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MedKoo Cat#: 527708 | Name: Silicon Phthalocyanine 4

Description:

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

Silicon Phthalocyanine 4, also known as Pc-4, is a drug potentially for the treatment of cutaneous neoplasms. Photoirradiation of the silicon phthalocyanine 4 photosensitizer with red light generates singlet oxygen and other reactive oxygen species to induce cell death. Pc 4 is absorbed into the epidermis in as little as 1 hour and the absorption increased with increasing time and dose. Silicon phthalocyanine 4 can be effectively delivered into human skin via topical application.

Chemical Structure

Silicon Phthalocyanine 4
Silicon Phthalocyanine 4
CAS#135719-28-7

Theoretical Analysis

MedKoo Cat#: 527708

Name: Silicon Phthalocyanine 4

CAS#: 135719-28-7

Chemical Formula: C39H35N9O2Si2

Exact Mass: 717.2452

Molecular Weight: 717.94

Elemental Analysis: C, 65.25; H, 4.91; N, 17.56; O, 4.46; Si, 7.82

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Silicon phthalocyanine 4; Pc-4; Pc 4; Pc4
IUPAC/Chemical Name
19-(((3-(dimethylamino)propyl)dimethylsilyl)oxy)-19H-6,11-(azeno)-17,21-(azeno[1]episoindoloazeno)benzo[7,8][1,3,5,10]tetraaza[2]silacycloundecino[4,3-a:11,1-a']diisoindol-19-ol
InChi Key
MQPOIOMXRKFQLZ-XSRQUKKKSA-N
InChi Code
InChI=1S/C39H35N9O2Si2/c1-46(2)22-13-23-51(3,4)50-52(49)47-36-28-18-9-10-19-29(28)38(47)44-34-26-16-7-8-17-27(26)35(41-34)45-39-31-21-12-11-20-30(31)37(48(39)52)43-33-25-15-6-5-14-24(25)32(40-33)42-36/h5-12,14-21,49H,13,22-23H2,1-4H3/b42-32-,42-36-,43-33-,43-37-,44-34-,44-38-,45-35-,45-39-
SMILES Code
O[Si]1(O[Si](C)(C)CCCN(C)C)N2/C(C3=C(C=CC=C3)/C2=N/C4=N/C(C5=C4C=CC=C5)=N\6)=N\C(C7=C/8C=CC=C7)=NC8=N/C9=C(C=CC=C%10)C%10=C6N91
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 717.94 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
1: Dimaano ML, Rozario C, Nerandzic MM, Donskey CJ, Lam M, Baron ED. The photodynamic antibacterial effects of silicon phthalocyanine (Pc) 4. Int J Mol Sci. 2015 Apr 8;16(4):7851-60. doi: 10.3390/ijms16047851. PubMed PMID: 25856680; PubMed Central PMCID: PMC4425053. 2: Master AM, Livingston M, Oleinick NL, Sen Gupta A. Optimization of a nanomedicine-based silicon phthalocyanine 4 photodynamic therapy (Pc 4-PDT) strategy for targeted treatment of EGFR-overexpressing cancers. Mol Pharm. 2012 Aug 6;9(8):2331-8. doi: 10.1021/mp300256e. PubMed PMID: 22775587; PubMed Central PMCID: PMC3498539. 3: Hutnick MA, Ahsanuddin S, Guan L, Lam M, Baron ED, Pokorski JK. PEGylated Dendrimers as Drug Delivery Vehicles for the Photosensitizer Silicon Phthalocyanine Pc 4 for Candidal Infections. Biomacromolecules. 2017 Feb 13;18(2):379-385. doi: 10.1021/acs.biomac.6b01436. PubMed PMID: 28117573. 4: Soler DC, Ohtola J, Sugiyama H, Rodriguez ME, Han L, Oleinick NL, Lam M, Baron ED, Cooper KD, McCormick TS. Activated T cells exhibit increased uptake of silicon phthalocyanine Pc 4 and increased susceptibility to Pc 4-photodynamic therapy-mediated cell death. Photochem Photobiol Sci. 2016 Jun 8;15(6):822-31. doi: 10.1039/c6pp00058d. PubMed PMID: 27161819; PubMed Central PMCID: PMC4928582. 5: Shen XM, Jiang XJ, Zhu YJ, Zhang HH, Huang JD. [Spectral properties, photodynamic anticancer activity and the interaction with albumin of silicon phthalocyanine axially modified by pyrimidine derivatives]. Guang Pu Xue Yu Guang Pu Fen Xi. 2013 Aug;33(8):2148-52. Chinese. PubMed PMID: 24159865. 6: Li J, Yang Y, Zhang P, Sounik JR, Kenney ME. Synthesis, properties and drug potential of the photosensitive alkyl- and alkylsiloxy-ligated silicon phthalocyanine Pc 227. Photochem Photobiol Sci. 2014 Dec;13(12):1690-8. doi: 10.1039/c4pp00321g. PubMed PMID: 25308695. 7: Lam M, Hsia AH, Liu Y, Guo M, Swick AR, Berlin JC, McCormick TS, Kenney ME, Oleinick NL, Cooper KD, Baron ED. Successful cutaneous delivery of the photosensitizer silicon phthalocyanine 4 for photodynamic therapy. Clin Exp Dermatol. 