OSA's Digital Library

Virtual Journal for Biomedical Optics

Virtual Journal for Biomedical Optics

| EXPLORING THE INTERFACE OF LIGHT AND BIOMEDICINE

  • Editors: Andrew Dunn and Anthony Durkin
  • Vol. 9, Iss. 4 — Apr. 1, 2014
« Show journal navigation

Luminescence and photosensitivity of gadolinium labeled hematoporphyrin monomethyl ether

Peng Wang, Feng Qin, Li Wang, Fajun Li, Yangdong Zheng, Yunfei Song, Zhiguo Zhang, and Wenwu Cao  »View Author Affiliations


Optics Express, Vol. 22, Issue 3, pp. 2414-2422 (2014)
http://dx.doi.org/10.1364/OE.22.002414


View Full Text Article

Acrobat PDF (2937 KB)





Browse Journals / Lookup Meetings

Browse by Journal and Year


   


Lookup Conference Papers

Close Browse Journals / Lookup Meetings

Article Tools

Share
Citations

Abstract

Photodynamic therapy for deep-lying lesions needs an appropriate imaging modality, precise evaluation of tissue oxygen and an effective photosensitizer. Gadolinium based metalloporphyrins Gd(III)-HMME is proposed in this study as a potential multifunctional theranostic agent, as photosensitizer, ratiometric oxygen sensor and MRI contrast agent. The time resolved spectroscopy revealed the luminescence peak of Gd(III)-HMME at 710 and 779 nm with a lifetime of 64 μs in oxygen-free methanol to be phosphorescent. This phosphorescence is strongly dependent on dissolved oxygen concentration. Its intensity in oxygen saturated methanol solution is 21% of that in deoxygenated solution. The singlet oxygen quantum yields ΦΔ of HMME and Gd(III)-HMME in air saturated methanol solution were determined to be 0.79 and 0.40 respectively using comparative spectra method. These phenomena indicate that the oxygen sensibility and production of singlet oxygen of Gd(III)-HMME can fulfill the requirement of PDT treatment.

© 2014 Optical Society of America

1. Introduction

Photodynamic therapy (PDT) and fluorescence imaging has long been used for treatment and diagnosis of superficial cancer. PDT requires photosensitizer (PS), light and molecular oxygen. When PSs are exposed to light of appropriate wavelength, they produce highly cytotoxic singlet oxygen (1O2) to destruct the diseased tissue and the fluorescence could be used for diagnosis and image guided resection [1

1. J. P. Celli, B. Q. Spring, I. Rizvi, C. L. Evans, K. S. Samkoe, S. Verma, B. W. Pogue, and T. Hasan, “Imaging and photodynamic therapy: mechanisms, monitoring, and optimization,” Chem. Rev. 110(5), 2795–2838 (2010). [CrossRef] [PubMed]

]. PDT is minimally invasive, has few side effects, rapid recovery from the treatment and could be operated repeatedly. However clinical applications of PDT treatment are restricted by the limited penetration of light. In recent years, interstitial PDT has been studied for treatment of larger and deeper lesions [2

2. S. Krishnamurthy, S. K. Powers, P. Witmer, and T. Brown, “Optimal light dose for interstitial photodynamic therapy in treatment for malignant brain tumors,” Lasers Surg. Med. 27(3), 224–234 (2000). [CrossRef] [PubMed]

, 3

3. A. Johansson, J. Axelsson, S. Andersson-Engels, and J. Swartling, “Realtime light dosimetry software tools for interstitial photodynamic therapy of the human prostate,” Med. Phys. 34(11), 4309–4321 (2007). [CrossRef] [PubMed]

]. This treatment approach needs images to provide the morphological and physiological information of the diseased tissues. MRI guided diffuse optical spectroscopy (DOS) and fluorescence tomography imaging (FTI) [4

4. A. Corlu, R. Choe, T. Durduran, M. A. Rosen, M. Schweiger, S. R. Arridge, M. D. Schnall, and A. G. Yodh, “Three-dimensional in vivo fluorescence diffuse optical tomography of breast cancer in humans,” Opt. Express 15(11), 6696–6716 (2007). [CrossRef] [PubMed]

] have been developed for diagnosis of tumors. With these technologies, the three-dimensional (3D) dosimetric planning of interstitial PDT can be realized. Another problem for interstitial PDT is to estimate the efficacy of PDT. Singlet oxygen luminescence dosimetry is the golden standard. However its clinical applications are limited due to its very low luminescence intensity [5

5. M. T. Jarvi, M. J. Niedre, M. S. Patterson, and B. C. Wilson, “Singlet oxygen luminescence dosimetry (SOLD) for photodynamic therapy: current status, Challenges and future prospects,” Photochem. Photobiol. 82(5), 1198–1210 (2006). [CrossRef] [PubMed]

]. The treatment planning must consider the three elements of PDT, not only light. Therefore, interstitial PDT would benefit from these multimodality methods with the theranostic agents that could function as MRI contrast agent (CA), photosensitizer and oxygen indicator at the same time.

