Synthesis and in vitro PDT evaluation of new porphyrins containing meso-epoxymethylaryl cationic groups.

Abstract:

OBJECTIVES:Photodynamic therapy (PDT) is an effective cancer treatment that uses photosensitizers, light, and oxygen to destroy malignant cells. Porphyrins, and in particular the cationic derivatives, are the most investigated photosensitizers for PDT. In this context, it is important to study new methodologies to develop efficient cationic photosensitizers for use in PDT. MATERIALS AND METHODS:New porphyrins bearing cationic epoxymethylaryl groups were synthesized and characterized. Their cellular uptake, intracellular localization, and phototoxicity were evaluated in human HEp2 cells, and compared with their methylated analogs. RESULTS:All cationic porphyrins were efficient generators of singlet oxygen, with quantum yields in the range 0.35-0.61. The two methylated derivatives (3 and 4) accumulated the most within cells at all times investigated, up to 24 hours. Of these two porphyrins, 4 was the most phototoxic to the cells (LD50  = 2.4 μM at 1.5 J/cm2 ); however, porphyrin 3 also showed high phototoxicity (LD50  = 7.4 μM at 1.5 J/cm2 ). The epoxymethyl-containing porphyrins were found to be less phototoxic than the methylated derivatives, with LD50  >  38 μM. The neutral porphyrins showed no phototoxicity up to the 100 μM concentrations investigated, and had the lowest singlet oxygen quantum yields. All cationic porphyrins localized mainly in the cell ER, Golgi apparatus, and lysosomes. CONCLUSION:Our results suggest that cationic methylated porphyrin derivatives are promising PDT photosensitizing agents. The epoxymethyl-containing derivatives showed increased efficacy relative to the neutral analogs, and are good candidates for further investigation. Lasers Surg. Med. 50:566-575, 2018. © 2018 Wiley Periodicals, Inc.

journal_name

Lasers Surg Med

authors

Carneiro J,Gonçalves A,Zhou Z,Griffin KE,Kaufman NEM,Vicente MDGH

doi

10.1002/lsm.22824

subject

Has Abstract

pub_date

2018-07-01 00:00:00

pages

566-575

issue

5

eissn

0196-8092

issn

1096-9101

journal_volume

50

pub_type

杂志文章
  • Limits of radial time constants to approximate thermal response of tissue.

    abstract::The time constant model, as an approximation to the bio-heat equation, was tested for non-ablating, deep penetrating (argon) laser beams in absorbing tissue phantoms (polyacrylamide) in air. Temperature responses were measured with a thermal camera, both during laser irradiation as well as after the laser beam was swi...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900130615

    authors: Meijering LJ,van Gemert MJ,Gijsbers GH,Welch AJ

    更新日期:1993-01-01 00:00:00

  • Laser modulation of angiogenic factor production by T-lymphocytes.

    abstract:BACKGROUND AND OBJECTIVE:In previous investigations, small variations in the energy densities of low level light therapy (LLLT) were found to produce significant differences in the proliferation of resting T-lymphocytes in vitro. Pulsing these cells with mitogen in addition to laser therapy produced inhibitory effects ...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/(sici)1096-9101(2000)26:4<357::aid-lsm3>3.

    authors: Agaiby AD,Ghali LR,Wilson R,Dyson M

    更新日期:2000-01-01 00:00:00

  • The effect of irrigation on peak temperatures in nerve root, dura, and intervertebral disc during laser-assisted foraminoplasty.

    abstract:BACKGROUND AND OBJECTIVE:The Holmium: YAG (Ho: YAG) laser has been used for the ablation of prolapsed discs but alternative techniques are available, and this application remains controversial. It also has potential for the decompression of nerve roots within narrowed foraminae with the technique of endoscopic laser fo...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1083

    authors: Hafez MI,Zhou S,Coombs RR,McCarthy ID

    更新日期:2001-01-01 00:00:00

  • Functional efficacy of glatiramer acetate treatment for laser-induced retinal damage in rats.

