Phthalocyanine
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MedKoo CAT#: 329457

CAS#: 574-93-6

Description: Phthalocyanine is an intensely blue-green-coloured aromatic macrocyclic compound that is widely used in dyeing. Phthalocyanine can be used as an agent for Photodynamic Therapy and Imaging. Phthalocyanines form coordination complexes with most elements of the periodic table. These complexes are also intensely colored and also are used as dyes or pigments.

Chemical Structure

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Phthalocyanine
CAS# 574-93-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329457
Name: Phthalocyanine
CAS#: 574-93-6
Chemical Formula: C32H18N8
Exact Mass: 514.17
Molecular Weight: 514.552
Elemental Analysis: C, 74.70; H, 3.53; N, 21.78

Price and Availability

Size Price Availability Quantity
100g USD -1
2g USD 80
5g USD 150
10g USD 350
25g USD 550
50g USD 850
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Synonym: Phthalocyanine; Heliogen Blue 7560; Heliogen Blue 7800; Heliogen Blue G; HSDB 4350; Irgazin Blue 3GT; Lionol Blue KW; Monolite Fast Blue GS; Pigment Blue Green Phthalocyanine U; Polymon Blue G;

IUPAC/Chemical Name: 29H, 31H-Phthalocyanine

InChi Key: IEQIEDJGQAUEQZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C32H18N8/c1-2-10-18-17(9-1)25-33-26(18)38-28-21-13-5-6-14-22(21)30(35-28)40-32-24-16-8-7-15-23(24)31(36-32)39-29-20-12-4-3-11-19(20)27(34-29)37-25/h1-16H,(H2,33,34,35,36,37,38,39,40)

SMILES Code: C1(/C2=N/3)=C(C=CC=C1)/C(N2)=N/C4=N/C(C5=C4C=CC=C5)=N\C(N6)=C7C=CC=CC7=C6/N=C8C9=C(C=CC=C9)C3=N/8

Appearance: Solid powder

Purity: >90% (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: Approximately 25% of all artificial organic pigments are phthalocyanine derivatives. Copper phthalocyanine (CuPc) dyes are produced by introducing solubilizing groups, such as one or more sulfonic acid functions. These dyes find extensive use in various areas of textile dyeing (Direct dyes for cotton), for spin dyeing and in the paper industry. Direct blue 86 is the sodium salt of CPC-sulfonic acid whereas direct blue 199 is the quaternary ammonium salt of the CPC-sulfonic acid. The quaternary ammonium salts of these sulfonic acids are used as solvent dyes because of their solubility in organic solvents, e.g. Solvent Blue 38 and Solvent Blue 48. The dye derived from cobalt phthalocyanine and an amine is Phthalogen Dye IBN. 1,3-Diiminoisoindolene, the intermediate formed during phthalocyanine manufacture, used in combination with a copper salt affords the dye GK 161. All major artists' pigment manufacturers produce variants of copper phthalocyanine, designated color index PB15 (blue) and color indexes PG7 and PG36 (green). Phthalocyanine is also commonly used as a dye in the manufacture of high-speed CD-R media. Most brands of CD-R use this dye except Taiyo Yuden (now CMC Pro) and Verbatim DataLife (which use cyanine and azo dyes, respectively). Metal phthalocyanines have long been examined as catalysts for redox reactions. Areas of interest are the oxygen reduction reaction and the sweetening of gas streams by removal of hydrogen sulfide. Phthalocyanine compounds have been investigated as donor materials in molecular electronics, e.g. organic field-effect transistors. Copper Phthalocyanine (CuPc) may possibly be used as storage in quantum computing, due to the length of time its electrons can remain in superposition

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Biological target: Phthalocyanine is an intensely blue-green-coloured aromatic macrocyclic compound that is widely used in dyeing.
In vitro activity: The photophysicochemical properties (fluorescence, singlet oxygen and photodegradation quantum yield) of these novel complexes were investigated in dimethylsulfoxide (DMSO) for both non-ionic and quaternized cationic phthalocyanine complexes and in aqueous solution for quaternized cationic phthalocyanine complexes. Studies indicate that the mechanism of BSA quenching by quaternized zinc(II) phthalocyanines was static quenching. Quaternized zinc(II) phthalocyanines interacted with ct-DNA by intercalation. Quaternized zinc(II) phthalocyanines caused a decrease in cell viability and triggered apoptotic cell death after PDT was applied at a concentration that did not have a toxic effect on their own. The results revealed that the synthesized water soluble quaternized zinc(II) phthalocyanine complexes (Q-Zn1c and Q-Zn2c) are promising potential photosensitizers for PDT. Reference: Photochem Photobiol Sci. 2023 May 11. https://pubmed.ncbi.nlm.nih.gov/37166570/
In vivo activity: The present study aimed to fabricate concanavalin A conjugated phthalocyanine-loaded cochleates (Formulation PhConA) as a glucose-sensitive lipidic system and estimate its efficacy in streptozotocin-induced male Sprague Dawley diabetic rats for 28 days. The in-vivo studies of the formulation PhConA improved the blood glucose levels along with defensive effect on the liver to overcome the hyperlipidemic effect. The rigid structure of cochleates prolongs the drug elimination from systemic circulation and extends its effect for a longer duration by decreasing the blood glucose level. Thus, the glucose-sensitive formulation PhConA showed significant improvement in diabetic rats within the period of 28 days by improving the oxidative defense and protecting the pancreatic β-cells. Reference: J Liposome Res. 2023 May 12:1-16. https://pubmed.ncbi.nlm.nih.gov/37171277/