In this study, gadolinium metalated hematoporphyrin methyl ether Gd(III)-HMME was synthesized and characterized with mass spectra and UV-visible spectra. Both the molecular weight and the electronic structure confirmed the successful synthesis of the metalloporphyrins. The weak fluorescence and strong room temperature phosphorescence were observed and proved with time resolved spectroscopy. The dependence of the luminescence spectra of Gd(III)-HMME on dissolved oxygen levels was determined, which shows that the fluorescence intensity is independent of oxygen levels while the phosphorescence is strongly dependent on oxygen level. The phosphorescence intensity decreased by 79% in oxygen saturated methanol. This phenomenon indicates the potential of Gd(III)-HMME to be an optical ratiometric oxygen indicator. The singlet oxygen quantum yields ΦΔ of Gd(III)-HMME and HMME were determined with a comparative method based on spectrophotometer using 1,3-diphenylisobenzofuran (DPBF) as singlet oxygen capture and 4,5,6,7,-tetrachloro-2’,4’,5′,7’-tetraiodofluorescein disodium salt (Rose Bengal) as a reference. Although the ΦΔ of Gd(III)-HMME is only half of that of HMME, the efficiency of photosensitization is high enough for the PDT purpose. The synergistic effect of oxygen sensing capability, photosensitivity, MRI enhancement, cell permeability and the necrosis affinity would give Gd(III)-HMME a wide potential application prospect.

2. Experimental

2.1 Chemicals

Anhydrous gadolinium(III) chloride (GdCl3), 1,3-diphenylisobenzofuran (DPBF) and 4,5,6,7,-tetrachloro-2’,4’,5′,7’-tetraiodofluorescein disodium salt (Rose Bengal) were obtained from J&K Scientific Ltd. Hematoporphyrin monomethyl ether (HMME) was purchased from Shanghai Xianhui Pharmacuetical Co. Ltd. All chemical reagents were analytical reagent grade and used without further purification.

Gd(III)-HMME was synthesized in imidazole at high temperature with gentle argon flow protection based on T. S. Srivastava’s method [22

22. T. S. Srivastava, “Lanthanide octaethylprophyrins: preparation, association, and interaction with axial ligands,” Bioinorg. Chem. 8(1), 61–76 (1978). [CrossRef] [PubMed]

]. 5 g imidazole, 12 mg HMME and 150 mg anhydrous GdCl3 were added into a 50 ml round bottom flask with argon flow protection for 30 min. Then, the mixture was heated and kept at 220 °C and stirred magnetically for 2 h protected with gentle argon flow. After cooling down to room temperature, the mixture was dissolved in 10 ml methanol and dialyzed (cutoff size = 800) against methanol for 5 times.

2.2 Instrumentation

Mass spectroscopy were recorded by liquid chromatography/mass spectra (LC/MS) analyzing system (Thermo Finnigan Surveyor LCQ DECA XP plus, USA). UV-visible absorption spectra were determined with miniature fiber optic spectrometer QE65000 (Ocean Optics, USA) equipped with the deuterium lamp. 532 nm solid laser (CLO Laser DPGL-500L, China) was used for excitation of photosensitizers. Laser power meter (Ophir Photonics Group, Israel) was used to determine the output power of the 532 nm laser. In the time resolved spectroscopy measurements, the laser pulses of 100 fs at 800 nm from Ti: sapphire femtosecond laser (Spectra-Physics, USA) passed through a double-frequency BBO crystal. The output pulses at 400 nm were used for the luminescence excitation of HMME and Gd(III)-HMME. The luminescence spectra were recorded every 2 ns with the spectrometer (Bruker Optics) and intensified charge coupled device (ICCD, IStar740, CCI010, Andor), which was trigged by synchronization and delay generator (SDG, Spectra-Physics, USA) and Digital Delay/Pulse Generator (Stanford Research Systems).

2.3 Oxygen sensitivity of luminescence spectra

The luminescence spectra in solutions with different dissolved oxygen concentrations were recorded. The oxygen and nitrogen flows were controlled with two gas mass flow meters and mixed in a bottle. The gas mixture was loaded into Gd(III)-HMME methanol solution with a needle and then kept above the solution surface. The dissolved oxygen level was then controlled by the ratio of flow rates of oxygen and nitrogen. The proportion of oxygen was set as 3%, 12.7%, 22.4% and 100%. A vacuum pump was used to get the solution deoxygenated. Optics fiber loading light at 405 nm was used for excitation and the luminescence spectra were measured using a miniature spectrometer QE65000.