    abstract:BACKGROUND AND OBJECTIVES:To functionally evaluate the efficacy of glatiramer acetate (Cop-1) as a neuroprotective treatment for laser-induced retinal injuries in rats. STUDY DESIGN/MATERIALS AND METHODS:Using standard lasering and flash ERG techniques, we evaluated the effect of photocoagulation and of Cop-1 treatmen...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.20610

    authors: Belokopytov M,Ben-Shlomo G,Rosner M,Belkin M,Dubinski G,Epstein Y,Ofri R

    更新日期:2008-03-01 00:00:00

  • Low power laser irradiation alters the rate of regeneration of the rat facial nerve.

    abstract::Low power laser irradiation has been reported to cause biological effects due to the photochemical and/or photophysical action of the radiation. This study determined quantitatively if transcutaneous low power laser irradiation can affect the regeneration of the rat facial nerve. The facial nerve was crushed unilatera...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900130113

    authors: Anders JJ,Borke RC,Woolery SK,Van de Merwe WP

    更新日期:1993-01-01 00:00:00

  • Short-term microbiological effects of photodynamic therapy in non-surgical periodontal treatment of residual pockets: A split-mouth RCT.

    abstract:BACKGROUND AND OBJECTIVE:Photodynamic therapy (PDT) has been used as a therapeutic alternative to treat periodontitis, especially in challenging sites that require additional periodontal therapy such as residual pockets. The aim of this split-mouth randomized trial was to evaluate the microbiological and clinical effec...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章,随机对照试验

    doi:10.1002/lsm.22449

    authors: Corrêa MG,Oliveira DH,Saraceni CH,Ribeiro FV,Pimentel SP,Cirano FR,Casarin RC

    更新日期:2016-12-01 00:00:00

  • Comparison of laser vascular welding, interrupted sutures, and continuous sutures in growing vascular anastomoses.

    abstract:BACKGROUND AND OBJECTIVES:The argon laser-assisted vascular anastomosis may solve the problems of conventional sutured anastomosis, such as vascular stenosis and arrest of growth owing to a foreign-body reaction to suture material. STUDY DESIGN/MATERIALS AND METHODS:Twelve argon laser-assisted vascular anastomoses, se...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900160105

    authors: Chikamatsu E,Sakurai T,Nishikimi N,Yano T,Nimura Y

    更新日期:1995-01-01 00:00:00

  • Water flux from partial-thickness skin wounds: comparative study of the effects of Er:YAG and Ho:YAG lasers.

    abstract:BACKGROUND AND OBJECTIVE:The clinical use of lasers to cut and coagulate tissue necessitates a better understanding of how the residual thermal damage affects healing. This study was designed to evaluate the effects of varying degrees of thermal damage on the healing process. STUDY DESIGN, MATERIALS AND METHODS:Partia...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/(SICI)1096-9101(1996)18:1<1::AID-LSM1>3.0.

    authors: Jaffe BH,Walsh JT Jr

    更新日期:1996-01-01 00:00:00

  • Moraxella catarrhalis is susceptible to antimicrobial photodynamic therapy with Photofrin.

    abstract:BACKGROUND AND OBJECTIVE:Moraxella catarrhalis is a significant cause of pediatric otitis media (OM), which is the most prevalent bacterial infection in children and primary reason for antibiotic administration in this population. Moreover, biofilm formation has been implicated as a primary mechanism of chronic or recu...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.22287

    authors: Luke-Marshall NR,Mang TS,Hansen LA,Campagnari AA

    更新日期:2014-11-01 00:00:00

  • The anti-inflammatory mechanism of 635 nm light-emitting-diode irradiation compared with existing COX inhibitors.

    abstract:BACKGROUND AND OBJECTIVES:Inhibition of cyclooxygenase (COX) and prostaglandin E(2) (PGE(2)) protects cells against cell injury in specific pathophysiological situations: inflammation and oxidative stress. Although the anti-inflammatory effects have been reported in clinical fields for specific wavelength irradiation d...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.20533

    authors: Lim W,Lee S,Kim I,Chung M,Kim M,Lim H,Park J,Kim O,Choi H

    更新日期:2007-08-01 00:00:00

  • Low-level laser therapy associated with high intensity resistance training on cardiac autonomic control of heart rate and skeletal muscle remodeling in wistar rats.

