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MedKoo Cat#: 500101 | Name: MPPa (Methyl pyropheophorbide-a)
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Description:

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

Pyropheophorbide-a methyl ester (MPPa) is a PDT photosensitizer, and is also a semisynthetic natural product derived from chlorophyll a. The absorption peak of MPPa in organic solvent and in cells was at 667 and 674 nm, respectively. 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide reduction assay showed that MPPa had no dark cytotoxicity.

Chemical Structure

MPPa (Methyl pyropheophorbide-a)
MPPa (Methyl pyropheophorbide-a)
CAS#6453-67-4

Theoretical Analysis

MedKoo Cat#: 500101

Name: MPPa (Methyl pyropheophorbide-a)

CAS#: 6453-67-4

Chemical Formula: C34H36N4O3

Exact Mass: 548.2787

Molecular Weight: 548.67

Elemental Analysis: C, 74.43; H, 6.61; N, 10.21; O, 8.75

Price and Availability

Size Price Availability Quantity
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,350.00 Ready to ship
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Synonym
MPPa; MPPA; NSC267052; NSC-267052; NSC 267052; Pyropheophorbidea; Methyl pyropheophorbide a.
IUPAC/Chemical Name
methyl 3-Phorbinepropanoate, 9-ethenyl-14-ethyl-4,8,13,18-tetramethyl-20-oxo-, (3S,4S)-
InChi Key
RYLBYBPLWNFWPG-CMMLGHQLSA-N
InChi Code
InChI=1S/C34H36N4O3/c1-8-20-16(3)24-13-26-18(5)22(10-11-31(40)41-7)33(37-26)23-12-30(39)32-19(6)27(38-34(23)32)15-29-21(9-2)17(4)25(36-29)14-28(20)35-24/h8,13-15,18,22,35,38H,1,9-12H2,2-7H3/b24-13-,25-14-,26-13-,27-15-,28-14-,29-15-,33-23-/t18-,22-/m0/s1
SMILES Code
CC1=C(/C=C(N=C2/C=C(N/C3=C\C4=N/C([C@@H](CCC(OC)=O)[C@@H]4C)=C5/C6)/C(C=C)=C3C)/C(CC)=C2C)NC5=C1C6=O
Appearance
Black solid powder
Purity
>30% (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
     
Biological target:
Pyropheophorbide-a methyl ester (MPPa) is a PDT photosensitizer.
In vitro activity:
This study demonstrated that PPME photosensitization activated NF-kappaB transcription factor in colon cancer cells. Unexpectedly, this activation occurred in two separate waves, i.e. a rapid and transient one and a second slower but sustained phase. The former was due to photosensitization by PPME localized in the cytoplasmic membrane which triggered interleukin-1 receptor internalization and the transduction pathways controlled by the interleukin-1 type I receptor. Reference: J Biol Chem. 1999 Jan 29;274(5):2988-3000. https://pubmed.ncbi.nlm.nih.gov/9915837/
In vivo activity:
By other in vitro studies, this study found MPPa-PDT induced apoptotic mainly via the mitochondrial/Caspase-9/Caspase-3 pathway and could restrain the cell cycle progression from the more sensitive G0/G1-phases. In vivo, the tumour growth was significantly inhibited after PDT, and many apoptotic cells could be seen by histopathological examinations. These results indicate the death way of cells induced by MPPa is mainly via mild apoptotic and the cure effect is obvious, suggesting that MPPa is a potential photosensitizer of photodynamic therapy for prostate cancer. Reference: Biochem Biophys Res Commun. 2006 Sep 22;348(2):413-20. https://pubmed.ncbi.nlm.nih.gov/16889752/
Solvent mg/mL mM
Solubility
Soluble in CHCl3 10.0 18.20
DMSO 2.5 4.56
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 548.67 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.