2.4 Singlet oxygen production

In this study, ΦΔ of HMME and Gd-HMME in air saturated methanol at room temperature were determined by a spectrophotometric method. In this relative method, there are two critical analytical reagents, singlet oxygen capture with typical absorption or fluorescence spectra and photosensitizer with well determined ΦΔ. At least three data are used in this analysis. They are: ΦΔ of the photosensitizer of the reference reagent, the absorption of excitation light and the photodegradation rates of singlet oxygen capture in each mixture solutions with different photosensitizers. The ΦΔ is determined based on Eq. (1).
ΦΔIabsk=ΦΔrefIabsrefkref,
(1)
where k is the degradation rate of the singlet oxygen capture DPBF, mainly induced by the reaction with singlet oxygen; the superscript ref stands for the reference reagent Rose Bengal; Iabs represents the absorption of excitation light by photosensitizer [23

23. A. Ogunsipe and T. Nyokong, “Photophysical and photochemical studies of sulphonated non-transition metal phthalocyanines in aqueous and non-aqueous media,” J. Photochem. Photobiol. Chem. 173(2), 211–220 (2005). [CrossRef]

]. Iabs is determined by concentrations of photosensitizers, extinction coefficients and incident light intensities as described by Eq. (2).
Iabs=I532(λ)×(1eε(λ)NL)dλ,
(2)
where I532(λ) is the emission spectra of the 532 nm laser, ε(λ) is the extinction spectra of each photosensitizer, N represents the concentration of that photosensitizer and L represents the is the light path in the cuvette.

Rose Bengal was used as the reference reagent ΦΔRB = 0.76 in air saturated methanol solution at room temperature [24

24. S. Mathai, T. A. Smith, and K. P. Ghiggino, “Singlet oxygen quantum yields of potential porphyrin-based photosensitisers for photodynamic therapy,” Photochem. Photobiol. Sci. 6(9), 995–1002 (2007). [CrossRef] [PubMed]

]. DPBF is a highly singlet oxygen selective indicator. DPBF has strong absorption at 415 nm and the product of chemical reaction between DPBF and singlet oxygen has no absorption in this range. The UV-visible absorption spectra in the range of 400 nm to 430 nm were uesd to monitor the photostability of DPBF under irradiation at 532 nm and the photodegradation in mixtures with photosensitizers. Four samples were prepared: (1) DPBF 30 μM; (2) DPBF 30 μM, Rose Bengal 1 μM; (3) DPBF 30 μM, HMME 2 μM; (4) DPBF 30 μM, Gd-HMME 2 μM. Each sample of 3 ml was put in silica curette of 1 cm length and illuminated with 532 nm laser at the same power density of 1 mW/cm2, corresponding to a photon density of 1.3 × 1013/cm3. The decrease of DPBF was monitored with UV-visible absorption spectroscopy simultaneously. The absorption spectra of DPBF were recorded every 3 min and the degradation rate of DPBF k was determined accordingly. In this experiment, all measurements were taken at room temperature under 1 atm.

3. Results and discussion

3.1 Synthesis and characterization

Figure 1
Fig. 1 Chemical structures of (a) HMME and (b) Gd(III)-HMME.
presents the chemical structures of HMME and Gd(III)-HMME, and the chloride ion is omitted in the figure. The ESI mass spectrum of Gd(III)-HMME has an intense peak at m/z = 803.05 (calc m/z = 803.17) corresponding to [Cl-Gd(III)-HMME + H+] as shown in Fig. 2
Fig. 2 Mass spectrum of Gd(III)-HMME (Positive ion ESI source). [HMME + H+]: HMME molecule attached with a proton; [Cl-Gd(III)-HMME]+: Gd(III)-HMME molecule attached with one chloride ion.
.

The UV-visible absorption spectra and luminescence spectra of HMME and Gd(III)-HMME are presented in Fig. 3
Fig. 3 Normalized absorption spectra (black solid line) of HMME and Gd(III)-HMME and the corresponding luminescence spectra (red solid line) in oxygen-free methanol solutions. The Soret bands and Q bands are labeled. The fluorescence emissions are labeled. Inset figure shows the weak fluorescence emission of Gd(III)-HMME. The strong room-temperature redshift luminescence emissions are marked as phosphorescence.
. The gadolinium ion has a relatively large ionic radius of 93.8 pm and its corresponding metalloporphyrins have an out-of-plane structure [25

25. H. Ryeng and A. Ghosh, “Do nonplanar distortions of porphyrins bring about strongly red-shifted electronic spectra? Controversy, consensus, new developments, and relevance to chelatases,” J. Am. Chem. Soc. 124(27), 8099–8103 (2002). [CrossRef] [PubMed]

]. The out- of-plane results in red shift of Q-band absorption peaks. The change of symmetry from D2h to C4v leads to the Q-band peak reduction. The Q-band peaks of HMME are at 499 nm, 530 nm, 568 nm and 624 nm [26

26. M. Gouterman, “Optical spectra and electronic structure of porphyrins and related rings,” in The Porphyrins, Part 3A(Academic Press, 1978).