    abstract:BACKGROUND AND OBJECTIVE:Phototherapy plus dynamic exercise can enhance physical performance and improve health. The aim of our study was to evaluate the effect of low-level laser therapy (LLLT) associated with high intensity resistance training (HIT) on cardiac autonomic and muscle metabolic responses in rats. STUDY ...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.22298

    authors: Paolillo FR,Arena R,Dutra DB,de Cassia Marqueti Durigan R,de Araujo HS,de Souza HC,Parizotto NA,Cipriano G Jr,Chiappa G,Borghi-Silva A

    更新日期:2014-12-01 00:00:00

  • Enhancement of bonding to enamel and dentin prepared by Er,Cr:YSGG laser.

    abstract:BACKGROUND AND OBJECTIVE:Erbium lasers are potential tools to remove caries and dental hard tissue but bond strengths of composites to those preparations are reported to be lower than conventional methods. The purpose of this study was to evaluate the effect of mechanical excavation and/or chemical alteration on bond s...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.20790

    authors: Obeidi A,McCracken MS,Liu PR,Litaker MS,Beck P,Rahemtulla F

    更新日期:2009-08-01 00:00:00

  • Photodynamic effects of toluidine blue on human oral keratinocytes and fibroblasts and Streptococcus sanguis evaluated in vitro.

    abstract:BACKGROUND AND OBJECTIVE:Some oral bacteria are susceptible to killing by red light after their sensitization with toluidine blue O (TBO). The photochemotherapy of periodontal disease in vivo would require a therapeutic window where bacteria could be killed without adjacent normal tissue damage. STUDY DESIGN/MATERIALS...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/(SICI)1096-9101(1996)18:3<253::AID-LSM6>3.

    authors: Soukos NS,Wilson M,Burns T,Speight PM

    更新日期:1996-01-01 00:00:00

  • Spectroscopic, morphologic, and cytotoxic studies on major fractions of hematoporphyrin derivative and Photofrin II.

    abstract::This study characterizes the special properties of hematoporphyrin derivative (HpD) (Photofrin I) and Photofrin II with respect to the absorption and fluorescence spectra of the subfractions of the compounds in both solution and cells. In addition, data are presented demonstrating variation in the spectral amplitudes ...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900070207

    authors: Sun CH,Duzman E,Mellott J,Liaw LH,Berns MW

    更新日期:1987-01-01 00:00:00

  • Flashlamp pulsed dye laser (PDL) suppression of keloid proliferation through down-regulation of TGF-beta1 expression and extracellular matrix expression.

    abstract:BACKGROUND AND OBJECTIVES:Keloids have been treated with flashlamp pulsed dye lasers (PDLs) with good results. We investigated whether PDL treatments induced keloid regression by decreasing growth factor-beta(1) (TGF-beta(1)) induction, thereby reducing fibroblast proliferation and collagen deposition. STUDY DESIGN/MA...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.10206

    authors: Kuo YR,Jeng SF,Wang FS,Chen TH,Huang HC,Chang PR,Yang KD

    更新日期:2004-01-01 00:00:00

  • Treatment of infantile hemangiomas with the 595-nm pulsed dye laser using different pulse widths in an Asian population.

    abstract:INTRODUCTION:The pulsed dye laser (PDL) using varying fluences and pulse durations have been used to treat hemangiomas. This study aims to examine the efficacy and safety of the 595-nm PDL for the treatment of infantile hemangiomas using short (1.5-3 milliseconds) versus long (10 milliseconds) pulse durations and high ...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.21159

    authors: Tay YK,Tan SK

    更新日期:2012-02-01 00:00:00

  • Safety measures in gynecological laser surgery.

    abstract::The advantages of the laser have been extolled in the literature but, in contrast, there is a paucity of information on the hazards involved in its surgical use. Recognition and prevention of risks is a mandatory requirement. The experience by encounter is described with counsel as to the prerequisite of taking precau...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900040207

    authors: Lobraico RV

    更新日期:1984-01-01 00:00:00

  • Histologic changes associated with talaporfin sodium-mediated photodynamic therapy in rat skin.