Preparing Stock Solutions

The following data is based on the product molecular weight 514.55 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. Kocaağa N, Türkkol A, Bilgin MD, Erdoğmuş A. The synthesis of novel water-soluble zinc (II) phthalocyanine based photosensitizers and exploring of photodynamic therapy activities on the PC3 cancer cell line. Photochem Photobiol Sci. 2023 May 11. doi: 10.1007/s43630-023-00428-y. Epub ahead of print. PMID: 37166570. 2. Liu S, Ma J, Xue EY, Wang S, Zheng Y, Ng DKP, Wang A, Zheng N. Polymeric Phthalocyanine-Based Nanosensitizers for Enhanced Photodynamic and Sonodynamic Therapies. Adv Healthc Mater. 2023 Apr 5:e2300481. doi: 10.1002/adhm.202300481. Epub ahead of print. PMID: 37019442. 3. Govardhane S, Shende P. Phthalocyanine-based glucose-responsive nanocochleates for dynamic prevention of β-cell damage in diabetes. J Liposome Res. 2023 May 12:1-16. doi: 10.1080/08982104.2023.2209642. Epub ahead of print. PMID: 37171277. 4. Feng HY, Yuan Y, Zhang Y, Liu HJ, Dong X, Yang SC, Liu XL, Lai X, Zhu MH, Wang J, Lu Q, Lin Q, Chen HZ, Lovell JF, Sun P, Fang C. Targeted Micellar Phthalocyanine for Lymph Node Metastasis Homing and Photothermal Therapy in an Orthotopic Colorectal Tumor Model. Nanomicro Lett. 2021 Jun 19;13(1):145. doi: 10.1007/s40820-021-00666-8. PMID: 34146159; PMCID: PMC8214644.
In vitro protocol: 1. Kocaağa N, Türkkol A, Bilgin MD, Erdoğmuş A. The synthesis of novel water-soluble zinc (II) phthalocyanine based photosensitizers and exploring of photodynamic therapy activities on the PC3 cancer cell line. Photochem Photobiol Sci. 2023 May 11. doi: 10.1007/s43630-023-00428-y. Epub ahead of print. PMID: 37166570. 2. Liu S, Ma J, Xue EY, Wang S, Zheng Y, Ng DKP, Wang A, Zheng N. Polymeric Phthalocyanine-Based Nanosensitizers for Enhanced Photodynamic and Sonodynamic Therapies. Adv Healthc Mater. 2023 Apr 5:e2300481. doi: 10.1002/adhm.202300481. Epub ahead of print. PMID: 37019442.
In vivo protocol: 1. Govardhane S, Shende P. Phthalocyanine-based glucose-responsive nanocochleates for dynamic prevention of β-cell damage in diabetes. J Liposome Res. 2023 May 12:1-16. doi: 10.1080/08982104.2023.2209642. Epub ahead of print. PMID: 37171277. 2. Feng HY, Yuan Y, Zhang Y, Liu HJ, Dong X, Yang SC, Liu XL, Lai X, Zhu MH, Wang J, Lu Q, Lin Q, Chen HZ, Lovell JF, Sun P, Fang C. Targeted Micellar Phthalocyanine for Lymph Node Metastasis Homing and Photothermal Therapy in an Orthotopic Colorectal Tumor Model. Nanomicro Lett. 2021 Jun 19;13(1):145. doi: 10.1007/s40820-021-00666-8. PMID: 34146159; PMCID: PMC8214644.

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1: Iqbal Z, Chen J, Chen Z, Huang M. Phthalocyanine-Biomolecule Conjugated Photosensitizers for Targeted Photodynamic Therapy and Imaging. Curr Drug Metab. 2015;16(9):816-32. Review. PubMed PMID: 26593738.

2: Acherar S, Colombeau L, Frochot C, Vanderesse R. Synthesis of Porphyrin, Chlorin and Phthalocyanine Derivatives by Azide-Alkyne Click Chemistry. Curr Med Chem. 2015;22(28):3217-54. Review. PubMed PMID: 26179994.

