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Chemical Structure| 868594-52-9 Chemical Structure| 868594-52-9
Chemical Structure| 868594-52-9

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Fmoc-NH-PEG8-CH2COOH is an 8-unit PEG derivative containing an Fmoc-protected amino group and a C2-carboxylic acid group. It is commonly used in peptide synthesis and bioconjugation.

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Product Citations

Astrid Haraldsson ;

Abstract: One of the major challenges in cancer treatment is delivering high enough doses of active substance specifically to cancer cells without accumulation in healthy organs. Pretargeting has emerged as a potential solution, where the delivery of a cancer recognizing (primary) agent and a cancer killing (secondary) agent are separated. Pretargeted cancer therapy utilizing PNA probes has proved to be a promising approach to selectively deliver toxic payloads to cancer cells while minimizing accumulation in healthy organs. The aim of this project was to develop a new set of secondary PNA probes specifically designed for PNA pretargeted delivery of cytotoxic drugs. A HER2-specific Affibody molecule, ZHER2:2891-SR-H6, was recombinantly produced in E. coli before being conjugated to a primary PNA hybridization probe, HP9, through sortase A-mediated ligation, to produce the primary agent, ZHER2:2891-SR-HP9. Circular dichroism (CD) spectroscopy confirmed the stability of the constructs with high melting temperatures of 71.2 and 73.7 °C. Surface plasmon resonance (SPR) analysis demonstrated high binding affinity to HER2, slightly affected by PNA conjugation. Three new secondary PNA hybridization probes were designed, differing mainly in prevalence and position of a hydrophilic PEG molecule. The probes were produced by solid phase peptide synthesis and conjugated to the cytotoxic drug DM1 through maleimide-cysteine coupling. Analytical RP-HPLC evaluation revealed a slightly higher apparent hydrophobicity for the probe with PEG in the main chain. All three secondary probes displayed high affinity to the primary probe with KD values between 498–505 pM. In vitro cytotoxicity studies on HER2-overexpressing cells demonstrated comparable potent cytotoxic activity for pre-incubated primary and secondary probes with IC50 values of 10–14 nM. These results indicate the successful development of three PNA-drug conjugates for pretargeted delivery of cytotoxic drugs.

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Alternative Products

Product Details of Fmoc-NH-PEG8-CH2COOH

CAS No. :868594-52-9
Formula : C33H47NO12
M.W : 649.73
SMILES Code : OC(COCCOCCOCCOCCOCCOCCOCCOCCNC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)=O
MDL No. :MFCD27635163
InChI Key :JRLUSGRARXJCNA-UHFFFAOYSA-N
Pubchem ID :57884377

Safety of Fmoc-NH-PEG8-CH2COOH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of Fmoc-NH-PEG8-CH2COOH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 868594-52-9 ]

[ 868594-52-9 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 868594-51-8 ]
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  • 2
  • [ 868594-52-9 ]
  • C143H174N19O26PolS4 [ No CAS ]
  • [ 71989-26-9 ]
  • H-(Lys)16-NH-[CH2CH2O]8-CH2CO-Gly-Ala-Cys-Arg-Arg-Glu-Thr-Ala-Trp-Ala-Cys-Gly-OH [ No CAS ]
  • 4
  • 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide [ No CAS ]
  • [ 868594-52-9 ]
  • 5
  • [ 86770-67-4 ]
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  • 6
  • [ 352439-36-2 ]
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  • 7
  • C22H43N3O10 [ No CAS ]
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  • 8
  • C37H55NO12 [ No CAS ]
  • [ 868594-52-9 ]
  • 9
  • [ 868594-52-9 ]
  • [ 50-28-2 ]
  • C51H69NO13 [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Compound (9). Fmoo-NH-PEG8-CH2CH2COOH (300 mg, 0.3 mmol) was activated by N- Hydroxysuccinimide (NHS) (34.5 mg, 0.3 mmol) in 1 mL of DMF for 3h, followed by the addition of 17β- estradiol (81.6 mg, 0.3 mmol,) and EDC (46.6 mg, 0.3 mmol). Reaction mixture was stirred at room temperature for 72h and monitored by reverse phase HPLC. Crude product was purified by HPLC reverse phase column (Zorbax300SB-C18, 21.2x150mm, 5uCrt) to give compound 9 Yield (41 mg, 16%). 1H NMR (500 MHz, MeOD-d4) 6 7.12 - 7.11 (d, 1H), 6.59 - 6.57 (m, 1H), 6.52-6.51 (d, 1H), 4.26 - 4.24 (m, 1H), 3.77 - 3.74 (t, 2H), 3.71 - 3.56 (m, 31 H), 3.34 - 3.32 (m, 2H), 2.83 - 2.80 (m, 2H), 2.59 - 2.56 (t, 2H), 2.36 - 2.31 (m, 1H), 2.17 - 2.14 (m, 1H), 2.09 - 2.05 (m, 1H), 2.01 - 1.97 (m, 1H), 1.92 - 1.88 (m, 1H), 1.59 - 1.19 (m, 8H), 0.81 (s, 3H). 13C NMR (500 MHz, MeOD-d4) 6171.62, 152.12, 141.58, 138.85, 135.04, 128.85, 125.00, 123.42, 122.38, 117.17, 112.27, 109.95, 78.73, 67.76, 67.74, 67.67, 67.59, 67.53, 67.14, 64.07, 63.81 , 47.54, 40.59, 38.02, 36.76, 34.26, 32.13, 26.94, 26.93, 26.88, 24.75, 23.83, 20.25, 7.90HRMS (ESI+) cald for C51H69NO13 [M + 1]*: 905.11 , found 905.19.
16% Compound (9). Fmoo-NH-PEG8-CH2CH2COOH (300 mg, 0.3 mmol) was activated by N- Hydroxysuccinimide (NHS) (34.5 mg, 0.3 mmol) in 1 mL of DMF for 3h, followed by the addition of 17β- estradiol (81.6 mg, 0.3 mmol,) and EDC (46.6 mg, 0.3 mmol). Reaction mixture was stirred at room temperature for 72h and monitored by reverse phase HPLC. Crude product was purified by HPLC reverse phase column (Zorbax300SB-C18, 21.2x150mm, 5uCrt) to give compound 9 Yield (41 mg, 16%). 1H NMR (500 MHz, MeOD-d4) 6 7.12 - 7.11 (d, 1H), 6.59 - 6.57 (m, 1H), 6.52-6.51 (d, 1H), 4.26 - 4.24 (m, 1H), 3.77 - 3.74 (t, 2H), 3.71 - 3.56 (m, 31 H), 3.34 - 3.32 (m, 2H), 2.83 - 2.80 (m, 2H), 2.59 - 2.56 (t, 2H), 2.36 - 2.31 (m, 1H), 2.17 - 2.14 (m, 1H), 2.09 - 2.05 (m, 1H), 2.01 - 1.97 (m, 1H), 1.92 - 1.88 (m, 1H), 1.59 - 1.19 (m, 8H), 0.81 (s, 3H). 13C NMR (500 MHz, MeOD-d4) 6171.62, 152.12, 141.58, 138.85, 135.04, 128.85, 125.00, 123.42, 122.38, 117.17, 112.27, 109.95, 78.73, 67.76, 67.74, 67.67, 67.59, 67.53, 67.14, 64.07, 63.81 , 47.54, 40.59, 38.02, 36.76, 34.26, 32.13, 26.94, 26.93, 26.88, 24.75, 23.83, 20.25, 7.90HRMS (ESI+) cald for C51H69NO13 [M + 1]*: 905.11 , found 905.19.
 

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