AlPcS4 | CAS#144082-45-1 | PDT photosensitizer

MedKoo Cat#: 406813 | Name: AlPcS4

Description:

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

AlPcS4 , also known as aluminum phthalocyanine tetrasulfonate Chloroaluminum tetrasulfophthalocyanine; or AlS4Pc, AlPcS4(a), is a potent photosensitizer, and is potentially useful in cancer sonodynamic therapy and cancer photodynamic therapy. Aluminum phthalocyanine disulfonate is a mixture of regional isomers, in which sulfonate group can be in 3- or 4- position in phenyl ring. Aluminum phthalocyanine disulfonate is also a Coloring Agent; Dermatologic Agent; Fluorescent Dye; Indicators and Reagent; Luminescent Agent; Photosensitizing Agent; Radiation-Sensitizing Agent.

Chemical Structure

AlPcS4

CAS#144082-45-1 (free acid)

Theoretical Analysis

MedKoo Cat#: 406813

Name: AlPcS4

CAS#: 144082-45-1 (free acid)

Chemical Formula: C32H16AlClN8O12S4

Exact Mass: 893.9274

Molecular Weight: 895.20

Elemental Analysis: C, 42.93; H, 1.80; Al, 3.01; Cl, 3.96; N, 12.52; O, 21.45; S, 14.33

Price and Availability

Size	Price	Availability
1mg	USD 120.00	Ready to ship
5mg	USD 350.00	Ready to ship
10mg	USD 550.00	Ready to ship
25mg	USD 1,250.00	Ready to ship
50mg	USD 2,250.00	Ready to ship

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Related CAS #

144082-45-1 (free acid) 118887-28-8 (sodium)

Synonym

AlPcS4 or AlS4Pc, or AlPcS4(a); Chloroaluminum tetrasulfophthalocyanine; Aluminum phthalocyanine tetrasulfonate tetrasodium; Al(III) Phthalocyanine Chloride Tetrasulfonic tetrasodium; MFCD#: MFCD00672294.

IUPAC/Chemical Name

Aluminate(4-), chloro[29H,31H-phthalocyanine-2,9,17,24-tetrasulfonato(6-)-N29,N30,N31,N32]-, (SP-5-13)-

InChi Key

ZFWXERRHYQLDNT-UHFFFAOYSA-M

InChi Code

InChI=1S/C32H16N8O12S4.Al.ClH/c41-53(42,43)13-1-5-17-21(9-13)29-35-25(17)33-26-18-6-2-14(54(44,45)46)10-22(18)31(36-26)40-32-24-12-16(56(50,51)52)4-8-20(24)28(38-32)34-27-19-7-3-15(55(47,48)49)11-23(19)30(37-27)39-29;;/h1-12H,(H4-2,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52);;1H/q-2;+3;/p-1

SMILES Code

Cl[Al]123N4C5=NC6=[N]1C(C7=C6C=C(C=C7)S(=O)(O)=O)=NC8=C9C=CC(S(=O)(O)=O)=CC9=C(N38)N=C(C%10=C%11C=CC(S(=O)(O)=O)=C%10)[N]2=C%11N=C4C%12=C5C=C(S(=O)(O)=O)C=C%12

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

Related CAS# CAS#33308-41-7 (Phthalocyanine tetrasulfonic acid) CAS#144082-45-1(Aluminum phthalocyanine tetrasulfonic acid) CAS#118887-28-8 (Aluminum phthalocyanine tetrasulfonate tetrasodium)

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#FSI71222

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

AlPcS4 is a photosensitizer.