, 27

27. T. C. Lei, G. F. Glazner, M. Duffy, L. Scherrer, S. Pendyala, B. Li, X. L. Wang, H. W. Wang, and Z. Huang, “Optical properties of hematoporphyrin monomethyl ether (HMME), a PDT photosensitizer,” Photodiagn. Photodyn. Ther. 9(3), 232–242 (2012). [CrossRef] [PubMed]

]. The Q-band peaks of Gd(III)-HMME are at 538 nm and 571 nm. The fluorescence intensity of Gd(III)-HMME decreased significantly and their peaks are in the mirror positions of the absorption spectra, in accordance with Franck-Condon principle. In addition, Gd(III)-HMME also exhibits strong room temperature luminescence emission and the peaks are at 712 nm and 780 nm.

3.2 Luminescence lifetimes of Gd(III)-HMME and HMME

Figure 4(a)
Fig. 4 The decay curves of the fluorescence emission of HMME and Gd(III)-HMME at 625 nm in methanol solution (a) and the decay curve luminescence emission of Gd(III)-HMME at 710 nm in oxygen-free methanol solution (b).
presents the luminescence decay curves of HMME and Gd(III)-HMME in air-saturated methanol solutions at 625 nm, respectively. The fluorescence lifetime of Gd(III)-HMME is smaller than that of HMME. Figure 4(b) shows the luminescence decay curves of Gd(III)-HMME in deaerated methanol. The lifetime of 51 μs indicates that the emission is from the triplet energy level. The electron configuration of trivalent gadolinium ion is [Xe]4f7. The heavy atom effect and the paramagnetism enhanced the singlet-triplet intersystem crossing [19

19. A. Harriman, “Luminescence of porphyrins and metalloporphyrins. Part 3. -Heavy-atom effects,” J. Chem. Soc., Faraday Trans. II 77(7), 1281–1291 (1981). [CrossRef]

]. This effect reduces the fluorescence intensity and makes strong phosphorescence possible. In contrast to Yb3+, Er3+ and Nd3+ [6

6. Y. Ni, “Metalloporphyrins and functional analogues as MRI contrast agents,” Curr. Med Imaging. Rev. 4(2), 96–112 (2008). [CrossRef]

], which have lower energy levels to the single states (S1 and S2) and triple states (T1) of porphyrins, Gd3+ ion cannot receive energy by means of the Förster resonance energy transfer. For these reasons, gadolinium porphyrins have very strong room temperature phosphorescent emission.

3.3 Oxygen dependence

The relationship between the luminescence intensity of Gd(III)-HMME and dissolved oxygen concentration was studied. Figure 5
Fig. 5 The luminescence spectra of Gd(III)-HMME in methanol solutions with different dissolved oxygen concentrations. The fluorescence and phosphorescence peaks are labeled respectively.
presents the luminescence spectra in methanol with different dissolved oxygen concentrations. The fluorescence intensities at 625 nm kept the same and the phosphorescence intensities at 710 nm depended strongly on dissolved oxygen concentrations and decreased by 79% in oxygen saturated methanol solution. The phosphorescence emission intensity and lifetime always comply with the Stern-Volmer relationship and the fluorescence offers an invariant referent. Therefore, the ratio between phosphorescence and fluorescence could be used for oxygen indication after calibration.

3.4 Singlet oxygen production

Figure 6
Fig. 6 The absorption spectra of DPBF in methanol solutions with (a) no photosensitizer (b) 1 μM Rose Bengal (c) 2 μM HMME (d) 2 μM Gd(III)-HMME with 532 nm laser illumination and recorded every 3 min.
shows the absorption spectra DPBF in methanol solution by itself and in the mixture solution of Rose Bengal, HMME and Gd(III)-HMME, respectively. The photostability of DPBF is excellent under the light excitation at 532 nm. The residual concentration of DPBF and the excitation time follows exponential relationship in solutions with photosensitizers.

Figure 7
Fig. 7 Relative consumptions of DPBF under irradiation mixed with different photosensitizers and recorded every 3 min.
shows the time dependence of relative consumption of DPBF in four circumstances. The concentrations of DPBF are determined with the absorption spectra shown in Fig. 6. The degradation rates of DPBF are determined by linear fitting. The degradation rates of DPBF, the absorption of excitation light at 532 nm and ΦΔ calculated according to Eq. (1) are presented in Table 1

Table 1. Chemicals, concentrations and calculated degradation rates k, absorption Iabs and sensitization efficiencies ΦΔ.

table-icon
View This Table
. Although the singlet oxygen quantum yield of Gd(III)-HMME (ΦΔ = 0.40) is only about one half of that of HMME (ΦΔ = 0.79) in air-saturated methanol solution at room temperature, the singlet oxygen generation is still more than sufficient for PDT purpose.

