WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H201724
CAS#: 215808-49-4
Description: Lemuteporfin, also known DRM05, QLT-0074 , is a diester derivative of benzoporphyrin derivative, is a neutral, uncharged benzoporphyrin molecule having symmetrical diethylene glycol groups; this maintains its amphiphilic character. It differs from another benzoporphyrin derivative, verteporfin, as it is a single regioisomer. verteporfin, consists of two regioisomers present in equal proportions and is negatively charged at neutral pH.
Hodoodo Cat#: H201724
Name: Lemuteporfin
CAS#: 215808-49-4
Chemical Formula: C44H48N4O10
Exact Mass: 792.34
Molecular Weight: 792.870
Elemental Analysis: C, 66.65; H, 6.10; N, 7.07; O, 20.18
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Synonym: QLT0074; QLT 0074; QLT-0074; DRM05; DRM 05; DRM-05; EA 6; Lemuteporfin.
IUPAC/Chemical Name: Dimethyl (2RS,21SR)-8-ethenyl-13,17-bis(3-(2-hydroxyethoxycarbonyl)-3-oxopropyl)-2,7,12,18-tetramethyl-2,21-dihydrobenzo(b)porphyrin-21,22-dicarboxylate
InChi Key: IKKAMLAWMNGIGM-CUFIPODPSA-N
InChi Code: InChI=1S/C44H48N4O10/c1-8-26-23(2)32-20-37-30-12-9-29(42(53)55-6)41(43(54)56-7)44(30,5)38(48-37)22-33-25(4)28(11-14-40(52)58-18-16-50)36(47-33)21-35-27(10-13-39(51)57-17-15-49)24(3)31(46-35)19-34(26)45-32/h8-9,12,19-22,41,45,47,49-50H,1,10-11,13-18H2,2-7H3/b31-19-,32-20-,33-22-,34-19-,35-21-,36-21-,37-20-,38-22-/t41-,44+/m0/s1
SMILES Code: CC(C(/C=C1C(C=C)=C(/C(N/1)=C/C2=N/C([C@@]3([C@@H](C(C(OC)=O)=CC=C32)C(OC)=O)C)=C\C4=C5C)C)=N/C6=C\C(N4)=C5CCC(OCCO)=O)=C6CCC(OCCO)=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, 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: Photocytotoxicity assays in vitro showed that lemuteporfin is a potent photo sensitizer with very little cytotoxicity at high concentrations (>3.0 microM) in the absence of light. Cytotoxicity and fluorescence quantification studies indicated rapid uptake and release of the photosensitizer by L1210 cells. The photosensitizer was taken up by rapidly proliferating L1210 cells and Con A activated splenocytes to a greater extent than by unstimulated splenocytes. Mouse studies revealed rapid delivery of lemuteporfin to plasma and skin. The capacity of lemuteporfin to photosensitize skin and control tumor growth was greatest at relatively early (30 min or less) light exposure times, indicating rapid clearance kinetics in vivo. Thus, lemuteporfin may be useful in therapies where a high potency and rapid clearance are required, thus minimizing the potential for unwanted skin photosensitivity. [ source: Photochem Photobiol. 2006, Jan-Feb;82(1):219-24] Lemuteporfin is a highly potent and selective topical photodynamic therapy (PDT) approach to sebaceous gland targeting for moderate to severe acne. The anticipated clinical profile for lemuteporfin will be to obtain substantial anti-sebaceous gland effects, approaching AccutaneTM efficacy in acne, with no risk of systemic toxicity or damage to surrounding skin structures. The cellular uptake of lemuteporfin was rapid, with maximum levels reached within 20 min. Mitogen-activated lymphoid cells accumulated more of the lemuteporfin than their quiescent equivalents, supporting selectivity. Photosensitizer fluorescence in the skin increased rapidly within the first few minutes following intravenous administration to mice, then decreased over the next 24 h. Skin photosensitivity reactions indicated rapid clearance of the photosensitizer. Lemuteporfin shares an absorption spectrum typical of benzoporphyrin derivatives and can be activated with light in the ultraviolet, blue and red parts of the spectrum. Favorable characteristics of benzoporphyrin photosensitizers include their absorption peak near 690 nm, a wavelength that penetrates tissue relatively efficiently. Another advantage is that upon activation, there is a high quantum yield of singlet oxygen. Lemuteporfin is presently being investigated clinically in photodynamic therapy. Source: Boch R, Canaan AJ, Cho A, Dolphin DD, Hong L, Jain AK, North JR, Richter AM, Smits C, Sternberg ED. Cellular and antitumor activity of a new diethylene glycol benzoporphyrin derivative (lemuteporfin). Photochem Photobiol. 2006 Jan-Feb;82(1):219-24.