In vitro activity:

The synergistic antitumor growth effect of AlPcS4/PDT (photodynamic therapy) and low‑dose chemotherapeutic agents on gastric cancer cells was investigated and compared by combining AlPcS4/PDT treatment with different low‑dose chemotherapeutic agents, namely, 5‑fluorouracil (5‑FU), doxorubicin (DOX), cisplatin (CDDP), mitomycin C (MMC), and vincristine (VCR). The inhibitory effect was increased in treatments that combined AlPcS4/PDT with all the low‑dose chemotherapeutic agents. An evident synergistic effect was obtained in the combination treatment of AlPcS4/PDT with low‑dose 5‑FU, DOX, and MMC by increasing AlPcS4 intracellular uptake ability, improving apoptosis‑inducing abilities, and prolonging apoptosis‑inducing time. The low‑dose chemotherapeutic agents prolonged the apoptosis‑inducing period of AlPcS4/PDT, and AlPcS4/PDT quickly improved apoptosis‑inducing abilities of chemotherapy even at low doses. Generally, the combination treatment of AlPcS4/PDT with low‑dose chemotherapeutic agents had significant antitumor growth effects in addition to a low dark‑cytotoxicity effect on gastric cancer in vitro. Reference: Oncol Rep. 2018 Jul;40(1):165-178. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6059740/

In vivo activity:

C57/B1 mice received 2 x 10(5) B16 melanoma cells subcutaneously and were randomized into study (PDT) and three control groups. AlpcS4 2.5 mg/kg was injected intraperitoneally and the mice were exposed to light (100 J/cm2). PDT caused massive tumor necrosis. PDT prolonged the survival of mice (41 +/- 13.4 days) compared to controls (15.8 +/- 3.8 days, P < .001). 31 days after injection with B16 cells, the tumor size was 2.6 +/- 0.3 cm in the control group and 1.6 +/- 0.2, 0.9 +/- 0.3, and 1.0 +/- 0.4 cm in the PDT groups (days 3, 6 and 12, respectively; P < .01). PDT increased skin temperature to 42.8 degrees C +/- 1.3 degrees C, 45.3 degrees C +/- 3.5 degrees C, and 51.7 degrees C +/- 2.7 degrees C at 40, 60, and 100 J/cm2, respectively (P < .01). Overall, photodynamic therapy was found to have significant effects in experimental melanoma in mice. Reference: Ann Surg Oncol. 1998 Apr-May;5(3):241-7. https://pubmed.ncbi.nlm.nih.gov/9607626/

Preparing Stock Solutions

The following data is based on the product molecular weight 895.20 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.

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. Xin J, Wang S, Zhang L, Xin B, He Y, Wang J, Wang S, Shen L, Zhang Z, Yao C. Comparison of the synergistic anticancer activity of AlPcS4 photodynamic therapy in combination with different low‑dose chemotherapeutic agents on gastric cancer cells. Oncol Rep. 2018 Jul;40(1):165-178. doi: 10.3892/or.2018.6438. Epub 2018 May 16. PMID: 29767247; PMCID: PMC6059740. 2. Haddad R, Blumenfeld A, Siegal A, Kaplan O, Cohen M, Skornick Y, Kashtan H. In vitro and in vivo effects of photodynamic therapy on murine malignant melanoma. Ann Surg Oncol. 1998 Apr-May;5(3):241-7. doi: 10.1007/BF02303780. PMID: 9607626.

In vitro protocol:

In vivo protocol:

1. Haddad R, Blumenfeld A, Siegal A, Kaplan O, Cohen M, Skornick Y, Kashtan H. In vitro and in vivo effects of photodynamic therapy on murine malignant melanoma. Ann Surg Oncol. 1998 Apr-May;5(3):241-7. doi: 10.1007/BF02303780. PMID: 9607626.