3: Kuzyniak W, Ermilov EA, Atilla D, Gürek AG, Nitzsche B, Derkow K, Hoffmann B, Steinemann G, Ahsen V, Höpfner M. Tetra-triethyleneoxysulfonyl substituted zinc phthalocyanine for photodynamic cancer therapy. Photodiagnosis Photodyn Ther. 2016 Mar;13:148-57. doi: 10.1016/j.pdpdt.2015.07.001. Review. PubMed PMID: 26162500.

4: Mfouo-Tynga I, Abrahamse H. Cell death pathways and phthalocyanine as an efficient agent for photodynamic cancer therapy. Int J Mol Sci. 2015 May 6;16(5):10228-41. doi: 10.3390/ijms160510228. Review. PubMed PMID: 25955645; PubMed Central PMCID: PMC4463643.

5: Sorokin AB. Phthalocyanine metal complexes in catalysis. Chem Rev. 2013 Oct 9;113(10):8152-91. doi: 10.1021/cr4000072. Review. PubMed PMID: 23782107.

6: Jiang Z, Shao J, Yang T, Wang J, Jia L. Pharmaceutical development, composition and quantitative analysis of phthalocyanine as the photosensitizer for cancer photodynamic therapy. J Pharm Biomed Anal. 2014 Jan;87:98-104. doi: 10.1016/j.jpba.2013.05.014. Review. PubMed PMID: 23746989.

7: Yaku H, Murashima T, Miyoshi D, Sugimoto N. Specific binding of anionic porphyrin and phthalocyanine to the G-quadruplex with a variety of in vitro and in vivo applications. Molecules. 2012 Sep 5;17(9):10586-613. doi: 10.3390/molecules170910586. Review. PubMed PMID: 22951397.

8: Jia X, Jia L. Nanoparticles improve biological functions of phthalocyanine photosensitizers used for photodynamic therapy. Curr Drug Metab. 2012 Oct;13(8):1119-22. Review. PubMed PMID: 22380016.

9: Liao PN, Pillai S, Kloz M, Gust D, Moore AL, Moore TA, Kennis JT, van Grondelle R, Walla PJ. On the role of excitonic interactions in carotenoid-phthalocyanine dyads and implications for photosynthetic regulation. Photosynth Res. 2012 Mar;111(1-2):237-43. doi: 10.1007/s11120-011-9690-9. Review. PubMed PMID: 21948493.

10: 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.

11: Bottari G, de la Torre G, Guldi DM, Torres T. Covalent and noncovalent phthalocyanine-carbon nanostructure systems: synthesis, photoinduced electron transfer, and application to molecular photovoltaics. Chem Rev. 2010 Nov 10;110(11):6768-816. doi: 10.1021/cr900254z. Review. PubMed PMID: 20364812.

12: Fukuda T, Kobayashi N. Hydrogenated tetraazaporphyrins--old but new core-modified phthalocyanine analogues. Dalton Trans. 2008 Sep 21;(35):4685-704. doi: 10.1039/b804181d. Review. PubMed PMID: 18728874.

13: Miller JD, Baron ED, Scull H, Hsia A, Berlin JC, McCormick T, Colussi V, Kenney ME, Cooper KD, Oleinick NL. Photodynamic therapy with the phthalocyanine photosensitizer Pc 4: the case experience with preclinical mechanistic and early clinical-translational studies. Toxicol Appl Pharmacol. 2007 Nov 1;224(3):290-9. Review. PubMed PMID: 17397888; PubMed Central PMCID: PMC2128784.

14: Gorman SA, Brown SB, Griffiths J. An overview of synthetic approaches to porphyrin, phthalocyanine, and phenothiazine photosensitizers for photodynamic therapy. J Environ Pathol Toxicol Oncol. 2006;25(1-2):79-108. Review. PubMed PMID: 16566711.

15: Valli L. Phthalocyanine-based Langmuir-Blodgett films as chemical sensors. Adv Colloid Interface Sci. 2005 Nov 30;116(1-3):13-44. Review. PubMed PMID: 16112639.

16: Huang J, Peng Y, Chen N. [Some spectrum methods on the structures of metal phthalocyanine]. Guang Pu Xue Yu Guang Pu Fen Xi. 2001 Feb;21(1):1-6. Review. Chinese. PubMed PMID: 12953564.

17: Ochsner M. Light scattering of human skin: a comparison between zinc (II)-phthalocyanine and photofrin II. J Photochem Photobiol B. 1996 Jan;32(1-2):3-9. Review. PubMed PMID: 8725049.

18: Hayatsu H. Cellulose bearing covalently linked copper phthalocyanine trisulphonate as an adsorbent selective for polycyclic compounds and its use in studies of environmental mutagens and carcinogens. J Chromatogr. 1992 Apr 24;597(1-2):37-56. Review. Erratum in: J Chromatogr 1992 Jun 19;603(1-2):304. PubMed PMID: 1381369.