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Conjugates of Tetrapyrrolic Macrocycles as Potential Anticancer Target-Oriented Photosensitizers

Topics in Current Chemistry volume 381, Article number: 10 (2023) Cite this article

Abstract

Photodynamic therapy is a minimally invasive treatment of tumors using photosensitizers, light, and reactive oxygen species, which can destroy cellular structures. With the development of photodynamic therapy, significant efforts have been made to create new efficient photosensitizers with improved delivery to cells, stability, and selectivity against cancer tissues. Naturally occurring tetrapyrrolic macrocycles, such as porphyrins and chlorins, are very attractive as photosensitizers, and their structural modification and conjugation with other biologically active molecules are promising approaches for creating new photosensitizers specifically targeting cancer cells. The present review aims to highlight recent developments in the design, preparation, and investigation of complex conjugates of tetrapyrrolic macrocycles, which can potentially be used as sensitizers for target-oriented photodynamic therapy of cancer. In this review, we discuss the structure, photodynamic effect, and anticancer activity of the following conjugates of tetrapyrrolic macrocycles: (1) conjugates obtained by modifying peripheral substituents in porphyrins and chlorins; (2) conjugates of porphyrins and chlorins with lipids, carbohydrates, steroids, and peptides; (3) conjugates of porphyrins and chlorins with anticancer drugs and some other biologically active molecules; (4) metal-containing conjugates. The question of how the conjugate structure affects its specificity, internalization, localization, and photoinduced toxicity within cancer cells is the focus of this review.

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Data availability

The authors confirm that the data supporting the findings of this study are available within the article.

Abbreviations

PDT:

Photodynamic therapy

PSs:

Photosensitizers

ROS:

Reactive oxygen species

SO:

Singlet oxygen

.OH:

Hydroxyl radical

HOO·:

Hydroperoxyl radical

O− 2 :

Superoxide

BODIPY:

Difluoro-4-bora-3a,4a-diaza-s-indacene

NO:

Nitric oxide

NOS:

Nitric oxide synthase

NF-κB:

Nuclear factor kappa-light-chain-enhancer of activated B cells

DNA:

Deoxyribonucleic acid

DMSO:

Dimethyl sulfoxide

ATP:

Adenosine triphosphate

DiR:

1,1′-Dioctadecyl-3,3,3′,3′-tetramethyl-indotricarbocyanine iodide

FRET:

Fluorescence resonance energy transfer

NIR:

Near-infrared

DCC:

N,N′-Dicyclohexylcarbodiimide

HOBt:

Hydroxybenzotriazole

EDC:

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide

DMAP:

4-Dimethylaminopyridine

HPPH:

2-(1-Hexyloxyethyl)-2-devinyl pyropheophorbide-a

PET:

Positron emission tomography

TNFSF13:

Tumor necrosis factor ligand superfamily member 13

LDL:

Low-density lipoprotein

M2-TAMs:

Tumor-associated macrophages

RIF:

Radiation-induced fibrosarcoma

ABCG2:

ATP-binding cassette super-family G member 2

α-MSH:

α-Melanocyte-stimulating hormone

CD133:

Prominin-1 (surface marker of colorectal cancer)

K6L9:

Peptide-Ac[D(K6L9)]NH2 (antimicrobial peptide, possessing membrane-lytic property)

cRGD:

Cyclic Arg-Gly-Asp

Lys:

Lysine

Gly:

Glycine

Ala:

Alanine

YY1:

Yin Yang 1 (transcriptional repressor protein)

RKIP:

Raf kinase inhibitor protein

BAX:

Bcl-2-like protein 4 (apoptosis regulator)

Bcl-2:

B-cell lymphoma 2 (apoptosis regulator)

HDAC:

Histone deacetylase

PSMA:

Prostate-specific membrane antigen

ADP:

Adenosine diphosphate

PARP:

Poly(ADP-ribose) polymerase

EPR:

Electron paramagnetic resonance

MR:

Magnetic resonance

DTPA:

Diethylenetriaminepentaacetic acid

EGFR:

Epidermal growth factor receptor

VEGFR:

Vascular endothelial growth factor

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Acknowledgements

This research was funded by Program for Basic Research in the Russian Federation for a long-term period (2021–2030) (no. 122030100170-5).

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  1. V.N. Orekhovich Institute of Biomedical Chemistry, 10, Pogodinskaya Street, 119435, Moscow, Russia

    Andrew M. Korolchuk, Vladimir A. Zolottsev & Alexander Y. Misharin

  2. Institute of Fine Chemical Technologies, MIREA-Russian Technological University, 86 Vernadskogo Av., Moscow, 119454, Russia

    Andrew M. Korolchuk

  3. RUDN University, 6, Miklukho-Maklaya Street, 117198, Moscow, Russia

    Vladimir A. Zolottsev

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Korolchuk, A.M., Zolottsev, V.A. & Misharin, A.Y. Conjugates of Tetrapyrrolic Macrocycles as Potential Anticancer Target-Oriented Photosensitizers. Top Curr Chem (Z) 381, 10 (2023). https://doi.org/10.1007/s41061-023-00421-0

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