Aluminum phthalocyanine disulfonate disodium | AlPcS2 disodium | CAS#68637-19-4 | PDT drug

MedKoo Cat#: 406812 | Name: Aluminum phthalocyanine disulfonate disodium

Description:

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

Aluminum phthalocyanine disulfonate sodium, also known as AlPcS2 disodium or AlS2Pc or AlPcS(2a), 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

Aluminum phthalocyanine disulfonate disodium

CAS#68637-19-4 (free acid)

Theoretical Analysis

MedKoo Cat#: 406812

Name: Aluminum phthalocyanine disulfonate disodium

CAS#: 68637-19-4 (free acid)

Chemical Formula: C32H14AlClN8Na2O6S2

Exact Mass: 0.0000

Molecular Weight: 779.05

Elemental Analysis: C, 49.34; H, 1.81; Al, 3.46; Cl, 4.55; N, 14.38; Na, 5.90; O, 12.32; S, 8.23

Price and Availability

Size	Price	Availability
1mg	USD 90.00	Ready to ship
5mg	USD 210.00	Ready to ship
10mg	USD 350.00	Ready to ship
25mg	USD 550.00	Ready to ship
50mg	USD 950.00	Ready to ship
100mg	USD 1,650.00	Ready to ship

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Related CAS #

134307-90-7 690206-42-9 68637-19-4 (free acid)

Synonym

Aluminum phthalocyanine disulfonate disodium; AlPcS(2a), AlPcS2; AlS2Pc; ClAlPcS2. Clalpcs; Disulfonated aluminum phthalocyanine; Al(III) Phthalocyanine chloride disulfonate disodium

IUPAC/Chemical Name

Aluminate(2-), chloro[29H,31H-phthalocyanine-C,C-disulfonato(4-)-κN29,κN30,κN31,κN32]-, sodium(1:2)

InChi Key

NHVAKUAEQKVVJJ-UHFFFAOYSA-K

InChi Code

InChI=1S/C32H16N8O6S2.Al.ClH.2Na/c41-47(42,43)15-9-11-21-23(13-15)31-38-29(21)36-27-19-7-3-1-5-17(19)25(34-27)33-26-18-6-2-4-8-20(18)28(35-26)37-30-22-12-10-16(48(44,45)46)14-24(22)32(39-30)40-31;;;;/h1-14H,(H2-2,33,34,35,36,37,38,39,40,41,42,43,44,45,46);;1H;;/q-2;+3;;2*+1/p-3

SMILES Code

Cl[Al]123N(C(C4=C5C=CC=C4)=N6)C5=NC7=[N]1C(C8=C7C=CC(S(=O)(O[Na])=O)=C8)=NC(N93)=C%10C=C(S(=O)(O[Na])=O)C=CC%10=C9N=C%11C%12=C(C=CC=C%12)C6=[N]%112

Appearance

Deep blue to black 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 water.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in water

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#YXM61227

QC Data

View QC data: current batch, Lot#YXM61227

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

N/A

In vitro activity:

As seen in the diagrams, cells in control group 1 that comprised of cells neither treated with AlPcSmix (sulfonated aluminum phthalocyanine mix) nor exposed to light appeared structurally unaltered and retained their characteristic morphology after 24 hours of incubation. The cells appeared healthy and uninjured and actively proliferated to confluence in 24 hours. PDT treated cells on the other hand (AlPcSmix+ irradiation) showed visible structural alteration with increasing level of damage proportional to the increase in PDT doses. Although there was significant cell damage in both cell populations, the side population incurred less damage than the total cell population at similar dose concentrations. There was however observable cell morphology alterations showing cell shrinkage, blebbing and detachment from the plate surface. Reference: Oncotarget. 2019 Jul 9; 10(43): 4380–4396. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6633885/

In vivo activity:

On the one hand, in comparison to control, mice injected with cells treated with PDT mediated by IC50 and IC70 AlPcNE (aluminum phthalocyanine) exhibited a delay in tumor development, which is even comparable to that induced by ICD-positive, MTX-treated cells (Fig. 4B). The increased resistance to tumor development was also reflected in the survival curves, as the mice injected with B16F10 cells treated with MTX or with PDT mediated by IC50 or IC70 AlPcNE showed higher survival rates than mice from the other groups (Fig. 4C-D). Reference: Photodiagnosis Photodyn Ther. 2021 Jun 13;35:102392. https://pubmed.ncbi.nlm.nih.gov/34133961/

