Hexaminolevulinate hydrochloride | Hexyl 5-aminolevulinate | CAS#140898-91-5 | photodynamic | PDT drug

MedKoo Cat#: 100423 | Name: Hexaminolevulinate HCl

Description:

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

Hexaminolevulinate hydrochloride, also known as hexyl 5-aminolevulinate HCl, is the hexyl ester of 5-aminolevulinic acid (ALA) with photodynamic properties. As a precursor of photoactive porphorins, hexyl 5-aminolevulinate induces the endogenous production of the photosensitizer protoporphyrin IX (PPIX) which accumulates selectively in tumor tissue. When exposed to specific wavelengths of light, PPIX is activated and, depending on the wavelength and/or intensity of light, either fluoresces, thereby allowing tumor imaging, or induces tumor cell apoptosis.

Chemical Structure

Hexaminolevulinate HCl

CAS#140898-91-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 100423

Name: Hexaminolevulinate HCl

CAS#: 140898-91-5 (HCl)

Chemical Formula: C11H22ClNO3

Exact Mass: 0.0000

Molecular Weight: 251.75

Elemental Analysis: C, 52.48; H, 8.81; Cl, 14.08; N, 5.56; O, 19.07

Price and Availability

Size	Price	Availability
200mg	USD 150.00	Ready to ship
500mg	USD 250.00	Ready to ship
1g	USD 425.00	Ready to ship
2g	USD 700.00	Ready to ship
5g	USD 1,450.00	Ready to ship
10g	USD 2,350.00	Ready to ship

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Related CAS #

140898-91-5 (HCl) 140898-97-1 (free)

Synonym

P-1206. Abbreviation: HAL. hexaminolevulinate; 5-Aminolevulinic acid hexyl ester; 5-ALA hexylester; US brand names: Hexvix; Cysview

IUPAC/Chemical Name

hexyl 5-amino-4-oxopentanoate hydrochloride.

InChi Key

LZYXPFZBAZTOCH-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H21NO3.ClH/c1-2-3-4-5-8-15-11(14)7-6-10(13)9-12;/h2-9,12H2,1H3;1H

SMILES Code

O=C(OCCCCCC)CCC(CN)=O.[H]Cl

Appearance

White to off-white 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, not in water

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TZC50722

QC Data

View QC data: current batch, Lot#TZC50722

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Hexaminolevulinate hydrochloride is a fluorescent agent.

In vitro activity:

To find optimal regime for hexaminolevulinate (HAL)-induced photodynamic extracorporeal purging of BM, experimental conditions for incubation of HAL in L1210 cell line, BM cells and their mixtures were examined. As the number of dead L1210 cells after 4-h incubation in serum-free medium was found to be dependent on cell density, the density of 8 × 105 cells/ml was chosen to keep the percentage of dead L1210 cells below 10%. The same cell density was used for BM cells as well as for cell mixtures. Production of PpIX by cells was analyzed by means of flow cytometry and fluorescence spectroscopy. PpIX production in the L1210 cells incubated for 4 h in serum-free medium with different amounts of HAL leveled off at the concentration of 20 μM (Figure 1a). In pure mouse BM, two main populations of living cells, could be clearly separated by flow cytometric analysis, namely granulocytes and mixed population. For both populations, the mild increase in PpIX production was observed even at 100 μM HAL (Figure 1b). The fluorescence signal of the remaining BM cells did not exceed the signal of either of the two populations. The absolute amounts of PpIX produced by HAL in the tumor cell line and BM cells were measured by means of fluorescence spectroscopy relative to protein content (Figure 1c). L1210 cells produced higher amounts of PpIX than mixture of BM cells. Reference: Bone Marrow Transplant. 2010 Oct;45(10):1553-61. https://doi.org/10.1038/bmt.2009.382

In vivo activity:

The median time to first SCC was significantly longer for mice treated with prophylactic HAL-PDT (2%, 6% and 20% HAL, 264 days) than mice exposed to UVR (186 days) and UVR + placebo-PDT (199 days) (P < 0.0001). The therapeutic efficacy of HAL-PDT showed cure rates of 23-61.5% (P = 0.11). Similar PpIX fluorescence intensity and severity of clinical reactions were seen for HAL-groups, although mice developed more intense hyper-pigmentation when treated with 20% MAL-PDT compared with 2% HAL-PDT. Reference: Exp Dermatol. 2010 Aug;19(8):e166-72. https://doi.org/10.1111/j.1600-0625.2009.01035.x

	Solvent	mg/mL	mM
Solubility
	DMSO	41.0	162.86

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 251.75 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:

1. Čunderlíková B, Vasovič V, Sieber F, Furre T, Nesland JM, Peng Q. Hexaminolevulinate-mediated photodynamic purging of leukemia cells from BM. Bone Marrow Transplant. 2010 Oct;45(10):1553-61. doi: 10.1038/bmt.2009.382. Epub 2010 Feb 1. PMID: 20118993. 2. Čunderlíková B, Vasovič V, Sieber F, Furre T, Borgen E, Nesland JM, Peng Q. Hexaminolevulinate-mediated photodynamic purging of marrow grafts with murine breast carcinoma. Bone Marrow Transplant. 2011 Aug;46(8):1118-27. doi: 10.1038/bmt.2010.277. Epub 2010 Nov 8. PMID: 21057550.

