14-Ethyl-9-(1-(hexyloxy)ethyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbine propanoic acid

  • CAT Number: M102904
  • CAS Number: 149402-51-7
  • Molecular Formula: C39H48N4O4
  • Molecular Weight: 636.837
  • Purity: ≥95%
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Photochlor, also known as HTTP, is a lipophilic, second-generation, chlorin-based photosensitizer. Upon intravenous administration, HPPH selectively accumulates in the cytoplasm of cancer or pre-cancerous cells. When laser light is applied, a photodynamic reaction between HPPH and oxygen occurs, resulting in the production of cytotoxic free radicals and singlet oxygen and free radical-mediated cell death. Compared to the first-generation photosensitizer porfimer sodium, HPPH shows improved pharmacokinetic properties and causes only mild skin photosensitivity which declines rapidly within a few days after administration.

Catalog Number M102904
CAS Number 149402-51-7
Molecular Formula

C39H48N4O4

Purity 95%
Storage Store at RT
InChI InChI=1S/C39H48N4O4/c1-8-10-11-12-15-47-24(7)36-22(5)30-17-29-21(4)26(13-14-35(45)46)38(42-29)27-16-34(44)37-23(6)31(43-39(27)37)18-32-25(9-2)20(3)28(40-32)19-33(36)41-30/h17-19,21,24,26,40-41H,8-16H2,1-7H3,(H,45,46)/t21-,24?,26-/m0/s1
InChIKey ODJVLHDVEGAIAW-USOGPTGWSA-N
SMILES CCCCCCOC(C)C1=C2C=C3C(=C(C(=CC4=NC5=C(CC(=O)C5=C4C)C6=NC(=CC(=C1C)N2)C(C6CCC(=O)O)C)N3)CC)C
Reference

</br>1: Sun G, Anderson MA, Gorospe EC, Leggett CL, Lutzke LS, Wong Kee Song LM, Levy M, Wang KK. Synergistic effects of photodynamic therapy with HPPH and gemcitabine in pancreatic cancer cell lines. Lasers Surg Med. 2012 Nov;44(9):755-61. doi: 10.1002/lsm.22073. Epub 2012 Sep 27. PubMed PMID: 23018618.</br>2: Nava HR, Allamaneni SS, Dougherty TJ, Cooper MT, Tan W, Wilding G, Henderson BW. Photodynamic therapy (PDT) using HPPH for the treatment of precancerous lesions associated with Barrett/’s esophagus. Lasers Surg Med. 2011 Sep;43(7):705-12. doi: 10.1002/lsm.21112. PubMed PMID: 22057498; PubMed Central PMCID: PMC3218433.</br>3: Srivatsan A, Ethirajan M, Pandey SK, Dubey S, Zheng X, Liu TH, Shibata M, Missert J, Morgan J, Pandey RK. Conjugation of cRGD peptide to chlorophyll a based photosensitizer (HPPH) alters its pharmacokinetics with enhanced tumor-imaging and photosensitizing (PDT) efficacy. Mol Pharm. 2011 Aug 1;8(4):1186-97. doi: 10.1021/mp200018y. Epub 2011 Jul 1. PubMed PMID: 21702452; PubMed Central PMCID: PMC3148296.</br>4: Sunar U, Rohrbach D, Rigual N, Tracy E, Keymel K, Cooper MT, Baumann H, Henderson BH. Monitoring photobleaching and hemodynamic responses to HPPH-mediated photodynamic therapy of head and neck cancer: a case report. Opt Express. 2010 Jul 5;18(14):14969-78. doi: 10.1364/OE.18.014969. PubMed PMID: 20639983; PubMed Central PMCID: PMC2964147.</br>5: Spernyak JA, White WH 3rd, Ethirajan M, Patel NJ, Goswami L, Chen Y, Turowski S, Missert JR, Batt C, Mazurchuk R, Pandey RK. Hexylether derivative of pyropheophorbide-a (HPPH) on conjugating with 3gadolinium(III) aminobenzyldiethylenetriaminepentaacetic acid shows potential for in vivo tumor imaging (MR, Fluorescence) and photodynamic therapy. Bioconjug Chem. 2010 May 19;21(5):828-35. doi: 10.1021/bc9005317. PubMed PMID: 20387862; PubMed Central PMCID: PMC2874103.</br>6: Zheng X, Morgan J, Pandey SK, Chen Y, Tracy E, Baumann H, Missert JR, Batt C, Jackson J, Bellnier DA, Henderson BW, Pandey RK. Conjugation of 2-(1/’-hexyloxyethyl)-2-devinylpyropheophorbide-a (HPPH) to carbohydrates changes its subcellular distribution and enhances photodynamic activity in vivo. J Med Chem. 2009 Jul 23;52(14):4306-18. doi: 10.1021/jm9001617. PubMed PMID: 19507863; PubMed Central PMCID: PMC2913405.</br>7: Weston MA, Patterson MS. Simple photodynamic therapy dose models fail to predict the survival of MLL cells after HPPH-PDT in vitro. Photochem Photobiol. 2009 May-Jun;85(3):750-9. doi: 10.1111/j.1751-1097.2008.00494.x. Epub 2008 Dec 18. PubMed PMID: 19140895.</br>8: Kim YC, Kang HE, Lee MG. Pharmacokinetics of phenytoin and its metabolite, 4/’-HPPH, after intravenous and oral administration of phenytoin to diabetic rats induced by alloxan or streptozotocin. Biopharm Drug Dispos. 2008 Jan;29(1):51-61. PubMed PMID: 18022993.</br>9: Brinkmann C, García F, Morey JV, McPartlin M, Singh S, Wheatley AE, Wright DS. Stepwise nucleophilic substitution of manganocene, syntheses and structures of the dimer [CpMn(hpp)]2 and the unusual manganate cage [LiMn(hpp)3]2 (hppH = 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2,a]pyrimidine). Dalton Trans. 2007 Apr 28;(16):1570-2. Epub 2007 Mar 15. PubMed PMID: 17426857.</br>10: Bellnier DA, Greco WR, Nava H, Loewen GM, Oseroff AR, Dougherty TJ. Mild skin photosensitivity in cancer patients following injection of Photochlor (2-[1-hexyloxyethyl]-2-devinyl pyropheophorbide-a; HPPH) for photodynamic therapy. Cancer Chemother Pharmacol. 2006 Jan;57(1):40-5. Epub 2005 Nov 5. PubMed PMID: 16001178.</br>

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