72072-06-1

Basic information

• Product Name: N-Boc-5-aminolevulinic acid
• Synonyms: N-Boc-5-aminolevulinic acid;5-(Tert-butoxycarbonylamino)-4-oxopentanoic acid;5-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-4-oxopentanoic acid
• CAS NO: 72072-06-1
• Molecular Formula: C₁₀H₁₇NO₅
• Molecular Weight: 231.25
• Mol File: 72072-06-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-Boc-5-aminolevulinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-5-aminolevulinic acid(72072-06-1)
• EPA Substance Registry System: N-Boc-5-aminolevulinic acid(72072-06-1)

Safety Data

• Hazardous Substances Data: 72072-06-1(Hazardous Substances Data)

Usage

Uses

Used in Photodynamic Therapy:
N-Boc-5-aminolevulinic acid is used as a precursor in photodynamic therapy for the production of protoporphyrin IX. N-Boc-5-aminolevulinic acid's fluorescence under specific light conditions helps in the visualization and detection of cancer cells, enabling more accurate and targeted treatment.
Used in Medical and Biochemical Research:
N-Boc-5-aminolevulinic acid is utilized as a research tool in various medical and biochemical studies. Its conversion to protoporphyrin IX and the subsequent fluorescence properties make it valuable for investigating cellular processes and mechanisms related to cancer and other diseases.
Used in Drug Development:
The N-Boc protected form of 5-ALA serves as a controlled delivery system for therapeutic applications. Its stability and ability to be metabolized into protoporphyrin IX make it a promising candidate for the development of new drugs and treatment strategies in oncology and other medical fields.
Used in Diagnostic Imaging:
N-Boc-5-aminolevulinic acid is employed in diagnostic imaging techniques, such as fluorescence imaging, to detect and visualize cancer cells. Its conversion to protoporphyrin IX allows for the identification of tumor margins and the assessment of treatment efficacy.
Used in Safety and Handling:
N-Boc-5-aminolevulinic acid is used as a reminder of the importance of proper handling and safety precautions when working with potentially hazardous chemicals. Its potential health risks emphasize the need for meticulous handling, storage, and disposal to ensure the safety of researchers and patients.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 5451-09-2 5-aminolevulinic acid hydrochloride 
• 537712-66-6 5-tert-butoxycarbonylamino-4-oxo-pentanoic acid methyl ester 
• 106-60-5 ALA 
• 178918-29-1 furan-2-ylmethylcarbamic acid tert-butyl ester 
• 617-89-0 furan-2-ylmethanamine 

Downstream Products

• 938074-94-3 C₂₁H₃₁N₃O₆ 
• 1006370-55-3 pentafluorophenyl 5-(tert-butoxycarbonylamino)levulinate 
• 106-60-5 ALA 
• 5451-09-2 5-aminolevulinic acid hydrochloride 

Relevant articles and documents

Development of a Prodrug of Camptothecin for Enhanced Treatment of Glioblastoma Multiforme

A novel therapeutic approach for glioblastoma multiforme (GBM) therapy has been carried out through in vitro and in vivo testing by using the prodrug camptothecin-20-O-(5-aminolevulinate) (CPT-ALA). The incorporation of ALA to CPT may promote uptake of the cytotoxic molecule by glioblastoma cells where the heme synthesis pathway is active, improving the therapeutic action and reducing the side effects over healthy tissue. The antitumor properties of CPT-ALA have been tested on different GBM cell lines (U87, U251, and C6) as well as in an orthotopic GBM model in rat, where potential toxicity in central nervous system cells was analyzed. In vitro results indicated no significant differences in the cytotoxic effect over the different GBM cell lines for CPT and CPT-ALA, albeit cell mortality induced by CPT over normal cell lines was significantly higher than CPT-ALA. Moreover, intracranial GBM in rat was significantly reduced (30% volume) with 2 weeks of CPT-ALA treatment with no significant side effects or alterations to the well-being of the animals tested. 5-ALA moiety enhances CPT diffusion into tumors due to solubility improvement and its metabolic-based targeting, increasing the CPT cytotoxic effect on malignant cells while reducing CPT diffusion to other proliferative healthy tissue. We demonstrate that CPT-ALA blocks proliferation of GBM cells, reducing the infiltrative capacity of GBM and promoting the success of surgical removal, which improves life expectancy by reducing tumor recurrence.

ALA hybrid 3-hydroxypyridone derivative as well as preparation method and application thereof

The invention designs and synthesizes a novel anti-tumor active compound with iron chelating property and photosensitive activity based on the principles of reasonable drug design, drug-likeness and the like. The invention aims to provide a preparation me

Peptide-targeted dendrimeric prodrugs of 5-aminolevulinic acid: A novel approach towards enhanced accumulation of protoporphyrin IX for photodynamic therapy

Photodynamic therapy (PDT) is a promising approach for the targeted treatment of cancer and various other human disorders. An effective, clinically approved approach in PDT involves the administration of 5-aminolevulinic acid (ALA) to generate elevated levels of the natural photosensitiser protoporphyrin IX (PpIX). The development of prodrugs of ALA is of considerable interest as a means to enhance the efficiency and cell selectivity of PpIX accumulation for PDT applications. In this work a novel peptide-targeted dendrimeric prodrug of 5-aminolevulinic acid (ALA) 13 was synthesised which displays nine copies of ALA on a core structure that is linked to a homing peptide for targeted delivery to a specific cancer cell type. The synthesis was accomplished effectively via a flexible, modular solid phase and solution phase route, using a combination of solid phase peptide synthesis and copper-catalysed azide-alkyne cycloaddition chemistry. The prodrug system shows a sustained and enhanced production of protoporphyrin IX (PpIX) in the MDA-MB-231 cell line that over-expresses the epidernal growth factor receptor (EGFR+) in comparison to equimolar ALA and the corresponding non-targeted ALA dendrimer (nine copies of ALA). This study provides a proof of concept for the development of a new generation of prodrugs for ALA-based photodynamic therapy that can deliver an enhanced ALA payload to specific tissue types.