In vivo protocol:

1. Togsverd-Bo K, Lerche CM, Poulsen T, Wulf HC, Haedersdal M. Photodynamic therapy with topical methyl- and hexylaminolevulinate for prophylaxis and treatment of UV-induced SCC in hairless mice. Exp Dermatol. 2010 Aug;19(8):e166-72. doi: 10.1111/j.1600-0625.2009.01035.x. PMID: 20100196. 2. Čunderlíková B, Vasovič V, Sieber F, Furre T, Nesland JM, Peng Q. Hexaminolevulinate-mediated photodynamic purging of leukemia cells from BM. Bone Marrow Transplant. 2010 Oct;45(10):1553-61. doi: 10.1038/bmt.2009.382. Epub 2010 Feb 1. PMID: 20118993.

1: Togsverd-Bo K, Lerche CM, Philipsen PA, HÃ¦dersdal M, Wulf HC. Artificial daylight photodynamic therapy with "non-inflammatory" doses of hexyl aminolevulinate only marginally delays SCC development in UV-exposed hairless mice. Photochem Photobiol Sci. 2013 Sep 24. [Epub ahead of print] PubMed PMID: 24064675. 2: Rink M, Babjuk M, Catto JW, Jichlinski P, Shariat SF, Stenzl A, Stepp H, Zaak D, Witjes JA. Hexyl aminolevulinate-guided fluorescence cystoscopy in the diagnosis and follow-up of patients with non-muscle-invasive bladder cancer: a critical review of the current literature. Eur Urol. 2013 Oct;64(4):624-38. doi: 10.1016/j.eururo.2013.07.007. Epub 2013 Jul 19. PubMed PMID: 23906669. 3: Togsverd-Bo K, Lerche CM, Philipsen PA, Poulsen T, Wulf HC, Haedersdal M. Porphyrin biodistribution in UV-exposed murine skin after methyl- and hexyl-aminolevulinate incubation. Exp Dermatol. 2012 Apr;21(4):260-4. doi: 10.1111/j.1600-0625.2012.01442.x. Epub 2012 Feb 10. PubMed PMID: 22320713. 4: Baglo Y, Sousa MM, Slupphaug G, Hagen L, HÃ¥vÃ¥g S, Helander L, Zub KA, Krokan HE, Gederaas OA. Photodynamic therapy with hexyl aminolevulinate induces carbonylation, posttranslational modifications and changed expression of proteins in cell survival and cell death pathways. Photochem Photobiol Sci. 2011 Jul;10(7):1137-45. doi: 10.1039/c0pp00369g. Epub 2011 Mar 30. PubMed PMID: 21448498. 5: Sievert KD, Kruck S. Hexyl aminolevulinate fluorescence cystoscopy in bladder cancer. Expert Rev Anticancer Ther. 2009 Aug;9(8):1055-63. doi: 10.1586/era.09.73. Review. PubMed PMID: 19671025. 6: Juzeniene A, Nielsen KP, Zhao L, Ryzhikov GA, Biryulina MS, Stamnes JJ, Stamnes K, Moan J. Changes in human skin after topical PDT with hexyl aminolevulinate. Photodiagnosis Photodyn Ther. 2008 Sep;5(3):176-81. doi: 10.1016/j.pdpdt.2008.07.001. Epub 2008 Aug 28. PubMed PMID: 19356652. 7: Berrahmoune S, Fotinos N, Bezdetnaya L, Lange N, Guedenet JC, Guillemin F, D'Hallewin MA. Analysis of differential PDT effect in rat bladder tumor models according to concentrations of intravesical hexyl-aminolevulinate. Photochem Photobiol Sci. 2008 Sep;7(9):1018-24. doi: 10.1039/b804921a. Epub 2008 Jul 23. PubMed PMID: 18754047. 8: Vaucher L, Jichlinski P, Lange N, Ritter-Schenk C, van den Bergh H, Kucera P. Hexyl-aminolevulinate-mediated photodynamic therapy: how to spare normal urothelium. An in vitro approach. Lasers Surg Med. 2007 Jan;39(1):67-75. PubMed PMID: 17096415. 9: Frampton JE, Plosker GL. Hexyl aminolevulinate in the detection of bladder cancer: profile report. BioDrugs. 2006;20(5):317-20. PubMed PMID: 17025378. 10: Frampton JE, Plosker GL. Hexyl aminolevulinate: in the detection of bladder cancer. Drugs. 2006;66(4):571-8; discussion 579-80. Review. PubMed PMID: 16597168.