1: Derycke AS, Kamuhabwa A, Gijsens A, Roskams T, De Vos D, Kasran A, Huwyler J, Missiaen L, de Witte PA. Transferrin-conjugated liposome targeting of photosensitizer AlPcS4 to rat bladder carcinoma cells. J Natl Cancer Inst. 2004 Nov 3;96(21):1620-30. doi: 10.1093/jnci/djh314. PMID: 15523091. 2: Turubanova VD, Balalaeva IV, Mishchenko TA, Catanzaro E, Alzeibak R, Peskova NN, Efimova I, Bachert C, Mitroshina EV, Krysko O, Vedunova MV, Krysko DV. Immunogenic cell death induced by a new photodynamic therapy based on photosens and photodithazine. J Immunother Cancer. 2019 Dec 16;7(1):350. doi: 10.1186/s40425-019-0826-3. PMID: 31842994; PMCID: PMC6916435. 3: Xin J, Wang S, Zhang L, Xin B, He Y, Wang J, Wang S, Shen L, Zhang Z, Yao C. Comparison of the synergistic anticancer activity of AlPcS4 photodynamic therapy in combination with different low‑dose chemotherapeutic agents on gastric cancer cells. Oncol Rep. 2018 Jul;40(1):165-178. doi: 10.3892/or.2018.6438. Epub 2018 May 16. PMID: 29767247; PMCID: PMC6059740. 4: Gijsens A, Derycke A, Missiaen L, De Vos D, Huwyler J, Eberle A, de Witte P. Targeting of the photocytotoxic compound AlPcS4 to Hela cells by transferrin conjugated PEG-liposomes. Int J Cancer. 2002 Sep 1;101(1):78-85. doi: 10.1002/ijc.10548. PMID: 12209592. 5: Xin J, Wang S, Wang J, Wang J, Fu L, Shen L, Zhang Z, Yao C. Nanosystem Integrated with Photosensitizer and Novel Targeting Chemotherapy Agent for Gastric Cancer Chemo-Photodynamic Combined Therapy. J Biomed Nanotechnol. 2018 Aug 1;14(8):1430-1447. doi: 10.1166/jbn.2018.2598. PMID: 29903058. 6: Peng Q, Moan J, Farrants GW, Danielsen HE, Rimington C. Location of P-II and AlPCS4 in human tumor LOX in vitro and in vivo by means of computer-enhanced video fluorescence microscopy. Cancer Lett. 1991 Jun 14;58(1-2):37-47. doi: 10.1016/0304-3835(91)90021-9. PMID: 1828713. 7: Hu Y, Yang Y, Wang H, Du H. Synergistic Integration of Layer-by-Layer Assembly of Photosensitizer and Gold Nanorings for Enhanced Photodynamic Therapy in the Near Infrared. ACS Nano. 2015 Sep 22;9(9):8744-54. doi: 10.1021/acsnano.5b03063. Epub 2015 Aug 14. PMID: 26267273. 8: Xin J, Wang S, Wang J, Fu L, Zhang Z, Yao C. A Nucleus-Targeted Nanosystem Integrated with Photodynamic Therapy and Chemotherapy. J Biomed Nanotechnol. 2022 Mar 1;18(3):837-848. doi: 10.1166/jbn.2022.3286. PMID: 35715898. 9: Allen CM, Langlois R, Sharman WM, La Madeleine C, Van Lier JE. Photodynamic properties of amphiphilic derivatives of aluminum tetrasulfophthalocyanine. Photochem Photobiol. 2002 Aug;76(2):208-16. doi: 10.1562/0031-8655(2002)076<0208:PPOADO>2.0.CO;2. PMID: 12194219. 10: da Silva NS, Ribeiro Cde M, Machado AH, Pacheco-Soares C. Ultrastructural changes in Tritrichomonas foetus after treatments with AlPcS4 and photodynamic therapy. Vet Parasitol. 2007 May 15;146(1-2):175-81. doi: 10.1016/j.vetpar.2007.02.006. Epub 2007 Mar 30. PMID: 17399904. 11: Kassab K, El Fadeel DA, Fadel M. Topical photodynamic therapy using transfersomal aluminum phthalocyanine tetrasulfonate: in vitro and in vivo study. Lasers Med Sci. 2013 Sep;28(5):1353-61. doi: 10.1007/s10103-012-1256-3. Epub 2013 Jan 5. PMID: 23291878. 