WO1989006122A1 - Utilisation de peptides de dithiol de thioredoxine, derives ou analogues de thioredoxine, dans des preparations de soin des cheveux - Google Patents

Utilisation de peptides de dithiol de thioredoxine, derives ou analogues de thioredoxine, dans des preparations de soin des cheveux Download PDF

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Publication number
WO1989006122A1
WO1989006122A1 PCT/US1988/004694 US8804694W WO8906122A1 WO 1989006122 A1 WO1989006122 A1 WO 1989006122A1 US 8804694 W US8804694 W US 8804694W WO 8906122 A1 WO8906122 A1 WO 8906122A1
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WIPO (PCT)
Prior art keywords
thioredoxin
cys
derived
waving
hair
Prior art date
Application number
PCT/US1988/004694
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English (en)
Inventor
Vincent P. Pigiet
Original Assignee
Repligen Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US07/140,353 external-priority patent/US4894223A/en
Priority claimed from US07/140,354 external-priority patent/US4935231A/en
Application filed by Repligen Corporation filed Critical Repligen Corporation
Publication of WO1989006122A1 publication Critical patent/WO1989006122A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/04—Depilatories

Definitions

  • Wavy hair is considered a desirable human hair feature, whereas straight hair is usually held in less favor. Because of these human demands to beautify the hair, there has evolved a multitude of hair care products with a variety of claims and promises. With hair care products designed to dye or wave the hair, it has been found that the structure of the hair shaft itself must be reckoned with in order to have a product which would give the desired results.
  • a key detail of the hair shaft, which is predominantly keratinaceous in nature, is that the keratin fibers are bonded together by disulfide crosslinkages. It is this detail of the hair structure which the subject invention is concerned with.
  • the prior art discloses the severance of the disulfide crosslink with, enter alia, various chemical agents.
  • keratin disulfides are reduced by use of either sulfites or bisulfites.
  • Sulfite and bisulfite waving have the advantage of being less damaging than a thioglycolate wave with less likelihood of overprocessing.
  • Drawbacks to the sulfite and bisulfite waving process are that they give soft waves and the permanent does not last as long as the thioglycolate wave.
  • An additional detraction of the bisulfite wave is the formation of keratin thiosulfates, commonly known as Bunte salts. The presence of residual
  • Bunte salts can lead to relaxation of the curl through disulfide exchange and to lanthionine formation causing irreversible hair damage. These Bunte salts can also affect the texture and feel of hair.
  • the subject invention concerns the surprising and advantageous discovery that the use of organic reducing agents such as thioglycolic acid, -cysteine ethylester, beta-mercaptoethylamine, cysteine, mercaptosuccinic acid, beta-mercapto propionic acid, dimercapto adipic acid, thiomalic acid, thioglycollamides, glycol thioglycollate, glycerol thioglycollate, thiolactic acid and salts thereof (referred to collectively as organic reducing agents) in hair care preparations can be dramatically improved upon by use of thioredoxin or a thioredoxin-derived, or thiored ⁇ xin-like, dithiol peptide in combination with organic reducing agents.
  • organic reducing agents such as thioglycolic acid, -cysteine ethylester, beta-mercaptoethylamine, cysteine, mercaptosucc
  • a further aspect of the subject invention is the discovery that the use of sulfite or bisulfite compounds in hair care preparations can also be improved upon by use of thioredoxin or thioredoxin-derived, or thioredoxin-like, dithiol peptide compounds.
  • thioredoxin compounds significantly reduces the amount of sulfite or bisulfite compounds needed to achieve the desired effect in the hair. This combination of thioredoxin compounds with sulfites or bisulfites facilitates waving the hair in a shorter time and makes it possible to cleave the Bunte salts formed from the hair fiber. Thus, the use of thioredoxin compounds enhances the reductive properties of sulfite and bisulfite compounds and additive dithiol peptides.
  • thioredoxin or a thioredoxin-derived, or thioredoxin-like, dithiol peptide to a hair care product containing an organic reducing agent, e.g., a preparation for straightening, waving, removing, or softening hair
  • an organic reducing agent e.g., a preparation for straightening, waving, removing, or softening hair
  • organic reducing agent e.g., a preparation for straightening, waving, removing, or softening hair
  • the TGA concentration can be reduced by a factor of 4 (to about 0.15 M) and still give the same amount of waving as a commercial waving lotion containing 0.6 M TGA This effect carries over to the other organic reducing agents also.
