Towards a general method for the stepwise solid-phase synthesis of peptide–oligonucleotide conjugates

Antopolsky, Maxim; Azhayeva, Elena; Tengvall, Unni; Azhayev, Alex

doi:10.1016/s0040-4039(01)02185-2

Cited by 39 publications

(33 citation statements)

References 8 publications

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“…3'-NLS,5'-RGD conjugate (16): The 3'-NLS conjugate 15 (0.45 mg, 0.088 mmol) was dissolved in an 80 % aqueous AcOH solution (0.4 mL) and the RGD peptide P3 in water (3 equiv, 0.175 mg) was added. The reaction mixture was stirred overnight at room temperature and the acetic acid was then lyophilized.…”

Section: Methodsmentioning

confidence: 99%

“…3'-NLS,5'-RGD conjugate (16): An aqueous solution of NLS peptide P2 (2 equiv, 0.12 mg) was added to a solution of oligonucleotide 18 b (0.2 mg, 0.047 mmol) in 0.1 m ammonium acetate buffer (0.3 mL, pH 4.6). The reaction mixture was stirred for 4 h at room temperature and the conjugate 16 was then purified by HPLC (0.180 mg, 70 %).…”

Section: Methodsmentioning

confidence: 99%

“…[15] The method suffers from the poor compatibility of the peptide and oligonucleotide chemistries and has not found much favour in spite of some promising advances in this area. [16] The second approach (the fragment approach) involves the separate solid phase assembly of peptide and oligonucleotide, deprotection and purification (when necessary), and the coupling of the two fragments in solution phase. This is done by introducing mutually reactive groups into each fragment during or after the solid phase synthesis and involves the formation of linkages like disulfide, [17] thioether, [18] amide, [19] maleimide, [20] oxime, [21] thiazolidine, [21a, b] and hydrazone.…”

Section: Introductionmentioning

confidence: 99%

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New Strategy for the Synthesis of 3′,5′‐Bifunctionalized Oligonucleotide Conjugates through Sequential Formation of Chemoselective Oxime Bonds

Edupuganti

Singh

Defrancq

et al. 2004

Chemistry A European J

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A convenient strategy for the synthesis of bifunctionalized oligonucleotide conjugates bearing two different reporters at the 3' and 5' ends of the oligonucleotide is presented. The method involves the preparation of oligonucleotides bearing an aldehyde and/or aminooxy functionality at each end, followed by reaction to form oxime bonds with appropriately functionalized reporters. The conjugation reactions are carried out under mild aqueous conditions with good reaction yield.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

New Strategy for the Synthesis of 3′,5′‐Bifunctionalized Oligonucleotide Conjugates through Sequential Formation of Chemoselective Oxime Bonds

Edupuganti

Singh

Defrancq

et al. 2004

Chemistry A European J

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“…The (MeO) 2 Tr group was removed with acetic acid and the resulting product was repurified. Analysis of the purified product by polyacrylamide gel electrophoresis show a broad band with less mobility than the corresponding 40 mer as described for other oligonucleotide-peptide conjugates [1,27]. Melting experiments performed with duplexes of oligonucleotide 3 with their complementary oligonucleotide gave the same melting temperatures when compared with their linear analogues ( Table 3).…”

mentioning

confidence: 60%

Synthesis of OligonucleotidePeptide Conjugates Carrying the c‐myc Peptide Epitope as Recognition System

Frieden¹,

Aviñó²,

Tarrasón³

et al. 2004

Chemistry & Biodiversity

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Oligonucleotidepeptide conjugates 1–3 were prepared by sequential addition of the appropriate Boc‐protected amino acids, followed by nucleoside phosphoramidites in the same support. These molecules are designed to be used for triplex formation and for the directed assembly of nanomaterials. The structures of the desired oligonucleotidepeptide conjugates were confirmed by mass spectrometry on small oligonucleotidepeptide conjugates, by gel electrophoresis, and by hybridization with complementary oligonucleotides. Oligonucleotides carrying the c‐myc peptide were specifically recognized by the anti‐c‐myc monoclonal antibody.

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“…Mel-P15 (amino acid sequence, GLPALISWIKRKRQQ) was synthesized by GL Biochem, Ltd. (Shanghai, China) via stepwise solid phase methodology (14). Then the peptide was purified using a Sephadex™ gel column.…”

Section: Methodsmentioning

confidence: 99%

The anti‑hepatocellular carcinoma activity of Mel‑P15 is mediated by natural killer cells

Cui

Peng

et al. 2017

Oncol Lett

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Abstract. Mel-P15 is a peptide derived from melittin, the main toxic component in the venom of the European honeybee Apis mellifera. In the present study, the antitumor effects of Mel-P15 and the underlying molecular mechanisms of these effects in vivo were investigated. Mel-P15 directly stimulated natural killer (NK) cell cytotoxicity in vitro, which was increased to 55.45% at a 4 µg/ml dose of Mel-P15. In the mouse liver cancer (H22) xenograft mice model, Mel-P15 suppressed tumor growth in vivo; the tumor inhibitory rate was 61.15% following treatment with 2 mg/kg Mel-P15. In addition, the immune response was activated following Mel-P15 treatment. Mel-P15 treatment increased the spleen and thymus indices, promoted splenocyte proliferation, stimulated NK cytotoxicity and upregulated the secretion of cytokines, including interleukin-2, interferon-γ and tumor necrosis factor-α. In addition, the tumor inhibitory effect of Mel-P15 on BEL-7402-bearing nude mice was abrogated by the selective depletion of NK cells via the intraperitoneal injection of an anti-asialo GM-1 antibody. The results suggest that Mel-P15 inhibits tumor growth in vivo by promoting NK cell cytotoxicity. Mel-P15 may therefore be a potential immunotherapy candidate for the treatment of hepatocellular carcinoma.

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Towards a general method for the stepwise solid-phase synthesis of peptide–oligonucleotide conjugates

Cited by 39 publications

References 8 publications

New Strategy for the Synthesis of 3′,5′‐Bifunctionalized Oligonucleotide Conjugates through Sequential Formation of Chemoselective Oxime Bonds

New Strategy for the Synthesis of 3′,5′‐Bifunctionalized Oligonucleotide Conjugates through Sequential Formation of Chemoselective Oxime Bonds

Synthesis of OligonucleotidePeptide Conjugates Carrying the c‐myc Peptide Epitope as Recognition System

The anti‑hepatocellular carcinoma activity of Mel‑P15 is mediated by natural killer cells

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