AkaLumine HCl | CAS#2558205-28-8 | luciferin analogue

MedKoo Cat#: 128013 | Name: AkaLumine HCl

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 HCl

CAS#2558205-28-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 128013

Name: AkaLumine HCl

CAS#: 2558205-28-8 (HCl)

Chemical Formula: C16H19ClN2O2S

Exact Mass: 338.0856

Molecular Weight: 338.85

Elemental Analysis: C, 56.71; H, 5.65; Cl, 10.46; N, 8.27; O, 9.44; S, 9.46

Price and Availability

Size	Price	Availability
5mg	USD 150.00	Ready to ship
10mg	USD 250.00	Ready to ship
25mg	USD 450.00	Ready to ship
50mg	USD 750.00	Ready to ship
100mg	USD 1,250.00	Ready to ship
1g	USD 4,450.00	2 Weeks

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Related CAS #

1176235-08-7 (free base) 2558205-28-8 (HCl)

Synonym

AkaLumine hydrochloride; TokeOni; AkaLumine (hydrochloride); AkaLumine HCl

IUPAC/Chemical Name

(S)-2-((1E,3E)-4-(4-(dimethylamino)phenyl)buta-1,3-dien-1-yl)-4,5-dihydrothiazole-4-carboxylic acid hydrochloride

InChi Key

PZCNKVAGZCXXHX-SSRSOBHISA-N

InChi Code

InChI=1S/C16H18N2O2S.ClH/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);1H/b5-3+,6-4+;/t14-;/m1./s1

SMILES Code

CN(C1=CC=C(/C=C/C=C/C2=N[C@@H](C(O)=O)CS2)C=C1)C.Cl

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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#T25D01P22

QC Data

View QC data: current batch, Lot#T25D01P22

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Km: 2.06 μM (recombinant Fluc protein)

In vitro activity:

Although the luminogenic properties of AkaLumine-HCl and D-luciferin for in vitro parasite detection were comparable at equal substrate concentrations, AkaLumine-HCl proved to be unsuitable for in vivo infection follow-up due to high background signals in the liver. Reference: 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.

In vivo activity:

oFluc and Akaluc were similarly bright in the pancreas for in vivo BLI; however, Akaluc was superior to oFluc for brain imaging, because its substrate, AkaLumine-HCl, was distributed to the brain more efficiently than the oFluc substrate, D-luciferin. We also demonstrated that the lights produced by oFluc and Akaluc were sufficiently spectrally distinct from each other for dual-color imaging in a single living mouse. Reference: Nakashiba T, Ogoh K, Iwano S, Sugiyama T, Mizuno-Iijima S, Nakashima K, Mizuno S, Sugiyama F, Yoshiki A, Miyawaki A, Abe K. Development of two mouse strains conditionally expressing bright luciferases with distinct emission spectra as new tools for in vivo imaging. Lab Anim (NY). 2023 Oct;52(10):247-257. doi: 10.1038/s41684-023-01238-6. Epub 2023 Sep 7. PMID: 37679611; PMCID: PMC10533401.

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	295.12
	H2O	50.0	147.56

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 338.85 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.

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

Formulation protocol:

In vitro protocol:

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. 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.

In vivo protocol:

Nakashiba T, Ogoh K, Iwano S, Sugiyama T, Mizuno-Iijima S, Nakashima K, Mizuno S, Sugiyama F, Yoshiki A, Miyawaki A, Abe K. Development of two mouse strains conditionally expressing bright luciferases with distinct emission spectra as new tools for in vivo imaging. Lab Anim (NY). 2023 Oct;52(10):247-257. doi: 10.1038/s41684-023-01238-6. Epub 2023 Sep 7. PMID: 37679611; PMCID: PMC10533401. Miyabara H, Hirano R, Watanabe S, Soriano JCC, Watanabe H, Kuchimaru T, Kitada N, Kadonosono T, Maki SA, Kondoh G, Kizaka-Kondoh S. In vivo optical imaging of tumor stromal cells with hypoxia-inducible factor activity. Cancer Sci. 2023 Oct;114(10):3935-3945. doi: 10.1111/cas.15907. Epub 2023 Jul 22. PMID: 37482942; PMCID: PMC10551579.

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.