  • a synergistic effect is also observed when thioredoxin or a thioredoxin- derived, or thioredoxin-like, dithiol peptide is added to a hair care product containing a sulfite or bisulfite compound.
  • thioredoxin compound significantly less bisulfite or sulfite is needed to effect the desired hair treatment
  • sodium or ammonium bisulfite is used in waving lotions at about 7.0% concentration levels.
  • the bisulfite concentration increases from about 0.01% to about 7.0%, the amount of hair curling increases with a leveling off occurring at about 7.0%.
  • the bisulfite concentration can be reduced by a factor of two to about 3.2% and still give the same amount of waving as a commercial waving lotion containing 7.0% bisulfite.
  • the concentration of thioredoxin or one of the thioredoxin-derived, or thioredoxin-like, dithiol peptides which can be used to enhance the effect of an organic reducing agent, or a sulfite or bisulfite compound ranges from about 1 to about 100 nmole/ml.
  • the optimal concentration for intact bacterial thioredoxin appears to be about 2 nmole/ml.
  • Thioredoxins are low molecular weight dithiol proteins that have the ability to reduce disulfides in typical organic compounds such as Eliman's reagent or disulfides as they exist naturally in a variety of proteins (Holmgren, A [1981] Trends in Biochemical Science 6:26-39).
  • Thioredoxin and thioredoxin-derived, or thioredoxin-like, dithiol peptides within the scope of the subject invention are exemplified by the following compounds:
  • thioredoxin isolated from Escherichia coli (Laurent, T.C., Moore, E.C., and Reichard, P. [1964] J. Biol. Chem. 239:3436-3445); (2) thioredoxins isolated from other sources, e.g., thioredoxin isolated from yeast (Porque, G.P., Baldesten, A, and Reichard, P. [1970] J. Biol. Chem. 245:2362-2379); Cvanobacterium (Gleason, F.K. and Holmgren, A [1983] in 'Thioredoxins, Structure and Function" [P. Gadal, ed.] Editions du Centre National de labericht Scientifique); rat (Guerara, J., Moore, E.C., and Ward, D. NM.
  • T* bacteriophage Soderberg, B.-O., Sjoberg, B.-M., Sonnerstam, U., and Branden, C.-I.
  • thioredoxin purification of mammalian thioredoxin (Luthman, M. and Holmgren, A [1982] Biochem. 121:6628-6633); further, thioredoxin from a human source can be used in the subject invention;
  • thioredoxin-derived peptides are the fragment containing residues 1 through 37 (i.e., T ⁇ -- produced by cyanogen bromide cleavage of thioredoxin from E. coli.
  • the important feature of these thioredoxin-derived dithiol peptides is that they contain the redox-active peptide sequence, Cys-X-Y-Cys, wherein X and Y, independently, can be any of the natural 20 amino acids.
  • redox-active sequences Cys-X-Y-Cys-Lys or Trp-Cys-X-Y-Cys-Lys, wherein X and Y are as defined above, for example, Cys-Gly-Pro-Cys-Lys or Trp-Cys-Gly-Pro-Cys-Lys can be used; and (4) thioredoxin-like dithiol peptides that inter alia have the intrinsic ability to catalyze the reduction of protein disulfides. These thioredoxin-like dithiol peptides will generally have the characteristic of containing a pair of cysteine residues which form a redox-active disulfide.
  • This example includes peptides, derived from natural sources or constructed synthetically, that include the same redox- active sequence as disclosed above, for example in E. coli thioredoxin, Cys-Gly-Pro-Cys, Cys-Gly-Pro-Cys-Lys, or Trp-Cys-Gly-
  • Other thioredoxin-like peptides include the class of seed proteins called purothionins that have intrinsic thioredoxin-like activity (Wada, K. and Buchanan, B3. [1983] in "Thioredoxins, Structure and Function" [Gadal, P., ed.] Editions du Centre National de la Recherche Scientifique).
  • Hair tresses were divided into small tresses approximately 1 cm wide. Each tress was treated with 2 ml of waving lotion. Half of the waving lotion (1 ml) was applied to the tress and combed through. An end paper was folded around the tress to assure that the tress was flat and that all ends were covered. The tress was rolled firmly and evenly on the smallest rods available in the TONI SPIN CURLERTM assortment After the tress was rolled the remaining waving lotion was applied and the tress kept for 15 minutes at room temperature. After 15 minutes the tress was rinsed for 30 seconds under warm running tap water, blotted dry, and maintained at room temperature for an additional 30 minutes. The tress was neutralized by applying 2 ml of hydrogen peroxide (0.5%).
  • the curling rod was removed and an additional 2 ml of hydrogen peroxide was applied.
  • the tress was rinsed for 30 seconds under warm running tap water, blotted dry, and allowed to completely air-dry before making any measurements.
  • RHL is the relative hair length
  • L « the length before waving
  • Lj the length after waving