    abstract:BACKGROUND AND OBJECTIVE:Alternative treatments are needed to achieve consistent and more complete port wine stain (PWS) removal, especially in darker skin types; photodynamic therapy (PDT) is a promising alternative treatment. To this end, we previously reported on Talaporfin Sodium (TS)-mediated PDT. It is essential ...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.22677

    authors: Moy WJ,Yao J,de Feraudy SM,White SM,Salvador J,Kelly KM,Choi B

    更新日期:2017-10-01 00:00:00

  • Choosing between intraoral or extraoral, red or infrared laser irradiation after impacted third molar extraction.

    abstract:BACKGROUND AND OBJECTIVE:Swelling and trismus are complications experienced by nearly all subjects after undergoing oral surgery for the removal of impacted teeth. The main purpose of this paper was to compare the effects of photobiomodulation therapy (PBMT) at two different wavelengths applied intra-orally and extra-o...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章,随机对照试验

    doi:10.1002/lsm.22488

    authors: Sierra SO,Deana AM,Bussadori SK,da Mota AC,Ferrari RA,do Vale KL,Fernandes KP

    更新日期:2016-07-01 00:00:00

  • In vitro evaluation of ablation parameters of normal and fibrous aorta using smooth excimer laser coronary angioplasty.

    abstract::A modified excimer laser energy delivery system was used to irradiate 100 segments of normal and fibrous aorta in vitro. The laser beam was scanned into 8 fiber bundles consisting of 50 fibers each resulting in a reduction of the applied pulse energy. The total repetition rate was increased to 150 Hz in order to keep ...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900130605

    authors: Xie DY,Hassenstein S,Oberhoff M,Hanke H,Baumbach A,Hohla K,Haase KK,Karsch KR

    更新日期:1993-01-01 00:00:00

  • Discrimination of cancerous and healthy colon tissues: A new laser-based method.

    abstract:BACKGROUND:Femtosecond (fs) Laser Ionisation Mass Spectrometry (fs-LIMS) on colon tissues are described and investigated using ionization/fragmentation processes in details to present a new application in this study. Linear Time of Flight (L-TOF) mass analyzer was utilized to investigate paraffin-embedded human tissue ...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.23033

    authors: Gündoğdu Y,Alptekin H,Karabağlı P,Şahin M,Kilic HŞ

    更新日期:2019-04-01 00:00:00

  • Alteration of spectral characteristics of human artery wall caused by 476-nm laser irradiation.

    abstract::Fluorescence spectroscopy is a promising new technique for discrimination of normal and atherosclerotic arterial tissues. It has been suggested that this technique be used as a guidance system for laser angiosurgery catheters; however, irradiation by 476-nm light can change the spectroscopic properties of arterial tis...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900090606

    authors: Chaudhry HW,Richards-Kortum R,Kolubayev T,Kittrell C,Partovi F,Kramer JR,Feld MS

    更新日期:1989-01-01 00:00:00

  • Treatment of port wine stains with photodynamic therapy, using pulsed dye laser as a light source, compared with pulsed dye laser alone: a pilot study.

    abstract:BACKGROUND AND OBJECTIVES:Laser-induced photo thermal damage has been combined with photodynamic therapy (PDT) using a systemic photosensitiser to treat vascular lesions. The efficacy of PDT using systemic 5-aminolaevulinic acid (5-ALA) as the photosensitiser and pulsed dye laser (PDL) as the light source in port wine ...

    journal_title:Lasers in surgery and medicine

    pub_type: 临床试验,杂志文章,随机对照试验

    doi:10.1002/lsm.20151

    authors: Evans AV,Robson A,Barlow RJ,Kurwa HA

    更新日期:2005-04-01 00:00:00

  • Massive air embolism complicating Nd-YAG laser endobronchial photoresection.