4. Conclusion

In conclusion, gadolinium porphyrin Gd(III)-HMME was synthesized and characterized with UV-visible spectra and mass spectra. The photophysical and photochemical properties were studied with spectral methods. Strong room-temperature phosphorescence was observed and further proved by time resolved spectroscopy analysis. The fluorescence intensity of Gd(III)-HMME is insensitive to dissolved oxygen concentration but its phosphorescence shows strong dependence on dissolved oxygen levels. This phenomenon makes Gd(III)-HMME a promising and potential ratiometric oxygen sensor. Although ΦΔ of Gd(III)-HMME is 0.4 in air saturated methanol solution at room temperature, only about half of that of Rose Bengal or HMME, the photosensitivity of Gd(III)-HMME is still relatively strong among metalloporphyrins. The inherent paramagnetism of Gd3+ and the physiochemical properties will help Gd(III)-HMME find various applications, especially for biomedical purposes like MRI-guided PDT treatment.

Acknowledgments

This work was financially supported by the National Key Basic Research Program of China (973 Program) under Grant No. 2013CB632900.

References and links

1.

J. P. Celli, B. Q. Spring, I. Rizvi, C. L. Evans, K. S. Samkoe, S. Verma, B. W. Pogue, and T. Hasan, “Imaging and photodynamic therapy: mechanisms, monitoring, and optimization,” Chem. Rev. 110(5), 2795–2838 (2010). [CrossRef] [PubMed]

2.

S. Krishnamurthy, S. K. Powers, P. Witmer, and T. Brown, “Optimal light dose for interstitial photodynamic therapy in treatment for malignant brain tumors,” Lasers Surg. Med. 27(3), 224–234 (2000). [CrossRef] [PubMed]

3.

A. Johansson, J. Axelsson, S. Andersson-Engels, and J. Swartling, “Realtime light dosimetry software tools for interstitial photodynamic therapy of the human prostate,” Med. Phys. 34(11), 4309–4321 (2007). [CrossRef] [PubMed]

4.

A. Corlu, R. Choe, T. Durduran, M. A. Rosen, M. Schweiger, S. R. Arridge, M. D. Schnall, and A. G. Yodh, “Three-dimensional in vivo fluorescence diffuse optical tomography of breast cancer in humans,” Opt. Express 15(11), 6696–6716 (2007). [CrossRef] [PubMed]

5.

M. T. Jarvi, M. J. Niedre, M. S. Patterson, and B. C. Wilson, “Singlet oxygen luminescence dosimetry (SOLD) for photodynamic therapy: current status, Challenges and future prospects,” Photochem. Photobiol. 82(5), 1198–1210 (2006). [CrossRef] [PubMed]

6.

Y. Ni, “Metalloporphyrins and functional analogues as MRI contrast agents,” Curr. Med Imaging. Rev. 4(2), 96–112 (2008). [CrossRef]

7.

M. Bottrill, L. Kwok, and N. J. Long, “Lanthanides in magnetic resonance imaging,” Chem. Soc. Rev. 35(6), 557–571 (2006). [CrossRef] [PubMed]

8.

H. S. He, J. P. Guo, Z. X. Zhao, W. K. Wong, W. Y. Wong, W. K. Lo, K. F. Li, L. Luo, and K. W. Cheah, “Synthesis, characterization and near-infrared photoluminescence of monoporphyrinate lanthanide complexes containing an anionic tripodal ligand,” Eur. J. Inorg. Chem. 2004(4), 837–845 (2004). [CrossRef]

9.

S. M. Borisov, G. Zenkl, and I. Klimant, “Phosphorescent platinum(II) and palladium(II) complexes with azatetrabenzoporphyrins-new red laser diode-compatible indicators for optical oxygen sensing,” ACS Appl. Mater. Interfaces 2(2), 366–374 (2010). [CrossRef] [PubMed]

10.

K. Koren, S. M. Borisov, R. Saf, and I. Klimant, “Strongly phosphorescent iridium(III)-porphyrins new oxygen indicators with tunable photophysical properties and functionalities,” Eur. J. Inorg. Chem. 2011(10), 1531–1534 (2011). [CrossRef] [PubMed]

11.

P. Mroz, J. Bhaumik, D. K. Dogutan, Z. Aly, Z. Kamal, L. Khalid, H. L. Kee, D. F. Bocian, D. Holten, J. S. Lindsey, and M. R. Hamblin, “Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: role of molecular charge, central metal and hydroxyl radical production,” Cancer Lett. 282(1), 63–76 (2009). [CrossRef] [PubMed]

12.

H. J. Vreman and D. K. Stevenson, “Metalloporphyrin-enhanced photodegradation of bilirubin in vitro,” Am. J. Dis. Child. 144(5), 590–594 (1990). [PubMed]

13.

S. D. Appleton, M. L. Chretien, B. E. McLaughlin, H. J. Vreman, D. K. Stevenson, J. F. Brien, K. Nakatsu, D. H. Maurice, and G. S. Marks, “Selective inhibition of heme oxygenase, without inhibition of nitric oxide synthase or soluble guanylyl cyclase, by metalloporphyrins at low concentrations,” Drug Metab. Dispos. 27(10), 1214–1219 (1999). [PubMed]

14.