  • TGA concentration ranging from about 0.01 M to about 0.6 M was evaluated in a solution containing ammonium bicarbonate in the same molar concentration as TGA at pH 8.6. The influence on waving was determined in the absence and presence of 10 nmole/ml of thioredoxin. Two hair lots were also used. The tresses were waved and the relative hair length determined as described above. The results showed that as the TGA concentration increased from about 0.01 M to about 0.6 M the amount of curling also increased and leveled off at approximately 0.4 M.
  • thioredoxin concentrations were varied from about 1 to about 10 nmole/ml.
  • the waving solution was solution (2) above.
  • the results showed that thioredoxin concentration can be decreased to as low as 2 nmole/ml before there is a noticeable decrease in the effect on waving.
  • an object of the subject invention is to be able to lower the pH and still obtain a high level of waving.
  • pH was decreased from 8.5 to 7.5 there was also a decrease in the amount of waving, both in the presence and absence of thioredoxin.
  • the amount of waving in the presence of thioredoxin and 0.2 M TGA was still greater than the amount of waving with the 0.2 M TGA alone at pH 8.6.
  • TGA becomes a less efficient reducing agent, contributing to the decreased waving, both in the presence and absence of thioredoxin.
  • the pH was adjusted with concentrated HQ.
  • the waving solutions contained 0.2 M TGA and 0.2 M NH,HC0 3 , and 0.2 M TGA, 0.2 M NH,HC0 3 , and 40 nmole/ml thioredoxin.
  • the experimental procedure was as described above.
  • Thioredoxin is purified either from a commercial source of E. coli. strain B (Grain Processing Corp., Minneapolis, MN) or from any of a number of common strains of E. coli grown by standard procedures (Pigiet, V. and Conley, R.R. [1977] J. Biol Chem. 252:6367-6372).
  • the protein is purified using standard procedures including chromatography on ion exchange and molecular sieve columns (Williams, C.H., Zanetti, G., Arscott, L.D., and McAllister, J.K. [1967] J. Biol. Chem.
  • Thioredoxin was at least 95% homogeneous as determined by SDS-polyacrylamide gel electrophoresis. The enzyme was stored in 5 ml aliquots in -20°C in 0.5M Tris, pH 7.4 with 1 mM EDTA
  • Thioredoxin protein is assayed immunologically using quantitative rocket immunoelectrophoresis as described in McEvoy et al., supra.
  • Example 3 Production of Thioredoxin Fragments
  • a sample of the CNBr digest was incubated with a 2-fold molar excess of DTT for 10 minutes at room temperature before being applied to a thiopropyl column equilibrated with 0.1M Tris, pH 7.5, containing 0.5M NaCl and 1 mM EDTA
  • the column was washed with two column volumes of the equilibrating buffer containing 2M urea to remove any T 3 ⁇ . 10 s that was non-specifically bound.
  • the column was then washed with an additional 2 column volumes of equilibrating buffer. ⁇ J . 37 was eluted from the column with 25mM DTT in equilibrating buffer.
  • the sample was analyzed for homogeneity by reverse phase high pressure liquid chromatography on a Waters u-Bondpak C 18 column attached to a Beckman Model 421 system monitored at 214 nm. A 0-60% gradient of acetonitrile containing 0.08 to 0.1% TFA (Buffer B) was used to elute the peptide at a flow rate of 2 ml min. The peptide was judged to be greater than 95% pure by this procedure. DTT was removed from the sample by exclusion chromatography.
  • T 1 . 37 was pooled, dried, and resuspended in sodium acetate buffer and adjusted to pH 8.0 with NH ⁇ OH. An aliquot of trypsin (Sigma -Chemical) was added to the incubation at 1% (w w) of peptide concentration. The reaction mixture was incubated at 37°C for 1 hr.
  • Residues 19 through 36 can be used in the same manner as residues 1-37, described herein.
  • the solvent system employed was 0.1% trifluoroacetic acid (Buffer A) and 0.08% trifluoroacetic acid in acetonitrile (Buffer B). A gradient from 0-30% B over 30 minutes and 30-60% over 15 minutes was used to separate the peptides at a flow rate of 2 mtymin.
  • T 31 . 36 was obtained synthetically and was reduced for several experiments.
  • the peptide was incubated at 37°C for 1 hr with a 5- fold molar excess of DTT.
  • the DTT was removed by HPLC as described for the isolation of ⁇ 32 .- . ⁇ 31 . 36 was taken to dryness, reconstituted with a minimal volume of TE buffer and used immediately in the waving assay. The procedure was only partially effective, with only 30% of the peptide reduced as determined by cleavage of a model Bunte salt
  • Tj.- peptide The effect of Tj.- peptide on waving is shown in Table 2.
  • the peptide has a comparable influence on waving as the intact thioredoxin. In this study the concentration used was twice as great as that of the intact thioredoxin.
  • ⁇ 2 . 37 peptide was varied from about 1 to about 80 nmoles/ml. The waving solution is the same as described in Table 2. The results showed that the ⁇ . 3 peptide can be decreased to as low as 1 nmole/ml before there is any noticeable decrease in the effect on waving.