    abstract::A 63 year old male underwent 6,900 rads of external radiation for a squamous cell carcinoma of the left main bronchus. Recurrence of the tumor 8 months later was treated with 6,618 joules and patency of the left main bronchus was restored. Four months later, he developed complete atelectasis of the left lung requiring...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900120316

    authors: Golish JA,Pena CM,Mehta AC

    更新日期:1992-01-01 00:00:00

  • Comparison of non-ablative and ablative fractional laser treatments in a postoperative scar study.

    abstract:BACKGROUND AND OBJECTIVE:Postoperative scarring after thyroidectomy is a problem for both patients and clinicians. Recently, both non-ablative and ablative fractional laser (NFL and AFL) systems have attracted attention as potential therapies for the revision of thyroidectomy scars. The present split-scar study was des...

    journal_title:Lasers in surgery and medicine

    pub_type: 临床试验,杂志文章

    doi:10.1002/lsm.22297

    authors: Shin JU,Gantsetseg D,Jung JY,Jung I,Shin S,Lee JH

    更新日期:2014-12-01 00:00:00

  • Evaluation of changes in oxygen tension as indicators of RIF-1 tumor response to Nd:YAG laser heating.

    abstract::Heat-induced oxygen tension changes in RIF-1 tumors in C3H male mice were analyzed in an attempt to correlate these changes with tumor response to Nd:YAG laser heating. A low power, microprocessor-controlled Nd:YAG laser was used to superficially heat 250-300 mm3 tumors to base temperatures of 44, 45, 46, or 48 degree...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900130308

    authors: Fahy AK,Waldow SM

    更新日期:1993-01-01 00:00:00

  • Risk factors for recurrence of vaginal intraepithelial neoplasia in the vaginal vault after laser vaporization.

    abstract:BACKGROUND:We sought to investigate risk factors for recurrence of vaginal intraepithelial neoplasia (VAIN) in the vaginal vault after laser vaporization. MATERIALS AND METHODS:Among 162 patients treated with laser vaporization in the vaginal vault after hysterectomy between March 1998 and August 2007, the clinical da...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.20741

    authors: Kim HS,Park NH,Park IA,Park JH,Chung HH,Kim JW,Song YS,Kang SB

    更新日期:2009-03-01 00:00:00

  • Effects of low intensity laser irradiation during healing of skin lesions in the rat.

    abstract:OBJECTIVE:To determine whether laser light can improve healing of skin wounds by killing wound bacteria while simultaneously accelerating host tissue activity. MATERIALS AND METHODS:Wounds on the rat dorsum were irradiated or sham-irradiated three times weekly from days 1 to 19 using 635 or 808 nm diode lasers at 1 or...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.20769

    authors: Nussbaum EL,Mazzulli T,Pritzker KP,Heras FL,Jing F,Lilge L

    更新日期:2009-07-01 00:00:00

  • Relation between skin surface temperature and minimal blanching during argon, Nd-YAG 532, and CW dye 585 laser therapy of port-wine stains.

    abstract::Laser photocoagulation has proven to be valuable in the treatment of port-wine stains. In this application, the minimal blanching technique is used as an indicator of suitable dosage since it has been demonstrated that the immediate appearance a white mark is required to achieve permanent blanching a few months later....

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.1900130119

    authors: Mordon S,Beacco C,Rotteleur G,Brunetaud JM

    更新日期:1993-01-01 00:00:00

  • Intracutaneous ALA photodynamic therapy: dose-dependent targeting of skin structures.

    abstract:BACKGROUND:Photodynamic therapy (PDT) using topical aminolevulinic acid (ALA) depends on local drug uptake, metabolism to porphyrins, and depth of light penetration using different wavelengths. Topical ALA-PDT has limited depth of drug penetration. We studied induced porphyrin distribution and PDT after intradermal ALA...

    journal_title:Lasers in surgery and medicine

    pub_type: 杂志文章

    doi:10.1002/lsm.21073

    authors: Sakamoto FH,Doukas AG,Farinelli WA,Tannous Z,Su Y,Smith NA,Zurakowski D,Anderson RR

    更新日期:2011-09-01 00:00:00