Preparing Stock Solutions

The following data is based on the product molecular weight 779.05 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. Tang WZ, Cui ZJ. Permanent Photodynamic Activation of the Cholecystokinin 2 Receptor. Biomolecules. 2020 Feb 4;10(2):236. doi: 10.3390/biom10020236. PMID: 32033232; PMCID: PMC7072308. 2. Chizenga EP, Chandran R, Abrahamse H. Photodynamic therapy of cervical cancer by eradication of cervical cancer cells and cervical cancer stem cells. Oncotarget. 2019 Jul 9;10(43):4380-4396. doi: 10.18632/oncotarget.27029. PMID: 31320992; PMCID: PMC6633885. 3. Morais JAV, Almeida LR, Rodrigues MC, Azevedo RB, Muehlmann LA. The induction of immunogenic cell death by photodynamic therapy in B16F10 cells in vitro is effected by the concentration of the photosensitizer. Photodiagnosis Photodyn Ther. 2021 Jun 13;35:102392. doi: 10.1016/j.pdpdt.2021.102392. Epub ahead of print. PMID: 34133961. 4. Longo JP, Lozzi SP, Simioni AR, Morais PC, Tedesco AC, Azevedo RB. Photodynamic therapy with aluminum-chloro-phthalocyanine induces necrosis and vascular damage in mice tongue tumors. J Photochem Photobiol B. 2009 Feb 9;94(2):143-6. doi: 10.1016/j.jphotobiol.2008.11.003. Epub 2008 Nov 21. PMID: 19097802.

In vitro protocol:

In vivo protocol:

1. Morais JAV, Almeida LR, Rodrigues MC, Azevedo RB, Muehlmann LA. The induction of immunogenic cell death by photodynamic therapy in B16F10 cells in vitro is effected by the concentration of the photosensitizer. Photodiagnosis Photodyn Ther. 2021 Jun 13;35:102392. doi: 10.1016/j.pdpdt.2021.102392. Epub ahead of print. PMID: 34133961. 2. Longo JP, Lozzi SP, Simioni AR, Morais PC, Tedesco AC, Azevedo RB. Photodynamic therapy with aluminum-chloro-phthalocyanine induces necrosis and vascular damage in mice tongue tumors. J Photochem Photobiol B. 2009 Feb 9;94(2):143-6. doi: 10.1016/j.jphotobiol.2008.11.003. Epub 2008 Nov 21. PMID: 19097802.