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The following data is based on the product molecular weight 792.87 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: | |
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1. Surface topographies for non-toxic bioadhesion control By Brennan, Anthony B.; Long, Christopher James; Bagan, Joseph W.; Schumacher, James Frederick; Spiecker, Mark M. From U.S. Pat. Appl. Publ. (2010), US 20100226943 A1 20100909.
2. Combination of photodynamic therapy and anti-vegf agents in the treatment of unwanted choroidal neovasculature By Strong, Andrew; Hao, Yong From PCT Int. Appl. (2010), WO 2010069073 A1 20100624.
3. Photodynamic therapy of sebaceous gland disorders By Tao, Jing-Song; Curaudeau, Alain H.; Hunt, David; Boniface, Graham; Rubinachik, Valery From PCT Int. Appl. (2009), WO 2009093144 A2 20090730.
4. Photodynamic therapy for the treatment of hidradenitis suppurativa By Tao, Jing-Song; Hunt, David W. C. From PCT Int. Appl. (2008), WO 2008052350 A1 20080508.
5. Fractionated versus Standard Continuous Light Delivery in Interstitial Photodynamic Therapy of Dunning Prostate Carcinomas By Xiao, Zhengwen; Halls, Steve; Dickey, Dwayne; Tulip, John; Moore, Ronald B. From Clinical Cancer Research (2007), 13(24), 7496-7505.
6. Interstitial photodynamic therapy of the canine prostate using intra-arterial administration of photosensitizer and computerized pulsed light delivery By Xiao, Zhengwen; Dickey, Dwayne; Owen, Richard J.; Tulip, John; Moore, Ronald From Journal of Urology (New York, NY, United States) (2007), 178(1), 308-313.
7. Ultraviolet B light stimulates interleukin-20 expression by human epithelial keratinocytes By Hunt, David W. C.; Boivin, Wendy A.; Fairley, Lindsay A.; Jovanovic, Miroslava M.; King, Diane E.; Salmon, Ruth A.; Utting, Oliver B. From Photochemistry and Photobiology (2006), 82(5), 1292-1300.
8. Cellular and antitumor activity of a new diethylene glycol benzoporphyrin derivative (lemuteporfin) By Boch, Ron; Canaan, Alice J.; Cho, Angela; Dolphin, David D.; Hong, Lina; Jain, Ashok K.; North, John R.; Richter, Anna M.; Smits, Claire; Sternberg, Ethan D. From Photochemistry and Photobiology (2006), 82(Jan./Feb.), 219-224.
9. Photodynamic therapy for the treatment of prostatic conditions By Rubinchik, Valery; Visser, Mitchell D. From PCT Int. Appl. (2005), WO 2005077457 A1 20050825.
10. Photodynamic therapy for the treatment of acne By Curaudeau, Alain H.; Neyndorff, Herma C.; Tao, Jing-Song; Lam, Morgan Chun; Curry, Patrick Mark; Rubinchik, Valery; Hunt, David W. C. From PCT Int. Appl. (2005), WO 2005074987 A1 20050818.
11. Photodynamic therapy for the treatment of prostatic conditions By Boch, Ronald Erwin; North, John Robert; Rubinchik, Valery; Visser, Mitchell D. From PCT Int. Appl. (2004), WO 2004071579 A2 20040826.
12. Photodynamic therapy for the treatment of hair loss By Simkin, Guillermo O.; Richter, Anna M.; Hunt, David W. C.; North, John Robert; Lutwyche, Peter; Boch, Ronald Erwin; Houle, Jean-Marie From U.S. Pat. Appl. Publ. (2004), US 20040029856 A1 20040212.
13. Compositions and methods for delivery of photosensitive drugs By Allemann, Eric; Konan, Yvette; Gurny, Robert; Boch, Ronald Erwin From PCT Int. Appl. (2003), WO 2003097096 A1 20031127.
