MPPa (Methyl pyropheophorbide-a)
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MedKoo CAT#: 500101

CAS#: 6453-67-4

Description: 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

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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: 548.27874
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
10.0mg USD 150.0 Same Day
25.0mg USD 250.0 Same Day
50.0mg USD 450.0 Same Day
100.0mg USD 850.0 Same Day
200.0mg USD 1450.0 Same Day
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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: O=C(OC)CC[C@@H]([C@@H]/1C)C(C2=C(N/3)C(C(C2)=O)=C(C)C3=C\4)=NC1=C/C5=C(C)C(C=C)=C(N5)/C=C6C(C)=C(CC)C4=N/6

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in CHCl3 10.0 18.2

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

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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.



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