Recalculate based on batch purity %
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:
1. Sun X, Leung WN. Photodynamic therapy with pyropheophorbide-a methyl ester in human lung carcinoma cancer cell: efficacy, localization and apoptosis. Photochem Photobiol. 2002 Jun;75(6):644-51. doi: 10.1562/0031-8655(2002)075<0644:ptwpam>2.0.co;2. PMID: 12081327. 2. Matroule JY, Bonizzi G, Morlière P, Paillous N, Santus R, Bours V, Piette J. Pyropheophorbide-a methyl ester-mediated photosensitization activates transcription factor NF-kappaB through the interleukin-1 receptor-dependent signaling pathway. J Biol Chem. 1999 Jan 29;274(5):2988-3000. doi: 10.1074/jbc.274.5.2988. PMID: 9915837. 3. Huang L, Lin H, Chen Q, Yu L, Bai D. MPPa-PDT suppresses breast tumor migration/invasion by inhibiting Akt-NF-κB-dependent MMP-9 expression via ROS. BMC Cancer. 2019 Nov 29;19(1):1159. doi: 10.1186/s12885-019-6374-x. PMID: 31783821; PMCID: PMC6884812. 4. Tian Y, Leung W, Yue K, Mak N. Cell death induced by MPPa-PDT in prostate carcinoma in vitro and in vivo. Biochem Biophys Res Commun. 2006 Sep 22;348(2):413-20. doi: 10.1016/j.bbrc.2006.07.071. Epub 2006 Jul 26. PMID: 16889752.
In vitro protocol:
1. Sun X, Leung WN. Photodynamic therapy with pyropheophorbide-a methyl ester in human lung carcinoma cancer cell: efficacy, localization and apoptosis. Photochem Photobiol. 2002 Jun;75(6):644-51. doi: 10.1562/0031-8655(2002)075<0644:ptwpam>2.0.co;2. PMID: 12081327. 2. Matroule JY, Bonizzi G, Morlière P, Paillous N, Santus R, Bours V, Piette J. Pyropheophorbide-a methyl ester-mediated photosensitization activates transcription factor NF-kappaB through the interleukin-1 receptor-dependent signaling pathway. J Biol Chem. 1999 Jan 29;274(5):2988-3000. doi: 10.1074/jbc.274.5.2988. PMID: 9915837.
In vivo protocol:
1. Huang L, Lin H, Chen Q, Yu L, Bai D. MPPa-PDT suppresses breast tumor migration/invasion by inhibiting Akt-NF-κB-dependent MMP-9 expression via ROS. BMC Cancer. 2019 Nov 29;19(1):1159. doi: 10.1186/s12885-019-6374-x. PMID: 31783821; PMCID: PMC6884812. 2. Tian Y, Leung W, Yue K, Mak N. Cell death induced by MPPa-PDT in prostate carcinoma in vitro and in vivo. Biochem Biophys Res Commun. 2006 Sep 22;348(2):413-20. doi: 10.1016/j.bbrc.2006.07.071. Epub 2006 Jul 26. PMID: 16889752.
1: Wu D, Liu Z, Fu Y, Zhang Y, Tang N, Wang Q, Tao L. Efficacy of 2-(1-hexyloxyethyl)-2-devinyl pyropheophorbide-a in photodynamic therapy of human esophageal squamous cancer cells. Oncol Lett. 2013 Oct;6(4):1111-1119. Epub 2013 Jul 25. PubMed PMID: 24137473; PubMed Central PMCID: PMC3796395. 2: Rigual N, Shafirstein G, Cooper MT, Baumann H, Bellnier DA, Sunar U, Tracy EC, Rohrbach DJ, Wilding G, Tan W, Sullivan M, Merzianu M, Henderson BW. Photodynamic therapy with 3-(1'-hexyloxyethyl) pyropheophorbide a for cancer of the oral cavity. Clin Cancer Res. 2013 Dec 1;19(23):6605-13. doi: 10.1158/1078-0432.CCR-13-1735. Epub 2013 Oct 2. PubMed PMID: 24088736. 3: Barnes CA, Rasmussen SL, Petrich JW, Rasmussen MA. Determination of the concentration of potential efflux pump inhibitors, pheophorbide a and pyropheophorbide a, in the feces of animals by fluorescence spectroscopy. J Agric Food Chem. 2012 Oct 24;60(42):10456-60. doi: 10.1021/jf3023063. Epub 2012 Oct 10. PubMed PMID: 23002917. 4: Zhou A, Wei Y, Wu B, Chen Q, Xing D. Pyropheophorbide A and c(RGDyK) comodified chitosan-wrapped upconversion nanoparticle for targeted near-infrared photodynamic therapy. Mol Pharm. 2012 Jun 4;9(6):1580-9. doi: 10.1021/mp200590y. Epub 2012 May 8. PubMed PMID: 22533630. 5: Golovina GV, Ol'shevskaia VA, Kalinina VN, Shtil' AA, Kuz'min VA. [Role of the medium acidity in the complexes formation of pyropheophorbide a with albumin and lipoproteins]. Bioorg Khim. 2011 Sep-Oct;37(5):718-20. Russian. PubMed PMID: 22332371. 6: Arian D, Kovbasyuk L, Mokhir A. Control of the photocatalytic activity of bimetallic complexes of pyropheophorbide-a by nucleic acids. Inorg Chem. 2011 Dec 5;50(23):12010-7. doi: 10.1021/ic201408h. Epub 2011 Nov 2. PubMed PMID: 22047611. 