Hexaminolevulinate HCl
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. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).
1: Togsverd-Bo K, Lerche CM, Philipsen PA, Hædersdal 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, Håvåg 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.
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, Håvåg 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.
| Chemical | |
|---|---|
| CAS Num | 140898-91-5 |
| Chemical Formula | C11H22ClNO3 |
| Molecular Weight | 251.75 |
| IUPAC Chemical Name | hexyl 5-amino-4-oxopentanoate hydrochloride. |
| Elemental Analysis | C, 52.48; H, 8.81; Cl, 14.08; N, 5.56; O, 19.07 |
| Synonym | P-1206. Abbreviation |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | O=C(OCCCCCC)CCC(CN)=O.[H]Cl |
| Biological | |
| Targets and Effects | photosensitizer |
| Pathways | Apoptosis |
| Physical | |
| 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). |
| Shelf Life | >2 years if stored properly |
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