  • the thioredoxin concentration in both A and B was 10 nmole/ml.
  • the Tj. 37 fragment concentration was 26 nmole/ml for A and 20 nmole/ml for B. A and B were run on two different days using two different lots of hair. The pH for all assays was 8.6.
  • the bisulfite waving solution consisted of 7% (w w) ammonium bisulfite, 4.65% (w w) ethanol, and 0.6% (w w) polyoxyethylene(23) lauryl ether.
  • the pH was adjusted to 7.5 with ammonium hydroxide. All dilutions of the 7% solution were made using a diluent consisting of all components except the ammonium bisulfite.
  • the neutralizer contained 23% hydrogen peroxide adjusted to pH 3.3 with dilute phosphoric acid. All solutions were overlayed with argon or nitrogen and stored in the dark at room temperature for up to 2 months.
  • Hair Waving Assay The influence of thioredoxin and active site peptides on bisulfite permanent waving was determined by direct hair waving assays. Tresses were divided into smaller tresses approximately 0.5 cm wide and 12 to 13 cm in length. Each tress weighed approximately 0.2 g. Intact tresses were shampooed before waving with SILKIENCETM for normal hair (The Gillette Company, Boston, MA). Each tress was shampooed and thoroughly rinsed two times before being combed through and allowed to air dry. Bleached-waved tresses were used as received with no additional treatment. Each tress was treated with a total of 3 ml of waving lotion.
  • the tress was saturated with neutralizer and resaturated after 90 seconds. After 10 minutes at room temperature, the rod was removed from the tress and the neutralizer worked down to the end of the tress. After an additional 2 minutes the tress was rinsed for 2 minutes with 40°C tap water and the hanging length was measured immediately while the tress was wet
  • Example 6 Influence of Thioredoxin
  • Thioredoxin was effective in increasing the waving obtained from a bisulfite solution in hair.
  • the increase in waving with the addition of thioredoxin was also more significant
  • the RHL with the addition of thioredoxin was 0.69 for intact hair compared to 0.68 for bleached-waved hair.
  • Thioredoxin in 3.2% bisulfite produced more waving than a 7% commercial preparation (CLAIROL KINDNESS 33 ').
  • the amount of dithiol required to give the maximal effect was 2-5uM.
  • thioredoxin affected the processing time required in treated hair.
  • the presence of thioredoxin significantly reduces the observed biphasic nature of the reaction.
  • thioredoxin increased the amount of waving at a reaction time as short as 15 minutes. Intact tresses were waved with a 3.2% bisulfite solution alone or containing 5 uM thioredoxin. As with treated hair, the greatest increase in waving with the addition of thioredoxin was at 45 minutes.
  • Example 7 Influence of Thioredoxin and Cysteine Methyl Ester
  • a stable sulfonated thioredoxin intermediate is formed and this intermediate could be recycled to reduced thioredoxin by the addition of a secondary reductant such as cysteine methyl ester or cysteine. Above neutral pH this intermediate is unstable and oxidized thioredoxin is formed.
  • the effect of reduced thioredoxin (5 uM) and various concentrations of cysteine methyl ester on permanent waving at neutral pH was determined. Cysteine methyl ester in the absence of thioredoxin increased the amount of waving though it was not as effective as intact thioredoxin. The presence of cysteine methyl ester had no effect on waving with intact thioredoxin.
  • Waving obtained with reduced thioredoxin in the absence of cysteine methyl ester was comparable to that using oxidized thioredoxin. Since the reduced form of the enzyme is necessary to cleave Bunte salts, this shows that thioredoxin may be involved in something other that Bunte salt cleavage when added directly to the bisulfite waving solution. The other possibility is that thioredoxin is reduced by the bisulfite and then cleaves Bunte salts.
  • ⁇ 1 . 36 is one of the ⁇ iimal active site peptides and is not limited by molecular size as is intact thioredoxin. Cysteine was used as the secondary reductant in the presence of reduced T 31 . 36 (2 uM) and 3.5% bisulfite.
  • Thioredoxin or a thioredoxin-derived, or thioredoxin-like, dithiol peptide can be incorporated, advantageously, into a standard lather shaving cream or brushless shaving cream to soften the hair. This softening of the hair complements the softening realized by the soap and water contact with such shaving creams.
  • the level of thioredoxin or a thioredoxin-derived, or thioredoxin-like, dithiol peptide used in such shaving creams can be varied as described above. Likewise, the percentage of soaps of such standard shaving creams can be reduced with the use of the compounds of the invention.
  • compositions and processes of the previous examples can be readily adapted by a person skilled in the art to be used to care for animal hair in general, e.g., dog, cat, horse, and the like.