ALA-HPO hybrid derivative with iron chelating property and PDT activity, preparation method and application thereof

The invention provides an ALA-HPO hybrid derivative shown as a formula (I) or a formula (II), and a preparation method thereof, and application of the ALA-HPO hybrid derivative in preparation of photodynamic therapy drugs. The formula (I) and the formula (II) are defined in the specification.

Synthesis method of 5-aminolevulinic acid hydrochloride

The invention relates to a synthesis method of 5-aminolevulinic acid hydrochloride (5-ALA), furfuryl amine (2-furylamine) is used as an initial raw material, and the target product is synthesized through four steps of amino protection, oxidation reaction, reduction reaction and hydrolysis decarboxylation. Reagents used in the synthesis method are low in price, easy to obtain, and environment-friendly and the operation is simple.

F-18-labeled 5-aminolevulinic acid derivative as well as synthetic method and application thereof

The invention discloses an F-18-labeled 5-aminolevulinic acid derivative as well as a synthetic method and an application thereof. A radioactive probe provided by the embodiment of the invention is long in half-life period of radioactivity, and the stabil

Light triggering of 5-aminolevulinic acid from fused coumarin ester cages

The evaluation of the photorelease of 5-aminolevulinic acid (5-ALA), a small molecule which has considerable interest in the area of medicine as a photosensitizer prodrug in PDT and cosmetic treatments, and in agriculture as a herbicide/insecticide, was carried out by using a series of fused coumarin derivatives with different substituents and ring fusions in the preparation of 5-ALA photosensitive ester cages, in order to tune the photophysical and photolytic properties of the resulting conjugates. This study was intended to assess the viability of the photorelease of 5-ALA from lipophilic conjugates since it has hydrophilic character, does not penetrate efficiently through the skin or cell membranes and appropriate derivatisation can enhance its lipophilicity and its application scope in biological environment. Photolytic studies were performed on the ester cages by irradiation in a photochemical reactor at 254, 300, 350 and 419 nm, using methanol/HEPES buffer 80 : 20 solutions as solvent. The data obtained confirmed the suitability of the tested photosensitive moieties for the release of 5-aminolevulinic acid at the various wavelengths of irradiation. As well as the photolysis, the photophysics of the compounds was characterised by both steady state and time-resolved methods which uncovered the presence of different fluorescing species. Additionally, an on-off experiment was carried out by using two excitation sources (cleave and probe) to enable fluorescence to follow the kinetics of the process and to ascertain optical control over the bond scission.

5-[(PIPERAZIN-1-YL)-3-OXO-PROPYL]-IMIDAZOLIDINE-2,4-DIONE DERIVATIVES AS ADAMTS INHIBITORS FOR THE TREATMENT OF OSTEOARTHRITIS

The present invention discloses compounds according to Formula (I), wherein R, R2, R3a, R3b, and Cy are as defined herein. The present invention discloses compounds inhibiting ADAMTS, methods for their production, pharmaceutical compositions comprising the same and methods for the prophylaxis and/or treatment of inflammatory conditions and/or diseases involving degradation of cartilage and/or disruption of cartilage homeostasis.

Study of the stability of the 5-aminolevulinic acid tyrosine ester in aqueous solution

Photodynamic therapy based on photoactivable porphyrins (PAPs) can treat various dermatological conditions. The side-effects as well as the non-selective or insufficient accumulation of PAPs in the targeted tissues limit performances. We studied the stability in solution at different temperatures (21 °C; 4 °C), different pH values (7.5; 2.0), and as a function of time of 5-aminolevulinic acid's Tyrosine-ester, a molecule presenting interesting properties to selectively produce PAPs in blood vessels after topical application. Solutions of this precursor can be kept up to 24 h at refrigerated temperatures and under acidic pH. At room temperature or physiological pH, they must be prepared minutes before their use. ARKAT-USA, Inc.

Novel multifunctional acyloxyalkyl ester prodrugs of 5-aminolevulinic acid display improved anticancer activity independent and dependent on photoactivation

Multifunctional acyloxyalkyl ester prodrugs of 5-aminolevulinic acid in cancer cell lines inhibited the proteasome and induced apoptosis and heme synthesis. The most potent prodrug was butyryloxymethyl 5-amino-4-oxopentanoate (1a). The metabolically released formaldehyde from the prodrugs was the dominant factor affecting cell viability by a ROS-dependent mechanism and was responsible for rapid phosphorylation of H2AX, suppression of the cell survival protein c-myc, and transient elevation in the expression of p21. 1a, which differs from 2a by releasing butyric instead of pivalic acid, was a more potent inducer of heme and acetylated H4 expression and induced apoptosis through activation of caspase 9. 1a and 1b specifically increased the level of the photosensitizer protoporphyrin 9, leading to enhancement of cell death by photodynamic therapy (PDT). The advantage of these multifunctional prodrugs over 5-ALA is their greater potency in the non-PDT mechanism of cancer cell killing and their ability to also augment PDT.