M. A. Oar, W. R. Dichtel, J. M. Serin, J. M. J. Frechet, J. E. Rogers, J. E. Slagle, P. A. Fleitz, L. S. Tan, T. Y. Ohulchanskyy, and P. N. Prasad, “Light-harvesting chromophores with metalated porphyrin cores for tuned photosensitization of singlet oxygen via two-photon excited FRET,” Chem. Mater. 18(16), 3682–3692 (2006). [CrossRef]

15.

C. Brushett, B. Qiu, E. Atalar, and X. Yang, “High-resolution MRI of deep-seated atherosclerotic arteries using motexafin gadolinium,” J. Magn. Reson. Imaging 27(1), 246–250 (2008). [CrossRef] [PubMed]

16.

Y. Ni, C. Pislaru, H. Bosmans, S. Pislaru, Y. Miao, F. Van de Werf, W. Semmler, and G. Marchal, “Validation of intracoronary delivery of metalloporphyrin as an in vivo “histochemical staining” for myocardial infarction with MR imaging,” Acad. Radiol. 5(Suppl 1), S37–S41, discussion S45–S46 (1998). [CrossRef] [PubMed]

17.

V. M. Runge, B. R. Carollo, C. R. Wolf, K. L. Nelson, and D. Y. Gelblum, “Gd DTPA: a review of clinical indications in central nervous system magnetic resonance imaging,” Radiographics 9(5), 929–958 (1989). [CrossRef] [PubMed]

18.

A. M. Evens, “Motexafin gadolinium: a redox-active tumor selective agent for the treatment of cancer,” Curr. Opin. Oncol. 16(6), 576–580 (2004). [CrossRef] [PubMed]

19.

A. Harriman, “Luminescence of porphyrins and metalloporphyrins. Part 3. -Heavy-atom effects,” J. Chem. Soc., Faraday Trans. II 77(7), 1281–1291 (1981). [CrossRef]

20.

E. G. Ermolina, R. T. Kuznetsova, T. A. Solodova, E. N. Telminov, T. N. Kopylova, G. V. Mayer, N. N. Semenishyn, N. V. Rusakova, and Y. V. Korovin, “Photophysics and oxygen sensing properties of tetraphenylporphyrin lanthanide complexes,” Dyes Pigments 97(1), 209–214 (2013). [CrossRef]

21.

J. Cheng, H. Liang, Q. Li, C. Peng, Z. Li, S. Shi, L. Yang, Z. Tian, Y. Tian, Z. Zhang, and W. Cao, “Hematoporphyrin monomethyl ether-mediated photodynamic effects on THP-1 cell-derived macrophages,” J. Photochem. Photobiol. B 101(1), 9–15 (2010). [CrossRef] [PubMed]

22.

T. S. Srivastava, “Lanthanide octaethylprophyrins: preparation, association, and interaction with axial ligands,” Bioinorg. Chem. 8(1), 61–76 (1978). [CrossRef] [PubMed]

23.

A. Ogunsipe and T. Nyokong, “Photophysical and photochemical studies of sulphonated non-transition metal phthalocyanines in aqueous and non-aqueous media,” J. Photochem. Photobiol. Chem. 173(2), 211–220 (2005). [CrossRef]

24.

S. Mathai, T. A. Smith, and K. P. Ghiggino, “Singlet oxygen quantum yields of potential porphyrin-based photosensitisers for photodynamic therapy,” Photochem. Photobiol. Sci. 6(9), 995–1002 (2007). [CrossRef] [PubMed]

25.

H. Ryeng and A. Ghosh, “Do nonplanar distortions of porphyrins bring about strongly red-shifted electronic spectra? Controversy, consensus, new developments, and relevance to chelatases,” J. Am. Chem. Soc. 124(27), 8099–8103 (2002). [CrossRef] [PubMed]

26.

M. Gouterman, “Optical spectra and electronic structure of porphyrins and related rings,” in The Porphyrins, Part 3A(Academic Press, 1978).

27.

T. C. Lei, G. F. Glazner, M. Duffy, L. Scherrer, S. Pendyala, B. Li, X. L. Wang, H. W. Wang, and Z. Huang, “Optical properties of hematoporphyrin monomethyl ether (HMME), a PDT photosensitizer,” Photodiagn. Photodyn. Ther. 9(3), 232–242 (2012). [CrossRef] [PubMed]

28.