12: Moor AC, Wagenaars-van Gompel AE, Hermanns RC, van der Meulen J, Smit J, Wilschut J, Brand A, Dubbelman TM, VanSteveninck J. Inhibition of various steps in the replication cycle of vesicular stomatitis virus contributes to its photoinactivation by AlPcS4 or Pc4 and red light. Photochem Photobiol. 1999 Mar;69(3):353-9. doi: 10.1562/0031-8655(1999)069<0353:iovsit>2.3.co;2. PMID: 10089828. 13: Dias LM, Sharifi F, de Keijzer MJ, Mesquita B, Desclos E, Kochan JA, de Klerk DJ, Ernst D, de Haan LR, Franchi LP, van Wijk AC, Scutigliani EM, Cavaco JEB, Tedesco AC, Huang X, Pan W, Ding B, Krawczyk PM, Heger M; Photodynamic Therapy Study Group. Attritional evaluation of lipophilic and hydrophilic metallated phthalocyanines for oncological photodynamic therapy. J Photochem Photobiol B. 2021 Mar;216:112146. doi: 10.1016/j.jphotobiol.2021.112146. Epub 2021 Jan 29. PMID: 33601256. 14: Plaetzer K, Kiesslich T, Krammer B, Hammerl P. Characterization of the cell death modes and the associated changes in cellular energy supply in response to AlPcS4-PDT. Photochem Photobiol Sci. 2002 Mar;1(3):172-7. doi: 10.1039/b108816e. PMID: 12659513. 15: Rück A, Heckelsmiller K, Kaufmann R, Grossman N, Haseroth E, Akgün N. Light- induced apoptosis involves a defined sequence of cytoplasmic and nuclear calcium release in AlPcS4-photosensitized rat bladder RR 1022 epithelial cells. Photochem Photobiol. 2000 Aug;72(2):210-6. doi: 10.1562/0031-8655(2000)072<0210:LIAIAD>2.0.CO;2. PMID: 10946575. 16: Dias LM, de Keijzer MJ, Ernst D, Sharifi F, de Klerk DJ, Kleijn TG, Desclos E, Kochan JA, de Haan LR, Franchi LP, van Wijk AC, Scutigliani EM, Fens MH, Barendrecht AD, Cavaco JEB, Huang X, Xu Y, Pan W, den Broeder MJ, Bogerd J, Schulz RW, Castricum KC, Thijssen VL, Cheng S, Ding B, Krawczyk PM, Heger M; Photodynamic Therapy Study Group. Metallated phthalocyanines and their hydrophilic derivatives for multi-targeted oncological photodynamic therapy. J Photochem Photobiol B. 2022 Sep;234:112500. doi: 10.1016/j.jphotobiol.2022.112500. Epub 2022 Jun 17. PMID: 35816857. 17: Daugelaviciene N, Grigaitis P, Gasiule L, Dabkeviciene D, Neniskyte U, Sasnauskiene A. Lysosome-targeted photodynamic treatment induces primary keratinocyte differentiation. J Photochem Photobiol B. 2021 May;218:112183. doi: 10.1016/j.jphotobiol.2021.112183. Epub 2021 Mar 29. PMID: 33831753. 18: Raznitsyna I, Kulikova P, Rogatkin D, Kulikov D, Bychenkov O, Chursinova Y, Bobrov M, Glazkov A. Fluorescence of radiation-induced tissue damage. Int J Radiat Biol. 2018 Feb;94(2):166-173. doi: 10.1080/09553002.2018.1420925. Epub 2018 Jan 16. PMID: 29297727. 19: Teixeira R, Serra VV, Botequim D, Paulo PMR, Andrade SM, Costa SMB. Fluorescence Spectroscopy of Porphyrins and Phthalocyanines: Some Insights into Supramolecular Self-Assembly, Microencapsulation, and Imaging Microscopy. Molecules. 2021 Jul 14;26(14):4264. doi: 10.3390/molecules26144264. PMID: 34299539; PMCID: PMC8306603. 20: Gondivkar SM, Gadbail AR, Choudhary MG, Vedpathak PR, Likhitkar MS. Photodynamic treatment outcomes of potentially-malignant lesions and malignancies of the head and neck region: A systematic review. J Investig Clin Dent. 2018 Feb;9(1). doi: 10.1111/jicd.12270. Epub 2017 May 8. PMID: 28480637.