7: Ethirajan M, Joshi P, William WH 3rd, Ohkubo K, Fukuzumi S, Pandey RK. Remarkable regioselective position-10 bromination of bacteriopyropheophorbide-a and ring-B reduced pyropheophorbide-a. Org Lett. 2011 Apr 15;13(8):1956-9. doi: 10.1021/ol200314v. Epub 2011 Mar 21. PubMed PMID: 21417431; PubMed Central PMCID: PMC3076286. 8: Xu J, Xia X, Leung AW, Xiang J, Jiang Y, Yu H, Bai D, Li X, Xu C. Sonodynamic action of pyropheophorbide-a methyl ester induces mitochondrial damage in liver cancer cells. Ultrasonics. 2011 May;51(4):480-4. doi: 10.1016/j.ultras.2010.11.014. Epub 2010 Dec 3. PubMed PMID: 21183195. 9: Bouslama L, Hayashi K, Lee JB, Ghorbel A, Hayashi T. Potent virucidal effect of pheophorbide a and pyropheophorbide a on enveloped viruses. J Nat Med. 2011 Jan;65(1):229-33. doi: 10.1007/s11418-010-0468-8. Epub 2010 Sep 11. PubMed PMID: 20835849. 10: Guelluy PH, Fontaine-Aupart MP, Grammenos A, Lécart S, Piette J, Hoebeke M. Optimizing photodynamic therapy by liposomal formulation of the photosensitizer pyropheophorbide-a methyl ester: in vitro and ex vivo comparative biophysical investigations in a colon carcinoma cell line. Photochem Photobiol Sci. 2010 Sep 24;9(9):1252-60. doi: 10.1039/c0pp00100g. Epub 2010 Aug 12. PubMed PMID: 20714673. 11: Xu J, Xia X, Wang X, Xu C, Wang P, Xiang J, Jiang Y, Leung AW. Sonodynamic action of pyropheophorbide-a methyl ester in liver cancer cells. J Ultrasound Med. 2010 Jul;29(7):1031-7. PubMed PMID: 20587426. 12: Stamati I, Kuimova MK, Lion M, Yahioglu G, Phillips D, Deonarain MP. Novel photosensitisers derived from pyropheophorbide-a: uptake by cells and photodynamic efficiency in vitro. Photochem Photobiol Sci. 2010 Jul 30;9(7):1033-41. doi: 10.1039/c0pp00038h. Epub 2010 Jun 8. PubMed PMID: 20532306. 13: Ghosh I, Saleh N, Nau WM. Selective time-resolved binding of copper(II) by pyropheophorbide-a methyl ester. Photochem Photobiol Sci. 2010 May;9(5):649-54. doi: 10.1039/c0pp00002g. Epub 2010 Feb 22. PubMed PMID: 20442923. 14: 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. 15: Cai J, Niedzwiedzki DM, Frank HA, Hamilton AD. Ultrafast energy transfer within pyropheophorbide-a tethered to self-assembling DNA quadruplex. Chem Commun (Camb). 2010 Jan 28;46(4):544-6. doi: 10.1039/b908435e. Epub 2009 Dec 7. PubMed PMID: 20062856; PubMed Central PMCID: PMC3655531. 16: Al-Omari S, Ali A. Photodynamic activity of pyropheophorbide methyl ester and pyropheophorbide a in dimethylformamide solution. Gen Physiol Biophys. 2009 Mar;28(1):70-7. PubMed PMID: 19390139. 17: Sengee GI, Badraa N, Shim YK. Synthesis and biological evaluation of new imidazolium and piperazinium salts of pyropheophorbide-a for photodynamic cancer therapy. Int J Mol Sci. 2008 Aug;9(8):1407-15. doi: 10.3390/ijms9081407. Epub 2008 Aug 13. PubMed PMID: 19325811; PubMed Central PMCID: PMC2635737. 18: Liu T, Wu LY, Choi JK, Berkman CE. In vitro targeted photodynamic therapy with a pyropheophorbide--a conjugated inhibitor of prostate-specific membrane antigen. Prostate. 2009 May 1;69(6):585-94. doi: 10.1002/pros.20909. PubMed PMID: 19142895; PubMed Central PMCID: PMC2719770. 19: Pandey SK, Sajjad M, Chen Y, Zheng X, Yao R, Missert JR, Batt C, Nabi HA, Oseroff AR, Pandey RK. Comparative positron-emission tomography (PET) imaging and phototherapeutic potential of 124I- labeled methyl- 3-(1'-iodobenzyloxyethyl)pyropheophorbide-a vs the corresponding glucose and galactose conjugates. J Med Chem. 2009 Jan 22;52(2):445-55. doi: 10.1021/jm8012213. PubMed PMID: 19090663; PubMed Central PMCID: PMC2699564. 20: Rancan F, Helmreich M, Mölich A, Ermilov EA, Jux N, Röder B, Hirsch A, Böhm F. Synthesis and in vitro testing of a pyropheophorbide-a-fullerene hexakis adduct immunoconjugate for photodynamic therapy. Bioconjug Chem. 2007 Jul-Aug;18(4):1078-86. Epub 2007 Jun 6. PubMed PMID: 17550226.
Chen L, Zuo W, Xiao Z, Jin Q, Liu J, Wu L, Liu N, Zhu X. A carrier-free metal-coordinated dual-photosensitizers nanotheranostic with glutathione-depletion for fluorescence/photoacoustic imaging-guided tumor phototherapy. J Colloid Interface Sci. 2021 Apr 30;600:243-255. doi: 10.1016/j.jcis.2021.04.131. Epub ahead of print. PMID: 34020121.