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Abstract

L'invention permet d'entretenir plus efficacement les cheveux grâce à une nouvelle préparation permettant de les onduler, de les raidir, de les assouplir, ou d'en enlever. Ladite préparation utilise comme ingrédient clé la thiorédoxine composée ou un peptide de dithiol dérivé de thiorédoxine ou analogue à celle-ci, conjointement avec un agent de réduction organique, ou un composé de sulfite ou de bisulfite. Cette invention permet de traiter les cheveaux à un pH inférieur afin de moins les abimer lorsqu'on les ondule, lorsqu'on les raidit ou lorsqu'on les assouplit. Lorsqu'on s'épile, les odeurs désagréables des produits dépilatoires sont réduites au minimum ou éliminés.
PCT/US1988/004694 1988-01-04 1988-12-29 Utilisation de peptides de dithiol de thioredoxine, derives ou analogues de thioredoxine, dans des preparations de soin des cheveux WO1989006122A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US140,354 1988-01-04
US07/140,353 US4894223A (en) 1985-08-28 1988-01-04 Use of thioredoxin, thioredoxin-derived, or thioredoxin-like dithiol peptides in hair care preparations
US140,353 1988-01-04
US07/140,354 US4935231A (en) 1985-08-28 1988-01-04 Use of thioredoxin, thioredoxin-derived, or thioredoxin-like dithiol peptides in hair care preparations

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002067875A1 (fr) * 2001-02-22 2002-09-06 L'oreal S.A. Compositions defrisantes comprenant au moins un compose d'hydroxyde et au moins un agent d'activation, et leurs procedes d'utilisation
WO2002085317A1 (fr) * 2001-04-20 2002-10-31 L'oreal S.A. Composition et procede de lanthionisation de fibres de keratine utilisant au moins un nucleophile organique et au moins un generateur d'ions hydroxydes
FR2877213A1 (fr) * 2004-10-29 2006-05-05 Michel Flork Composition depilatoire
EP2559422A1 (fr) * 2011-08-17 2013-02-20 The Procter & Gamble Company Article d'épilation efficace
US9248085B2 (en) 2011-08-17 2016-02-02 The Procter & Gamble Company Effective depilatory article

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0183506A2 (fr) * 1984-11-26 1986-06-04 Repligen Corporation Utilisation du thiorédoxine et d'autres peptides dithiolés pour les soins de la chevelure

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0183506A2 (fr) * 1984-11-26 1986-06-04 Repligen Corporation Utilisation du thiorédoxine et d'autres peptides dithiolés pour les soins de la chevelure

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002067875A1 (fr) * 2001-02-22 2002-09-06 L'oreal S.A. Compositions defrisantes comprenant au moins un compose d'hydroxyde et au moins un agent d'activation, et leurs procedes d'utilisation
WO2002085317A1 (fr) * 2001-04-20 2002-10-31 L'oreal S.A. Composition et procede de lanthionisation de fibres de keratine utilisant au moins un nucleophile organique et au moins un generateur d'ions hydroxydes
FR2877213A1 (fr) * 2004-10-29 2006-05-05 Michel Flork Composition depilatoire
WO2006048526A2 (fr) * 2004-10-29 2006-05-11 Producciones Infovision Composition depilatoire non irritante a action rapide
WO2006048526A3 (fr) * 2004-10-29 2006-08-31 Producciones Infovision Composition depilatoire non irritante a action rapide
EP2559422A1 (fr) * 2011-08-17 2013-02-20 The Procter & Gamble Company Article d'épilation efficace
WO2013025871A3 (fr) * 2011-08-17 2013-04-18 The Procter & Gamble Company Article dépilatoire efficace
US9248085B2 (en) 2011-08-17 2016-02-02 The Procter & Gamble Company Effective depilatory article

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