R. Battino, T. R. Rettich, and T. Tominaga, “The solubility of oxygen and ozone in liquids,” J. Phys. Chem. Ref. Data 12(2), 163–178 (1983). [CrossRef]

OCIS Codes
(160.4760) Materials : Optical properties
(160.5690) Materials : Rare-earth-doped materials
(300.6500) Spectroscopy : Spectroscopy, time-resolved
(160.1435) Materials : Biomaterials

ToC Category:
Spectroscopy

History
Original Manuscript: November 14, 2013
Revised Manuscript: December 27, 2013
Manuscript Accepted: December 29, 2013
Published: January 28, 2014

Virtual Issues
Vol. 9, Iss. 4 Virtual Journal for Biomedical Optics

Citation
Peng Wang, Feng Qin, Li Wang, Fajun Li, Yangdong Zheng, Yunfei Song, Zhiguo Zhang, and Wenwu Cao, "Luminescence and photosensitivity of gadolinium labeled hematoporphyrin monomethyl ether," Opt. Express 22, 2414-2422 (2014)
http://www.opticsinfobase.org/vjbo/abstract.cfm?URI=oe-22-3-2414


Sort:  Author  |  Year  |  Journal  |  Reset  

References

  1. J. P. Celli, B. Q. Spring, I. Rizvi, C. L. Evans, K. S. Samkoe, S. Verma, B. W. Pogue, T. Hasan, “Imaging and photodynamic therapy: mechanisms, monitoring, and optimization,” Chem. Rev. 110(5), 2795–2838 (2010). [CrossRef] [PubMed]
  2. S. Krishnamurthy, S. K. Powers, P. Witmer, T. Brown, “Optimal light dose for interstitial photodynamic therapy in treatment for malignant brain tumors,” Lasers Surg. Med. 27(3), 224–234 (2000). [CrossRef] [PubMed]
  3. A. Johansson, J. Axelsson, S. Andersson-Engels, J. Swartling, “Realtime light dosimetry software tools for interstitial photodynamic therapy of the human prostate,” Med. Phys. 34(11), 4309–4321 (2007). [CrossRef] [PubMed]
  4. A. Corlu, R. Choe, T. Durduran, M. A. Rosen, M. Schweiger, S. R. Arridge, M. D. Schnall, A. G. Yodh, “Three-dimensional in vivo fluorescence diffuse optical tomography of breast cancer in humans,” Opt. Express 15(11), 6696–6716 (2007). [CrossRef] [PubMed]
  5. M. T. Jarvi, M. J. Niedre, M. S. Patterson, B. C. Wilson, “Singlet oxygen luminescence dosimetry (SOLD) for photodynamic therapy: current status, Challenges and future prospects,” Photochem. Photobiol. 82(5), 1198–1210 (2006). [CrossRef] [PubMed]
  6. Y. Ni, “Metalloporphyrins and functional analogues as MRI contrast agents,” Curr. Med Imaging. Rev. 4(2), 96–112 (2008). [CrossRef]
  7. M. Bottrill, L. Kwok, N. J. Long, “Lanthanides in magnetic resonance imaging,” Chem. Soc. Rev. 35(6), 557–571 (2006). [CrossRef] [PubMed]
  8. H. S. He, J. P. Guo, Z. X. Zhao, W. K. Wong, W. Y. Wong, W. K. Lo, K. F. Li, L. Luo, K. W. Cheah, “Synthesis, characterization and near-infrared photoluminescence of monoporphyrinate lanthanide complexes containing an anionic tripodal ligand,” Eur. J. Inorg. Chem. 2004(4), 837–845 (2004). [CrossRef]
  9. S. M. Borisov, G. Zenkl, I. Klimant, “Phosphorescent platinum(II) and palladium(II) complexes with azatetrabenzoporphyrins-new red laser diode-compatible indicators for optical oxygen sensing,” ACS Appl. Mater. Interfaces 2(2), 366–374 (2010). [CrossRef] [PubMed]
  10. K. Koren, S. M. Borisov, R. Saf, I. Klimant, “Strongly phosphorescent iridium(III)-porphyrins new oxygen indicators with tunable photophysical properties and functionalities,” Eur. J. Inorg. Chem. 2011(10), 1531–1534 (2011). [CrossRef] [PubMed]
  11. P. Mroz, J. Bhaumik, D. K. Dogutan, Z. Aly, Z. Kamal, L. Khalid, H. L. Kee, D. F. Bocian, D. Holten, J. S. Lindsey, M. R. Hamblin, “Imidazole metalloporphyrins as photosensitizers for photodynamic therapy: role of molecular charge, central metal and hydroxyl radical production,” Cancer Lett. 282(1), 63–76 (2009). [CrossRef] [PubMed]
  12. H. J. Vreman, D. K. Stevenson, “Metalloporphyrin-enhanced photodegradation of bilirubin in vitro,” Am. J. Dis. Child. 144(5), 590–594 (1990). [PubMed]
  13. S. D. Appleton, M. L. Chretien, B. E. McLaughlin, H. J. Vreman, D. K. Stevenson, J. F. Brien, K. Nakatsu, D. H. Maurice, G. S. Marks, “Selective inhibition of heme oxygenase, without inhibition of nitric oxide synthase or soluble guanylyl cyclase, by metalloporphyrins at low concentrations,” Drug Metab. Dispos. 27(10), 1214–1219 (1999). [PubMed]