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J Photochem Photobiol B. 2015 Jan;142:186-96. doi: 10.1016/j.jphotobiol.2014.12.003. Epub 2014 Dec 9. PubMed PMID: 25545333. 4: Trinidad AJ, Hong SJ, Peng Q, Madsen SJ, Hirschberg H. Combined concurrent photodynamic and gold nanoshell loaded macrophage-mediated photothermal therapies: an in vitro study on squamous cell head and neck carcinoma. Lasers Surg Med. 2014 Apr;46(4):310-8. doi: 10.1002/lsm.22235. Epub 2014 Mar 20. PubMed PMID: 24648368; PubMed Central PMCID: PMC4142684. 5: Wang F, Zamora G, Sun CH, Trinidad A, Chun C, Kwon YJ, Berg K, Madsen SJ, Hirschberg H. Increased sensitivity of glioma cells to 5-fluorocytosine following photo-chemical internalization enhanced nonviral transfection of the cytosine deaminase suicide gene. J Neurooncol. 2014 May;118(1):29-37. doi: 10.1007/s11060-014-1410-9. Epub 2014 Mar 8. PubMed PMID: 24610460; PubMed Central PMCID: PMC4153358. 6: Madsen SJ, Gach HM, Hong SJ, Uzal FA, Peng Q, Hirschberg H. Increased nanoparticle-loaded exogenous macrophage migration into the brain following PDT-induced blood-brain barrier disruption. Lasers Surg Med. 2013 Oct;45(8):524-32. doi: 10.1002/lsm.22172. Epub 2013 Aug 30. PubMed PMID: 24037939; PubMed Central PMCID: PMC4026156. 7: Randles EG, Bergethon PR. Reaction field analysis and lipid bilayer location for lipophilic fluorophores. J Phys Chem B. 2013 Sep 5;117(35):10193-202. doi: 10.1021/jp402861x. Epub 2013 Aug 22. PubMed PMID: 23967904. 8: Vikdal M, Generalov R, Berg K. The photosensitizer disulfonated aluminum phthalocyanine reduces uptake and alters trafficking of fluid phase endocytosed drugs in vascular endothelial cells--impact on efficacy of photochemical internalization. Biochem Pharmacol. 2013 Sep 15;86(6):748-58. doi: 10.1016/j.bcp.2013.07.011. Epub 2013 Jul 20. PubMed PMID: 23876343. 9: Mathews MS, Shih EC, Zamora G, Sun CH, Cho SK, Kwon YJ, Hirschberg H. Glioma cell growth inhibition following photochemical internalization enhanced non-viral PTEN gene transfection. Lasers Surg Med. 2012 Nov;44(9):746-54. doi: 10.1002/lsm.22082. Epub 2012 Sep 27. Erratum in: Lasers Surg Med. 2012 Dec;44(10):865. PubMed PMID: 23018764; PubMed Central PMCID: PMC4141883. 10: Mathews MS, Blickenstaff JW, Shih EC, Zamora G, Vo V, Sun CH, Hirschberg H, Madsen SJ. Photochemical internalization of bleomycin for glioma treatment. J Biomed Opt. 2012 May;17(5):058001. doi: 10.1117/1.JBO.17.5.058001. PubMed PMID: 22612148; PubMed Central PMCID: PMC3381024. 11: Mathews MS, Vo V, Shih EC, Zamora G, Sun CH, Madsen SJ, Hirschberg H. Photochemical internalization-mediated delivery of chemotherapeutic agents in human breast tumor cell lines. J Environ Pathol Toxicol Oncol. 2012;31(1):49-59. PubMed PMID: 22591284; PubMed Central PMCID: PMC4124822. 12: Kessel D. Inhibition of endocytic processes by photodynamic therapy. Lasers Surg Med. 2011 Sep;43(7):542-7. doi: 10.1002/lsm.21067. PubMed PMID: 22057481; PubMed Central PMCID: PMC3211108. 13: Gupta S, Dwarakanath BS, Chaudhury NK, Mishra AK, Muralidhar K, Jain V. In vitro and in vivo targeted delivery of photosensitizers to the tumor cells for enhanced photodynamic effects. J Cancer Res Ther. 2011 Jul-Sep;7(3):314-24. doi: 10.4103/0973-1482.87035. PubMed PMID: 22044814. 14: Mathews MS, Chighvinadze D, Gach HM, Uzal FA, Madsen SJ, Hirschberg H. Cerebral edema following photodynamic therapy using endogenous and exogenous photosensitizers in normal brain. Lasers Surg Med. 2011 Nov;43(9):892-900. doi: 10.1002/lsm.21135. PubMed PMID: 22006731; PubMed Central PMCID: PMC4124831. 15: Berg K, Nordstrand S, Selbo PK, Tran DT, Angell-Petersen E, Høgset A. Disulfonated tetraphenyl chlorin (TPCS2a), a novel photosensitizer developed for clinical utilization of photochemical internalization. Photochem Photobiol Sci. 2011 Oct;10(10):1637-51. doi: 10.1039/c1pp05128h. Epub 2011 Jul 20. PubMed PMID: 21773635. 16: Gupta S, Dwarakanath BS, Muralidhar K, Koru-Sengul T, Jain V. Non-monotonic changes in clonogenic cell survival induced by disulphonated aluminum phthalocyanine photodynamic treatment in a human glioma cell line. J Transl Med. 2010 Apr 30;8:43. doi: 10.1186/1479-5876-8-43. PubMed PMID: 20433757; PubMed Central PMCID: PMC2885318. 17: Woodhams J, Lou PJ, Selbo PK, Mosse A, Oukrif D, MacRobert A, Novelli M, Peng Q, Berg K, Bown SG. Intracellular re-localisation by photochemical internalisation enhances the cytotoxic effect of gelonin--quantitative studies in normal rat liver. J Control Release. 2010 Mar 19;142(3):347-53. doi: 10.1016/j.jconrel.2009.11.017. Epub 2009 Nov 22. PubMed PMID: 19932724. 18: Krestyn E, Kolarova H, Bajgar R, Tomankova K. Photodynamic properties of ZnTPPS(4), ClAlPcS(2) and ALA in human melanoma G361 cells. Toxicol In Vitro. 2010 Feb;24(1):286-91. doi: 10.1016/j.tiv.2009.08.015. Epub 2009 Aug 29. PubMed PMID: 19720133. 19: Norum OJ, Bruland ØS, Gorunova L, Berg K. Photochemical internalization of bleomycin before external-beam radiotherapy improves locoregional control in a human sarcoma model. Int J Radiat Oncol Biol Phys. 2009 Nov 1;75(3):878-85. doi: 10.1016/j.ijrobp.2009.04.039. Epub 2009 Aug 6. PubMed PMID: 19665318. 20: Tomankova K, Kolarova H, Kolar P, Kejlova K, Jirova D. Study of cytotoxic effect of photodynamically and sonodynamically activated sensitizers in vitro. Toxicol In Vitro. 2009 Dec;23(8):1465-71. doi: 10.1016/j.tiv.2009.07.006. Epub 2009 Jul 10. PubMed PMID: 19595758.