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MedKoo Cat#: 561056 | Name: AkaLumine free base
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Description:

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

AkaLumine is a luciferin analogue. The bioluminescence produced by AkaLumine in reactions with native firefly luciferase is in the near-infrared wavelength ranges (λmax=677 nm), and yields significantly increased target-detection sensitivity from deep tissues with maximal signals attained at very low concentrations, as compared with D-luciferin and emerging synthetic luciferin CycLuc1.

Chemical Structure

AkaLumine free base
AkaLumine free base
CAS#1176235-08-7 (free base)

Theoretical Analysis

MedKoo Cat#: 561056

Name: AkaLumine free base

CAS#: 1176235-08-7 (free base)

Chemical Formula: C16H18N2O2S

Exact Mass: 302.1089

Molecular Weight: 302.39

Elemental Analysis: C, 63.55; H, 6.00; N, 9.26; O, 10.58; S, 10.60

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
25mg USD 950.00 2 Weeks
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Related CAS #
1176235-08-7 (free base) 2558205-28-8 (HCl)
Synonym
AkaLumine; Aka Lumine
IUPAC/Chemical Name
2-[(1E,3E)-4-(4-Dimethylaminophenyl)buta-1,3-dienyl]-4,5-dihydrothiazole-4-carboxylic acid
InChi Key
ULTVSKXCSMDCHR-GGWOSOGESA-N
InChi Code
InChI=1S/C16H18N2O2S/c1-18(2)13-9-7-12(8-10-13)5-3-4-6-15-17-14(11-21-15)16(19)20/h3-10,14H,11H2,1-2H3,(H,19,20)/b5-3+,6-4+
SMILES Code
O=C(C1N=C(/C=C/C=C/C2=CC=C(N(C)C)C=C2)SC1)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
>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
Certificate of Analysis
View CoA: current batch, Lot#A20O09B28
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 302.39 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: Su Y, Walker JR, Park Y, Smith TP, Liu LX, Hall MP, Labanieh L, Hurst R, Wang DC, Encell LP, Kim N, Zhang F, Kay MA, Casey KM, Majzner RG, Cochran JR, Mackall CL, Kirkland TA, Lin MZ. Novel NanoLuc substrates enable bright two-population bioluminescence imaging in animals. Nat Methods. 2020 Aug;17(8):852-860. doi: 10.1038/s41592-020-0889-6. Epub 2020 Jul 13. PMID: 32661427. 2: Ogawa H, Ono R, Noguchi Y, Kitada N, Saito-Moriya R, Maki SA, Akiyama H, Itabashi H, Hiyama M. Absorption Spectra for Firefly Bioluminescence Substrate Analog: TokeOni in Various pH Solutions. Photochem Photobiol. 2021 Sep;97(5):1016-1022. doi: 10.1111/php.13458. Epub 2021 Jun 21. PMID: 34081790. 3: Hendrickx S, Bulté D, Mabille D, Mols R, Claes M, Ilbeigi K, Ahmad R, Dirkx L, Van Acker SI, Caljon G. Comparison of Bioluminescent Substrates in Natural Infection Models of Neglected Parasitic Diseases. Int J Mol Sci. 2022 Dec 16;23(24):16074. doi: 10.3390/ijms232416074. PMID: 36555716; PMCID: PMC9781651. 4: Su Y, Walker JR, Hall MP, Klein MA, Wu X, Encell LP, Casey KM, Liu LX, Hong G, Lin MZ, Kirkland TA. An optimized bioluminescent substrate for non-invasive imaging in the brain. Nat Chem Biol. 2023 Jun;19(6):731-739. doi: 10.1038/s41589-023-01265-x. Epub 2023 Feb 9. PMID: 36759751; PMCID: PMC10229426. 5: Kuchimaru T, Iwano S, Kiyama M, Mitsumata S, Kadonosono T, Niwa H, Maki S, Kizaka-Kondoh S. A luciferin analogue generating near-infrared bioluminescence achieves highly sensitive deep-tissue imaging. Nat Commun. 2016 Jun 14;7:11856. doi: 10.1038/ncomms11856. PMID: 27297211; PMCID: PMC4911627. 6: Lim W, Kim B, Jo G, Yang DH, Park MH, Hyun H. Bioluminescence and near- infrared fluorescence imaging for detection of metastatic bone tumors. Lasers Med Sci. 2020 Feb;35(1):115-120. doi: 10.1007/s10103-019-02801-9. Epub 2019 Jun 1. PMID: 31154597. 7: Nakayama J, Saito R, Hayashi Y, Kitada N, Tamaki S, Han Y, Semba K, Maki SA. High Sensitivity In Vivo Imaging of Cancer Metastasis Using a Near-Infrared Luciferin Analogue seMpai. Int J Mol Sci. 2020 Oct 24;21(21):7896. doi: 10.3390/ijms21217896. PMID: 33114327; PMCID: PMC7660630. 8: Zambito G, Gaspar N, Ridwan Y, Hall MP, Shi C, Kirkland TA, Encell LP, Löwik C, Mezzanotte L. Evaluating Brightness and Spectral Properties of Click Beetle and Firefly Luciferases Using Luciferin Analogues: Identification of Preferred Pairings of Luciferase and Substrate for In Vivo Bioluminescence Imaging. Mol Imaging Biol. 2020 Dec;22(6):1523-1531. doi: 10.1007/s11307-020-01523-7. Epub 2020 Sep 14. PMID: 32926287; PMCID: PMC7666294. 9: Zhong C, Kayamori K, Koide S, Shinoda D, Oshima M, Nakajima-Takagi Y, Nagai Y, Mimura N, Sakaida E, Yamazaki S, Iwano S, Miyawaki A, Ito R, Tohyama K, Yamaguchi K, Furukawa Y, Lennox W, Sheedy J, Weetall M, Iwama A. Efficacy of the novel tubulin polymerization inhibitor PTC-028 for myelodysplastic syndrome. Cancer Sci. 2020 Dec;111(12):4336-4347. doi: 10.1111/cas.14684. Epub 2020 Nov 2. PMID: 33037737; PMCID: PMC7734154. 10: Yeh HW, Xiong Y, Wu T, Chen M, Ji A, Li X, Ai HW. ATP-Independent Bioluminescent Reporter Variants To Improve in Vivo Imaging. ACS Chem Biol. 2019 May 17;14(5):959-965. doi: 10.1021/acschembio.9b00150. Epub 2019 Apr 17. PMID: 30969754; PMCID: PMC6528180. 11: Gaspar N, Walker JR, Zambito G, Marella-Panth K, Lowik C, Kirkland TA, Mezzanotte L. Evaluation of NanoLuc substrates for bioluminescence imaging of transferred cells in mice. J Photochem Photobiol B. 2021 Mar;216:112128. doi: 10.1016/j.jphotobiol.2021.112128. Epub 2021 Jan 26. PMID: 33529963. 12: Viviani VR, Bevilaqua VR, de Souza DR, Pelentir GF, Kakiuchi M, Hirano T. A Very Bright Far-Red Bioluminescence Emitting Combination Based on Engineered Railroad Worm Luciferase and 6'-Amino-Analogs for Bioimaging Purposes. Int J Mol Sci. 2020 Dec 30;22(1):303. doi: 10.3390/ijms22010303. PMID: 33396708; PMCID: PMC7794784.