  14. M. A. Oar, W. R. Dichtel, J. M. Serin, J. M. J. Frechet, J. E. Rogers, J. E. Slagle, P. A. Fleitz, L. S. Tan, T. Y. Ohulchanskyy, P. N. Prasad, “Light-harvesting chromophores with metalated porphyrin cores for tuned photosensitization of singlet oxygen via two-photon excited FRET,” Chem. Mater. 18(16), 3682–3692 (2006). [CrossRef]
  15. C. Brushett, B. Qiu, E. Atalar, X. Yang, “High-resolution MRI of deep-seated atherosclerotic arteries using motexafin gadolinium,” J. Magn. Reson. Imaging 27(1), 246–250 (2008). [CrossRef] [PubMed]
  16. Y. Ni, C. Pislaru, H. Bosmans, S. Pislaru, Y. Miao, F. Van de Werf, W. Semmler, G. Marchal, “Validation of intracoronary delivery of metalloporphyrin as an in vivo “histochemical staining” for myocardial infarction with MR imaging,” Acad. Radiol. 5(Suppl 1), S37–S41, discussion S45–S46 (1998). [CrossRef] [PubMed]
  17. V. M. Runge, B. R. Carollo, C. R. Wolf, K. L. Nelson, D. Y. Gelblum, “Gd DTPA: a review of clinical indications in central nervous system magnetic resonance imaging,” Radiographics 9(5), 929–958 (1989). [CrossRef] [PubMed]
  18. A. M. Evens, “Motexafin gadolinium: a redox-active tumor selective agent for the treatment of cancer,” Curr. Opin. Oncol. 16(6), 576–580 (2004). [CrossRef] [PubMed]
  19. A. Harriman, “Luminescence of porphyrins and metalloporphyrins. Part 3. -Heavy-atom effects,” J. Chem. Soc., Faraday Trans. II 77(7), 1281–1291 (1981). [CrossRef]
  20. E. G. Ermolina, R. T. Kuznetsova, T. A. Solodova, E. N. Telminov, T. N. Kopylova, G. V. Mayer, N. N. Semenishyn, N. V. Rusakova, Y. V. Korovin, “Photophysics and oxygen sensing properties of tetraphenylporphyrin lanthanide complexes,” Dyes Pigments 97(1), 209–214 (2013). [CrossRef]
  21. J. Cheng, H. Liang, Q. Li, C. Peng, Z. Li, S. Shi, L. Yang, Z. Tian, Y. Tian, Z. Zhang, W. Cao, “Hematoporphyrin monomethyl ether-mediated photodynamic effects on THP-1 cell-derived macrophages,” J. Photochem. Photobiol. B 101(1), 9–15 (2010). [CrossRef] [PubMed]
  22. T. S. Srivastava, “Lanthanide octaethylprophyrins: preparation, association, and interaction with axial ligands,” Bioinorg. Chem. 8(1), 61–76 (1978). [CrossRef] [PubMed]
  23. A. Ogunsipe, T. Nyokong, “Photophysical and photochemical studies of sulphonated non-transition metal phthalocyanines in aqueous and non-aqueous media,” J. Photochem. Photobiol. Chem. 173(2), 211–220 (2005). [CrossRef]
  24. S. Mathai, T. A. Smith, K. P. Ghiggino, “Singlet oxygen quantum yields of potential porphyrin-based photosensitisers for photodynamic therapy,” Photochem. Photobiol. Sci. 6(9), 995–1002 (2007). [CrossRef] [PubMed]
  25. H. Ryeng, A. Ghosh, “Do nonplanar distortions of porphyrins bring about strongly red-shifted electronic spectra? Controversy, consensus, new developments, and relevance to chelatases,” J. Am. Chem. Soc. 124(27), 8099–8103 (2002). [CrossRef] [PubMed]
  26. M. Gouterman, “Optical spectra and electronic structure of porphyrins and related rings,” in The Porphyrins, Part 3A(Academic Press, 1978).
  27. T. C. Lei, G. F. Glazner, M. Duffy, L. Scherrer, S. Pendyala, B. Li, X. L. Wang, H. W. Wang, Z. Huang, “Optical properties of hematoporphyrin monomethyl ether (HMME), a PDT photosensitizer,” Photodiagn. Photodyn. Ther. 9(3), 232–242 (2012). [CrossRef] [PubMed]
  28. R. Battino, T. R. Rettich, T. Tominaga, “The solubility of oxygen and ozone in liquids,” J. Phys. Chem. Ref. Data 12(2), 163–178 (1983). [CrossRef]

Cited By

Alert me when this paper is cited

OSA is able to provide readers links to articles that cite this paper by participating in CrossRef's Cited-By Linking service. CrossRef includes content from more than 3000 publishers and societies. In addition to listing OSA journal articles that cite this paper, citing articles from other participating publishers will also be listed.


« Previous Article  |  Next Article »

OSA is a member of CrossRef.

CrossCheck Deposited