z. Syrosingopine and UK5099 synergistically suppress non-small cell lung cancer by activating the integrated stress response. Cell Death Dis. 2024 Jun 19;15(6):431. doi: 10.1038/s41419-024-06821-4. PMID: 38898028; PMCID: PMC11187063. 7: Buyse C, Mignion L, Joudiou N, Melloul S, Driesschaert B, Gallez B. Sensitive simultaneous measurements of oxygenation and extracellular pH by EPR using a stable monophosphonated trityl radical and lithium phthalocyanine. Free Radic Biol Med. 2024 Mar;213:11-18. doi: 10.1016/j.freeradbiomed.2024.01.012. Epub 2024 Jan 11. PMID: 38218552; PMCID: PMC10923140. 8: Winter M, Nait Eldjoudi A, Guette C, Hondermarck H, Bourette RP, Fovez Q, Laine W, Ghesquiere B, Adriaenssens E, Kluza J, Le Bourhis X. Mitochondrial adaptation decreases drug sensitivity of persistent triple negative breast cancer cells surviving combinatory and sequential chemotherapy. Neoplasia. 2023 Dec;46:100949. doi: 10.1016/j.neo.2023.100949. Epub 2023 Nov 11. PMID: 37956532; PMCID: PMC10661600. 9: Wang J, Saiki N, Tanimura A, Noma T, Niwa A, Nakahata T, Saito MK. UK-5099, a mitochondrial pyruvate carrier inhibitor, recovers impaired neutrophil maturation caused by AK2 deficiency in human pluripotent stem cell models. Biochem Biophys Res Commun. 2023 Dec 20;687:149211. doi: 10.1016/j.bbrc.2023.149211. Epub 2023 Nov 3. PMID: 37949028. 10: Jeon KI, Kumar A, Callan CL, DeMagistris M, MacRae S, Nehrke K, Huxlin KR. Blocking Mitochondrial Pyruvate Transport Alters Corneal Myofibroblast Phenotype: A New Target for Treating Fibrosis. Invest Ophthalmol Vis Sci. 2023 Oct 3;64(13):36. doi: 10.1167/iovs.64.13.36. PMID: 37870848; PMCID: PMC10599161. 11: Zeng Q, Si H, Lv K, Mo J, Wang X, Yan B, Zhang J. Determination and pharmacokinetics study of UK-5099 in mouse plasma by LC-MS/MS. BMC Vet Res. 2022 Apr 20;18(1):145. doi: 10.1186/s12917-022-03245-0. PMID: 35443692; PMCID: PMC9020015. 12: Hegazy L, Gill LE, Pyles KD, Kaiho C, Kchouk S, Finck BN, McCommis KS, Elgendy B. Identification of Novel Mitochondrial Pyruvate Carrier Inhibitors by Homology Modeling and Pharmacophore-Based Virtual Screening. Biomedicines. 2022 Feb 2;10(2):365. doi: 10.3390/biomedicines10020365. PMID: 35203575; PMCID: PMC8962382. 13: Buyse C, Joudiou N, Corbet C, Feron O, Mignion L, Flament J, Gallez B. Impact of Inhibition of the Mitochondrial Pyruvate Carrier on the Tumor Extracellular pH as Measured by CEST-MRI. Cancers (Basel). 2021 Aug 25;13(17):4278. doi: 10.3390/cancers13174278. PMID: 34503089; PMCID: PMC8428345. 14: Liu X, Flores AA, Situ L, Gu W, Ding H, Christofk HR, Lowry WE, Jung ME. Development of Novel Mitochondrial Pyruvate Carrier Inhibitors to Treat Hair Loss. J Med Chem. 2021 Feb 25;64(4):2046-2063. doi: 10.1021/acs.jmedchem.0c01570. Epub 2021 Feb 3. PMID: 33534563; PMCID: PMC8939290. 15: Guimarães NC, Alves DS, Vilela WR, de-Souza-Ferreira E, Gomes BRB, Ott D, Murgott J, E N de Souza P, de Sousa MV, Galina A, Roth J, Fabro de Bem A, Veiga- Souza FH. Mitochondrial pyruvate carrier as a key regulator of fever and neuroinflammation. Brain Behav Immun. 2021 Feb;92:90-101. doi: 10.1016/j.bbi.2020.11.031. Epub 2020 Nov 24. PMID: 33242651. 16: Burrell JA, Richard AJ, King WT, Stephens JM. Mitochondrial Pyruvate Carriers are not Required for Adipogenesis but are Regulated by High-Fat Feeding in Brown Adipose Tissue. Obesity (Silver Spring). 2020 Feb;28(2):293-302. doi: 10.1002/oby.22678. PMID: 31970913; PMCID: PMC6986308. 17: Yamashita Y, Vinogradova EV, Zhang X, Suciu RM, Cravatt BF. A Chemical Proteomic Probe for the Mitochondrial Pyruvate Carrier Complex. Angew Chem Int Ed Engl. 2020 Mar 2;59(10):3896-3899. doi: 10.1002/anie.201914391. Epub 2020 Feb 11. PMID: 31863675; PMCID: PMC7323913. 18: Herbst EAF, George MAJ, Brebner K, Holloway GP, Kane DA. Lactate is oxidized outside of the mitochondrial matrix in rodent brain. Appl Physiol Nutr Metab. 2018 May;43(5):467-474. doi: 10.1139/apnm-2017-0450. Epub 2017 Dec 5. PMID: 29206478. 19: Wilkins LR, Brautigan DL, Wu H, Yarmohammadi H, Kubicka E, Serbulea V, Leitinger N, Liu W, Haaga JR. Cinnamic Acid Derivatives Enhance the Efficacy of Transarterial Embolization in a Rat Model of Hepatocellular Carcinoma. Cardiovasc Intervent Radiol. 2017 Mar;40(3):430-437. doi: 10.1007/s00270-016-1515-y. Epub 2016 Nov 21. PMID: 27872984; PMCID: PMC5520990. 20: Simchowitz L, Textor JA, Cragoe EJ Jr. Cell volume regulation in human neutrophils: 2-(aminomethyl)phenols as Cl- channel inhibitors. Am J Physiol. 1993 Jul;265(1 Pt 1):C143-55. doi: 10.1152/ajpcell.1993.265.1.C143. PMID: 8393278.