2011 Aug;36(6):645-51. doi: 10.1111/j.1365-2230.2010.03989.x. Review. PubMed PMID: 21623875; PubMed Central PMCID: PMC3140567. 8: Doane T, Chomas A, Srinivasan S, Burda C. Observation and photophysical characterization of silicon phthalocyanine J-aggregate dimers in aqueous solutions. Chemistry. 2014 Jun 23;20(26):8030-9. doi: 10.1002/chem.201304885. PubMed PMID: 24861009. 9: Baron ED, Malbasa CL, Santo-Domingo D, Fu P, Miller JD, Hanneman KK, Hsia AH, Oleinick NL, Colussi VC, Cooper KD. Silicon phthalocyanine (Pc 4) photodynamic therapy is a safe modality for cutaneous neoplasms: results of a phase 1 clinical trial. Lasers Surg Med. 2010 Dec;42(10):728-35. doi: 10.1002/lsm.20984. PubMed PMID: 21246576; PubMed Central PMCID: PMC3149858. 10: Yang Y, Samas B, Kennedy VO, Macikenas D, Chaloux BL, Miller JA, Speer RL Jr, Protasiewicz J, Pinkerton AA, Kenney ME. Long, directional interactions in cofacial silicon phthalocyanine oligomers. J Phys Chem A. 2011 Nov 17;115(45):12474-85. doi: 10.1021/jp2019445. PubMed PMID: 21805980. 11: Céspedes-Guirao FJ, Martín-Gomis L, Ohkubo K, Fukuzumi S, Fernández-Lázaro F, Sastre-Santos A. Synthesis and photophysics of silicon phthalocyanine-perylenebisimide triads connected through rigid and flexible bridges. Chemistry. 2011 Aug 8;17(33):9153-63. doi: 10.1002/chem.201100320. PubMed PMID: 21714016. 12: Lam M, Dimaano ML, Oyetakin-White P, Retuerto MA, Chandra J, Mukherjee PK, Ghannoum MA, Cooper KD, Baron ED. Silicon phthalocyanine 4 phototoxicity in Trichophyton rubrum. Antimicrob Agents Chemother. 2014 Jun;58(6):3029-34. doi: 10.1128/AAC.01448-13. PubMed PMID: 24614382; PubMed Central PMCID: PMC4068425. 13: El-Khouly ME, Kang ES, Kay KY, Choi CS, Aaraki Y, Ito O. Silicon-phthalocyanine-cored fullerene dendrimers: synthesis and prolonged charge-separated states with dendrimer generations. Chemistry. 2007;13(10):2854-63. PubMed PMID: 17177216. 14: Kinsella TJ, Baron ED, Colussi VC, Cooper KD, Hoppel CL, Ingalls ST, Kenney ME, Li X, Oleinick NL, Stevens SR, Remick SC. Preliminary clinical and pharmacologic investigation of photodynamic therapy with the silicon phthalocyanine photosensitizer pc 4 for primary or metastatic cutaneous cancers. Front Oncol. 2011 Jun 30;1:14. doi: 10.3389/fonc.2011.00014. PubMed PMID: 22649754; PubMed Central PMCID: PMC3355859. 15: Lam M, Lee Y, Deng M, Hsia AH, Morrissey KA, Yan C, Azzizudin K, Oleinick NL, McCormick TS, Cooper KD, Baron ED. Photodynamic therapy with the silicon phthalocyanine pc 4 induces apoptosis in mycosis fungoides and sezary syndrome. Adv Hematol. 2010;2010:896161. doi: 10.1155/2010/896161. PubMed PMID: 21197103; PubMed Central PMCID: PMC3004392. 16: Ermilov EA, Liu JY, Ng DK, Röder B. Spectroscopic study of electron and energy transfer in novel silicon phthalocyanine--boron dipyrromethene triads. Phys Chem Chem Phys. 2009 Aug 14;11(30):6430-40. doi: 10.1039/b823432a. PubMed PMID: 19809675. 17: Martín-Gomis L, Ohkubo K, Fernández-Lázaro F, Fukuzumi S, Sastre-Santos A. Multistep electron transfer systems based on silicon phthalocyanine, [60]fullerene and trinitrofluorenone. Chem Commun (Camb). 2010 Jun 14;46(22):3944-6. doi: 10.1039/c002077j. PubMed PMID: 20419189. 18: Ozawa K, Ishii K. Photophysical and magnetic properties of magnetic silica gel-supported silicon phthalocyanine complexes. Phys Chem Chem Phys. 2009 Feb 21;11(7):1019-22. doi: 10.1039/b811128f. PubMed PMID: 19543597. 19: Ishii K, Sakai N. Wavelength-tunable excited-state absorption and optical limiting effects in the Q band region based on silicon phthalocyanine oligomers. Phys Chem Chem Phys. 2010 Dec 21;12(47):15354-7. doi: 10.1039/c0cp01172j. PubMed PMID: 20941425. 20: Zhang GC, Huang JD, Chen YM, Sun JC, Liu H, Chen NS, Huang JL. [A silicon phthalocyanine axially substituted by nipagin: synthesis, molecular spectroscopic properties, and in vitro photodynamic activities]. Guang Pu Xue Yu Guang Pu Fen Xi. 2005 Oct;25(10):1622-6. Chinese. PubMed PMID: 16395898.